From 7f69ef4097ff89197f7d7bafac6c02e8900d2707 Mon Sep 17 00:00:00 2001 From: Steven Kearnes Date: Mon, 24 May 2021 11:31:50 -0600 Subject: [PATCH 1/5] Add hein-dataset.pbtxt --- hein-dataset.pbtxt | 47584 +++++++++++++++++++++++++++++++++++++++++++ 1 file changed, 47584 insertions(+) create mode 100644 hein-dataset.pbtxt diff --git a/hein-dataset.pbtxt b/hein-dataset.pbtxt new file mode 100644 index 00000000..2ac2c659 --- /dev/null +++ b/hein-dataset.pbtxt @@ -0,0 +1,47584 @@ +name: "Development of an automated kinetic profiling system with online HPLC for reaction optimization" +description: "Reactions from DOI: 10.1039/c9re00086k" +reactions { + inputs { + key: "1" + value { + components { + identifiers { + type: SMILES + value: "O=C(CC(OC)=O)C1CC1" + } + amount { + moles { + value: 276.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + addition_order: 1 + } + } + inputs { + key: "MeI" + value { + components { + identifiers { + type: SMILES + value: "CI" + } + amount { + moles { + value: 276.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + } + addition_order: 1 + } + } + inputs { + key: "base" + value { + components { + identifiers { + type: SMILES + value: "C(=O)([O-])[O-].[K+].[K+]" + } + amount { + moles { + value: 414.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: ROUND_BOTTOM_FLASK + volume { + value: 500.0 + units: MILLILITER + } + } + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + atmosphere { + type: NITROGEN + } + } + stirring { + type: STIR_BAR + } + } + notes { + procedure_details: "To a 500 ml round bottomed flask equipped with a magnetic stir bar under N2 atmosphere was\ncharged methyl 3-cyclopropyl-3-oxopropanoate 1 (39.2 g, 276 mmol), MeI (17.2 ml, 276 mmol)\nand K2CO3 (57.2 g, 414 mmol). The mixture was agitated at 25 \302\260C for 16 h. The reaction mixture\nwas diluted with Et2O (100 ml) and filtered. The solids were rinsed with Et2O (100 ml) and the\nfiltrate was concentrated to a crude oil. The crude oil was purified by normal phase column\nchromatography to give methyl 3-cyclopropyl-2-methyl-3-oxopropanoate 2 in 79% yield." + } + workups { + type: ADDITION + details: "The reaction mixture was diluted with Et2O (100 mL)." + input { + components { + identifiers { + type: SMILES + value: "CCOCC" + } + amount { + volume { + value: 100.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: FILTRATION + keep_phase: "filtrate" + } + workups { + type: WASH + details: "The solids were rinsed with Et2O (100 mL)." + input { + components { + identifiers { + type: SMILES + value: "CCOCC" + } + amount { + volume { + value: 100.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated to a crude oil." + } + workups { + type: OTHER_CHROMATOGRAPHY + details: "The crude oil was purified by normal phase column chromatography." + } + outcomes { + reaction_time { + value: 16.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "O=C(C(C)C(OC)=O)C1CC1" + } + is_desired_product: true + measurements { + type: YIELD + percentage { + value: 79.0 + } + } + } + } + provenance { + doi: "10.1039/c9re00086k" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" + record_created { + time { + value: "05/24/2021, 11:30:49" + } + person { + username: "skearnes" + name: "Steven Kearnes" + orcid: "0000-0003-4579-4388" + organization: "Relay Therapeutics" + email: "skearnes@relaytx.com" + } + } + } + reaction_id: "SYNTHESIS_OF_2" +} +reactions { + inputs { + key: "2" + value { + components { + identifiers { + type: SMILES + value: "O=C(C(C)C(OC)=O)C1CC1" + } + amount { + moles { + value: 64.0 + units: MILLIMOLE + } + } + reaction_role: REACTANT + preparations { + type: SYNTHESIZED + reaction_id: "SYNTHESIS_OF_2" + } + } + addition_order: 1 + } + } + inputs { + key: "NaHMDS" + value { + components { + identifiers { + type: SMILES + value: "C[Si](C)(C)N([Na])[Si](C)(C)C" + } + amount { + moles { + value: 96.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 96.0 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 2 + addition_duration { + value: 30.0 + units: MINUTE + } + } + } + inputs { + key: "THF" + value { + components { + identifiers { + type: SMILES + value: "C1CCOC1" + } + amount { + volume { + value: 100.0 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "THF rinse" + value { + components { + identifiers { + type: SMILES + value: "C1CCOC1" + } + amount { + volume { + value: 50.0 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + addition_order: 3 + addition_time { + value: 30.0 + units: MINUTE + } + } + } + inputs { + key: "Ts2O in THF" + value { + components { + identifiers { + type: SMILES + value: "CC1=CC=C(C=C1)S(=O)(=O)OS(=O)(=O)C2=CC=C(C=C2)C" + } + amount { + moles { + value: 96.0 + units: MILLIMOLE + } + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "C1CCOC1" + } + amount { + volume { + value: 200.0 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + addition_order: 4 + addition_duration { + value: 1.0 + units: HOUR + } + } + } + setup { + vessel { + type: ROUND_BOTTOM_FLASK + preparations { + type: OVEN_DRIED + } + volume { + value: 1000.0 + units: MILLILITER + } + } + } + conditions { + temperature { + setpoint { + value: -78.0 + units: CELSIUS + } + } + pressure { + atmosphere { + type: NITROGEN + } + } + stirring { + type: STIR_BAR + } + } + notes { + procedure_details: "To an oven-dried 1000 ml round bottomed flask equipped with a magnetic stir bar under N2\natmosphere was added methyl 3-cyclopropyl-2-methyl-3-oxopropanoate 2 (10.0 g, 64.0 mmol)\nand THF (100 ml). The mixture was cooled to -78 \302\260C and 1M NaHMDS solution (96.0 ml, 96.0\nmmol) was added over 30 min, maintaining the internal temperature below -60 \302\260C, followed by\na THF rinse (50 ml). The mixture was aged for 1 h at -78 \302\260C and Ts2O (31.3 g, 96.0 mmol) in THF\n(200 ml) was added over 1 h, maintaining the internal temperature below -60 \302\260C. The mixture\nwas aged for 20 min at -78 \302\260C, then warmed to 25 \302\260C and aged for 2 h. A thick slurry formed. The\nreaction was quenched with 300 ml of 0.5M NaHCO3 solution and the phases were separated.\nThe aqueous layer was back-extracted twice with 100 ml of EtOAc. The organic layers were\ncombined and washed with 200 ml of saturated NaCl solution, dried over MgSO4 and filtered.\nUpon concentration to an oil, the crude product was purified by normal phase column\nchromatography to give (E)-methyl 3-cyclopropyl-2-methyl-3-(tosyloxy)acrylate 3-(E) in 30%\nyield and (Z)-methyl 3-cyclopropyl-2-methyl-3-(tosyloxy)acrylate 3-(Z) in 54% yield." + } + workups { + type: WAIT + details: "The mixture was aged for 20 min at -78 \302\260C." + duration { + value: 20.0 + units: MINUTE + } + } + workups { + type: TEMPERATURE + details: "Warmed to 25 \302\260C." + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: WAIT + details: "Aged for 2 h." + duration { + value: 2.0 + units: HOUR + } + } + workups { + type: ADDITION + details: "The reaction was quenched with 300 ml of 0.5M NaHCO3 solution." + input { + components { + identifiers { + type: SMILES + value: "[Na+].OC([O-])=O" + } + amount { + moles { + value: 150.0 + units: MILLIMOLE + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 300.0 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: WORKUP + } + } + } + workups { + type: EXTRACTION + details: "The phases were separated." + keep_phase: "organic" + } + workups { + type: EXTRACTION + details: "The aqueous layer was back-extracted twice with 100 mL of EtOAc." + input { + components { + identifiers { + type: SMILES + value: "O=C(OCC)C" + } + amount { + volume { + value: 100.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + keep_phase: "organic" + } + workups { + type: EXTRACTION + details: "The aqueous layer was back-extracted twice with 100 mL of EtOAc." + input { + components { + identifiers { + type: SMILES + value: "O=C(OCC)C" + } + amount { + volume { + value: 100.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + keep_phase: "organic" + } + workups { + type: WASH + details: "The organic layers were combined and washed with 200 mL of saturated NaCl solution." + input { + components { + identifiers { + type: SMILES + value: "[Na+].[Cl-]" + } + amount { + moles { + value: 1.23 + units: MOLE + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 200.0 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: WORKUP + } + } + } + workups { + type: DRY_WITH_MATERIAL + details: "Dried over MgSO4." + input { + components { + identifiers { + type: SMILES + value: "[Mg+2].[O-]S([O-])(=O)=O" + } + reaction_role: WORKUP + } + } + } + workups { + type: FILTRATION + keep_phase: "filtrate" + } + workups { + type: CONCENTRATION + details: "Concentration to an oil." + } + workups { + type: OTHER_CHROMATOGRAPHY + details: "The crude product was purified by normal phase column chromatography." + } + outcomes { + reaction_time { + value: 16.0 + units: HOUR + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + type: YIELD + percentage { + value: 30.0 + } + } + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\OS(=O)(c2ccc(C)cc2)=O)=O" + } + is_desired_product: true + measurements { + type: YIELD + percentage { + value: 54.0 + } + } + } + } + provenance { + doi: "10.1039/c9re00086k" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" + record_created { + time { + value: "05/24/2021, 11:30:49" + } + person { + username: "skearnes" + name: "Steven Kearnes" + orcid: "0000-0003-4579-4388" + organization: "Relay Therapeutics" + email: "skearnes@relaytx.com" + } + } + } + reaction_id: "SYNTHESIS_OF_3E" +} +reactions { + inputs { + key: "base" + value { + components { + identifiers { + type: SMILES + value: "O=P([O-])([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 387.0 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 387.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + preparations { + type: SPARGED + details: "To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to 10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in preparation for automated dispensing (387 \302\265l, 0.387 mmol)." + } + } + addition_order: 2 + } + } + inputs { + key: "boronic acid" + value { + components { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + amount { + moles { + value: 142.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: NONE + } + } + addition_order: 1 + } + } + inputs { + key: "internal standard" + value { + components { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 13.0 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + addition_order: 1 + } + } + inputs { + key: "palladium precatalyst" + value { + components { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + amount { + moles { + value: 6.44 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + addition_order: 1 + } + } + inputs { + key: "solvents" + value { + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 1.0 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 10.0 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "vinyl tosylate" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + amount { + moles { + value: 129.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: SYNTHESIZED + reaction_id: "SYNTHESIS_OF_3E" + } + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + details: "Reactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01)." + material { + type: GLASS + details: "borosilicate" + } + attachments { + type: CAP + } + volume { + value: 4.0 + units: MILLILITER + } + } + is_automated: true + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + atmosphere { + type: NITROGEN + } + } + stirring { + type: STIR_BAR + details: "Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir discs (VP 782N6)." + rate { + rpm: 300 + } + } + } + notes { + procedure_details: "To a 4 ml reaction vial equipped with a magnetic\ntumble stir disc under N2 atmosphere was charged (E)-methyl 3-cyclopropyl-2-methyl-3-\n(tosyloxy)acrylate 3-(E) (40.0 mg, 0.129 mmol), (3-(benzyloxy)phenyl)boronic acid 4 (32.3 mg,\n0.142 mmol), palladium precatalyst 5 (5.96 mg, 6.44 \302\265mol) and 1,3,5-trimethoxybenzene (2.17\nmg, 0.013 mmol). ACN (1000 \302\265l) and water (10 \302\265l) were added and the mixture agitated to\ndissolve all solids. To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to\n10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in\npreparation for automated dispensing (387 \302\265l, 0.387 mmol). Finally, to a 96-well sample dilution\nplate was charged 400 \302\265l of a 9:1 mixture of acetonitrile and aqueous pH 3.5 ammonium formate\nbuffer." + } + workups { + type: ALIQUOT + details: "Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales 17P687)\ncapped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075)." + amount { + volume { + value: 20.0 + units: MICROLITER + } + } + is_automated: true + } + workups { + type: ADDITION + input { + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 360.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 40.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=C[O-].[NH4+]" + } + amount { + mass { + value: 504.0 + units: MICROGRAM + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=CO" + } + amount { + volume { + value: 316.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + } + stirring { + type: CUSTOM + details: "Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample." + } + is_automated: true + } + outcomes { + reaction_time { + value: 0.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 490.5643 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5050449 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 325.94662 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 880.28033 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.7006886 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09134269 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3745.1382 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 11.490035 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.11178655 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 29.23686 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.08969831 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0010517306 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 233.54845 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.32623914 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 715.8811 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1351.4216 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8877739 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.06384829 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 5268.786 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 7.359862 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.071604095 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 44.23908 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.061796684 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 702.0792 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.98072046 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011499143 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 324.20193 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.45287117 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.005138412 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 95.72977 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.133723 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 397.07077 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5546602 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 198.12094 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.27675116 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 20.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 428.29874 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.365469 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 313.6642 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 822.3286 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6216846 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.08867061 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3498.5737 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 11.153882 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.10851612 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 62.32241 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.19869149 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0023296974 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 30.16609 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0961732 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0010912099 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 610.46533 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1024.2686 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6778488 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0567482 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3162.5361 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.1805334 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05040141 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 87.37809 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14313358 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 987.0381 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6168617 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018958027 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 745.2726 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.220827 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013851869 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 123.86116 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2028963 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 722.6898 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1838342 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 616.6899 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0101963 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 40.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 383.23358 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2016225 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 318.9301 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 814.8354 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.5549028 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.08641192 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3372.003 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 10.572859 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.10286334 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 34.14686 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.10706691 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 114.41904 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.358759 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004206521 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 47.8732 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15010563 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0017031434 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 119.32299 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.37413526 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 36.79529 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.11537102 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 652.619 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1194.7474 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8306967 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.061917823 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2810.0898 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.3058653 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041891765 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 85.43835 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.13091612 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 865.70105 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3265028 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015553512 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 706.9754 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0832896 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.012291329 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 61.12777 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.09366532 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 859.7436 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3173743 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 705.6751 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0812972 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 60.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 314.66492 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9548198 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 329.55426 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 809.42194 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4561114 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0830706 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3333.8533 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 10.11625 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.098421 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 49.84937 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15126301 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 181.53438 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.55084825 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.006458806 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 74.44391 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.22589274 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0025630468 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 148.88913 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.45178944 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 63.25725 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1919479 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 395.85754 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 551.0915 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.392146 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.047085162 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1992.6111 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.033657 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04897245 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 58.44582 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14764357 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 821.37537 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0749266 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02432893 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 506.41293 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2792808 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014515103 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 117.70281 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.29733628 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 372.1861 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9402022 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 294.07016 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.74286866 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 80.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 243.61258 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7168878 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 339.8197 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 786.8825 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3155882 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.07831782 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3218.6992 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 9.471786 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.092151 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 67.9222 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.19987717 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 301.77158 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.88803434 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01041238 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 125.80776 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.37021914 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0042006173 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 177.2651 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5216446 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 93.00232 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.27368137 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 603.6911 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 911.8526 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5104622 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05108685 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3346.3354 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.543125 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05392907 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 83.64434 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.13855487 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1156.3579 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.9154794 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02245938 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 658.2517 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0903783 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.012371759 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 131.60469 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.21800004 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 541.7727 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8974336 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 366.86035 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.60769546 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 100.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 169.65173 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.49360135 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 343.70193 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 728.2881 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.1189528 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.07166722 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3004.7722 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 8.742378 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0850546 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 86.28066 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2510334 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 428.4157 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2464746 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014615164 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 193.61691 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.56332797 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0063916883 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 13.52521 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.039351568 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 176.63995 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5139336 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 118.06918 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.343522 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 649.5333 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 771.60944 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1879444 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.040178657 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3042.3625 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.683921 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.045569867 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 100.7443 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1551026 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1500.3427 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3098779 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02708378 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 874.53674 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3464079 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015276748 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 222.17567 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3420543 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 542.3678 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8350115 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 398.40033 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.613364 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 120.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 109.13497 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.32137117 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 339.59164 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 643.5442 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8950531 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.064094484 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2681.613 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 7.896581 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.076825835 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 100.06422 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.29466042 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 574.0514 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6904167 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.019820474 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 274.3153 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8077799 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009165313 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 20.66049 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.060839217 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 200.85059 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.59144735 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 138.23174 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.40705281 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 604.3044 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 655.67224 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0850034 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.036696985 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2815.5234 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.659115 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.045328528 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 92.21374 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15259486 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1573.511 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6038387 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03053053 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 829.938 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3733774 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015582752 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 140.65965 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.23276292 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 447.2571 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.740119 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 310.2557 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5134097 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 140.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 60.38027 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.19043896 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 317.0584 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 515.684 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6264639 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.055010263 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2227.2803 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 7.0248265 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.06834454 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 105.29844 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.33211055 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 674.6495 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.1278398 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.024949346 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 340.70404 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0745782 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.012192487 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 25.19804 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.07947444 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 184.41487 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5816432 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 146.69202 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.46266562 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 642.08673 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 744.65045 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.159735 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.039224554 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1928.0988 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.0028634 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029214857 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 126.3622 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.19679926 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1495.7598 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.329529 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.027314194 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1026.3999 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5985378 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01813749 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 145.24654 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.22621013 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 735.385 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1453048 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 617.72815 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9620634 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 160.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 44.54001 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.13462421 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 330.84695 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 446.32227 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3490294 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04562687 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2026.8601 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.126277 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.059602547 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 116.70929 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.35275915 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 840.43274 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.5402462 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029784894 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 441.8522 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3355185 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015153193 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 30.7321 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.092889175 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 180.73694 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5462856 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 155.70004 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4706105 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 606.96387 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 401.1194 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.660862 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.022351675 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2209.2422 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.6398249 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.035411853 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 97.77308 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1610855 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1944.2611 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.2032566 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.037558824 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1060.2756 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7468513 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.019820299 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 175.32437 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.28885472 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 369.90964 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6094426 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 318.3014 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.52441573 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 180.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 30.64968 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.09879517 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 310.2346 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 348.18863 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1223398 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.037959777 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1645.9138 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.305384 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.051616084 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 117.48207 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.37868783 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 921.96686 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.9718378 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03484539 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 505.8974 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.630693 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018502332 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 36.73896 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.11842316 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 185.83974 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.59902966 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 152.22482 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.49067646 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 567.297 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 328.69232 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5794008 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.019596493 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1739.7715 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.066774 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029836643 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 92.59261 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16321717 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1929.8845 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4018946 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.039887894 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1096.3264 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.932544 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.021927224 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 166.07944 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.29275572 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 404.59076 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.71319044 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 313.58432 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.55276924 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 200.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 28.68432 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.08853642 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 323.9833 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 284.07956 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.876834 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02965628 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1479.9105 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.5678606 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.044440717 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 124.31583 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.38371062 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1057.3331 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.263542 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.038265683 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 600.56476 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8536904 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.021032527 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 43.88113 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.13544257 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 172.72215 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5331205 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 158.4213 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.48897982 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 602.468 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 210.31886 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3490955 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011807107 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1645.6871 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.7315757 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.026575502 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 97.67627 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16212688 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2323.574 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.856759 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04522127 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1315.0062 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.1826987 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.024765555 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 210.32072 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.34909856 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 340.37592 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.56496924 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 336.2645 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.558145 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 220.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 24.93064 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.075440325 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 330.46835 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 225.00632 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.680871 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.023028418 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1308.0616 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.9582057 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.038509384 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 128.87866 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.38998792 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1181.5482 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5753748 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041921984 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 680.4693 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0591059 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.023363233 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 45.67683 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.13821848 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 174.9575 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5294229 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 164.19093 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.49684316 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 603.614 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 163.20898 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.27038634 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009145007 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1535.3284 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.54356 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.024746295 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 94.26455 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15616694 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2394.6643 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.9672115 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.046516348 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1374.4773 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.2770798 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02583643 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 211.12552 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3497691 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 318.91513 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.52834284 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 326.55954 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5410072 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 240.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 26.57664 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.08107862 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 327.7885 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 168.9886 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.51554155 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.017436648 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1121.9783 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4228725 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.033301126 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 129.62038 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.39543903 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1225.0444 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.7373016 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04382061 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 721.6462 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.2015605 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.024979565 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 50.59142 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15434165 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 163.18925 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.49784926 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 162.28036 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.49507645 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 643.4803 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 133.17241 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.20695648 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0069996817 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1428.1073 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.219349 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.021592045 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 118.31726 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18387084 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2678.0527 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.1618257 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.048798237 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1557.4137 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4202974 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02746142 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 250.3684 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3890848 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 362.23596 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5629325 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 333.10718 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.51766497 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 260.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 24.20987 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.07927073 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 305.40744 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 121.36669 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.39739272 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013440616 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 905.4163 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.964618 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.028842768 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 125.72504 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.41166332 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1256.0547 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.112718 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.048222445 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 743.80566 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.435454 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02763339 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 47.39398 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1551828 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 154.5202 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.50594777 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 158.46892 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5188771 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 592.47723 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 129.01923 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.21776234 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.007365158 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1079.4044 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8218496 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.017724775 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 129.4827 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.21854459 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2359.647 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.9826794 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04669771 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1425.6514 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.406255 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.027302092 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 278.7184 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47042885 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 384.48944 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.64895225 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 360.33954 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6081914 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 280.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 23.5109 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.07104027 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 330.9517 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 97.56874 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.29481262 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009971153 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 912.90796 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.7584326 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.026836792 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 140.23824 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4237423 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1372.8275 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.1481204 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.048637543 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 822.15027 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4842002 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.028186481 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 51.36434 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15520193 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 162.96536 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.49241433 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 166.90186 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.50430876 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 613.7262 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 101.09229 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16471888 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0055711223 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1069.2329 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7421987 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016949851 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 144.32611 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.23516369 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2615.3103 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.2613635 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04996534 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1552.9507 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.530364 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02871027 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 182.77211 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.29780728 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 396.75885 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6464754 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 357.5042 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5825142 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 300.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 20.42933 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.058420755 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 349.69302 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 78.89827 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.22562152 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.007630971 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 861.55457 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4637454 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.023969779 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 144.63573 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.41360772 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1476.7015 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.222851 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.049513772 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 894.82697 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.5588927 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029033966 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 58.04648 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16599268 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 167.25285 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47828478 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 175.61722 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.50220394 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 579.51855 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 107.15103 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18489663 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.006253574 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 934.06915 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.611802 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015681222 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 158.63225 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2737311 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2506.6794 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.3254514 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.050716784 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1488.8368 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.5690928 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029149696 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 166.39949 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.28713402 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 410.3987 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.70817184 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 358.8953 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.61929905 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 320.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 19.01272 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.056037106 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 339.28802 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 58.71957 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.17306702 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0058534727 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 779.89667 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.2986271 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.022363342 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 140.25708 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.41338646 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1457.2977 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.295164 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.050361656 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 887.22186 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6149518 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029670026 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 60.47698 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.17824672 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 167.6381 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.49408785 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 171.97375 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5068665 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 568.2288 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 104.60272 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18408556 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.006226142 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 559.96545 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.98545766 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009587517 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 214.24644 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.37704256 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2526.1135 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.445592 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.052125458 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1505.0272 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6486287 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030052137 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 99.67055 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.17540565 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 520.1095 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.91531694 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 461.5186 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8122055 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 340.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 16.04706 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.047764704 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 335.96063 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 47.83313 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1423772 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0048154816 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 734.9989 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.1877532 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.021284651 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 138.03235 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.41085872 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1451.1887 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.3195205 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05064724 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 883.0879 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6285458 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02982427 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 53.86236 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16032343 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 153.6596 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.45737386 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 168.70898 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.50216895 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 585.7142 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 95.6284 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16326803 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0055220514 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 613.869 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0480692 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.010196665 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 196.39613 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.33531055 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2635.5989 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.4998035 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.052761097 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1576.1028 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6909077 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030531848 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 135.31206 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.23102063 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 482.08636 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8230744 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 466.55176 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.79655194 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 360.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 347.95087 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 44.8533 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.128907 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004359892 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 727.8157 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0917196 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020350339 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 136.9742 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.39365956 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1485.8125 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.270179 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.050068703 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 907.9047 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.60929 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029605787 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 55.47123 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15942259 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 159.984 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.45978904 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 170.89839 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.49115667 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 520.3527 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 77.13166 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14822957 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0050134202 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 723.8187 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3910154 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013533189 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 139.85641 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.26877233 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2295.7617 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.4119334 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0517308 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1379.1016 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6503205 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030071333 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 153.48312 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.29495978 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 366.80933 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7049244 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 327.41812 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6292234 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 380.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 345.06076 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 43.24135 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.12531517 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.00423841 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 717.384 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0790079 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020226667 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 141.52655 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.41014966 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1493.6417 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.3286343 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0507541 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 911.6586 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6420236 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029977191 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 52.68863 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15269378 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 157.70892 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.45704684 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 174.20726 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5048597 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 546.2235 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 78.96692 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14456889 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004889609 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 264.59402 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.48440614 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2353.6716 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.3089905 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.050523773 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1460.2281 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6733162 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030332249 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 116.79911 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.21383026 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 501.0801 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9173537 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 716.94025 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3125402 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 400.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 345.27353 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 42.03334 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.121739246 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0041174646 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 719.3501 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.083421 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020269603 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 144.45079 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.41836625 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1510.9755 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.376169 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.051311463 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 924.7942 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6784394 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030390376 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 62.91556 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18221948 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 160.7762 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4656488 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 176.38095 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5108441 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 539.2308 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 76.26696 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14143658 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004783668 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 737.3046 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3673266 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013302721 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 151.69688 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.28132087 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2373.2065 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.401096 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05160373 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1431.9214 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6554887 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030129973 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 166.95341 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.30961403 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 378.6112 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.70213205 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 351.80756 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6524249 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 420.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 344.08658 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 42.18785 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.12260824 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004146856 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 714.0694 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0752609 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020190213 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 140.12799 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.40724632 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1504.2207 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.3716345 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05125829 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 915.12164 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.659568 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030176258 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 58.08021 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16879533 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 160.49721 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.46644425 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 176.57321 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.51316506 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 544.5192 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 87.60475 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16088459 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0054414384 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 376.66702 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.69174236 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0067299614 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 206.62315 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3794598 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2368.87 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.3503885 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.051009174 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1469.4111 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6985476 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030618532 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 148.63918 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.27297324 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 466.1165 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8560148 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 506.89618 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.93090594 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 440.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 323.3988 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 43.22353 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.13365397 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004520444 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 675.2211 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0878901 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020313084 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 131.53835 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.40673727 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1423.306 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.4010863 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05160362 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 868.68164 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6861005 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030477302 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 53.50764 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16545404 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 155.51894 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.48088902 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 165.12938 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.51060605 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 553.90564 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 81.38737 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14693365 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.00496959 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 778.1406 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.4048253 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013667546 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 145.40936 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2625165 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2449.0198 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.4213667 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.051841408 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1473.6844 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6605334 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030187212 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 150.3723 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2714764 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 397.0655 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7168468 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 340.70834 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6151018 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 460.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 328.4415 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 41.09112 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1251094 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.00423145 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 675.737 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0574045 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02001649 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 130.8688 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.39845395 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1438.4254 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.3795485 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05135108 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 873.1023 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6583192 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030162087 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 52.15836 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15880564 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 152.10603 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.46311453 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 166.02023 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5054789 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 601.4948 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 86.86591 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14441672 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0048844623 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 903.48706 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5020696 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014613635 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 136.29887 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.22660026 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2678.0342 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.452298 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.052204084 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1615.292 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.685463 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030470068 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 189.94456 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.31578755 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 419.25156 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.69701606 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 350.94153 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.58344895 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 480.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 321.20267 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 42.82974 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.13334179 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004509886 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 649.7465 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0228553 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.019680358 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 127.35521 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.39649487 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1379.8949 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.2960258 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05037176 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 848.71155 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6422927 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029980246 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 58.23689 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18130885 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 145.50868 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.45301205 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 157.1752 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4893334 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 564.08527 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 81.67859 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14479831 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0048973686 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 840.99756 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.490905 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014505015 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 125.10358 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.22178133 + } + retention_time { + value: 2.33 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2534.617 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.4933224 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.052685104 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1528.0685 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.708932 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030736355 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 163.3043 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2895029 + } + retention_time { + value: 2.91 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "Oc1cccc(OCc2ccccc2)c1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 406.84534 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.721248 + } + retention_time { + value: 1.92 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + } + is_desired_product: false + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 324.3944 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5750805 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + doi: "10.1039/c9re00086k" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" + record_created { + time { + value: "05/24/2021, 11:30:49" + } + person { + username: "skearnes" + name: "Steven Kearnes" + orcid: "0000-0003-4579-4388" + organization: "Relay Therapeutics" + email: "skearnes@relaytx.com" + } + } + } +} +reactions { + inputs { + key: "base" + value { + components { + identifiers { + type: SMILES + value: "O=P([O-])([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 387.0 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 387.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + preparations { + type: SPARGED + details: "To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to 10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in preparation for automated dispensing (387 \302\265l, 0.387 mmol)." + } + } + addition_order: 2 + } + } + inputs { + key: "boronic acid" + value { + components { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + amount { + moles { + value: 142.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: NONE + } + } + addition_order: 1 + } + } + inputs { + key: "internal standard" + value { + components { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 13.0 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + addition_order: 1 + } + } + inputs { + key: "palladium precatalyst" + value { + components { + identifiers { + type: SMILES + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + } + amount { + moles { + value: 6.44 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + addition_order: 1 + } + } + inputs { + key: "solvents" + value { + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 1.0 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 10.0 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "vinyl tosylate" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + amount { + moles { + value: 129.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: SYNTHESIZED + reaction_id: "SYNTHESIS_OF_3E" + } + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + details: "Reactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01)." + material { + type: GLASS + details: "borosilicate" + } + attachments { + type: CAP + } + volume { + value: 4.0 + units: MILLILITER + } + } + is_automated: true + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + atmosphere { + type: NITROGEN + } + } + stirring { + type: STIR_BAR + details: "Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir discs (VP 782N6)." + rate { + rpm: 500 + } + } + } + notes { + procedure_details: "To a 4 ml reaction vial equipped with a magnetic\ntumble stir disc under N2 atmosphere was charged (E)-methyl 3-cyclopropyl-2-methyl-3-\n(tosyloxy)acrylate 3-(E) (40.0 mg, 0.129 mmol), (3-(benzyloxy)phenyl)boronic acid 4 (32.3 mg,\n0.142 mmol), palladium precatalyst 5 (5.96 mg, 6.44 \302\265mol) and 1,3,5-trimethoxybenzene (2.17\nmg, 0.013 mmol). ACN (1000 \302\265l) and water (10 \302\265l) were added and the mixture agitated to\ndissolve all solids. To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to\n10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in\npreparation for automated dispensing (387 \302\265l, 0.387 mmol). Finally, to a 96-well sample dilution\nplate was charged 400 \302\265l of a 9:1 mixture of acetonitrile and aqueous pH 3.5 ammonium formate\nbuffer." + } + workups { + type: ALIQUOT + details: "Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales 17P687)\ncapped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075)." + amount { + volume { + value: 20.0 + units: MICROLITER + } + } + is_automated: true + } + workups { + type: ADDITION + input { + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 360.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 40.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=C[O-].[NH4+]" + } + amount { + mass { + value: 504.0 + units: MICROGRAM + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=CO" + } + amount { + volume { + value: 316.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + } + stirring { + type: CUSTOM + details: "Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample." + } + is_automated: true + } + outcomes { + reaction_time { + value: 0.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 789.43243 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1584.4377 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0070593 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.06788276 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 5982.962 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 7.578814 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.07373428 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 40.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 454.74182 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 673.57666 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.4812287 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.050098117 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2993.4353 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.5827136 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.064043224 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 443.38528 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9750264 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0114323795 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 207.45828 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.45621112 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.005176308 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 60.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 430.06973 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 556.34735 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2936213 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04375286 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2584.6316 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.009797 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.058469314 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 565.3064 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3144529 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015412223 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 265.04095 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.61627436 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0069924337 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 80.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 440.8866 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 502.88892 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.140631 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03857842 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2446.2454 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.548468 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.053981047 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 714.5022 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6206032 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.019001896 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 334.97397 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.75977355 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.008620619 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 100.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 456.32468 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 455.9279 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9991304 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03379259 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2324.6816 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.094359 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.049563017 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 849.3778 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8613453 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.021824645 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 400.40454 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.87745535 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009955872 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 120.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 679.77155 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 584.8447 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8603548 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02909892 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 3198.0068 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.7045317 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.045770388 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1410.6091 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0751224 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.024331225 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 667.9669 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.98263437 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011149264 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 140.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 683.0257 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 507.21786 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7426044 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.025116364 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2972.5066 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.351969 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.042340305 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1560.7131 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.2849991 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.026792072 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 736.8374 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0787843 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.012240211 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 160.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 702.9632 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 447.78397 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6369949 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.021544442 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2815.0942 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.004611 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.038960863 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1729.5242 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4603338 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.028847905 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 814.47943 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1586374 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013146248 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 180.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 652.37384 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 352.0839 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5396965 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018253615 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2405.987 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.6880496 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.035881035 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1697.528 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6020784 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030509891 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 801.60516 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2287512 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013941781 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 200.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 629.8367 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 301.3809 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47850642 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016184043 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2176.3796 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4554667 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.033618234 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1743.4241 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.7680573 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.032456025 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 825.0061 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.309873 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014862212 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 220.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 695.24066 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 280.38925 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.40329814 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01364035 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2241.119 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.2235153 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03136158 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2013.4865 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.8961 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03395735 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 953.68744 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3717372 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015564142 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 240.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 693.8551 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 234.85779 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.33848247 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011448154 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2095.3333 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.0198429 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029380051 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2091.4084 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.0141861 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.035341937 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 986.9314 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.4223883 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016138844 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 260.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 674.97577 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 188.2771 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.27893907 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009434276 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1912.9745 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.8341382 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.027573328 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2093.6548 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.1018221 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.036369484 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 992.59247 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.4705602 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016685417 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 280.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 716.32935 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 164.93059 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.23024407 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.007787315 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1906.018 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6608121 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.025887042 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2280.0366 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.1829445 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.037320662 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1080.6761 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5086302 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01711737 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 300.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 705.07166 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 133.43137 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1892451 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0064006476 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1775.5997 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.518325 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.024500785 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2295.6685 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.2559361 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.038176503 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1081.5221 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5339179 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.017404292 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 320.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 697.50214 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 108.68061 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15581402 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.005269942 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1692.2268 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4261243 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.023603763 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2331.4653 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.3425925 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.039192565 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1108.8933 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5898064 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018038422 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 340.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 701.7939 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 87.97259 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.12535389 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004239719 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1617.8046 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3052418 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.022427697 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2375.411 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.3847697 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0396871 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1120.1104 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5960674 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01810946 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 360.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 710.95105 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 52.94001 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.07446365 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0025185095 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1588.911 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.234909 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02174343 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2450.737 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4471247 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.040418226 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1153.3949 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6223266 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018407404 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 380.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 666.0584 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 57.31877 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.086056665 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0029106087 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1451.6746 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.1795003 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.021204358 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2311.4653 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.470364 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.040690713 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1094.749 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.643623 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01864904 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 400.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 461.35196 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 27.16534 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.058882028 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.001991508 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 985.88586 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.1369495 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020790381 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1619.4565 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5102408 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041158274 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 764.2314 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6565039 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01879519 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 420.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 454.0849 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 30.65263 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.06750418 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0022831266 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 954.605 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.102261 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020452898 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1605.3832 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5354252 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041453566 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 745.94147 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6427357 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018638972 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 440.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 475.99625 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 30.83437 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.064778596 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0021909417 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 994.1477 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.088562 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02031962 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1699.5409 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5704923 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041864734 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 795.173 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6705445 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018954499 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 460.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 471.93872 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 30.08823 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.06375453 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0021563056 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 985.13983 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0874317 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020308623 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1689.8529 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.580662 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041983977 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 792.7329 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.679737 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0190588 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + doi: "10.1039/c9re00086k" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" + record_created { + time { + value: "05/24/2021, 11:30:49" + } + person { + username: "skearnes" + name: "Steven Kearnes" + orcid: "0000-0003-4579-4388" + organization: "Relay Therapeutics" + email: "skearnes@relaytx.com" + } + } + } +} +reactions { + inputs { + key: "base" + value { + components { + identifiers { + type: SMILES + value: "O=P([O-])([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 387.0 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 387.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + preparations { + type: SPARGED + details: "To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to 10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in preparation for automated dispensing (387 \302\265l, 0.387 mmol)." + } + } + addition_order: 2 + } + } + inputs { + key: "boronic acid" + value { + components { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + amount { + moles { + value: 142.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: NONE + } + } + addition_order: 1 + } + } + inputs { + key: "internal standard" + value { + components { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 13.0 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + addition_order: 1 + } + } + inputs { + key: "palladium precatalyst" + value { + components { + identifiers { + type: SMILES + value: "Cl[Pd](Cl)[P](C1=CC=CC=C1)(C2=CC=CC2[Fe]C3C(P(C4=CC=CC=C4)C5=CC=CC=C5)=CC=C3)C6=CC=CC=C6" + } + amount { + moles { + value: 6.44 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + addition_order: 1 + } + } + inputs { + key: "solvents" + value { + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 1.0 + units: MILLILITER + } + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 10.0 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "vinyl tosylate" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + amount { + moles { + value: 129.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: SYNTHESIZED + reaction_id: "SYNTHESIS_OF_3E" + } + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + details: "Reactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01)." + material { + type: GLASS + details: "borosilicate" + } + attachments { + type: CAP + } + volume { + value: 4.0 + units: MILLILITER + } + } + is_automated: true + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + atmosphere { + type: NITROGEN + } + } + stirring { + type: STIR_BAR + details: "Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir discs (VP 782N6)." + rate { + rpm: 500 + } + } + } + notes { + procedure_details: "To a 4 ml reaction vial equipped with a magnetic\ntumble stir disc under N2 atmosphere was charged (E)-methyl 3-cyclopropyl-2-methyl-3-\n(tosyloxy)acrylate 3-(E) (40.0 mg, 0.129 mmol), (3-(benzyloxy)phenyl)boronic acid 4 (32.3 mg,\n0.142 mmol), palladium precatalyst 5 (5.96 mg, 6.44 \302\265mol) and 1,3,5-trimethoxybenzene (2.17\nmg, 0.013 mmol). ACN (1000 \302\265l) and water (10 \302\265l) were added and the mixture agitated to\ndissolve all solids. To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to\n10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in\npreparation for automated dispensing (387 \302\265l, 0.387 mmol). Finally, to a 96-well sample dilution\nplate was charged 400 \302\265l of a 9:1 mixture of acetonitrile and aqueous pH 3.5 ammonium formate\nbuffer." + } + workups { + type: ALIQUOT + details: "Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales 17P687)\ncapped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075)." + amount { + volume { + value: 20.0 + units: MICROLITER + } + } + is_automated: true + } + workups { + type: ADDITION + input { + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 360.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 40.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=C[O-].[NH4+]" + } + amount { + mass { + value: 504.0 + units: MICROGRAM + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=CO" + } + amount { + volume { + value: 316.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + } + stirring { + type: CUSTOM + details: "Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample." + } + is_automated: true + } + outcomes { + reaction_time { + value: 0.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 755.68005 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1534.0931 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0300827 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.06866146 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 5833.023 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 7.718905 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.075097226 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 40.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 443.52127 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 90.9476 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.20505804 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.006935473 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1017.21106 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.293489 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.022313353 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1433.5057 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.2321014 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.037897035 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 728.82434 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6432681 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018645013 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 60.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 431.1147 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 45.96372 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.106616 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0036059662 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 813.1333 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8861184 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018350046 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1407.1703 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.2640278 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03827138 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 713.1201 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.654131 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.018768266 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 80.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 433.5336 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 772.1005 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7809473 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.017326837 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1529.3625 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5276678 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04136261 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 769.7663 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7755631 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020146072 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 100.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 700.0409 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1171.0416 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6728189 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016274856 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2466.9658 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.524031 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04131997 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1246.6309 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7807972 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02020546 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 120.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 679.9285 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1130.1597 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6621742 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016171293 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2409.983 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5444653 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041559566 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1228.3345 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8065642 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02049782 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 140.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 684.47345 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1124.7384 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.643217 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015986858 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2410.9324 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5223167 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04129987 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1224.923 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7895844 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02030516 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 160.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 696.4937 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1138.4735 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6345782 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015902812 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2457.5005 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5283887 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041371062 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1254.5891 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8012928 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020438008 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 180.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 687.6207 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1105.4827 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6076925 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01564124 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2425.4854 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5273592 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041358992 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1244.3849 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8096966 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02053336 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 200.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 655.5416 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1056.302 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6113424 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01567675 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2292.252 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4967296 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.040999856 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1180.3575 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8005836 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020429961 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 220.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 710.05457 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1131.6302 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5937229 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015505331 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2493.4158 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5115833 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041174017 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1282.2495 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8058465 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020489676 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 240.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 419.6252 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 679.06256 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6182597 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01574405 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1475.0951 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.515268 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04121722 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 755.45825 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8003167 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020426933 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 260.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 460.23026 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 736.36505 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5999928 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0155663295 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1629.7455 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5411525 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041520722 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 840.4871 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8262318 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020720975 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 280.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 696.9243 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1115.1511 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6001036 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015567408 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2436.858 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4965892 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.040998206 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1259.9215 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8078312 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020512195 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 300.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 680.42126 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1088.0696 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5991116 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015557757 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2376.4417 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.492603 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04095147 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1157.8455 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7016597 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01930754 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 320.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 693.795 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1108.9601 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5983974 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015550807 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2426.0205 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4967396 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04099997 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1256.7375 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8113961 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020552643 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 340.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 700.07263 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1114.72 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.592292 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015491408 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2449.2773 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4986045 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04102184 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1267.7947 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8109473 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020547552 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 360.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 677.1683 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1063.2148 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5700895 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0152754 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2374.582 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.506635 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041115995 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1223.2388 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8064029 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020495988 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 380.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 614.97955 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 971.79895 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5802133 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015373895 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2139.427 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4788585 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.040790312 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1107.0168 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8000872 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020424329 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 400.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 697.96716 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1109.1903 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5891726 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01546106 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2434.4636 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.4879344 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.040896725 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1257.3499 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8014455 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02043974 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 420.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 506.37045 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 793.6947 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.567419 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015249421 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1779.9458 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.515106 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04121532 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 916.95886 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.810846 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0205464 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 440.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 466.39795 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 707.43713 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5168102 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014757046 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1590.958 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.41116 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.039996535 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 816.2998 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7502217 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.019858541 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 460.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 452.79462 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 707.4815 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5624777 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015201346 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1583.7922 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.497816 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.041012593 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 815.89453 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8019087 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020444997 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + doi: "10.1039/c9re00086k" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" + record_created { + time { + value: "05/24/2021, 11:30:49" + } + person { + username: "skearnes" + name: "Steven Kearnes" + orcid: "0000-0003-4579-4388" + organization: "Relay Therapeutics" + email: "skearnes@relaytx.com" + } + } + } +} +reactions { + inputs { + key: "base" + value { + components { + identifiers { + type: SMILES + value: "O=P([O-])([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 300.0 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 300.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + preparations { + type: SPARGED + details: "To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to 10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in preparation for automated dispensing (387 \302\265l, 0.387 mmol)." + } + } + addition_order: 2 + } + } + inputs { + key: "boronic acid" + value { + components { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + amount { + moles { + value: 110.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: NONE + } + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 250.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "internal standard" + value { + components { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 10.0 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 100.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "palladium precatalyst" + value { + components { + identifiers { + type: SMILES + value: "Cl[Pd](Cl)[P](C1=CC=CC=C1)(C2=CC=CC2[Fe]C3C(P(C4=CC=CC=C4)C5=CC=CC=C5)=CC=C3)C6=CC=CC=C6" + } + amount { + moles { + value: 1.0 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 250.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "solvents" + value { + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 10.0 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "vinyl tosylate" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + amount { + moles { + value: 100.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: SYNTHESIZED + reaction_id: "SYNTHESIS_OF_3E" + } + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 250.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + details: "Reactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01)." + material { + type: GLASS + details: "borosilicate" + } + attachments { + type: CAP + } + volume { + value: 4.0 + units: MILLILITER + } + } + is_automated: true + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + atmosphere { + type: NITROGEN + } + } + stirring { + type: STIR_BAR + details: "Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir discs (VP 782N6)." + rate { + rpm: 500 + } + } + } + notes { + procedure_details: "To a 4 ml reaction vial equipped with a magnetic\ntumble stir disc under N2 atmosphere was charged (E)-methyl 3-cyclopropyl-2-methyl-3-\n(tosyloxy)acrylate 3-(E) (40.0 mg, 0.129 mmol), (3-(benzyloxy)phenyl)boronic acid 4 (32.3 mg,\n0.142 mmol), palladium precatalyst 5 (5.96 mg, 6.44 \302\265mol) and 1,3,5-trimethoxybenzene (2.17\nmg, 0.013 mmol). ACN (1000 \302\265l) and water (10 \302\265l) were added and the mixture agitated to\ndissolve all solids. To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to\n10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in\npreparation for automated dispensing (387 \302\265l, 0.387 mmol). Finally, to a 96-well sample dilution\nplate was charged 400 \302\265l of a 9:1 mixture of acetonitrile and aqueous pH 3.5 ammonium formate\nbuffer." + } + workups { + type: ALIQUOT + details: "Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales 17P687)\ncapped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075)." + amount { + volume { + value: 20.0 + units: MICROLITER + } + } + is_automated: true + } + workups { + type: ADDITION + input { + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 360.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 40.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=C[O-].[NH4+]" + } + amount { + mass { + value: 504.0 + units: MICROGRAM + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=CO" + } + amount { + volume { + value: 316.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + } + stirring { + type: CUSTOM + details: "Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample." + } + is_automated: true + } + outcomes { + reaction_time { + value: 0.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 251.12868 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 460.132 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8322558 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2325.931 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 9.261909 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 5.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 224.31285 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 343.407 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5309289 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1882.4817 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 8.392216 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 122.49629 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5460957 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0064030816 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 59.93792 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.26720682 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0030318087 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 10.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 230.34326 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 297.72034 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2925073 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1742.1005 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 7.5630627 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 227.84863 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.98916996 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011598215 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 111.85833 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.48561582 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.005509943 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 15.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 253.29059 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 287.48743 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1350102 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1756.9401 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.93646 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 306.38214 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2096074 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014182888 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 148.35155 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.58569705 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0066454946 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 20.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 211.81667 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 228.26155 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0776374 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1441.8502 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.807067 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 300.33057 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.4178798 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016624924 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 138.56844 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6541904 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.007422641 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 25.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 214.94334 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 220.16705 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0243027 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1428.4741 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.645817 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 337.79297 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5715442 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01842667 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 157.84058 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.73433566 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.008331993 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 30.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 222.19221 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 206.6496 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9300487 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1392.3435 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.2663918 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 363.57492 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6363081 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.019186039 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 166.68742 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.75019467 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0085119335 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 35.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 214.92139 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 190.25092 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8852116 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1330.5581 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.190906 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 381.6656 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7758381 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020822058 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 177.83766 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.82745445 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009388546 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 40.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 224.78731 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 178.89474 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7958401 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1298.4664 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.776422 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 402.01013 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7884022 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020969374 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 186.99767 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.83188707 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009438841 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 45.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 235.25168 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 179.50269 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.76302403 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1338.8685 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.691218 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 445.71573 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8946335 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.022214957 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 208.34721 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8856354 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.010048685 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 50.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 223.31474 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 164.8724 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.73829603 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1265.1046 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.665119 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 447.56308 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0041807 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.023499418 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 209.091 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.93630624 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0106236115 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 55.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 216.93741 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 151.15038 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.69674647 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1197.0447 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.5179267 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 449.36118 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0713863 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02428742 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 210.07495 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9683666 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.010987379 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 60.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 246.52484 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 161.63391 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6556496 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1322.7485 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.365579 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 524.45044 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.1273735 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02494388 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 245.8711 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9973482 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011316212 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 65.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 226.5036 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 145.09882 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.64060265 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1236.9221 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.4609385 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 507.16718 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.239113 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.026254049 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 237.76834 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0497332 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011910588 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 70.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 224.91002 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 131.73769 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5857351 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1143.7059 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.085171 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 495.1958 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.2017508 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.025815967 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 230.73193 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0258856 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011640005 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 75.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 220.8618 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 123.58422 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5595545 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1108.5471 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.019189 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 494.56046 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.2392304 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.026255425 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 230.9048 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0454719 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011862238 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 80.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 208.84625 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 113.45226 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5432334 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1046.921 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.012879 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 485.80243 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3261247 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.027274275 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 227.46716 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0891608 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.012357946 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 85.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 213.95546 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 108.40001 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5066475 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1031.2479 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.8199186 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 513.39154 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3995252 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.028134914 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 238.28084 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1136937 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.012636302 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 90.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 220.71236 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 105.88336 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47973463 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1051.4462 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.7638755 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 521.65234 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3634942 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.027712442 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 243.85387 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1048492 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01253595 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 95.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 225.1136 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 106.96274 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47515005 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1074.9697 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.7752323 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 538.74316 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3932056 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.028060816 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 257.2243 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1426421 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.012964761 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 100.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 211.09848 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 96.94833 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4592564 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1003.8419 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.755325 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 523.9155 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4818537 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02910023 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 244.23254 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1569602 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013127218 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 105.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 210.94897 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 90.7617 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.43025428 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 975.63495 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.624981 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 521.7221 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4732146 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.028998937 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 243.12743 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1525414 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01307708 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 110.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 197.51227 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 83.65161 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.42352614 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 892.4936 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.518674 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 492.88657 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4954731 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029259922 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 230.82874 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1686805 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0132602 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 115.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 210.5581 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 84.86391 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4030427 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 950.13464 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.512458 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 537.3851 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.5521936 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029924981 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 250.28844 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1886905 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013487239 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + doi: "10.1039/c9re00086k" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" + record_created { + time { + value: "05/24/2021, 11:30:49" + } + person { + username: "skearnes" + name: "Steven Kearnes" + orcid: "0000-0003-4579-4388" + organization: "Relay Therapeutics" + email: "skearnes@relaytx.com" + } + } + } +} +reactions { + inputs { + key: "base" + value { + components { + identifiers { + type: SMILES + value: "O=P([O-])([O-])[O-].[K+].[K+].[K+]" + } + amount { + moles { + value: 300.0 + units: MICROMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 300.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + preparations { + type: SPARGED + details: "To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to 10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in preparation for automated dispensing (387 \302\265l, 0.387 mmol)." + } + } + addition_order: 2 + } + } + inputs { + key: "boronic acid" + value { + components { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + amount { + moles { + value: 110.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: NONE + } + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 250.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "internal standard" + value { + components { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + amount { + moles { + value: 10.0 + units: MICROMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 100.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "palladium precatalyst" + value { + components { + identifiers { + type: SMILES + value: "Cl[Pd](Cl)[P](C1=CC=CC=C1)(C2=CC=CC2[Fe]C3C(P(C4=CC=CC=C4)C5=CC=CC=C5)=CC=C3)C6=CC=CC=C6" + } + amount { + moles { + value: 1.0 + units: MICROMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 250.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "solvents" + value { + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 10.0 + units: MICROLITER + } + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + inputs { + key: "vinyl tosylate" + value { + components { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + amount { + moles { + value: 100.0 + units: MICROMOLE + } + } + reaction_role: REACTANT + preparations { + type: SYNTHESIZED + reaction_id: "SYNTHESIS_OF_3E" + } + } + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 250.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + details: "Reactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01)." + material { + type: GLASS + details: "borosilicate" + } + attachments { + type: CAP + } + volume { + value: 4.0 + units: MILLILITER + } + } + is_automated: true + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + } + conditions { + temperature { + setpoint { + value: 25.0 + units: CELSIUS + } + } + pressure { + atmosphere { + type: NITROGEN + } + } + stirring { + type: STIR_BAR + details: "Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir discs (VP 782N6)." + rate { + rpm: 500 + } + } + } + notes { + procedure_details: "To a 4 ml reaction vial equipped with a magnetic\ntumble stir disc under N2 atmosphere was charged (E)-methyl 3-cyclopropyl-2-methyl-3-\n(tosyloxy)acrylate 3-(E) (40.0 mg, 0.129 mmol), (3-(benzyloxy)phenyl)boronic acid 4 (32.3 mg,\n0.142 mmol), palladium precatalyst 5 (5.96 mg, 6.44 \302\265mol) and 1,3,5-trimethoxybenzene (2.17\nmg, 0.013 mmol). ACN (1000 \302\265l) and water (10 \302\265l) were added and the mixture agitated to\ndissolve all solids. To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to\n10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in\npreparation for automated dispensing (387 \302\265l, 0.387 mmol). Finally, to a 96-well sample dilution\nplate was charged 400 \302\265l of a 9:1 mixture of acetonitrile and aqueous pH 3.5 ammonium formate\nbuffer." + } + workups { + type: ALIQUOT + details: "Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales 17P687)\ncapped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075)." + amount { + volume { + value: 20.0 + units: MICROLITER + } + } + is_automated: true + } + workups { + type: ADDITION + input { + components { + identifiers { + type: SMILES + value: "CC#N" + } + amount { + volume { + value: 360.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O" + } + amount { + volume { + value: 40.0 + units: MICROLITER + } + volume_includes_solutes: true + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=C[O-].[NH4+]" + } + amount { + mass { + value: 504.0 + units: MICROGRAM + } + } + reaction_role: WORKUP + } + components { + identifiers { + type: SMILES + value: "O=CO" + } + amount { + volume { + value: 316.0 + units: MICROLITER + } + volume_includes_solutes: false + } + reaction_role: WORKUP + } + } + stirring { + type: CUSTOM + details: "Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample." + } + is_automated: true + } + outcomes { + reaction_time { + value: 0.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 214.43896 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 366.40317 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7086594 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1959.6674 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 9.138578 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 48.70964 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2271492 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0026633698 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 24.01273 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.11197932 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.001270551 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 5.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 184.28227 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 230.27904 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2495995 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1391.4832 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 7.550825 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 227.77298 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2360005 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014492353 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 111.78756 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6066105 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.006882785 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 10.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 211.12502 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 204.6626 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9693906 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1339.4518 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.3443537 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 325.0173 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5394542 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01805041 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 151.29233 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7166007 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.008130766 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 15.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 218.08653 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 189.95229 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.870995 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1322.0558 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 6.06207 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 391.77557 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7964226 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.021063413 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 183.51106 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8414599 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009547456 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 20.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 257.01898 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 195.8778 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7621141 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1440.2578 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.603702 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 507.54977 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.9747559 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.023154408 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 234.11978 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9109046 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.010335397 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 25.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 198.15588 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 129.99352 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6560164 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1039.9495 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.2481384 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 410.7822 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0730255 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.024306636 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 191.2985 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.96539396 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01095365 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 30.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 200.28362 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 121.94792 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.60887617 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1028.6123 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.135779 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 457.06238 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.282076 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.026757795 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 211.28294 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0549188 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011969426 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 35.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 217.45705 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 110.84234 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5097206 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1024.5057 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.711302 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 508.75443 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.339563 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.027431842 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 235.08241 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0810522 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.012265943 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 40.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 216.26643 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 100.09444 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4628293 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1006.9278 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.6559596 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 539.86145 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4962795 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029269377 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 249.01039 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1514057 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013064194 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 45.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 214.521 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 86.94685 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.40530694 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 951.93884 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.437509 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 545.7865 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.5442102 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.029831372 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 252.33632 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.176278 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.013346402 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 50.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 223.83688 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 82.16212 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.36706245 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 954.34174 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.263559 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 585.89276 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6174986 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.030690696 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 270.6734 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2092439 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0137204435 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 55.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 201.92815 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 71.93629 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.35624695 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 849.9856 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.209347 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 543.7628 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.692853 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.031574238 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 251.73604 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2466614 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014144995 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 60.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 213.18584 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 66.21473 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3105963 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 882.4792 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.1394835 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 588.3727 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.759905 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.032360442 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 271.1428 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2718613 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01443092 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 65.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 205.53284 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 59.55063 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2897378 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 816.761 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.9738708 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 568.2125 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.7645826 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.032415286 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 263.2247 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2806941 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01453114 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 70.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 220.63264 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 58.0082 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.26291758 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 858.04517 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.8890219 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 615.72107 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.790707 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.032721598 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 285.4902 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2939618 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014681678 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 75.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 224.66998 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 56.16369 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.24998306 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 865.7765 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.8535476 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 635.4445 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.8283463 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.033162925 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 295.09143 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3134439 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014902728 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 80.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 213.83128 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 51.75714 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.24204662 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 808.3491 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.7803128 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 611.63257 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.8603513 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03353819 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 281.53125 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3166046 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01493859 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 85.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 200.57803 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 44.61722 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2224432 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 773.153 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.8546245 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 596.404 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.973426 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.034864016 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 275.2119 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3720939 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01556819 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 90.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 197.5107 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 38.9466 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1971873 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 737.7882 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.7354343 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 557.40753 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.8221638 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.033090435 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 262.45062 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.328792 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015076872 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 95.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 179.3816 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 37.24174 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2076118 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 660.9548 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.6846297 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 528.8864 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.948387 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.034570426 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 244.51305 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3630887 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015466013 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 100.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 217.57083 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 39.19144 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18013187 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 783.1327 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.599438 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 634.8852 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.9180622 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.03421486 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 292.6897 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3452617 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015263743 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 105.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 224.14577 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 38.10116 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16998385 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 816.08594 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.6408715 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 678.8243 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.0284946 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.035509706 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 314.0771 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.401218 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01589864 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 110.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 217.49643 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 35.46846 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16307606 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 775.35864 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.5649257 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 653.1895 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.0032196 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.035213348 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 300.9266 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3835933 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015698664 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + outcomes { + reaction_time { + value: 115.0 + units: MINUTE + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 192.77646 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 29.09146 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15090774 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 694.42114 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.602209 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 587.3497 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.0467916 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.035724238 + } + retention_time { + value: 2.85 + units: MINUTE + } + } + reaction_role: PRODUCT + } + products { + identifiers { + type: SMILES + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + } + is_desired_product: false + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 271.76675 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.4097507 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015995454 + } + retention_time { + value: 2.78 + units: MINUTE + } + } + reaction_role: PRODUCT + } + analyses { + key: "Offline HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + analyses { + key: "Online HPLC-UV" + value { + type: LC + details: "Column: Imtakt Unison UK-C18 3 \302\265m 10x2 mm (UK020)\nColumn Temperature: 55 \302\260C\npH 3.5 Ammonium Formate Buffer: 12.6 g ammonium formate + 7.9 ml formic acid to 1 L water\nMobile Phase A: 40 ml pH 3.5 ammonium formate buffer + 3960 ml Water\nMobile Phase B: 40 ml pH 3.5 ammonium formate buffer + 360 ml Water + 3600 ml ACN\nInjection volume: 20 \302\265l\nWavelength Monitored: 210 nm\nTime (min) Flow (ml/min) %MPA %MPB\n0.00 1.00 95.0 5.0\n3.50 1.00 0.0 100.0\n3.90 1.00 0.0 100.0\n3.91 1.00 95.0 5.0\n4.00 1.00 95.0 5.0" + is_of_isolated_species: false + instrument_manufacturer: "Agilent" + } + } + } + provenance { + doi: "10.1039/c9re00086k" + publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" + record_created { + time { + value: "05/24/2021, 11:30:49" + } + person { + username: "skearnes" + name: "Steven Kearnes" + orcid: "0000-0003-4579-4388" + organization: "Relay Therapeutics" + email: "skearnes@relaytx.com" + } + } + } +} From efad7e648a192785c20a6f97dbbdf100751f383c Mon Sep 17 00:00:00 2001 From: Steven Kearnes Date: Tue, 25 May 2021 15:26:21 -0600 Subject: [PATCH 2/5] fix product duplication --- hein-dataset.pbtxt | 9629 ++++++++++++++++++-------------------------- 1 file changed, 3877 insertions(+), 5752 deletions(-) diff --git a/hein-dataset.pbtxt b/hein-dataset.pbtxt index 2ac2c659..c78d2499 100644 --- a/hein-dataset.pbtxt +++ b/hein-dataset.pbtxt @@ -160,7 +160,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/24/2021, 11:30:49" + value: "05/25/2021, 15:22:39" } person { username: "skearnes" @@ -541,7 +541,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/24/2021, 11:30:49" + value: "05/25/2021, 15:22:39" } person { username: "skearnes" @@ -833,7 +833,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -842,42 +842,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 490.5643 + value: 325.94662 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 1.5050449 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 325.94662 + value: 715.8811 } retention_time { value: 1.65 @@ -885,7 +876,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -946,53 +937,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 3745.1382 + value: 1351.4216 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 11.490035 + value: 1.8877739 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.11178655 + value: 0.06384829 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -1001,9 +985,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -1011,10 +994,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 490.5643 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -1025,19 +1008,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5050449 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 233.54845 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.32623914 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -1046,10 +1057,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 29.23686 + value: 3745.1382 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -1060,10 +1071,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.08969831 + value: 11.490035 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -1075,70 +1086,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0010517306 + value: 0.11178655 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 5268.786 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 7.359862 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.071604095 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -1151,7 +1154,7 @@ reactions { value: 0.0 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -1165,43 +1168,35 @@ reactions { value: 0.0 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 44.23908 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 0.061796684 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -1210,9 +1205,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -1220,10 +1214,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 29.23686 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -1234,66 +1228,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 0.08969831 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 233.54845 + value: 0.0010517306 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.32623914 + value: 702.0792 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 715.8811 + value: 0.98072046 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -1301,71 +1282,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.011499143 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1351.4216 + value: 0.0 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.8877739 + value: 0.0 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.06384829 + value: 0.0 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -1373,10 +1351,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 5268.786 + value: 324.20193 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -1387,10 +1365,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 7.359862 + value: 0.45287117 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -1402,56 +1380,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.071604095 + value: 0.005138412 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 44.23908 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.061796684 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -1459,10 +1430,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 702.0792 + value: 95.72977 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -1473,25 +1444,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.98072046 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.011499143 + value: 0.133723 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -1500,60 +1456,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 324.20193 + value: 0.0 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.45287117 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.005138412 + value: 0.0 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -1561,10 +1494,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 95.72977 + value: 397.07077 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -1575,10 +1508,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.133723 + value: 0.5546602 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -1587,45 +1520,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 397.07077 + value: 0.0 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5546602 + value: 0.0 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -1683,7 +1608,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -1692,42 +1617,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 428.29874 + value: 313.6642 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 1.365469 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 313.6642 + value: 610.46533 } retention_time { value: 1.65 @@ -1735,7 +1651,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -1796,53 +1712,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 3498.5737 + value: 1024.2686 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 11.153882 + value: 1.6778488 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.10851612 + value: 0.0567482 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -1851,9 +1760,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -1861,10 +1769,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 428.29874 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -1874,20 +1782,48 @@ reactions { uses_internal_standard: true is_normalized: true uses_authentic_standard: false + float_value { + value: 1.365469 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false float_value { value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -1896,10 +1832,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 62.32241 + value: 3498.5737 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -1910,10 +1846,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.19869149 + value: 11.153882 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -1925,70 +1861,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0023296974 + value: 0.10851612 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 30.16609 + value: 3162.5361 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.0961732 + value: 5.1805334 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0010912099 + value: 0.05040141 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -2001,7 +1929,7 @@ reactions { value: 0.0 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -2015,43 +1943,35 @@ reactions { value: 0.0 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 87.37809 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 0.14313358 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -2060,9 +1980,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -2070,10 +1989,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 62.32241 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -2084,66 +2003,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 0.19869149 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.0023296974 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 987.0381 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 610.46533 + value: 1.6168617 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -2151,71 +2057,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.018958027 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1024.2686 + value: 30.16609 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.6778488 + value: 0.0961732 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0567482 + value: 0.0010912099 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -2223,10 +2126,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3162.5361 + value: 745.2726 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -2237,10 +2140,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 5.1805334 + value: 1.220827 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -2252,56 +2155,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.05040141 + value: 0.013851869 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 87.37809 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.14313358 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -2309,10 +2205,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 987.0381 + value: 123.86116 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -2323,25 +2219,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.6168617 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.018958027 + value: 0.2028963 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -2350,60 +2231,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 745.2726 + value: 0.0 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.220827 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.013851869 + value: 0.0 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -2411,10 +2269,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 123.86116 + value: 722.6898 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -2425,10 +2283,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.2028963 + value: 1.1838342 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -2437,45 +2295,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 722.6898 + value: 0.0 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.1838342 + value: 0.0 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -2533,7 +2383,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -2542,42 +2392,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 383.23358 + value: 318.9301 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 1.2016225 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 318.9301 + value: 652.619 } retention_time { value: 1.65 @@ -2585,7 +2426,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -2646,53 +2487,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 3372.003 + value: 1194.7474 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 10.572859 + value: 1.8306967 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.10286334 + value: 0.061917823 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -2701,9 +2535,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -2711,10 +2544,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 34.14686 + value: 383.23358 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -2725,19 +2558,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.10706691 + value: 1.2016225 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -2746,10 +2607,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 114.41904 + value: 3372.003 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -2760,10 +2621,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.358759 + value: 10.572859 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -2775,70 +2636,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.004206521 + value: 0.10286334 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 47.8732 + value: 2810.0898 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.15010563 + value: 4.3058653 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0017031434 + value: 0.041891765 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -2848,10 +2701,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 34.14686 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -2862,46 +2715,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 0.10706691 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 119.32299 + value: 85.43835 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.37413526 + value: 0.13091612 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -2910,9 +2755,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -2920,10 +2764,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 36.79529 + value: 114.41904 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -2934,66 +2778,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.11537102 + value: 0.358759 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.004206521 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 865.70105 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 652.619 + value: 1.3265028 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -3001,71 +2832,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.015553512 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1194.7474 + value: 47.8732 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.8306967 + value: 0.15010563 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.061917823 + value: 0.0017031434 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -3073,10 +2901,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2810.0898 + value: 706.9754 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -3087,10 +2915,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3058653 + value: 1.0832896 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -3102,56 +2930,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.041891765 + value: 0.012291329 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 85.43835 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.13091612 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -3159,10 +2980,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 865.70105 + value: 61.12777 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -3173,25 +2994,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.3265028 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.015553512 + value: 0.09366532 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -3200,60 +3006,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 706.9754 + value: 119.32299 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.0832896 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.012291329 + value: 0.37413526 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -3261,10 +3044,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 61.12777 + value: 859.7436 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -3275,10 +3058,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.09366532 + value: 1.3173743 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -3287,45 +3070,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 859.7436 + value: 36.79529 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.3173743 + value: 0.11537102 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -3383,7 +3158,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -3392,42 +3167,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 314.66492 + value: 329.55426 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.9548198 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 329.55426 + value: 395.85754 } retention_time { value: 1.65 @@ -3435,7 +3201,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -3496,53 +3262,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 3333.8533 + value: 551.0915 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 10.11625 + value: 1.392146 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.098421 + value: 0.047085162 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -3551,9 +3310,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -3561,10 +3319,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 49.84937 + value: 314.66492 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -3575,19 +3333,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.15126301 + value: 0.9548198 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -3596,10 +3382,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 181.53438 + value: 3333.8533 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -3610,10 +3396,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.55084825 + value: 10.11625 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -3625,70 +3411,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.006458806 + value: 0.098421 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 74.44391 + value: 1992.6111 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.22589274 + value: 5.033657 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0025630468 + value: 0.04897245 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -3698,10 +3476,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 49.84937 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -3712,46 +3490,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 0.15126301 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 148.88913 + value: 58.44582 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.45178944 + value: 0.14764357 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -3760,9 +3530,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -3770,10 +3539,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 63.25725 + value: 181.53438 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -3784,66 +3553,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.1919479 + value: 0.55084825 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.006458806 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 821.37537 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 395.85754 + value: 2.0749266 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -3851,71 +3607,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.02432893 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 551.0915 + value: 74.44391 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.392146 + value: 0.22589274 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.047085162 + value: 0.0025630468 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -3923,10 +3676,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1992.6111 + value: 506.41293 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -3937,10 +3690,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 5.033657 + value: 1.2792808 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -3952,56 +3705,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.04897245 + value: 0.014515103 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 58.44582 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.14764357 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -4009,10 +3755,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 821.37537 + value: 117.70281 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -4023,25 +3769,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.0749266 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.02432893 + value: 0.29733628 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -4050,60 +3781,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 506.41293 + value: 148.88913 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.2792808 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.014515103 + value: 0.45178944 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -4111,10 +3819,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 117.70281 + value: 372.1861 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -4125,10 +3833,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.29733628 + value: 0.9402022 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -4137,45 +3845,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 372.1861 + value: 63.25725 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.9402022 + value: 0.1919479 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -4233,7 +3933,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -4242,42 +3942,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 243.61258 + value: 339.8197 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.7168878 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 339.8197 + value: 603.6911 } retention_time { value: 1.65 @@ -4285,7 +3976,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -4346,53 +4037,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 3218.6992 + value: 911.8526 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 9.471786 + value: 1.5104622 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.092151 + value: 0.05108685 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -4401,9 +4085,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -4411,10 +4094,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 67.9222 + value: 243.61258 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -4425,19 +4108,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.19987717 + value: 0.7168878 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -4446,10 +4157,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 301.77158 + value: 3218.6992 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -4460,10 +4171,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.88803434 + value: 9.471786 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -4475,70 +4186,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.01041238 + value: 0.092151 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 125.80776 + value: 3346.3354 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.37021914 + value: 5.543125 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0042006173 + value: 0.05392907 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -4548,10 +4251,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 67.9222 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -4562,46 +4265,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 0.19987717 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 177.2651 + value: 83.64434 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5216446 + value: 0.13855487 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -4610,9 +4305,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -4620,10 +4314,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 93.00232 + value: 301.77158 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -4634,66 +4328,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.27368137 + value: 0.88803434 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.01041238 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1156.3579 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 603.6911 + value: 1.9154794 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -4701,71 +4382,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.02245938 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 911.8526 + value: 125.80776 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.5104622 + value: 0.37021914 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.05108685 + value: 0.0042006173 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -4773,10 +4451,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3346.3354 + value: 658.2517 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -4787,10 +4465,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 5.543125 + value: 1.0903783 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -4802,56 +4480,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.05392907 + value: 0.012371759 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 83.64434 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.13855487 + value: 0.0 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -4859,10 +4530,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1156.3579 + value: 131.60469 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -4873,25 +4544,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.9154794 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.02245938 + value: 0.21800004 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -4900,60 +4556,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 658.2517 + value: 177.2651 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.0903783 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.012371759 + value: 0.5216446 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -4961,10 +4594,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 131.60469 + value: 541.7727 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -4975,10 +4608,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.21800004 + value: 0.8974336 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -4987,45 +4620,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 541.7727 + value: 93.00232 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.8974336 + value: 0.27368137 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -5083,7 +4708,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -5092,42 +4717,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 169.65173 + value: 343.70193 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.49360135 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 343.70193 + value: 649.5333 } retention_time { value: 1.65 @@ -5135,7 +4751,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -5196,53 +4812,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 3004.7722 + value: 771.60944 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 8.742378 + value: 1.1879444 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0850546 + value: 0.040178657 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -5251,9 +4860,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -5261,10 +4869,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 86.28066 + value: 169.65173 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -5275,19 +4883,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.2510334 + value: 0.49360135 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -5296,10 +4932,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 428.4157 + value: 3004.7722 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -5310,10 +4946,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.2464746 + value: 8.742378 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -5325,70 +4961,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.014615164 + value: 0.0850546 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 193.61691 + value: 3042.3625 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.56332797 + value: 4.683921 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0063916883 + value: 0.045569867 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -5398,10 +5026,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 13.52521 + value: 86.28066 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -5412,46 +5040,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.039351568 + value: 0.2510334 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 176.63995 + value: 100.7443 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5139336 + value: 0.1551026 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -5460,9 +5080,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -5470,10 +5089,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 118.06918 + value: 428.4157 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -5484,66 +5103,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.343522 + value: 1.2464746 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.014615164 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1500.3427 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 649.5333 + value: 2.3098779 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -5551,71 +5157,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.02708378 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 771.60944 + value: 193.61691 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.1879444 + value: 0.56332797 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.040178657 + value: 0.0063916883 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -5623,10 +5226,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3042.3625 + value: 874.53674 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -5637,10 +5240,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.683921 + value: 1.3464079 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -5652,56 +5255,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.045569867 + value: 0.015276748 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 100.7443 + value: 13.52521 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.1551026 + value: 0.039351568 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -5709,10 +5305,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1500.3427 + value: 222.17567 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -5723,25 +5319,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.3098779 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.02708378 + value: 0.3420543 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -5750,60 +5331,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 874.53674 + value: 176.63995 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.3464079 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.015276748 + value: 0.5139336 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -5811,10 +5369,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 222.17567 + value: 542.3678 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -5825,10 +5383,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.3420543 + value: 0.8350115 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -5837,45 +5395,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 542.3678 + value: 118.06918 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.8350115 + value: 0.343522 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -5933,7 +5483,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -5942,42 +5492,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 109.13497 + value: 339.59164 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.32137117 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 339.59164 + value: 604.3044 } retention_time { value: 1.65 @@ -5985,7 +5526,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -6046,53 +5587,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 2681.613 + value: 655.67224 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 7.896581 + value: 1.0850034 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.076825835 + value: 0.036696985 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -6101,9 +5635,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -6111,10 +5644,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 100.06422 + value: 109.13497 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -6125,19 +5658,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.29466042 + value: 0.32137117 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -6146,10 +5707,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 574.0514 + value: 2681.613 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -6160,10 +5721,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.6904167 + value: 7.896581 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -6175,70 +5736,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.019820474 + value: 0.076825835 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 274.3153 + value: 2815.5234 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.8077799 + value: 4.659115 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.009165313 + value: 0.045328528 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -6248,10 +5801,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 20.66049 + value: 100.06422 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -6262,46 +5815,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.060839217 + value: 0.29466042 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 200.85059 + value: 92.21374 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.59144735 + value: 0.15259486 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -6310,9 +5855,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -6320,10 +5864,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 138.23174 + value: 574.0514 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -6334,66 +5878,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.40705281 + value: 1.6904167 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.019820474 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1573.511 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 604.3044 + value: 2.6038387 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -6401,71 +5932,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.03053053 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 655.67224 + value: 274.3153 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.0850034 + value: 0.8077799 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.036696985 + value: 0.009165313 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -6473,10 +6001,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2815.5234 + value: 829.938 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -6487,10 +6015,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.659115 + value: 1.3733774 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -6502,56 +6030,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.045328528 + value: 0.015582752 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 92.21374 + value: 20.66049 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.15259486 + value: 0.060839217 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -6559,10 +6080,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1573.511 + value: 140.65965 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -6573,25 +6094,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.6038387 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.03053053 + value: 0.23276292 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -6600,60 +6106,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 829.938 + value: 200.85059 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.3733774 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.015582752 + value: 0.59144735 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -6661,10 +6144,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 140.65965 + value: 447.2571 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -6675,10 +6158,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.23276292 + value: 0.740119 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -6687,45 +6170,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 447.2571 + value: 138.23174 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.740119 + value: 0.40705281 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -6783,7 +6258,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -6792,42 +6267,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 60.38027 + value: 317.0584 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.19043896 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 317.0584 + value: 642.08673 } retention_time { value: 1.65 @@ -6835,7 +6301,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -6896,53 +6362,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 2227.2803 + value: 744.65045 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 7.0248265 + value: 1.159735 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.06834454 + value: 0.039224554 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -6951,9 +6410,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -6961,10 +6419,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 105.29844 + value: 60.38027 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -6975,19 +6433,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.33211055 + value: 0.19043896 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -6996,10 +6482,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 674.6495 + value: 2227.2803 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -7010,10 +6496,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.1278398 + value: 7.0248265 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -7025,70 +6511,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.024949346 + value: 0.06834454 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 340.70404 + value: 1928.0988 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.0745782 + value: 3.0028634 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.012192487 + value: 0.029214857 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -7098,10 +6576,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 25.19804 + value: 105.29844 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -7112,46 +6590,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.07947444 + value: 0.33211055 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 184.41487 + value: 126.3622 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5816432 + value: 0.19679926 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -7160,9 +6630,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -7170,10 +6639,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 146.69202 + value: 674.6495 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -7184,66 +6653,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.46266562 + value: 2.1278398 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.024949346 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1495.7598 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 642.08673 + value: 2.329529 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -7251,71 +6707,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.027314194 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 744.65045 + value: 340.70404 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.159735 + value: 1.0745782 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.039224554 + value: 0.012192487 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -7323,10 +6776,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1928.0988 + value: 1026.3999 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -7337,10 +6790,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.0028634 + value: 1.5985378 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -7352,56 +6805,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.029214857 + value: 0.01813749 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 126.3622 + value: 25.19804 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.19679926 + value: 0.07947444 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -7409,10 +6855,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1495.7598 + value: 145.24654 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -7423,25 +6869,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.329529 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.027314194 + value: 0.22621013 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -7450,60 +6881,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1026.3999 + value: 184.41487 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.5985378 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.01813749 + value: 0.5816432 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -7511,10 +6919,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 145.24654 + value: 735.385 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -7525,10 +6933,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.22621013 + value: 1.1453048 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -7537,45 +6945,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 735.385 + value: 146.69202 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.1453048 + value: 0.46266562 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -7633,7 +7033,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -7642,42 +7042,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 44.54001 + value: 330.84695 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.13462421 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 330.84695 + value: 606.96387 } retention_time { value: 1.65 @@ -7685,7 +7076,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -7746,53 +7137,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 2026.8601 + value: 401.1194 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 6.126277 + value: 0.660862 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.059602547 + value: 0.022351675 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -7801,9 +7185,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -7811,10 +7194,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 116.70929 + value: 44.54001 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -7825,19 +7208,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.35275915 + value: 0.13462421 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -7846,10 +7257,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 840.43274 + value: 2026.8601 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -7860,10 +7271,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.5402462 + value: 6.126277 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -7875,70 +7286,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.029784894 + value: 0.059602547 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 441.8522 + value: 2209.2422 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.3355185 + value: 3.6398249 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.015153193 + value: 0.035411853 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -7948,10 +7351,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 30.7321 + value: 116.70929 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -7962,46 +7365,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.092889175 + value: 0.35275915 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 180.73694 + value: 97.77308 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5462856 + value: 0.1610855 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -8010,9 +7405,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -8020,10 +7414,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 155.70004 + value: 840.43274 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -8034,66 +7428,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.4706105 + value: 2.5402462 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.029784894 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1944.2611 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 606.96387 + value: 3.2032566 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -8101,71 +7482,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.037558824 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 401.1194 + value: 441.8522 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.660862 + value: 1.3355185 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.022351675 + value: 0.015153193 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -8173,10 +7551,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2209.2422 + value: 1060.2756 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -8187,10 +7565,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.6398249 + value: 1.7468513 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -8202,56 +7580,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.035411853 + value: 0.019820299 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 97.77308 + value: 30.7321 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.1610855 + value: 0.092889175 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -8259,10 +7630,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1944.2611 + value: 175.32437 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -8273,25 +7644,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.2032566 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.037558824 + value: 0.28885472 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -8300,60 +7656,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1060.2756 + value: 180.73694 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.7468513 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.019820299 + value: 0.5462856 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -8361,10 +7694,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 175.32437 + value: 369.90964 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -8375,10 +7708,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.28885472 + value: 0.6094426 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -8387,45 +7720,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 369.90964 + value: 155.70004 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.6094426 + value: 0.4706105 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -8483,7 +7808,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -8492,42 +7817,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 30.64968 + value: 310.2346 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.09879517 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 310.2346 + value: 567.297 } retention_time { value: 1.65 @@ -8535,7 +7851,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -8596,53 +7912,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1645.9138 + value: 328.69232 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 5.305384 + value: 0.5794008 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.051616084 + value: 0.019596493 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -8651,9 +7960,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -8661,10 +7969,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 117.48207 + value: 30.64968 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -8675,19 +7983,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.37868783 + value: 0.09879517 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -8696,10 +8032,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 921.96686 + value: 1645.9138 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -8710,10 +8046,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.9718378 + value: 5.305384 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -8725,70 +8061,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.03484539 + value: 0.051616084 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 505.8974 + value: 1739.7715 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.630693 + value: 3.066774 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.018502332 + value: 0.029836643 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -8798,10 +8126,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 36.73896 + value: 117.48207 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -8812,46 +8140,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.11842316 + value: 0.37868783 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 185.83974 + value: 92.59261 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.59902966 + value: 0.16321717 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -8860,9 +8180,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -8870,10 +8189,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 152.22482 + value: 921.96686 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -8884,66 +8203,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.49067646 + value: 2.9718378 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.03484539 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1929.8845 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 567.297 + value: 3.4018946 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -8951,71 +8257,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.039887894 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 328.69232 + value: 505.8974 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5794008 + value: 1.630693 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.019596493 + value: 0.018502332 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -9023,10 +8326,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1739.7715 + value: 1096.3264 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -9037,10 +8340,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.066774 + value: 1.932544 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -9052,56 +8355,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.029836643 + value: 0.021927224 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 92.59261 + value: 36.73896 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.16321717 + value: 0.11842316 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -9109,10 +8405,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1929.8845 + value: 166.07944 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -9123,25 +8419,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.4018946 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.039887894 + value: 0.29275572 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -9150,60 +8431,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1096.3264 + value: 185.83974 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.932544 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.021927224 + value: 0.59902966 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -9211,10 +8469,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 166.07944 + value: 404.59076 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -9225,10 +8483,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.29275572 + value: 0.71319044 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -9237,45 +8495,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 404.59076 + value: 152.22482 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.71319044 + value: 0.49067646 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -9333,7 +8583,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -9342,42 +8592,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 28.68432 + value: 323.9833 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.08853642 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 323.9833 + value: 602.468 } retention_time { value: 1.65 @@ -9385,7 +8626,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -9446,53 +8687,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1479.9105 + value: 210.31886 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 4.5678606 + value: 0.3490955 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.044440717 + value: 0.011807107 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -9501,9 +8735,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -9511,10 +8744,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 124.31583 + value: 28.68432 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -9525,19 +8758,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.38371062 + value: 0.08853642 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -9546,10 +8807,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1057.3331 + value: 1479.9105 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -9560,10 +8821,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.263542 + value: 4.5678606 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -9575,70 +8836,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.038265683 + value: 0.044440717 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 600.56476 + value: 1645.6871 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.8536904 + value: 2.7315757 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.021032527 + value: 0.026575502 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -9648,10 +8901,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 43.88113 + value: 124.31583 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -9662,46 +8915,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.13544257 + value: 0.38371062 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 172.72215 + value: 97.67627 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5331205 + value: 0.16212688 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -9710,9 +8955,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -9720,10 +8964,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 158.4213 + value: 1057.3331 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -9734,66 +8978,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.48897982 + value: 3.263542 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.038265683 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2323.574 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 602.468 + value: 3.856759 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -9801,71 +9032,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.04522127 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 210.31886 + value: 600.56476 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.3490955 + value: 1.8536904 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.011807107 + value: 0.021032527 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -9873,10 +9101,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1645.6871 + value: 1315.0062 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -9887,10 +9115,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.7315757 + value: 2.1826987 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -9902,56 +9130,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.026575502 + value: 0.024765555 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 97.67627 + value: 43.88113 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.16212688 + value: 0.13544257 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -9959,10 +9180,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2323.574 + value: 210.32072 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -9973,25 +9194,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.856759 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.04522127 + value: 0.34909856 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -10000,60 +9206,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1315.0062 + value: 172.72215 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.1826987 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.024765555 + value: 0.5331205 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -10061,10 +9244,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 210.32072 + value: 340.37592 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -10075,10 +9258,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.34909856 + value: 0.56496924 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -10087,45 +9270,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 340.37592 + value: 158.4213 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.56496924 + value: 0.48897982 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -10183,7 +9358,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -10192,42 +9367,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 24.93064 + value: 330.46835 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.075440325 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 330.46835 + value: 603.614 } retention_time { value: 1.65 @@ -10235,7 +9401,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -10296,53 +9462,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1308.0616 + value: 163.20898 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 3.9582057 + value: 0.27038634 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.038509384 + value: 0.009145007 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -10351,9 +9510,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -10361,10 +9519,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 128.87866 + value: 24.93064 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -10375,19 +9533,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.38998792 + value: 0.075440325 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -10396,10 +9582,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1181.5482 + value: 1308.0616 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -10410,10 +9596,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.5753748 + value: 3.9582057 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -10425,70 +9611,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.041921984 + value: 0.038509384 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 680.4693 + value: 1535.3284 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.0591059 + value: 2.54356 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.023363233 + value: 0.024746295 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -10498,10 +9676,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 45.67683 + value: 128.87866 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -10512,46 +9690,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.13821848 + value: 0.38998792 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 174.9575 + value: 94.26455 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5294229 + value: 0.15616694 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -10560,9 +9730,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -10570,10 +9739,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 164.19093 + value: 1181.5482 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -10584,66 +9753,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.49684316 + value: 3.5753748 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.041921984 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2394.6643 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 603.614 + value: 3.9672115 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -10651,71 +9807,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.046516348 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 163.20898 + value: 680.4693 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.27038634 + value: 2.0591059 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.009145007 + value: 0.023363233 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -10723,10 +9876,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1535.3284 + value: 1374.4773 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -10737,10 +9890,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.54356 + value: 2.2770798 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -10752,56 +9905,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.024746295 + value: 0.02583643 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 94.26455 + value: 45.67683 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.15616694 + value: 0.13821848 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -10809,10 +9955,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2394.6643 + value: 211.12552 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -10823,25 +9969,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.9672115 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.046516348 + value: 0.3497691 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -10850,60 +9981,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1374.4773 + value: 174.9575 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.2770798 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.02583643 + value: 0.5294229 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -10911,10 +10019,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 211.12552 + value: 318.91513 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -10925,10 +10033,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.3497691 + value: 0.52834284 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -10937,45 +10045,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 318.91513 + value: 164.19093 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.52834284 + value: 0.49684316 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -11033,7 +10133,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -11042,42 +10142,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 26.57664 + value: 327.7885 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.08107862 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 327.7885 + value: 643.4803 } retention_time { value: 1.65 @@ -11085,7 +10176,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -11146,53 +10237,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1121.9783 + value: 133.17241 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 3.4228725 + value: 0.20695648 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.033301126 + value: 0.0069996817 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -11201,9 +10285,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -11211,10 +10294,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 129.62038 + value: 26.57664 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -11225,19 +10308,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.39543903 + value: 0.08107862 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -11246,10 +10357,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1225.0444 + value: 1121.9783 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -11260,10 +10371,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.7373016 + value: 3.4228725 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -11275,70 +10386,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.04382061 + value: 0.033301126 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 721.6462 + value: 1428.1073 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.2015605 + value: 2.219349 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.024979565 + value: 0.021592045 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -11348,10 +10451,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 50.59142 + value: 129.62038 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -11362,46 +10465,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.15434165 + value: 0.39543903 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 163.18925 + value: 118.31726 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.49784926 + value: 0.18387084 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -11410,9 +10505,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -11420,10 +10514,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 162.28036 + value: 1225.0444 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -11434,66 +10528,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.49507645 + value: 3.7373016 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.04382061 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2678.0527 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 643.4803 + value: 4.1618257 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -11501,71 +10582,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.048798237 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 133.17241 + value: 721.6462 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.20695648 + value: 2.2015605 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0069996817 + value: 0.024979565 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -11573,10 +10651,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1428.1073 + value: 1557.4137 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -11587,10 +10665,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.219349 + value: 2.4202974 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -11602,56 +10680,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.021592045 + value: 0.02746142 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 118.31726 + value: 50.59142 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.18387084 + value: 0.15434165 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -11659,10 +10730,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2678.0527 + value: 250.3684 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -11673,25 +10744,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.1618257 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.048798237 + value: 0.3890848 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -11700,60 +10756,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1557.4137 + value: 163.18925 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.4202974 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.02746142 + value: 0.49784926 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -11761,10 +10794,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 250.3684 + value: 362.23596 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -11775,10 +10808,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.3890848 + value: 0.5629325 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -11787,45 +10820,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 362.23596 + value: 162.28036 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.5629325 + value: 0.49507645 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -11883,7 +10908,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -11892,42 +10917,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 24.20987 + value: 305.40744 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.07927073 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 305.40744 + value: 592.47723 } retention_time { value: 1.65 @@ -11935,7 +10951,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -11996,53 +11012,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 905.4163 + value: 129.01923 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.964618 + value: 0.21776234 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.028842768 + value: 0.007365158 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -12051,9 +11060,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -12061,10 +11069,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 125.72504 + value: 24.20987 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -12075,19 +11083,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.41166332 + value: 0.07927073 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -12096,10 +11132,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1256.0547 + value: 905.4163 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -12110,10 +11146,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.112718 + value: 2.964618 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -12125,70 +11161,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.048222445 + value: 0.028842768 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 743.80566 + value: 1079.4044 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.435454 + value: 1.8218496 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.02763339 + value: 0.017724775 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -12198,10 +11226,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 47.39398 + value: 125.72504 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -12212,46 +11240,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.1551828 + value: 0.41166332 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 154.5202 + value: 129.4827 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.50594777 + value: 0.21854459 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -12260,9 +11280,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -12270,10 +11289,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 158.46892 + value: 1256.0547 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -12284,66 +11303,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5188771 + value: 4.112718 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.048222445 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2359.647 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 592.47723 + value: 3.9826794 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -12351,71 +11357,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.04669771 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 129.01923 + value: 743.80566 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.21776234 + value: 2.435454 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.007365158 + value: 0.02763339 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -12423,10 +11426,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1079.4044 + value: 1425.6514 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -12437,10 +11440,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.8218496 + value: 2.406255 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -12452,56 +11455,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.017724775 + value: 0.027302092 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 129.4827 + value: 47.39398 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.21854459 + value: 0.1551828 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -12509,10 +11505,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2359.647 + value: 278.7184 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -12523,25 +11519,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.9826794 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.04669771 + value: 0.47042885 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -12550,60 +11531,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1425.6514 + value: 154.5202 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.406255 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.027302092 + value: 0.50594777 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -12611,10 +11569,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 278.7184 + value: 384.48944 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -12625,10 +11583,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.47042885 + value: 0.64895225 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -12637,45 +11595,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 384.48944 + value: 158.46892 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.64895225 + value: 0.5188771 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -12733,7 +11683,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -12742,42 +11692,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 23.5109 + value: 330.9517 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.07104027 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 330.9517 + value: 613.7262 } retention_time { value: 1.65 @@ -12785,7 +11726,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -12846,53 +11787,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 912.90796 + value: 101.09229 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.7584326 + value: 0.16471888 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.026836792 + value: 0.0055711223 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -12901,9 +11835,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -12911,10 +11844,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 140.23824 + value: 23.5109 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -12925,19 +11858,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.4237423 + value: 0.07104027 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -12946,10 +11907,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1372.8275 + value: 912.90796 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -12960,10 +11921,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.1481204 + value: 2.7584326 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -12975,70 +11936,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.048637543 + value: 0.026836792 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 822.15027 + value: 1069.2329 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.4842002 + value: 1.7421987 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.028186481 + value: 0.016949851 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -13048,10 +12001,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 51.36434 + value: 140.23824 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -13062,46 +12015,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.15520193 + value: 0.4237423 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 162.96536 + value: 144.32611 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.49241433 + value: 0.23516369 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -13110,9 +12055,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -13120,10 +12064,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 166.90186 + value: 1372.8275 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -13134,66 +12078,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.50430876 + value: 4.1481204 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.048637543 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2615.3103 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 613.7262 + value: 4.2613635 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -13201,71 +12132,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.04996534 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 101.09229 + value: 822.15027 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.16471888 + value: 2.4842002 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0055711223 + value: 0.028186481 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -13273,10 +12201,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1069.2329 + value: 1552.9507 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -13287,10 +12215,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.7421987 + value: 2.530364 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -13302,56 +12230,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.016949851 + value: 0.02871027 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 144.32611 + value: 51.36434 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.23516369 + value: 0.15520193 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -13359,10 +12280,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2615.3103 + value: 182.77211 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -13373,25 +12294,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.2613635 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.04996534 + value: 0.29780728 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -13400,60 +12306,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1552.9507 + value: 162.96536 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.530364 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.02871027 + value: 0.49241433 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -13461,10 +12344,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 182.77211 + value: 396.75885 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -13475,10 +12358,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.29780728 + value: 0.6464754 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -13487,45 +12370,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 396.75885 + value: 166.90186 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.6464754 + value: 0.50430876 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -13583,7 +12458,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -13592,42 +12467,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 20.42933 + value: 349.69302 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.058420755 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 349.69302 + value: 579.51855 } retention_time { value: 1.65 @@ -13635,7 +12501,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -13696,53 +12562,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 861.55457 + value: 107.15103 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.4637454 + value: 0.18489663 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.023969779 + value: 0.006253574 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -13751,9 +12610,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -13761,10 +12619,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 144.63573 + value: 20.42933 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -13775,19 +12633,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.41360772 + value: 0.058420755 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -13796,10 +12682,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1476.7015 + value: 861.55457 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -13810,10 +12696,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.222851 + value: 2.4637454 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -13825,70 +12711,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.049513772 + value: 0.023969779 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 894.82697 + value: 934.06915 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.5588927 + value: 1.611802 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.029033966 + value: 0.015681222 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -13898,10 +12776,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 58.04648 + value: 144.63573 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -13912,46 +12790,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16599268 + value: 0.41360772 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 167.25285 + value: 158.63225 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.47828478 + value: 0.2737311 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -13960,9 +12830,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -13970,10 +12839,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 175.61722 + value: 1476.7015 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -13984,66 +12853,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.50220394 + value: 4.222851 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.049513772 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2506.6794 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 579.51855 + value: 4.3254514 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -14051,71 +12907,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.050716784 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 107.15103 + value: 894.82697 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.18489663 + value: 2.5588927 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.006253574 + value: 0.029033966 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -14123,10 +12976,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 934.06915 + value: 1488.8368 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -14137,10 +12990,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.611802 + value: 2.5690928 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -14152,56 +13005,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.015681222 + value: 0.029149696 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 158.63225 + value: 58.04648 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.2737311 + value: 0.16599268 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -14209,10 +13055,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2506.6794 + value: 166.39949 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -14223,25 +13069,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3254514 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.050716784 + value: 0.28713402 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -14250,60 +13081,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1488.8368 + value: 167.25285 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.5690928 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.029149696 + value: 0.47828478 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -14311,10 +13119,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 166.39949 + value: 410.3987 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -14325,10 +13133,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.28713402 + value: 0.70817184 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -14337,45 +13145,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 410.3987 + value: 175.61722 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.70817184 + value: 0.50220394 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -14433,7 +13233,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -14442,42 +13242,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 19.01272 + value: 339.28802 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.056037106 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 339.28802 + value: 568.2288 } retention_time { value: 1.65 @@ -14485,7 +13276,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -14546,53 +13337,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 779.89667 + value: 104.60272 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.2986271 + value: 0.18408556 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.022363342 + value: 0.006226142 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -14601,9 +13385,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -14611,10 +13394,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 140.25708 + value: 19.01272 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -14625,19 +13408,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.41338646 + value: 0.056037106 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -14646,10 +13457,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1457.2977 + value: 779.89667 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -14660,10 +13471,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.295164 + value: 2.2986271 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -14675,70 +13486,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.050361656 + value: 0.022363342 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 887.22186 + value: 559.96545 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6149518 + value: 0.98545766 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.029670026 + value: 0.009587517 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -14748,10 +13551,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 60.47698 + value: 140.25708 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -14762,46 +13565,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.17824672 + value: 0.41338646 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 167.6381 + value: 214.24644 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.49408785 + value: 0.37704256 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -14810,9 +13605,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -14820,10 +13614,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 171.97375 + value: 1457.2977 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -14834,66 +13628,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5068665 + value: 4.295164 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.050361656 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2526.1135 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 568.2288 + value: 4.445592 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -14901,71 +13682,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.052125458 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 104.60272 + value: 887.22186 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.18408556 + value: 2.6149518 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.006226142 + value: 0.029670026 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -14973,10 +13751,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 559.96545 + value: 1505.0272 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -14987,10 +13765,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.98545766 + value: 2.6486287 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -15002,56 +13780,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.009587517 + value: 0.030052137 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 214.24644 + value: 60.47698 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.37704256 + value: 0.17824672 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -15059,10 +13830,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2526.1135 + value: 99.67055 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -15073,25 +13844,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.445592 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.052125458 + value: 0.17540565 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -15100,60 +13856,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1505.0272 + value: 167.6381 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6486287 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030052137 + value: 0.49408785 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -15161,10 +13894,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 99.67055 + value: 520.1095 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -15175,10 +13908,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.17540565 + value: 0.91531694 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -15187,45 +13920,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 520.1095 + value: 171.97375 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.91531694 + value: 0.5068665 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -15283,7 +14008,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -15292,42 +14017,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 16.04706 + value: 335.96063 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.047764704 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 335.96063 + value: 585.7142 } retention_time { value: 1.65 @@ -15335,7 +14051,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -15396,53 +14112,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 734.9989 + value: 95.6284 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.1877532 + value: 0.16326803 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.021284651 + value: 0.0055220514 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -15451,9 +14160,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -15461,10 +14169,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 138.03235 + value: 16.04706 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -15475,19 +14183,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.41085872 + value: 0.047764704 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -15496,10 +14232,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1451.1887 + value: 734.9989 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -15510,10 +14246,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3195205 + value: 2.1877532 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -15525,70 +14261,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.05064724 + value: 0.021284651 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 883.0879 + value: 613.869 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6285458 + value: 1.0480692 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.02982427 + value: 0.010196665 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -15598,10 +14326,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 53.86236 + value: 138.03235 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -15612,46 +14340,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16032343 + value: 0.41085872 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 153.6596 + value: 196.39613 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.45737386 + value: 0.33531055 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -15660,9 +14380,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -15670,10 +14389,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 168.70898 + value: 1451.1887 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -15684,66 +14403,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.50216895 + value: 4.3195205 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.05064724 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2635.5989 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 585.7142 + value: 4.4998035 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -15751,71 +14457,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.052761097 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 95.6284 + value: 883.0879 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.16326803 + value: 2.6285458 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0055220514 + value: 0.02982427 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -15823,10 +14526,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 613.869 + value: 1576.1028 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -15837,10 +14540,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.0480692 + value: 2.6909077 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -15852,56 +14555,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.010196665 + value: 0.030531848 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 196.39613 + value: 53.86236 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.33531055 + value: 0.16032343 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -15909,10 +14605,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2635.5989 + value: 135.31206 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -15923,25 +14619,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.4998035 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.052761097 + value: 0.23102063 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -15950,60 +14631,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1576.1028 + value: 153.6596 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6909077 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030531848 + value: 0.45737386 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -16011,10 +14669,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 135.31206 + value: 482.08636 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -16025,10 +14683,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.23102063 + value: 0.8230744 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -16037,45 +14695,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 482.08636 + value: 168.70898 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.8230744 + value: 0.50216895 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -16133,7 +14783,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -16142,42 +14792,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 347.95087 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 347.95087 + value: 520.3527 } retention_time { value: 1.65 @@ -16185,7 +14826,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -16246,53 +14887,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 727.8157 + value: 77.13166 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.0917196 + value: 0.14822957 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.020350339 + value: 0.0050134202 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -16301,9 +14935,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -16311,10 +14944,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 136.9742 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -16325,19 +14958,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.39365956 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -16346,10 +15007,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1485.8125 + value: 727.8157 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -16360,10 +15021,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.270179 + value: 2.0917196 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -16375,70 +15036,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.050068703 + value: 0.020350339 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 907.9047 + value: 723.8187 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.60929 + value: 1.3910154 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.029605787 + value: 0.013533189 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -16448,10 +15101,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 55.47123 + value: 136.9742 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -16462,46 +15115,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.15942259 + value: 0.39365956 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 159.984 + value: 139.85641 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.45978904 + value: 0.26877233 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -16510,9 +15155,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -16520,10 +15164,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 170.89839 + value: 1485.8125 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -16534,66 +15178,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.49115667 + value: 4.270179 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.050068703 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2295.7617 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 520.3527 + value: 4.4119334 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -16601,71 +15232,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0517308 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 77.13166 + value: 907.9047 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.14822957 + value: 2.60929 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0050134202 + value: 0.029605787 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -16673,10 +15301,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 723.8187 + value: 1379.1016 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -16687,10 +15315,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.3910154 + value: 2.6503205 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -16702,56 +15330,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.013533189 + value: 0.030071333 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 139.85641 + value: 55.47123 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.26877233 + value: 0.15942259 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -16759,10 +15380,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2295.7617 + value: 153.48312 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -16773,25 +15394,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.4119334 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0517308 + value: 0.29495978 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -16800,60 +15406,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1379.1016 + value: 159.984 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6503205 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030071333 + value: 0.45978904 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -16861,10 +15444,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 153.48312 + value: 366.80933 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -16875,10 +15458,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.29495978 + value: 0.7049244 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -16887,45 +15470,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 366.80933 + value: 170.89839 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.7049244 + value: 0.49115667 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -16983,7 +15558,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -16992,42 +15567,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 345.06076 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 345.06076 + value: 546.2235 } retention_time { value: 1.65 @@ -17035,7 +15601,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -17096,53 +15662,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 717.384 + value: 78.96692 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.0790079 + value: 0.14456889 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.020226667 + value: 0.004889609 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -17151,9 +15710,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -17161,10 +15719,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 141.52655 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -17175,19 +15733,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.41014966 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -17196,10 +15782,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1493.6417 + value: 717.384 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -17210,10 +15796,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3286343 + value: 2.0790079 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -17225,70 +15811,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0507541 + value: 0.020226667 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 911.6586 + value: 0.0 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6420236 + value: 0.0 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.029977191 + value: 0.0 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -17298,10 +15876,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 52.68863 + value: 141.52655 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -17312,46 +15890,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.15269378 + value: 0.41014966 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 157.70892 + value: 264.59402 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.45704684 + value: 0.48440614 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -17360,9 +15930,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -17370,10 +15939,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 174.20726 + value: 1493.6417 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -17384,66 +15953,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5048597 + value: 4.3286343 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.0507541 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2353.6716 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 546.2235 + value: 4.3089905 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -17451,71 +16007,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.050523773 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 78.96692 + value: 911.6586 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.14456889 + value: 2.6420236 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.004889609 + value: 0.029977191 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -17523,10 +16076,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1460.2281 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -17537,10 +16090,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 2.6733162 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -17552,56 +16105,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.030332249 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 264.59402 + value: 52.68863 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.48440614 + value: 0.15269378 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -17609,10 +16155,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2353.6716 + value: 116.79911 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -17623,25 +16169,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3089905 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.050523773 + value: 0.21383026 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -17650,60 +16181,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1460.2281 + value: 157.70892 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6733162 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030332249 + value: 0.45704684 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -17711,10 +16219,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 116.79911 + value: 501.0801 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -17725,10 +16233,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.21383026 + value: 0.9173537 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -17737,45 +16245,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 501.0801 + value: 174.20726 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.9173537 + value: 0.5048597 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -17833,7 +16333,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -17842,42 +16342,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 345.27353 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 345.27353 + value: 539.2308 } retention_time { value: 1.65 @@ -17885,7 +16376,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -17946,53 +16437,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 719.3501 + value: 76.26696 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.083421 + value: 0.14143658 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.020269603 + value: 0.004783668 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -18001,9 +16485,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -18011,10 +16494,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 144.45079 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -18025,19 +16508,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.41836625 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -18046,10 +16557,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1510.9755 + value: 719.3501 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -18060,10 +16571,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.376169 + value: 2.083421 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -18075,70 +16586,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.051311463 + value: 0.020269603 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 924.7942 + value: 737.3046 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6784394 + value: 1.3673266 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.030390376 + value: 0.013302721 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -18148,10 +16651,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 62.91556 + value: 144.45079 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -18162,46 +16665,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.18221948 + value: 0.41836625 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 160.7762 + value: 151.69688 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.4656488 + value: 0.28132087 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -18210,9 +16705,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -18220,10 +16714,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 176.38095 + value: 1510.9755 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -18234,66 +16728,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5108441 + value: 4.376169 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.051311463 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2373.2065 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 539.2308 + value: 4.401096 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -18301,71 +16782,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.05160373 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 76.26696 + value: 924.7942 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.14143658 + value: 2.6784394 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.004783668 + value: 0.030390376 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -18373,10 +16851,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 737.3046 + value: 1431.9214 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -18387,10 +16865,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.3673266 + value: 2.6554887 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -18402,56 +16880,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.013302721 + value: 0.030129973 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 151.69688 + value: 62.91556 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.28132087 + value: 0.18221948 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -18459,10 +16930,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2373.2065 + value: 166.95341 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -18473,25 +16944,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.401096 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.05160373 + value: 0.30961403 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -18500,60 +16956,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1431.9214 + value: 160.7762 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6554887 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030129973 + value: 0.4656488 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -18561,10 +16994,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 166.95341 + value: 378.6112 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -18575,10 +17008,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.30961403 + value: 0.70213205 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -18587,45 +17020,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 378.6112 + value: 176.38095 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.70213205 + value: 0.5108441 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -18683,7 +17108,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -18692,42 +17117,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 344.08658 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 344.08658 + value: 544.5192 } retention_time { value: 1.65 @@ -18735,7 +17151,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -18796,53 +17212,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 714.0694 + value: 87.60475 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.0752609 + value: 0.16088459 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.020190213 + value: 0.0054414384 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -18851,9 +17260,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -18861,10 +17269,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 140.12799 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -18875,19 +17283,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.40724632 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -18896,10 +17332,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1504.2207 + value: 714.0694 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -18910,10 +17346,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3716345 + value: 2.0752609 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -18925,70 +17361,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.05125829 + value: 0.020190213 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 915.12164 + value: 376.66702 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.659568 + value: 0.69174236 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.030176258 + value: 0.0067299614 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -18998,10 +17426,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 58.08021 + value: 140.12799 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -19012,46 +17440,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16879533 + value: 0.40724632 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 160.49721 + value: 206.62315 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.46644425 + value: 0.3794598 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -19060,9 +17480,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -19070,10 +17489,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 176.57321 + value: 1504.2207 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -19084,66 +17503,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.51316506 + value: 4.3716345 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.05125829 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2368.87 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 544.5192 + value: 4.3503885 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -19151,71 +17557,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.051009174 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 87.60475 + value: 915.12164 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.16088459 + value: 2.659568 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0054414384 + value: 0.030176258 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -19223,10 +17626,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 376.66702 + value: 1469.4111 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -19237,10 +17640,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.69174236 + value: 2.6985476 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -19252,56 +17655,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0067299614 + value: 0.030618532 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 206.62315 + value: 58.08021 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.3794598 + value: 0.16879533 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -19309,10 +17705,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2368.87 + value: 148.63918 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -19323,25 +17719,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3503885 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.051009174 + value: 0.27297324 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -19350,60 +17731,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1469.4111 + value: 160.49721 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6985476 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030618532 + value: 0.46644425 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -19411,10 +17769,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 148.63918 + value: 466.1165 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -19425,10 +17783,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.27297324 + value: 0.8560148 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -19437,45 +17795,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 466.1165 + value: 176.57321 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.8560148 + value: 0.51316506 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -19533,7 +17883,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -19542,42 +17892,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 323.3988 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 323.3988 + value: 553.90564 } retention_time { value: 1.65 @@ -19585,7 +17926,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -19646,53 +17987,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 675.2211 + value: 81.38737 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.0878901 + value: 0.14693365 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.020313084 + value: 0.00496959 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -19701,9 +18035,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -19711,10 +18044,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 131.53835 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -19725,19 +18058,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.40673727 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -19746,10 +18107,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1423.306 + value: 675.2211 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -19760,10 +18121,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.4010863 + value: 2.0878901 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -19775,70 +18136,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.05160362 + value: 0.020313084 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 868.68164 + value: 778.1406 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6861005 + value: 1.4048253 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.030477302 + value: 0.013667546 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -19848,10 +18201,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 53.50764 + value: 131.53835 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -19862,46 +18215,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16545404 + value: 0.40673727 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 155.51894 + value: 145.40936 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.48088902 + value: 0.2625165 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -19910,9 +18255,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -19920,10 +18264,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 165.12938 + value: 1423.306 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -19934,66 +18278,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.51060605 + value: 4.4010863 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.05160362 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2449.0198 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 553.90564 + value: 4.4213667 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -20001,71 +18332,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.051841408 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 81.38737 + value: 868.68164 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.14693365 + value: 2.6861005 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.00496959 + value: 0.030477302 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -20073,10 +18401,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 778.1406 + value: 1473.6844 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -20087,10 +18415,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.4048253 + value: 2.6605334 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -20102,56 +18430,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.013667546 + value: 0.030187212 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 145.40936 + value: 53.50764 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.2625165 + value: 0.16545404 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -20159,10 +18480,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2449.0198 + value: 150.3723 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -20173,25 +18494,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.4213667 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.051841408 + value: 0.2714764 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -20200,60 +18506,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1473.6844 + value: 155.51894 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6605334 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030187212 + value: 0.48088902 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -20261,10 +18544,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 150.3723 + value: 397.0655 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -20275,10 +18558,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.2714764 + value: 0.7168468 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -20287,45 +18570,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 397.0655 + value: 165.12938 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.7168468 + value: 0.51060605 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -20383,7 +18658,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -20392,42 +18667,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 328.4415 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 328.4415 + value: 601.4948 } retention_time { value: 1.65 @@ -20435,7 +18701,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -20496,53 +18762,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 675.737 + value: 86.86591 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.0574045 + value: 0.14441672 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.02001649 + value: 0.0048844623 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -20551,9 +18810,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -20561,10 +18819,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 130.8688 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -20575,19 +18833,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.39845395 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -20596,10 +18882,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1438.4254 + value: 675.737 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -20610,10 +18896,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3795485 + value: 2.0574045 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -20625,70 +18911,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.05135108 + value: 0.02001649 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 873.1023 + value: 903.48706 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6583192 + value: 1.5020696 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.030162087 + value: 0.014613635 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -20698,10 +18976,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 52.15836 + value: 130.8688 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -20712,46 +18990,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.15880564 + value: 0.39845395 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 152.10603 + value: 136.29887 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.46311453 + value: 0.22660026 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -20760,9 +19030,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -20770,10 +19039,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 166.02023 + value: 1438.4254 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -20784,66 +19053,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5054789 + value: 4.3795485 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.05135108 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2678.0342 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 601.4948 + value: 4.452298 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -20851,71 +19107,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.052204084 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 86.86591 + value: 873.1023 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.14441672 + value: 2.6583192 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0048844623 + value: 0.030162087 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -20923,10 +19176,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 903.48706 + value: 1615.292 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -20937,10 +19190,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.5020696 + value: 2.685463 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -20952,56 +19205,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.014613635 + value: 0.030470068 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 136.29887 + value: 52.15836 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.22660026 + value: 0.15880564 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -21009,10 +19255,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2678.0342 + value: 189.94456 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -21023,25 +19269,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.452298 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.052204084 + value: 0.31578755 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -21050,60 +19281,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1615.292 + value: 152.10603 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.685463 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030470068 + value: 0.46311453 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -21111,10 +19319,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 189.94456 + value: 419.25156 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -21125,10 +19333,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.31578755 + value: 0.69701606 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -21137,45 +19345,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 419.25156 + value: 166.02023 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.69701606 + value: 0.5054789 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -21233,7 +19433,7 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -21242,42 +19442,33 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 321.20267 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 321.20267 + value: 564.08527 } retention_time { value: 1.65 @@ -21285,7 +19476,7 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" float_value { @@ -21346,53 +19537,46 @@ reactions { units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 649.7465 + value: 81.67859 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.0228553 + value: 0.14479831 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.019680358 + value: 0.0048973686 } retention_time { - value: 1.83 + value: 2.4 units: MINUTE } } @@ -21401,9 +19585,8 @@ reactions { products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -21411,10 +19594,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 127.35521 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } @@ -21425,19 +19608,47 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.39649487 + value: 0.0 } retention_time { - value: 2.33 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 3.09 + units: MINUTE + } + } + reaction_role: CATALYST } products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -21446,10 +19657,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1379.8949 + value: 649.7465 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -21460,10 +19671,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.2960258 + value: 2.0228553 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } @@ -21475,70 +19686,62 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.05037176 + value: 0.019680358 } retention_time { - value: 2.85 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 848.71155 + value: 840.99756 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6422927 + value: 1.490905 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.029980246 + value: 0.014505015 } retention_time { - value: 2.78 + value: 1.83 units: MINUTE } } - reaction_role: PRODUCT + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" + value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" } is_desired_product: false measurements { @@ -21548,10 +19751,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 58.23689 + value: 127.35521 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } @@ -21562,46 +19765,38 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.18130885 + value: 0.39649487 } retention_time { - value: 2.91 + value: 2.33 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" - } - is_desired_product: false measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 145.50868 + value: 125.10358 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.45301205 + value: 0.22178133 } retention_time { - value: 1.92 + value: 2.33 units: MINUTE } } @@ -21610,9 +19805,8 @@ reactions { products { identifiers { type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" + value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" } - is_desired_product: false measurements { analysis_key: "Online HPLC-UV" type: AREA @@ -21620,10 +19814,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 157.1752 + value: 1379.8949 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } @@ -21634,66 +19828,53 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.4893334 + value: 4.2960258 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" - } measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.0 + value: 0.05037176 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 2534.617 } retention_time { - value: 3.09 + value: 2.85 units: MINUTE } } - reaction_role: CATALYST - } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 564.08527 + value: 4.4933224 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } @@ -21701,71 +19882,68 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.052685104 } retention_time { - value: 1.65 + value: 2.85 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" } + is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 81.67859 + value: 848.71155 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.14479831 + value: 2.6422927 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0048973686 + value: 0.029980246 } retention_time { - value: 2.4 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -21773,10 +19951,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 840.99756 + value: 1528.0685 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -21787,10 +19965,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.490905 + value: 2.708932 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } @@ -21802,56 +19980,49 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.014505015 + value: 0.030736355 } retention_time { - value: 1.83 + value: 2.78 units: MINUTE } } - reaction_role: REACTANT + reaction_role: PRODUCT } products { identifiers { type: SMILES - value: "C12=CC=CC=C1C3=C(C=CC=C3)N2" + value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 125.10358 + value: 58.23689 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.22178133 + value: 0.18130885 } retention_time { - value: 2.33 + value: 2.91 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "COC(/C(C)=C(C1CC1)/c2cccc(OCc3ccccc3)c2)=O" - } measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -21859,10 +20030,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2534.617 + value: 163.3043 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -21873,25 +20044,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.4933224 - } - retention_time { - value: 2.85 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.052685104 + value: 0.2895029 } retention_time { - value: 2.85 + value: 2.91 units: MINUTE } } @@ -21900,60 +20056,37 @@ reactions { products { identifiers { type: SMILES - value: "COC(/C(C)=C(C1CC1)\\c2cccc(OCc3ccccc3)c2)=O" + value: "Oc1cccc(OCc2ccccc2)c1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1528.0685 + value: 145.50868 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.708932 - } - retention_time { - value: 2.78 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.030736355 + value: 0.45301205 } retention_time { - value: 2.78 + value: 1.92 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "NC(C=CC=C1)=C1C2=CC=CC=C2C3=CC(OCC4=CC=CC=C4)=CC=C3" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -21961,10 +20094,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 163.3043 + value: 406.84534 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -21975,10 +20108,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.2895029 + value: 0.721248 } retention_time { - value: 2.91 + value: 1.92 units: MINUTE } } @@ -21987,45 +20120,37 @@ reactions { products { identifiers { type: SMILES - value: "Oc1cccc(OCc2ccccc2)c1" + value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" } is_desired_product: false measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 406.84534 + value: 157.1752 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.721248 + value: 0.4893334 } retention_time { - value: 1.92 + value: 3.09 units: MINUTE } } - reaction_role: PRODUCT - } - products { - identifiers { - type: SMILES - value: "c1(COc2cccc(c3cccc(OCc4ccccc4)c3)c2)ccccc1" - } - is_desired_product: false measurements { analysis_key: "Offline HPLC-UV" type: AREA @@ -22080,7 +20205,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/24/2021, 11:30:49" + value: "05/25/2021, 15:22:39" } person { username: "skearnes" @@ -28302,7 +26427,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/24/2021, 11:30:49" + value: "05/25/2021, 15:22:39" } person { username: "skearnes" @@ -34524,7 +32649,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/24/2021, 11:30:49" + value: "05/25/2021, 15:22:39" } person { username: "skearnes" @@ -41047,7 +39172,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/24/2021, 11:30:49" + value: "05/25/2021, 15:22:39" } person { username: "skearnes" @@ -47570,7 +45695,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/24/2021, 11:30:49" + value: "05/25/2021, 15:22:39" } person { username: "skearnes" From 8b25514eb27f5ad202a7f3f72ee7bc4cbb93d27b Mon Sep 17 00:00:00 2001 From: Steven Kearnes Date: Wed, 26 May 2021 15:25:50 -0600 Subject: [PATCH 3/5] Fix catalyst SMILES --- hein-dataset.pbtxt | 9388 ++++++++++++++++++++++---------------------- 1 file changed, 4694 insertions(+), 4694 deletions(-) diff --git a/hein-dataset.pbtxt b/hein-dataset.pbtxt index c78d2499..ccee9d37 100644 --- a/hein-dataset.pbtxt +++ b/hein-dataset.pbtxt @@ -160,7 +160,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/25/2021, 15:22:39" + value: "05/26/2021, 15:23:46" } person { username: "skearnes" @@ -541,7 +541,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/25/2021, 15:22:39" + value: "05/26/2021, 15:23:46" } person { username: "skearnes" @@ -639,7 +639,7 @@ reactions { components { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } amount { moles { @@ -833,7 +833,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -842,66 +842,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 325.94662 + value: 880.28033 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 715.8811 + value: 2.7006886 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09134269 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 880.28033 + value: 1351.4216 } retention_time { value: 2.4 @@ -909,13 +893,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.7006886 + value: 1.8877739 } retention_time { value: 2.4 @@ -923,45 +907,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.09134269 + value: 0.06384829 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1351.4216 + value: 325.94662 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.8877739 + value: 715.8811 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -969,23 +972,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.06384829 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -1608,7 +1608,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -1617,66 +1617,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 313.6642 + value: 822.3286 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 610.46533 + value: 2.6216846 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.08867061 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 822.3286 + value: 1024.2686 } retention_time { value: 2.4 @@ -1684,13 +1668,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.6216846 + value: 1.6778488 } retention_time { value: 2.4 @@ -1698,45 +1682,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.08867061 + value: 0.0567482 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 1024.2686 + value: 313.6642 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.6778488 + value: 610.46533 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -1744,23 +1747,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0567482 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -2380,6 +2380,99 @@ reactions { value: 40.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 814.8354 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.5549028 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.08641192 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1194.7474 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8306967 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.061917823 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -2442,100 +2535,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 814.8354 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.5549028 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.08641192 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 1194.7474 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.8306967 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.061917823 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -3158,7 +3158,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -3167,66 +3167,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 329.55426 + value: 809.42194 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 395.85754 + value: 2.4561114 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0830706 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 809.42194 + value: 551.0915 } retention_time { value: 2.4 @@ -3234,13 +3218,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.4561114 + value: 1.392146 } retention_time { value: 2.4 @@ -3248,45 +3232,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0830706 + value: 0.047085162 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 551.0915 + value: 329.55426 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.392146 + value: 395.85754 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -3294,23 +3297,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.047085162 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -3930,6 +3930,99 @@ reactions { value: 80.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 786.8825 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3155882 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.07831782 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 911.8526 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5104622 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.05108685 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -3992,100 +4085,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 786.8825 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.3155882 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.07831782 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 911.8526 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5104622 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.05108685 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -4708,7 +4708,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -4717,66 +4717,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 343.70193 + value: 728.2881 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 649.5333 + value: 2.1189528 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.07166722 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 728.2881 + value: 771.60944 } retention_time { value: 2.4 @@ -4784,13 +4768,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 2.1189528 + value: 1.1879444 } retention_time { value: 2.4 @@ -4798,45 +4782,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.07166722 + value: 0.040178657 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 771.60944 + value: 343.70193 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.1879444 + value: 649.5333 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -4844,23 +4847,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.040178657 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -5480,6 +5480,99 @@ reactions { value: 120.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 643.5442 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8950531 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.064094484 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 655.67224 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0850034 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.036696985 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -5542,100 +5635,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 643.5442 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.8950531 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.064094484 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 655.67224 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.0850034 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.036696985 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -6258,7 +6258,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -6267,66 +6267,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 317.0584 + value: 515.684 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 642.08673 + value: 1.6264639 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.055010263 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 515.684 + value: 744.65045 } retention_time { value: 2.4 @@ -6334,13 +6318,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.6264639 + value: 1.159735 } retention_time { value: 2.4 @@ -6348,45 +6332,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.055010263 + value: 0.039224554 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 744.65045 + value: 317.0584 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.159735 + value: 642.08673 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -6394,23 +6397,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.039224554 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -7030,6 +7030,99 @@ reactions { value: 160.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 446.32227 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3490294 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.04562687 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 401.1194 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.660862 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.022351675 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -7092,100 +7185,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 446.32227 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.3490294 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.04562687 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 401.1194 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.660862 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.022351675 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -7808,7 +7808,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -7817,66 +7817,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 310.2346 + value: 348.18863 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 567.297 + value: 1.1223398 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.037959777 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 348.18863 + value: 328.69232 } retention_time { value: 2.4 @@ -7884,13 +7868,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 1.1223398 + value: 0.5794008 } retention_time { value: 2.4 @@ -7898,45 +7882,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.037959777 + value: 0.019596493 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 328.69232 + value: 310.2346 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.5794008 + value: 567.297 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -7944,23 +7947,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.019596493 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -8580,6 +8580,99 @@ reactions { value: 200.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 284.07956 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.876834 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.02965628 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 210.31886 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3490955 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.011807107 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -8642,100 +8735,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 284.07956 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.876834 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.02965628 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 210.31886 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.3490955 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.011807107 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -9358,7 +9358,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -9367,66 +9367,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 330.46835 + value: 225.00632 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 603.614 + value: 0.680871 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.023028418 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 225.00632 + value: 163.20898 } retention_time { value: 2.4 @@ -9434,13 +9418,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.680871 + value: 0.27038634 } retention_time { value: 2.4 @@ -9448,45 +9432,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.023028418 + value: 0.009145007 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 163.20898 + value: 330.46835 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.27038634 + value: 603.614 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -9494,23 +9497,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.009145007 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -10130,6 +10130,99 @@ reactions { value: 240.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 168.9886 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.51554155 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.017436648 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 133.17241 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.20695648 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0069996817 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -10192,100 +10285,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 168.9886 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.51554155 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.017436648 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 133.17241 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.20695648 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0069996817 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -10908,7 +10908,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -10917,66 +10917,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 305.40744 + value: 121.36669 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 592.47723 + value: 0.39739272 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.013440616 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 121.36669 + value: 129.01923 } retention_time { value: 2.4 @@ -10984,13 +10968,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.39739272 + value: 0.21776234 } retention_time { value: 2.4 @@ -10998,45 +10982,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.013440616 + value: 0.007365158 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 129.01923 + value: 305.40744 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.21776234 + value: 592.47723 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -11044,23 +11047,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.007365158 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -11680,6 +11680,99 @@ reactions { value: 280.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 97.56874 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.29481262 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.009971153 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 101.09229 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16471888 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0055711223 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -11742,100 +11835,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 97.56874 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.29481262 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.009971153 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 101.09229 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.16471888 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0055711223 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -12458,7 +12458,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -12467,66 +12467,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 349.69302 + value: 78.89827 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 579.51855 + value: 0.22562152 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.007630971 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 78.89827 + value: 107.15103 } retention_time { value: 2.4 @@ -12534,13 +12518,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.22562152 + value: 0.18489663 } retention_time { value: 2.4 @@ -12548,45 +12532,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.007630971 + value: 0.006253574 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 107.15103 + value: 349.69302 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.18489663 + value: 579.51855 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -12594,23 +12597,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.006253574 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -13230,6 +13230,99 @@ reactions { value: 320.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 58.71957 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.17306702 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0058534727 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 104.60272 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18408556 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.006226142 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -13292,100 +13385,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 58.71957 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.17306702 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0058534727 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 104.60272 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.18408556 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.006226142 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -14008,7 +14008,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -14017,66 +14017,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 335.96063 + value: 47.83313 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 585.7142 + value: 0.1423772 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0048154816 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 47.83313 + value: 95.6284 } retention_time { value: 2.4 @@ -14084,13 +14068,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.1423772 + value: 0.16326803 } retention_time { value: 2.4 @@ -14098,45 +14082,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0048154816 + value: 0.0055220514 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 95.6284 + value: 335.96063 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.16326803 + value: 585.7142 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -14144,23 +14147,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0055220514 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -14780,6 +14780,99 @@ reactions { value: 360.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 44.8533 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.128907 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.004359892 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 77.13166 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14822957 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0050134202 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -14842,100 +14935,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 44.8533 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.128907 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.004359892 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 77.13166 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.14822957 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0050134202 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } - products { - identifiers { - type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -15558,7 +15558,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -15567,66 +15567,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 345.06076 + value: 43.24135 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 546.2235 + value: 0.12531517 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.00423841 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 43.24135 + value: 78.96692 } retention_time { value: 2.4 @@ -15634,13 +15618,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.12531517 + value: 0.14456889 } retention_time { value: 2.4 @@ -15648,45 +15632,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.00423841 + value: 0.004889609 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 78.96692 + value: 345.06076 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.14456889 + value: 546.2235 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -15694,23 +15697,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.004889609 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -16333,7 +16333,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -16342,66 +16342,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 345.27353 + value: 42.03334 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 539.2308 + value: 0.121739246 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0041174646 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 42.03334 + value: 76.26696 } retention_time { value: 2.4 @@ -16409,13 +16393,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.121739246 + value: 0.14143658 } retention_time { value: 2.4 @@ -16423,45 +16407,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.0041174646 + value: 0.004783668 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 76.26696 + value: 345.27353 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.14143658 + value: 539.2308 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -16469,23 +16472,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.004783668 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -17108,7 +17108,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -17117,66 +17117,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 344.08658 + value: 42.18785 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 544.5192 + value: 0.12260824 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004146856 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 42.18785 + value: 87.60475 } retention_time { value: 2.4 @@ -17184,13 +17168,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.12260824 + value: 0.16088459 } retention_time { value: 2.4 @@ -17198,45 +17182,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.004146856 + value: 0.0054414384 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 87.60475 + value: 344.08658 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.16088459 + value: 544.5192 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -17244,23 +17247,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0054414384 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -17883,7 +17883,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -17892,66 +17892,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 323.3988 + value: 43.22353 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 553.90564 + value: 0.13365397 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004520444 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 43.22353 + value: 81.38737 } retention_time { value: 2.4 @@ -17959,13 +17943,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.13365397 + value: 0.14693365 } retention_time { value: 2.4 @@ -17973,45 +17957,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.004520444 + value: 0.00496959 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 81.38737 + value: 323.3988 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.14693365 + value: 553.90564 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -18019,23 +18022,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.00496959 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -18655,65 +18655,6 @@ reactions { value: 460.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 328.4415 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 601.4948 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -18810,7 +18751,66 @@ reactions { products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 328.4415 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 601.4948 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } + products { + identifiers { + type: SMILES + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -19433,7 +19433,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -19442,66 +19442,50 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 321.20267 + value: 42.82974 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: false - is_normalized: false + uses_internal_standard: true + is_normalized: true uses_authentic_standard: false float_value { - value: 564.08527 + value: 0.13334179 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004509886 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 42.82974 + value: 81.67859 } retention_time { value: 2.4 @@ -19509,13 +19493,13 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: AREA uses_internal_standard: true is_normalized: true uses_authentic_standard: false float_value { - value: 0.13334179 + value: 0.14479831 } retention_time { value: 2.4 @@ -19523,45 +19507,64 @@ reactions { } } measurements { - analysis_key: "Online HPLC-UV" + analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" uses_internal_standard: true is_normalized: true uses_authentic_standard: true float_value { - value: 0.004509886 + value: 0.0048973686 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { - analysis_key: "Offline HPLC-UV" + analysis_key: "Online HPLC-UV" type: AREA uses_internal_standard: false is_normalized: false uses_authentic_standard: false float_value { - value: 81.67859 + value: 321.20267 } retention_time { - value: 2.4 + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.14479831 + value: 564.08527 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -19569,23 +19572,20 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0048973686 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -20205,7 +20205,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/25/2021, 15:22:39" + value: "05/26/2021, 15:23:46" } person { username: "skearnes" @@ -20302,7 +20302,7 @@ reactions { components { identifiers { type: SMILES - value: "CS(O[Pd]1([P](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC4[Fe]C5C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C5)C8=CC=CC=C8C9=C([NH2]1)C=CC=C9)(=O)=O" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } amount { moles { @@ -20496,7 +20496,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -20505,57 +20505,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 789.43243 + value: 1584.4377 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 2.0070593 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 1584.4377 + value: 0.06788276 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 2.0070593 + value: 789.43243 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -20563,18 +20566,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.06788276 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -20751,6 +20751,56 @@ reactions { value: 40.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 673.57666 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.4812287 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.050098117 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -20784,56 +20834,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 673.57666 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.4812287 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.050098117 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -21012,7 +21012,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -21021,57 +21021,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 430.06973 + value: 556.34735 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.2936213 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 556.34735 + value: 0.04375286 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.2936213 + value: 430.06973 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -21079,18 +21082,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.04375286 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -21270,7 +21270,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -21279,57 +21279,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 440.8866 + value: 502.88892 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.140631 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 502.88892 + value: 0.03857842 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.140631 + value: 440.8866 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -21337,18 +21340,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.03857842 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -21528,7 +21528,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -21537,57 +21537,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 456.32468 + value: 455.9279 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.9991304 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 455.9279 + value: 0.03379259 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.9991304 + value: 456.32468 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -21595,18 +21598,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.03379259 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -21783,39 +21783,6 @@ reactions { value: 120.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 679.77155 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -21866,6 +21833,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 679.77155 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -22044,7 +22044,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -22053,57 +22053,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 683.0257 + value: 507.21786 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.7426044 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 507.21786 + value: 0.025116364 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.7426044 + value: 683.0257 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -22111,18 +22114,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.025116364 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -22302,7 +22302,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -22311,57 +22311,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 702.9632 + value: 447.78397 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.6369949 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 447.78397 + value: 0.021544442 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.6369949 + value: 702.9632 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -22369,18 +22372,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.021544442 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -22560,7 +22560,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -22569,57 +22569,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 652.37384 + value: 352.0839 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.5396965 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 352.0839 + value: 0.018253615 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.5396965 + value: 652.37384 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -22627,18 +22630,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.018253615 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -22815,6 +22815,56 @@ reactions { value: 200.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 301.3809 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47850642 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016184043 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -22848,56 +22898,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 301.3809 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.47850642 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.016184043 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -23076,7 +23076,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -23085,57 +23085,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 695.24066 + value: 280.38925 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.40329814 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 280.38925 + value: 0.01364035 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.40329814 + value: 695.24066 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -23143,18 +23146,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.01364035 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -23334,7 +23334,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -23343,57 +23343,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 693.8551 + value: 234.85779 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.33848247 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 234.85779 + value: 0.011448154 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.33848247 + value: 693.8551 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -23401,18 +23404,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.011448154 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -23592,7 +23592,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -23601,57 +23601,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 674.97577 + value: 188.2771 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.27893907 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 188.2771 + value: 0.009434276 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.27893907 + value: 674.97577 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -23659,18 +23662,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.009434276 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -23847,39 +23847,6 @@ reactions { value: 280.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 716.32935 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -23930,6 +23897,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 716.32935 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -24108,7 +24108,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -24117,57 +24117,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 705.07166 + value: 133.43137 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.1892451 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 133.43137 + value: 0.0064006476 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.1892451 + value: 705.07166 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -24175,18 +24178,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0064006476 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -24366,7 +24366,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -24375,57 +24375,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 697.50214 + value: 108.68061 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.15581402 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 108.68061 + value: 0.005269942 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.15581402 + value: 697.50214 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -24433,18 +24436,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.005269942 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -24624,7 +24624,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -24633,57 +24633,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 701.7939 + value: 87.97259 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.12535389 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 87.97259 + value: 0.004239719 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.12535389 + value: 701.7939 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -24691,18 +24694,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.004239719 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -24879,6 +24879,56 @@ reactions { value: 360.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 52.94001 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.07446365 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0025185095 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -24912,56 +24962,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 52.94001 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.07446365 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0025185095 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -25140,7 +25140,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -25149,57 +25149,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 666.0584 + value: 57.31877 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.086056665 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 57.31877 + value: 0.0029106087 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.086056665 + value: 666.0584 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -25207,18 +25210,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0029106087 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -25398,7 +25398,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -25407,57 +25407,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 461.35196 + value: 27.16534 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.058882028 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 27.16534 + value: 0.001991508 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.058882028 + value: 461.35196 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -25465,18 +25468,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.001991508 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -25656,7 +25656,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -25665,57 +25665,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 454.0849 + value: 30.65263 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.06750418 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 30.65263 + value: 0.0022831266 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.06750418 + value: 454.0849 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -25723,18 +25726,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0022831266 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -25911,39 +25911,6 @@ reactions { value: 440.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 475.99625 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -25994,6 +25961,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 475.99625 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -26172,7 +26172,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -26181,57 +26181,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 471.93872 + value: 30.08823 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.06375453 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 30.08823 + value: 0.0021563056 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.06375453 + value: 471.93872 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -26239,18 +26242,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0021563056 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -26427,7 +26427,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/25/2021, 15:22:39" + value: "05/26/2021, 15:23:46" } person { username: "skearnes" @@ -26524,7 +26524,7 @@ reactions { components { identifiers { type: SMILES - value: "Cl[Pd](Cl)[P](C1=CC=CC=C1)(C2=CC=CC2[Fe]C3C(P(C4=CC=CC=C4)C5=CC=CC=C5)=CC=C3)C6=CC=CC=C6" + value: "Cl[Pd](Cl)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC1[Fe]C1C=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1" } amount { moles { @@ -26718,7 +26718,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -26727,57 +26727,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 755.68005 + value: 1534.0931 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 2.0300827 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 1534.0931 + value: 0.06866146 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 2.0300827 + value: 755.68005 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -26785,18 +26788,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.06866146 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -26976,7 +26976,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -26985,57 +26985,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 443.52127 + value: 90.9476 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.20505804 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 90.9476 + value: 0.006935473 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.20505804 + value: 443.52127 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -27043,18 +27046,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.006935473 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -27231,6 +27231,56 @@ reactions { value: 60.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 45.96372 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.106616 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0036059662 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -27264,56 +27314,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 45.96372 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.106616 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0036059662 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -27492,7 +27492,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -27501,38 +27501,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 433.5336 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -27541,17 +27537,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 433.5336 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -27559,18 +27562,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -27750,7 +27750,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -27759,38 +27759,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 700.0409 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -27799,17 +27795,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 700.0409 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -27817,18 +27820,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -28008,7 +28008,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -28017,38 +28017,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 679.9285 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -28057,17 +28053,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 679.9285 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -28075,18 +28078,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -28263,6 +28263,56 @@ reactions { value: 140.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -28296,56 +28346,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -28524,7 +28524,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -28533,38 +28533,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 696.4937 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -28573,17 +28569,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 696.4937 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -28591,18 +28594,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -28782,7 +28782,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -28791,38 +28791,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 687.6207 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -28831,17 +28827,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 687.6207 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -28849,18 +28852,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -29040,7 +29040,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -29049,38 +29049,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 655.5416 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -29089,17 +29085,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 655.5416 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -29107,18 +29110,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -29295,6 +29295,56 @@ reactions { value: 220.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -29328,56 +29378,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -29556,7 +29556,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -29565,38 +29565,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 419.6252 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -29605,17 +29601,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 419.6252 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -29623,18 +29626,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -29814,7 +29814,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -29823,38 +29823,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 460.23026 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -29863,17 +29859,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 460.23026 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -29881,18 +29884,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -30072,7 +30072,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -30081,38 +30081,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 696.9243 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -30121,17 +30117,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 696.9243 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -30139,18 +30142,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -30327,6 +30327,56 @@ reactions { value: 300.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -30360,56 +30410,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -30588,7 +30588,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -30597,38 +30597,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 693.795 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -30637,17 +30633,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 693.795 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -30655,18 +30658,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -30846,7 +30846,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -30855,38 +30855,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 700.07263 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -30895,17 +30891,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 700.07263 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -30913,18 +30916,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -31104,7 +31104,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -31113,38 +31113,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 677.1683 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -31153,17 +31149,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 677.1683 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -31171,18 +31174,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -31359,6 +31359,56 @@ reactions { value: 380.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -31392,56 +31442,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -31620,7 +31620,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -31629,38 +31629,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 697.96716 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -31669,17 +31665,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 697.96716 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -31687,18 +31690,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -31878,7 +31878,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -31887,38 +31887,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 506.37045 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -31927,17 +31923,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 506.37045 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -31945,18 +31948,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -32136,7 +32136,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -32145,38 +32145,34 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 466.39795 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { value: 0.0 } @@ -32185,17 +32181,24 @@ reactions { units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 466.39795 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -32203,18 +32206,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -32391,6 +32391,56 @@ reactions { value: 460.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.0 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -32424,56 +32474,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -32649,7 +32649,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/25/2021, 15:22:39" + value: "05/26/2021, 15:23:46" } person { username: "skearnes" @@ -32774,7 +32774,7 @@ reactions { components { identifiers { type: SMILES - value: "Cl[Pd](Cl)[P](C1=CC=CC=C1)(C2=CC=CC2[Fe]C3C(P(C4=CC=CC=C4)C5=CC=CC=C5)=CC=C3)C6=CC=CC=C6" + value: "Cl[Pd](Cl)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC1[Fe]C1C=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1" } amount { moles { @@ -32983,7 +32983,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -32992,57 +32992,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 251.12868 + value: 460.132 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.8322558 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 460.132 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.8322558 + value: 251.12868 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -33050,18 +33053,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -33241,7 +33241,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -33250,57 +33250,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.31285 + value: 343.407 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.5309289 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 343.407 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.5309289 + value: 224.31285 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -33308,18 +33311,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -33499,7 +33499,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -33508,57 +33508,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 230.34326 + value: 297.72034 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.2925073 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 297.72034 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.2925073 + value: 230.34326 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -33566,18 +33569,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -33754,39 +33754,6 @@ reactions { value: 15.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 253.29059 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -33837,6 +33804,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 253.29059 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -34015,7 +34015,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -34024,57 +34024,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 211.81667 + value: 228.26155 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.0776374 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 228.26155 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.0776374 + value: 211.81667 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -34082,18 +34085,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -34273,7 +34273,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -34282,57 +34282,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 214.94334 + value: 220.16705 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.0243027 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 220.16705 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.0243027 + value: 214.94334 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -34340,18 +34343,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -34531,7 +34531,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -34540,57 +34540,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 222.19221 + value: 206.6496 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.9300487 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 206.6496 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.9300487 + value: 222.19221 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -34598,18 +34601,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -34786,6 +34786,56 @@ reactions { value: 35.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 190.25092 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8852116 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -34819,56 +34869,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 190.25092 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.8852116 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.09 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -35047,7 +35047,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -35056,57 +35056,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.78731 + value: 178.89474 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.7958401 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 178.89474 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.7958401 + value: 224.78731 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -35114,18 +35117,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -35305,7 +35305,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -35314,57 +35314,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 235.25168 + value: 179.50269 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.76302403 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 179.50269 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.76302403 + value: 235.25168 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -35372,18 +35375,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -35563,7 +35563,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -35572,57 +35572,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 223.31474 + value: 164.8724 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.73829603 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 164.8724 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.73829603 + value: 223.31474 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -35630,18 +35633,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -35818,39 +35818,6 @@ reactions { value: 55.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 216.93741 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -35901,6 +35868,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 216.93741 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -36079,7 +36079,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -36088,57 +36088,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 246.52484 + value: 161.63391 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.6556496 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 161.63391 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.6556496 + value: 246.52484 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -36146,18 +36149,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -36337,7 +36337,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -36346,57 +36346,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 226.5036 + value: 145.09882 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.64060265 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 145.09882 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.64060265 + value: 226.5036 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -36404,18 +36407,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -36595,7 +36595,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -36604,57 +36604,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.91002 + value: 131.73769 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.5857351 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 131.73769 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.5857351 + value: 224.91002 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -36662,18 +36665,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -36850,6 +36850,56 @@ reactions { value: 75.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 123.58422 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5595545 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -36883,56 +36933,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 123.58422 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.5595545 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.09 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -37111,7 +37111,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -37120,57 +37120,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 208.84625 + value: 113.45226 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.5432334 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 113.45226 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.5432334 + value: 208.84625 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -37178,18 +37181,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -37369,7 +37369,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -37378,57 +37378,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 213.95546 + value: 108.40001 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.5066475 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 108.40001 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.5066475 + value: 213.95546 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -37436,18 +37439,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -37627,7 +37627,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -37636,57 +37636,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 220.71236 + value: 105.88336 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.47973463 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 105.88336 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.47973463 + value: 220.71236 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -37694,18 +37697,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -37882,39 +37882,6 @@ reactions { value: 95.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 225.1136 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -37965,6 +37932,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 225.1136 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -38143,7 +38143,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -38152,57 +38152,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 211.09848 + value: 96.94833 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.4592564 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 96.94833 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.4592564 + value: 211.09848 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -38210,18 +38213,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -38401,7 +38401,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -38410,57 +38410,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 210.94897 + value: 90.7617 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.43025428 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 90.7617 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.43025428 + value: 210.94897 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -38468,18 +38471,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -38659,7 +38659,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -38668,57 +38668,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 197.51227 + value: 83.65161 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.42352614 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 83.65161 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.42352614 + value: 197.51227 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -38726,18 +38729,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -38914,6 +38914,56 @@ reactions { value: 115.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 84.86391 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4030427 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -38947,56 +38997,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 84.86391 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.4030427 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.09 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -39172,7 +39172,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/25/2021, 15:22:39" + value: "05/26/2021, 15:23:46" } person { username: "skearnes" @@ -39297,7 +39297,7 @@ reactions { components { identifiers { type: SMILES - value: "Cl[Pd](Cl)[P](C1=CC=CC=C1)(C2=CC=CC2[Fe]C3C(P(C4=CC=CC=C4)C5=CC=CC=C5)=CC=C3)C6=CC=CC=C6" + value: "Cl[Pd](Cl)<-P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC1[Fe]C1C=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1" } amount { moles { @@ -39506,7 +39506,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -39515,57 +39515,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 214.43896 + value: 366.40317 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.7086594 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 366.40317 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.7086594 + value: 214.43896 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -39573,18 +39576,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -39764,7 +39764,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -39773,57 +39773,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 184.28227 + value: 230.27904 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 1.2495995 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 230.27904 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 1.2495995 + value: 184.28227 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -39831,18 +39834,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -40022,7 +40022,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -40031,57 +40031,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 211.12502 + value: 204.6626 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.9693906 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 204.6626 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.9693906 + value: 211.12502 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -40089,18 +40092,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -40277,39 +40277,6 @@ reactions { value: 15.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 218.08653 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -40360,6 +40327,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 218.08653 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -40538,7 +40538,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -40547,57 +40547,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 257.01898 + value: 195.8778 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.7621141 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 195.8778 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.7621141 + value: 257.01898 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -40605,18 +40608,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -40796,7 +40796,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -40805,57 +40805,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 198.15588 + value: 129.99352 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.6560164 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 129.99352 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.6560164 + value: 198.15588 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -40863,18 +40866,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -41054,7 +41054,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -41063,57 +41063,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 200.28362 + value: 121.94792 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.60887617 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 121.94792 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.60887617 + value: 200.28362 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -41121,18 +41124,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -41309,6 +41309,56 @@ reactions { value: 35.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 110.84234 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5097206 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -41342,56 +41392,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 110.84234 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.5097206 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.09 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -41570,7 +41570,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -41579,57 +41579,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 216.26643 + value: 100.09444 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.4628293 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 100.09444 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.4628293 + value: 216.26643 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -41637,18 +41640,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -41828,7 +41828,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -41837,57 +41837,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 214.521 + value: 86.94685 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.40530694 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 86.94685 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.40530694 + value: 214.521 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -41895,18 +41898,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -42086,7 +42086,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -42095,57 +42095,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 223.83688 + value: 82.16212 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.36706245 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 82.16212 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.36706245 + value: 223.83688 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -42153,18 +42156,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -42341,39 +42341,6 @@ reactions { value: 55.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 201.92815 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -42424,6 +42391,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 201.92815 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -42602,7 +42602,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -42611,57 +42611,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 213.18584 + value: 66.21473 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.3105963 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 66.21473 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.3105963 + value: 213.18584 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -42669,18 +42672,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -42860,7 +42860,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -42869,57 +42869,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 205.53284 + value: 59.55063 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.2897378 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 59.55063 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.2897378 + value: 205.53284 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -42927,18 +42930,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -43118,7 +43118,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -43127,57 +43127,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 220.63264 + value: 58.0082 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.26291758 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 58.0082 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.26291758 + value: 220.63264 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -43185,18 +43188,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -43373,6 +43373,56 @@ reactions { value: 75.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 56.16369 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.24998306 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.09 + } + retention_time { + value: 2.4 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -43406,56 +43456,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 56.16369 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 0.24998306 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.09 - } - retention_time { - value: 2.4 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -43634,7 +43634,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -43643,57 +43643,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 213.83128 + value: 51.75714 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.24204662 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 51.75714 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.24204662 + value: 213.83128 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -43701,18 +43704,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -43892,7 +43892,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -43901,57 +43901,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 200.57803 + value: 44.61722 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.2224432 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 44.61722 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.2224432 + value: 200.57803 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -43959,18 +43962,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -44150,7 +44150,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -44159,57 +44159,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 197.5107 + value: 38.9466 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.1971873 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 38.9466 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.1971873 + value: 197.5107 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -44217,18 +44220,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -44405,39 +44405,6 @@ reactions { value: 95.0 units: MINUTE } - products { - identifiers { - type: SMILES - value: "COc1cc(OC)cc(OC)c1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 179.3816 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - float_value { - value: 0.009 - } - retention_time { - value: 1.65 - units: MINUTE - } - } - reaction_role: INTERNAL_STANDARD - } products { identifiers { type: SMILES @@ -44488,6 +44455,39 @@ reactions { } reaction_role: REACTANT } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 179.3816 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + float_value { + value: 0.009 + } + retention_time { + value: 1.65 + units: MINUTE + } + } + reaction_role: INTERNAL_STANDARD + } products { identifiers { type: SMILES @@ -44666,7 +44666,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -44675,57 +44675,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 217.57083 + value: 39.19144 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.18013187 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 39.19144 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.18013187 + value: 217.57083 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -44733,18 +44736,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -44924,7 +44924,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -44933,57 +44933,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.14577 + value: 38.10116 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.16998385 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 38.10116 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.16998385 + value: 224.14577 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -44991,18 +44994,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -45182,7 +45182,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -45191,57 +45191,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 217.49643 + value: 35.46846 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.16307606 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 35.46846 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.16307606 + value: 217.49643 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -45249,18 +45252,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -45440,7 +45440,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -45449,57 +45449,60 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 192.77646 + value: 29.09146 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false float_value { - value: 0.009 + value: 0.15090774 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD - } - products { - identifiers { - type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" - } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 29.09146 + value: 0.09 } retention_time { value: 2.4 units: MINUTE } } + reaction_role: REACTANT + } + products { + identifiers { + type: SMILES + value: "COc1cc(OC)cc(OC)c1" + } measurements { analysis_key: "Online HPLC-UV" type: AREA - uses_internal_standard: true - is_normalized: true + uses_internal_standard: false + is_normalized: false uses_authentic_standard: false float_value { - value: 0.15090774 + value: 192.77646 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } @@ -45507,18 +45510,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.09 + value: 0.009 } retention_time { - value: 2.4 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -45695,7 +45695,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/25/2021, 15:22:39" + value: "05/26/2021, 15:23:46" } person { username: "skearnes" From 99ac2c75dbe6d2aa3eba91ecf3f59c393b60cece Mon Sep 17 00:00:00 2001 From: Steven Kearnes Date: Thu, 1 Jul 2021 14:58:34 -0400 Subject: [PATCH 4/5] updates --- hein-dataset.pbtxt | 39 +++++++++++++++++---------------------- 1 file changed, 17 insertions(+), 22 deletions(-) diff --git a/hein-dataset.pbtxt b/hein-dataset.pbtxt index ccee9d37..e271e4f7 100644 --- a/hein-dataset.pbtxt +++ b/hein-dataset.pbtxt @@ -160,7 +160,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/26/2021, 15:23:46" + value: "07/01/2021, 14:56:43" } person { username: "skearnes" @@ -339,18 +339,13 @@ reactions { stirring { type: STIR_BAR } + conditions_are_dynamic: true } notes { + forms_precipitate: true + is_exothermic: true procedure_details: "To an oven-dried 1000 ml round bottomed flask equipped with a magnetic stir bar under N2\natmosphere was added methyl 3-cyclopropyl-2-methyl-3-oxopropanoate 2 (10.0 g, 64.0 mmol)\nand THF (100 ml). The mixture was cooled to -78 \302\260C and 1M NaHMDS solution (96.0 ml, 96.0\nmmol) was added over 30 min, maintaining the internal temperature below -60 \302\260C, followed by\na THF rinse (50 ml). The mixture was aged for 1 h at -78 \302\260C and Ts2O (31.3 g, 96.0 mmol) in THF\n(200 ml) was added over 1 h, maintaining the internal temperature below -60 \302\260C. The mixture\nwas aged for 20 min at -78 \302\260C, then warmed to 25 \302\260C and aged for 2 h. A thick slurry formed. The\nreaction was quenched with 300 ml of 0.5M NaHCO3 solution and the phases were separated.\nThe aqueous layer was back-extracted twice with 100 ml of EtOAc. The organic layers were\ncombined and washed with 200 ml of saturated NaCl solution, dried over MgSO4 and filtered.\nUpon concentration to an oil, the crude product was purified by normal phase column\nchromatography to give (E)-methyl 3-cyclopropyl-2-methyl-3-(tosyloxy)acrylate 3-(E) in 30%\nyield and (Z)-methyl 3-cyclopropyl-2-methyl-3-(tosyloxy)acrylate 3-(Z) in 54% yield." } - workups { - type: WAIT - details: "The mixture was aged for 20 min at -78 \302\260C." - duration { - value: 20.0 - units: MINUTE - } - } workups { type: TEMPERATURE details: "Warmed to 25 \302\260C." @@ -507,8 +502,8 @@ reactions { } outcomes { reaction_time { - value: 16.0 - units: HOUR + value: 20.0 + units: MINUTE } products { identifiers { @@ -541,7 +536,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/26/2021, 15:23:46" + value: "07/01/2021, 14:56:43" } person { username: "skearnes" @@ -724,7 +719,7 @@ reactions { } } is_automated: true - automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1).\n\nReactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01). Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir\ndiscs (VP 782N6). Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales\n17P687) capped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075).\n\nAutomated sampling procedure: The reaction vial, aqueous K3PO4 vial and dilution plate were\nsealed and placed on the Chemspeed Swing robot deck for automated initiation, sampling,\ndilution and HPLC injection (Figure S3). The robot deck was inerted under positive pressure N2\natmosphere, tumble stirring was initiated (300-500 rpm), and the reaction vial temperature set\nto 25 \302\260C. To the reaction vial was transferred 1M aqueous K3PO4 by needle. This was immediately\nfollowed by transfer of a 20 \302\265l aliquot from the reaction vial to the dilution plate by needle. Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample. A 50 \302\265l aliquot was then transferred from the\ndilution plate to the injection port of the HPLC selection valve, over-filling the 20 \302\265l loop with\ndiluted sample. Once the loop was filled, the valve was switched and the HPLC run triggered,\nallowing the HPLC pump to push the mobile phase through the loop, moving the sample into the\nHPLC column. The valve was then rinsed with 1000 \302\265l of acetonitrile. This sampling, dilution and\ninjection procedure was repeated every 5-20 minutes until reaction completion.\n" } conditions { temperature { @@ -20205,7 +20200,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/26/2021, 15:23:46" + value: "07/01/2021, 14:56:43" } person { username: "skearnes" @@ -20387,7 +20382,7 @@ reactions { } } is_automated: true - automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1).\n\nReactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01). Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir\ndiscs (VP 782N6). Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales\n17P687) capped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075).\n\nAutomated sampling procedure: The reaction vial, aqueous K3PO4 vial and dilution plate were\nsealed and placed on the Chemspeed Swing robot deck for automated initiation, sampling,\ndilution and HPLC injection (Figure S3). The robot deck was inerted under positive pressure N2\natmosphere, tumble stirring was initiated (300-500 rpm), and the reaction vial temperature set\nto 25 \302\260C. To the reaction vial was transferred 1M aqueous K3PO4 by needle. This was immediately\nfollowed by transfer of a 20 \302\265l aliquot from the reaction vial to the dilution plate by needle. Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample. A 50 \302\265l aliquot was then transferred from the\ndilution plate to the injection port of the HPLC selection valve, over-filling the 20 \302\265l loop with\ndiluted sample. Once the loop was filled, the valve was switched and the HPLC run triggered,\nallowing the HPLC pump to push the mobile phase through the loop, moving the sample into the\nHPLC column. The valve was then rinsed with 1000 \302\265l of acetonitrile. This sampling, dilution and\ninjection procedure was repeated every 5-20 minutes until reaction completion.\n" } conditions { temperature { @@ -26427,7 +26422,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/26/2021, 15:23:46" + value: "07/01/2021, 14:56:43" } person { username: "skearnes" @@ -26609,7 +26604,7 @@ reactions { } } is_automated: true - automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1).\n\nReactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01). Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir\ndiscs (VP 782N6). Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales\n17P687) capped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075).\n\nAutomated sampling procedure: The reaction vial, aqueous K3PO4 vial and dilution plate were\nsealed and placed on the Chemspeed Swing robot deck for automated initiation, sampling,\ndilution and HPLC injection (Figure S3). The robot deck was inerted under positive pressure N2\natmosphere, tumble stirring was initiated (300-500 rpm), and the reaction vial temperature set\nto 25 \302\260C. To the reaction vial was transferred 1M aqueous K3PO4 by needle. This was immediately\nfollowed by transfer of a 20 \302\265l aliquot from the reaction vial to the dilution plate by needle. Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample. A 50 \302\265l aliquot was then transferred from the\ndilution plate to the injection port of the HPLC selection valve, over-filling the 20 \302\265l loop with\ndiluted sample. Once the loop was filled, the valve was switched and the HPLC run triggered,\nallowing the HPLC pump to push the mobile phase through the loop, moving the sample into the\nHPLC column. The valve was then rinsed with 1000 \302\265l of acetonitrile. This sampling, dilution and\ninjection procedure was repeated every 5-20 minutes until reaction completion.\n" } conditions { temperature { @@ -32649,7 +32644,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/26/2021, 15:23:46" + value: "07/01/2021, 14:56:43" } person { username: "skearnes" @@ -32874,7 +32869,7 @@ reactions { } } is_automated: true - automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1).\n\nReactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01). Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir\ndiscs (VP 782N6). Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales\n17P687) capped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075).\n\nAutomated sampling procedure: The reaction vial, aqueous K3PO4 vial and dilution plate were\nsealed and placed on the Chemspeed Swing robot deck for automated initiation, sampling,\ndilution and HPLC injection (Figure S3). The robot deck was inerted under positive pressure N2\natmosphere, tumble stirring was initiated (300-500 rpm), and the reaction vial temperature set\nto 25 \302\260C. To the reaction vial was transferred 1M aqueous K3PO4 by needle. This was immediately\nfollowed by transfer of a 20 \302\265l aliquot from the reaction vial to the dilution plate by needle. Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample. A 50 \302\265l aliquot was then transferred from the\ndilution plate to the injection port of the HPLC selection valve, over-filling the 20 \302\265l loop with\ndiluted sample. Once the loop was filled, the valve was switched and the HPLC run triggered,\nallowing the HPLC pump to push the mobile phase through the loop, moving the sample into the\nHPLC column. The valve was then rinsed with 1000 \302\265l of acetonitrile. This sampling, dilution and\ninjection procedure was repeated every 5-20 minutes until reaction completion.\n" } conditions { temperature { @@ -39172,7 +39167,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/26/2021, 15:23:46" + value: "07/01/2021, 14:56:43" } person { username: "skearnes" @@ -39397,7 +39392,7 @@ reactions { } } is_automated: true - automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1)." + automation_platform: "Automated reaction monitoring was carried out on a Chemspeed Swing liquid handling robot\nequipped with an adjustable-pitch four needle (0.8 mm ID) liquid dispense tool, a V&P Scientific\ntumble stirrer and a Huber Unistat 82T chiller. The robot was integrated with an Agilent 1100\nHPLC-UV system through installation of a two position, 6-port HPLC valve on the Chemspeed\nSwing deck and connection to the Agilent 1100 through 0.17 mm ID tubing. Bilateral\ncommunication was established between the Chemspeed Autosuite software and the HPLC\nvalve. Also, unilateral communication was established between the Chemspeed Autosuite\nsoftware and the Agilent 1100 HPLC-UV (Figure S1).\n\nReactions were carried out in sealed 4 ml borosilicate glass vials with red pressure relief caps (CG4912-01). Vigorous agitation was achieved with parylene-coated NdFeB magnetic tumble stir\ndiscs (VP 782N6). Reaction aliquots were sampled into 96-well dilution plates (Analytical Sales\n17P687) capped with pre-slit silicone/PTFE cap mats (Analytical Sales 965075).\n\nAutomated sampling procedure: The reaction vial, aqueous K3PO4 vial and dilution plate were\nsealed and placed on the Chemspeed Swing robot deck for automated initiation, sampling,\ndilution and HPLC injection (Figure S3). The robot deck was inerted under positive pressure N2\natmosphere, tumble stirring was initiated (300-500 rpm), and the reaction vial temperature set\nto 25 \302\260C. To the reaction vial was transferred 1M aqueous K3PO4 by needle. This was immediately\nfollowed by transfer of a 20 \302\265l aliquot from the reaction vial to the dilution plate by needle. Upon\ntransfer, a 200 \302\265l N2 cushion was drawn by the needle, followed by a 200 \302\265l aliquot from the\ndilution plate. The 200 ul aliquot and N2 cushion were then re-dispensed to the dilution plate at\n10 ml/min flow rate to effectively mix the sample. A 50 \302\265l aliquot was then transferred from the\ndilution plate to the injection port of the HPLC selection valve, over-filling the 20 \302\265l loop with\ndiluted sample. Once the loop was filled, the valve was switched and the HPLC run triggered,\nallowing the HPLC pump to push the mobile phase through the loop, moving the sample into the\nHPLC column. The valve was then rinsed with 1000 \302\265l of acetonitrile. This sampling, dilution and\ninjection procedure was repeated every 5-20 minutes until reaction completion.\n" } conditions { temperature { @@ -45695,7 +45690,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "05/26/2021, 15:23:46" + value: "07/01/2021, 14:56:43" } person { username: "skearnes" From db6970832489b3d7637e3970d507061944beb8fd Mon Sep 17 00:00:00 2001 From: Steven Kearnes Date: Thu, 1 Jul 2021 15:07:13 -0400 Subject: [PATCH 5/5] updates --- hein-dataset.pbtxt | 11217 ++++++++++++++++++++++--------------------- 1 file changed, 5609 insertions(+), 5608 deletions(-) diff --git a/hein-dataset.pbtxt b/hein-dataset.pbtxt index e271e4f7..a7b52ea8 100644 --- a/hein-dataset.pbtxt +++ b/hein-dataset.pbtxt @@ -160,7 +160,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "07/01/2021, 14:56:43" + value: "07/01/2021, 15:05:35" } person { username: "skearnes" @@ -340,6 +340,7 @@ reactions { type: STIR_BAR } conditions_are_dynamic: true + details: "Complicated temperature schedule; see notes.procedure_details." } notes { forms_precipitate: true @@ -536,7 +537,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "07/01/2021, 14:56:43" + value: "07/01/2021, 15:05:35" } person { username: "skearnes" @@ -828,7 +829,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -837,10 +838,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 880.28033 + value: 3745.1382 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -851,10 +852,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.7006886 + value: 11.490035 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -866,10 +867,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09134269 + value: 0.11178655 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -880,10 +881,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1351.4216 + value: 5268.786 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -894,10 +895,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.8877739 + value: 7.359862 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -909,10 +910,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.06384829 + value: 0.071604095 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -921,7 +922,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -930,10 +931,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 325.94662 + value: 880.28033 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.7006886 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -941,11 +956,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09134269 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -956,10 +974,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 715.8811 + value: 1351.4216 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8877739 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -967,20 +999,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.06384829 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -989,24 +1024,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 490.5643 + value: 325.94662 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 1.5050449 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -1017,33 +1050,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 233.54845 + value: 715.8811 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.32623914 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -1052,10 +1083,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3745.1382 + value: 490.5643 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -1066,25 +1097,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 11.490035 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.11178655 + value: 1.5050449 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -1095,10 +1111,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 5268.786 + value: 233.54845 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -1109,29 +1125,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 7.359862 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.071604095 + value: 0.32623914 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -1603,7 +1604,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -1612,10 +1613,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 822.3286 + value: 3498.5737 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -1626,10 +1627,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.6216846 + value: 11.153882 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -1641,10 +1642,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.08867061 + value: 0.10851612 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -1655,10 +1656,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1024.2686 + value: 3162.5361 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -1669,10 +1670,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.6778488 + value: 5.1805334 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -1684,10 +1685,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0567482 + value: 0.05040141 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -1696,7 +1697,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -1705,10 +1706,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 313.6642 + value: 822.3286 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6216846 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -1716,11 +1731,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.08867061 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -1731,10 +1749,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 610.46533 + value: 1024.2686 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6778488 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -1742,20 +1774,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0567482 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -1764,24 +1799,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 428.29874 + value: 313.6642 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 1.365469 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -1792,33 +1825,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 610.46533 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -1827,10 +1858,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3498.5737 + value: 428.29874 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -1841,25 +1872,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 11.153882 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.10851612 + value: 1.365469 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -1870,10 +1886,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3162.5361 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -1884,29 +1900,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 5.1805334 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.05040141 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -2378,7 +2379,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -2387,10 +2388,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 814.8354 + value: 3372.003 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -2401,10 +2402,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.5549028 + value: 10.572859 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -2416,10 +2417,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.08641192 + value: 0.10286334 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -2430,10 +2431,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1194.7474 + value: 2810.0898 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -2444,10 +2445,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.8306967 + value: 4.3058653 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -2459,10 +2460,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.061917823 + value: 0.041891765 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -2471,7 +2472,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -2480,10 +2481,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 318.9301 + value: 814.8354 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.5549028 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -2491,11 +2506,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.08641192 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -2506,10 +2524,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 652.619 + value: 1194.7474 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8306967 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -2517,20 +2549,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.061917823 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -2539,24 +2574,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 383.23358 + value: 318.9301 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 1.2016225 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -2567,33 +2600,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 652.619 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -2602,10 +2633,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3372.003 + value: 383.23358 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -2616,25 +2647,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 10.572859 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.10286334 + value: 1.2016225 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -2645,10 +2661,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2810.0898 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -2659,29 +2675,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.3058653 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.041891765 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -3153,7 +3154,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -3162,10 +3163,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 809.42194 + value: 3333.8533 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3176,10 +3177,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.4561114 + value: 10.11625 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3191,10 +3192,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0830706 + value: 0.098421 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3205,10 +3206,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 551.0915 + value: 1992.6111 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3219,10 +3220,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.392146 + value: 5.033657 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3234,10 +3235,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.047085162 + value: 0.04897245 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3246,7 +3247,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -3255,10 +3256,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 329.55426 + value: 809.42194 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.4561114 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -3266,11 +3281,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0830706 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -3281,10 +3299,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 395.85754 + value: 551.0915 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.392146 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -3292,20 +3324,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.047085162 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -3314,24 +3349,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 314.66492 + value: 329.55426 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.9548198 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -3342,33 +3375,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 395.85754 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -3377,10 +3408,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3333.8533 + value: 314.66492 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -3391,25 +3422,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 10.11625 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.098421 + value: 0.9548198 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -3420,10 +3436,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1992.6111 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -3434,29 +3450,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 5.033657 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.04897245 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -3928,7 +3929,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -3937,10 +3938,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 786.8825 + value: 3218.6992 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3951,10 +3952,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.3155882 + value: 9.471786 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3966,10 +3967,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.07831782 + value: 0.092151 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3980,10 +3981,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 911.8526 + value: 3346.3354 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -3994,10 +3995,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.5104622 + value: 5.543125 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -4009,10 +4010,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.05108685 + value: 0.05392907 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -4021,7 +4022,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -4030,10 +4031,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 339.8197 + value: 786.8825 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.3155882 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -4041,11 +4056,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.07831782 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -4056,10 +4074,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 603.6911 + value: 911.8526 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5104622 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -4067,20 +4099,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.05108685 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -4089,24 +4124,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 243.61258 + value: 339.8197 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.7168878 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -4117,33 +4150,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 603.6911 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -4152,10 +4183,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3218.6992 + value: 243.61258 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -4166,25 +4197,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 9.471786 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.092151 + value: 0.7168878 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -4195,10 +4211,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3346.3354 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -4209,29 +4225,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 5.543125 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.05392907 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -4703,7 +4704,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -4712,10 +4713,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 728.2881 + value: 3004.7722 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -4726,10 +4727,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.1189528 + value: 8.742378 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -4741,10 +4742,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.07166722 + value: 0.0850546 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -4755,10 +4756,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 771.60944 + value: 3042.3625 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -4769,10 +4770,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.1879444 + value: 4.683921 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -4784,10 +4785,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.040178657 + value: 0.045569867 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -4796,7 +4797,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -4805,10 +4806,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 343.70193 + value: 728.2881 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.1189528 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -4816,11 +4831,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.07166722 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -4831,10 +4849,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 649.5333 + value: 771.60944 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1879444 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -4842,20 +4874,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.040178657 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -4864,24 +4899,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 169.65173 + value: 343.70193 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.49360135 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -4892,33 +4925,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 649.5333 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -4927,10 +4958,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3004.7722 + value: 169.65173 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -4941,25 +4972,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 8.742378 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0850546 + value: 0.49360135 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -4970,10 +4986,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3042.3625 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -4984,29 +5000,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.683921 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.045569867 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -5478,7 +5479,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -5487,10 +5488,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 643.5442 + value: 2681.613 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -5501,10 +5502,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.8950531 + value: 7.896581 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -5516,10 +5517,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.064094484 + value: 0.076825835 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -5530,10 +5531,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 655.67224 + value: 2815.5234 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -5544,10 +5545,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.0850034 + value: 4.659115 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -5559,10 +5560,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.036696985 + value: 0.045328528 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -5571,7 +5572,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -5580,10 +5581,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 339.59164 + value: 643.5442 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8950531 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -5591,11 +5606,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.064094484 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -5606,10 +5624,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 604.3044 + value: 655.67224 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0850034 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -5617,20 +5649,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.036696985 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -5639,24 +5674,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 109.13497 + value: 339.59164 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.32137117 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -5667,33 +5700,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 604.3044 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -5702,10 +5733,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2681.613 + value: 109.13497 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -5716,25 +5747,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 7.896581 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.076825835 + value: 0.32137117 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -5745,10 +5761,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2815.5234 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -5759,29 +5775,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.659115 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.045328528 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -6253,7 +6254,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -6262,10 +6263,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 515.684 + value: 2227.2803 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -6276,10 +6277,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.6264639 + value: 7.0248265 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -6291,10 +6292,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.055010263 + value: 0.06834454 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -6305,10 +6306,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 744.65045 + value: 1928.0988 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -6319,10 +6320,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.159735 + value: 3.0028634 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -6334,10 +6335,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.039224554 + value: 0.029214857 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -6346,7 +6347,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -6355,10 +6356,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 317.0584 + value: 515.684 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6264639 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -6366,11 +6381,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.055010263 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -6381,10 +6399,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 642.08673 + value: 744.65045 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.159735 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -6392,20 +6424,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.039224554 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -6414,24 +6449,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 60.38027 + value: 317.0584 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.19043896 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -6442,33 +6475,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 642.08673 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -6477,10 +6508,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2227.2803 + value: 60.38027 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -6491,25 +6522,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 7.0248265 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.06834454 + value: 0.19043896 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -6520,10 +6536,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1928.0988 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -6534,29 +6550,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.0028634 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.029214857 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -7028,7 +7029,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -7037,10 +7038,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 446.32227 + value: 2026.8601 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7051,10 +7052,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.3490294 + value: 6.126277 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7066,10 +7067,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.04562687 + value: 0.059602547 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7080,10 +7081,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 401.1194 + value: 2209.2422 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7094,10 +7095,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.660862 + value: 3.6398249 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7109,10 +7110,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.022351675 + value: 0.035411853 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7121,7 +7122,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -7130,10 +7131,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 330.84695 + value: 446.32227 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.3490294 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -7141,11 +7156,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.04562687 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -7156,10 +7174,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 606.96387 + value: 401.1194 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.660862 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -7167,20 +7199,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.022351675 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -7189,24 +7224,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 44.54001 + value: 330.84695 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.13462421 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -7217,33 +7250,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 606.96387 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -7252,10 +7283,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2026.8601 + value: 44.54001 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -7266,25 +7297,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 6.126277 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.059602547 + value: 0.13462421 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -7295,10 +7311,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2209.2422 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -7309,29 +7325,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.6398249 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.035411853 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -7803,7 +7804,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -7812,10 +7813,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 348.18863 + value: 1645.9138 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7826,10 +7827,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.1223398 + value: 5.305384 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7841,10 +7842,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.037959777 + value: 0.051616084 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7855,10 +7856,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 328.69232 + value: 1739.7715 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7869,10 +7870,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5794008 + value: 3.066774 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7884,10 +7885,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.019596493 + value: 0.029836643 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -7896,7 +7897,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -7905,10 +7906,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 310.2346 + value: 348.18863 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1223398 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -7916,11 +7931,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.037959777 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -7931,10 +7949,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 567.297 + value: 328.69232 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5794008 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -7942,20 +7974,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.019596493 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -7964,24 +7999,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 30.64968 + value: 310.2346 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.09879517 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -7992,33 +8025,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 567.297 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -8027,10 +8058,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1645.9138 + value: 30.64968 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -8041,25 +8072,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 5.305384 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.051616084 + value: 0.09879517 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -8070,10 +8086,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1739.7715 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -8084,29 +8100,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.066774 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.029836643 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -8578,7 +8579,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -8587,10 +8588,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 284.07956 + value: 1479.9105 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -8601,10 +8602,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.876834 + value: 4.5678606 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -8616,10 +8617,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.02965628 + value: 0.044440717 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -8630,10 +8631,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 210.31886 + value: 1645.6871 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -8644,10 +8645,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.3490955 + value: 2.7315757 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -8659,10 +8660,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.011807107 + value: 0.026575502 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -8671,7 +8672,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -8680,10 +8681,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 323.9833 + value: 284.07956 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.876834 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -8691,11 +8706,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.02965628 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -8706,10 +8724,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 602.468 + value: 210.31886 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3490955 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -8717,20 +8749,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.011807107 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -8739,24 +8774,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 28.68432 + value: 323.9833 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.08853642 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -8767,33 +8800,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 602.468 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -8802,10 +8833,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1479.9105 + value: 28.68432 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -8816,25 +8847,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 4.5678606 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.044440717 + value: 0.08853642 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -8845,10 +8861,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1645.6871 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -8859,29 +8875,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.7315757 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.026575502 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -9353,7 +9354,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -9362,10 +9363,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 225.00632 + value: 1308.0616 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -9376,10 +9377,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.680871 + value: 3.9582057 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -9391,10 +9392,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.023028418 + value: 0.038509384 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -9405,10 +9406,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 163.20898 + value: 1535.3284 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -9419,10 +9420,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.27038634 + value: 2.54356 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -9434,10 +9435,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.009145007 + value: 0.024746295 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -9446,7 +9447,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -9455,10 +9456,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 330.46835 + value: 225.00632 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.680871 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -9466,11 +9481,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.023028418 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -9481,10 +9499,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 603.614 + value: 163.20898 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.27038634 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -9492,20 +9524,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.009145007 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -9514,24 +9549,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 24.93064 + value: 330.46835 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.075440325 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -9542,33 +9575,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 603.614 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -9577,10 +9608,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1308.0616 + value: 24.93064 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -9591,25 +9622,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.9582057 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.038509384 + value: 0.075440325 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -9620,10 +9636,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1535.3284 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -9634,29 +9650,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.54356 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.024746295 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -10128,7 +10129,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -10137,10 +10138,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 168.9886 + value: 1121.9783 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10151,10 +10152,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.51554155 + value: 3.4228725 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10166,10 +10167,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.017436648 + value: 0.033301126 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10180,10 +10181,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 133.17241 + value: 1428.1073 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10194,10 +10195,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.20695648 + value: 2.219349 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10209,10 +10210,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0069996817 + value: 0.021592045 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10221,7 +10222,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -10230,10 +10231,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 327.7885 + value: 168.9886 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.51554155 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -10241,11 +10256,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.017436648 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -10256,10 +10274,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 643.4803 + value: 133.17241 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.20695648 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -10267,20 +10299,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0069996817 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -10289,24 +10324,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 26.57664 + value: 327.7885 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.08107862 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -10317,33 +10350,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 643.4803 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -10352,10 +10383,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1121.9783 + value: 26.57664 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -10366,25 +10397,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 3.4228725 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.033301126 + value: 0.08107862 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -10395,10 +10411,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1428.1073 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -10409,29 +10425,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.219349 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.021592045 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -10903,7 +10904,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -10912,10 +10913,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 121.36669 + value: 905.4163 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10926,10 +10927,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.39739272 + value: 2.964618 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10941,10 +10942,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.013440616 + value: 0.028842768 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10955,10 +10956,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 129.01923 + value: 1079.4044 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10969,10 +10970,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.21776234 + value: 1.8218496 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10984,10 +10985,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.007365158 + value: 0.017724775 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -10996,7 +10997,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -11005,10 +11006,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 305.40744 + value: 121.36669 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.39739272 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -11016,11 +11031,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.013440616 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -11031,10 +11049,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 592.47723 + value: 129.01923 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.21776234 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -11042,20 +11074,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.007365158 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -11064,24 +11099,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 24.20987 + value: 305.40744 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.07927073 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -11092,33 +11125,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 592.47723 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -11127,10 +11158,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 905.4163 + value: 24.20987 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -11141,25 +11172,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.964618 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.028842768 + value: 0.07927073 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -11170,10 +11186,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1079.4044 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -11184,29 +11200,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.8218496 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.017724775 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -11678,7 +11679,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -11687,10 +11688,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 97.56874 + value: 912.90796 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -11701,10 +11702,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.29481262 + value: 2.7584326 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -11716,10 +11717,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.009971153 + value: 0.026836792 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -11730,10 +11731,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 101.09229 + value: 1069.2329 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -11744,10 +11745,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16471888 + value: 1.7421987 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -11759,10 +11760,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0055711223 + value: 0.016949851 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -11771,7 +11772,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -11780,10 +11781,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 330.9517 + value: 97.56874 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.29481262 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -11791,11 +11806,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.009971153 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -11806,10 +11824,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 613.7262 + value: 101.09229 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16471888 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -11817,20 +11849,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0055711223 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -11839,24 +11874,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 23.5109 + value: 330.9517 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.07104027 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -11867,33 +11900,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 613.7262 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -11902,10 +11933,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 912.90796 + value: 23.5109 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -11916,25 +11947,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.7584326 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.026836792 + value: 0.07104027 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -11945,10 +11961,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1069.2329 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -11959,29 +11975,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.7421987 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.016949851 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -12453,7 +12454,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -12462,10 +12463,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 78.89827 + value: 861.55457 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -12476,10 +12477,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.22562152 + value: 2.4637454 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -12491,10 +12492,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.007630971 + value: 0.023969779 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -12505,10 +12506,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 107.15103 + value: 934.06915 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -12519,10 +12520,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.18489663 + value: 1.611802 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -12534,10 +12535,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.006253574 + value: 0.015681222 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -12546,7 +12547,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -12555,10 +12556,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 349.69302 + value: 78.89827 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.22562152 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -12566,11 +12581,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.007630971 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -12581,10 +12599,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 579.51855 + value: 107.15103 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18489663 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -12592,20 +12624,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.006253574 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -12614,24 +12649,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 20.42933 + value: 349.69302 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.058420755 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -12642,33 +12675,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 579.51855 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -12677,10 +12708,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 861.55457 + value: 20.42933 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -12691,25 +12722,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.4637454 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.023969779 + value: 0.058420755 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -12720,10 +12736,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 934.06915 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -12734,29 +12750,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.611802 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.015681222 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -13228,7 +13229,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -13237,10 +13238,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 58.71957 + value: 779.89667 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -13251,10 +13252,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.17306702 + value: 2.2986271 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -13266,10 +13267,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0058534727 + value: 0.022363342 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -13280,10 +13281,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 104.60272 + value: 559.96545 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -13294,10 +13295,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.18408556 + value: 0.98545766 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -13309,10 +13310,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.006226142 + value: 0.009587517 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -13321,7 +13322,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -13330,10 +13331,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 339.28802 + value: 58.71957 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.17306702 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -13341,11 +13356,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0058534727 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -13356,10 +13374,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 568.2288 + value: 104.60272 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.18408556 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -13367,20 +13399,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.006226142 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -13389,24 +13424,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 19.01272 + value: 339.28802 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.056037106 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -13417,33 +13450,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 568.2288 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -13452,10 +13483,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 779.89667 + value: 19.01272 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -13466,25 +13497,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.2986271 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.022363342 + value: 0.056037106 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -13495,10 +13511,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 559.96545 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -13509,29 +13525,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.98545766 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.009587517 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -14003,7 +14004,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -14012,10 +14013,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 47.83313 + value: 734.9989 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14026,10 +14027,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.1423772 + value: 2.1877532 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14041,10 +14042,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0048154816 + value: 0.021284651 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14055,10 +14056,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 95.6284 + value: 613.869 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14069,10 +14070,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16326803 + value: 1.0480692 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14084,10 +14085,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0055220514 + value: 0.010196665 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14096,7 +14097,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -14105,10 +14106,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 335.96063 + value: 47.83313 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1423772 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -14116,11 +14131,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0048154816 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -14131,10 +14149,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 585.7142 + value: 95.6284 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16326803 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -14142,20 +14174,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0055220514 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -14164,24 +14199,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 16.04706 + value: 335.96063 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.047764704 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -14192,33 +14225,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 585.7142 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -14227,10 +14258,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 734.9989 + value: 16.04706 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -14241,25 +14272,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.1877532 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.021284651 + value: 0.047764704 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -14270,10 +14286,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 613.869 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -14284,29 +14300,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.0480692 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.010196665 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -14778,7 +14779,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -14787,10 +14788,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 44.8533 + value: 727.8157 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14801,10 +14802,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.128907 + value: 2.0917196 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14816,10 +14817,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.004359892 + value: 0.020350339 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14830,10 +14831,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 77.13166 + value: 723.8187 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14844,10 +14845,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.14822957 + value: 1.3910154 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14859,10 +14860,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0050134202 + value: 0.013533189 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -14871,7 +14872,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -14880,10 +14881,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 347.95087 + value: 44.8533 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.128907 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -14891,11 +14906,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004359892 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -14906,10 +14924,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 520.3527 + value: 77.13166 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14822957 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -14917,20 +14949,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0050134202 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -14939,24 +14974,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 347.95087 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -14967,33 +15000,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 520.3527 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -15002,10 +15033,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 727.8157 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -15016,25 +15047,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.0917196 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.020350339 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -15045,10 +15061,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 723.8187 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -15059,29 +15075,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.3910154 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.013533189 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -15553,7 +15554,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -15562,10 +15563,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 43.24135 + value: 717.384 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -15576,10 +15577,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.12531517 + value: 2.0790079 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -15591,10 +15592,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.00423841 + value: 0.020226667 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -15605,10 +15606,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 78.96692 + value: 0.0 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -15619,10 +15620,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.14456889 + value: 0.0 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -15634,10 +15635,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.004889609 + value: 0.0 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -15646,7 +15647,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -15655,10 +15656,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 345.06076 + value: 43.24135 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.12531517 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -15666,11 +15681,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.00423841 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -15681,10 +15699,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 546.2235 + value: 78.96692 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14456889 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -15692,20 +15724,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004889609 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -15714,24 +15749,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 345.06076 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -15742,33 +15775,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 546.2235 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -15777,10 +15808,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 717.384 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -15791,25 +15822,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.0790079 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.020226667 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -15823,7 +15839,7 @@ reactions { value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -15837,26 +15853,11 @@ reactions { value: 0.0 } retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0 - } - retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -16328,7 +16329,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -16337,10 +16338,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 42.03334 + value: 719.3501 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -16351,10 +16352,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.121739246 + value: 2.083421 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -16366,10 +16367,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0041174646 + value: 0.020269603 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -16380,10 +16381,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 76.26696 + value: 737.3046 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -16394,10 +16395,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.14143658 + value: 1.3673266 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -16409,10 +16410,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.004783668 + value: 0.013302721 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -16421,7 +16422,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -16430,10 +16431,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 345.27353 + value: 42.03334 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.121739246 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -16441,11 +16456,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0041174646 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -16456,10 +16474,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 539.2308 + value: 76.26696 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14143658 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -16467,20 +16499,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004783668 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -16489,24 +16524,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 345.27353 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -16517,33 +16550,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 539.2308 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -16552,10 +16583,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 719.3501 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -16566,25 +16597,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.083421 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.020269603 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -16595,10 +16611,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 737.3046 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -16609,29 +16625,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.3673266 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.013302721 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -17103,7 +17104,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -17112,10 +17113,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 42.18785 + value: 714.0694 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17126,10 +17127,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.12260824 + value: 2.0752609 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17141,10 +17142,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.004146856 + value: 0.020190213 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17155,10 +17156,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 87.60475 + value: 376.66702 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17169,10 +17170,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16088459 + value: 0.69174236 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17184,10 +17185,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0054414384 + value: 0.0067299614 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17196,7 +17197,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -17205,10 +17206,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 344.08658 + value: 42.18785 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.12260824 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -17216,11 +17231,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004146856 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -17231,10 +17249,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 544.5192 + value: 87.60475 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16088459 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -17242,20 +17274,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0054414384 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -17264,24 +17299,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 344.08658 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -17292,33 +17325,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 544.5192 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -17327,10 +17358,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 714.0694 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -17341,25 +17372,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.0752609 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.020190213 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -17370,10 +17386,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 376.66702 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -17384,29 +17400,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.69174236 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.0067299614 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -17878,7 +17879,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -17887,10 +17888,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 43.22353 + value: 675.2211 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17901,10 +17902,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.13365397 + value: 2.0878901 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17916,10 +17917,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.004520444 + value: 0.020313084 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17930,10 +17931,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 81.38737 + value: 778.1406 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17944,10 +17945,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.14693365 + value: 1.4048253 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17959,10 +17960,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.00496959 + value: 0.013667546 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -17971,7 +17972,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -17980,10 +17981,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 323.3988 + value: 43.22353 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.13365397 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -17991,11 +18006,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004520444 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -18006,10 +18024,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 553.90564 + value: 81.38737 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14693365 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -18017,20 +18049,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.00496959 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -18039,24 +18074,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 323.3988 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -18067,33 +18100,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 553.90564 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -18102,10 +18133,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 675.2211 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -18116,25 +18147,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.0878901 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.020313084 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -18145,10 +18161,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 778.1406 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -18159,29 +18175,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.4048253 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.013667546 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -18653,7 +18654,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -18662,10 +18663,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 41.09112 + value: 675.737 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -18676,10 +18677,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.1251094 + value: 2.0574045 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -18691,10 +18692,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.00423145 + value: 0.02001649 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -18705,10 +18706,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 86.86591 + value: 903.48706 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -18719,10 +18720,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.14441672 + value: 1.5020696 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -18734,10 +18735,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0048844623 + value: 0.014613635 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -18746,7 +18747,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -18755,10 +18756,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 328.4415 + value: 41.09112 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1251094 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -18766,11 +18781,14 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.00423145 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } @@ -18781,10 +18799,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 601.4948 + value: 86.86591 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.14441672 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -18792,20 +18824,23 @@ reactions { analysis_key: "Offline HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0048844623 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -18814,24 +18849,22 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 328.4415 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } @@ -18842,33 +18875,31 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 601.4948 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } measurements { analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false + type: CUSTOM + details: "Concentration (M)" float_value { - value: 0.0 + value: 0.009 } retention_time { - value: 3.09 + value: 1.65 units: MINUTE } } - reaction_role: CATALYST + reaction_role: INTERNAL_STANDARD } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "CS(=O)(=O)O[Pd]1(<-P(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC2[Fe]C2C=CC=C2P(C2=CC=CC=C2)C2=CC=CC=C2)<-NC2=C(C=CC=C2)C2=CC=CC=C21" } measurements { analysis_key: "Online HPLC-UV" @@ -18877,10 +18908,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 675.737 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -18891,25 +18922,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.0574045 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.02001649 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -18920,10 +18936,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 903.48706 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } @@ -18934,29 +18950,14 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.5020696 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.014613635 + value: 0.0 } retention_time { - value: 1.83 + value: 3.09 units: MINUTE } } - reaction_role: REACTANT + reaction_role: CATALYST } products { identifiers { @@ -19425,6 +19426,99 @@ reactions { value: 480.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 649.7465 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0228553 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.019680358 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 840.99756 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.490905 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Offline HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.014505015 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -19640,99 +19734,6 @@ reactions { } reaction_role: CATALYST } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 649.7465 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.0228553 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.019680358 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 840.99756 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.490905 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Offline HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.014505015 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -20200,7 +20201,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "07/01/2021, 14:56:43" + value: "07/01/2021, 15:05:35" } person { username: "skearnes" @@ -20491,7 +20492,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -20500,10 +20501,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1584.4377 + value: 5982.962 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -20514,10 +20515,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.0070593 + value: 7.578814 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -20529,10 +20530,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.06788276 + value: 0.07373428 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -20541,7 +20542,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -20550,10 +20551,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 789.43243 + value: 1584.4377 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0070593 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -20561,20 +20576,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.06788276 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -20583,24 +20601,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 5982.962 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 7.578814 + value: 789.43243 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -20608,18 +20612,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.07373428 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -20749,7 +20750,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -20758,10 +20759,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 673.57666 + value: 2993.4353 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -20772,10 +20773,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.4812287 + value: 6.5827136 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -20787,10 +20788,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.050098117 + value: 0.064043224 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -20799,7 +20800,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -20808,10 +20809,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 454.74182 + value: 673.57666 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.4812287 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -20819,20 +20834,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.050098117 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -20841,24 +20859,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2993.4353 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.5827136 + value: 454.74182 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -20866,18 +20870,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.064043224 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -21007,7 +21008,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -21016,10 +21017,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 556.34735 + value: 2584.6316 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21030,10 +21031,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.2936213 + value: 6.009797 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21045,10 +21046,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.04375286 + value: 0.058469314 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21057,7 +21058,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -21066,10 +21067,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 430.06973 + value: 556.34735 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2936213 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -21077,20 +21092,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.04375286 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -21099,24 +21117,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2584.6316 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.009797 + value: 430.06973 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -21124,18 +21128,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.058469314 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -21265,7 +21266,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -21274,10 +21275,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 502.88892 + value: 2446.2454 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21288,10 +21289,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.140631 + value: 5.548468 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21303,10 +21304,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.03857842 + value: 0.053981047 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21315,7 +21316,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -21324,10 +21325,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 440.8866 + value: 502.88892 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.140631 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -21335,20 +21350,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.03857842 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -21357,24 +21375,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2446.2454 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.548468 + value: 440.8866 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -21382,18 +21386,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.053981047 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -21523,7 +21524,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -21532,10 +21533,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 455.9279 + value: 2324.6816 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21546,10 +21547,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.9991304 + value: 5.094359 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21561,10 +21562,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.03379259 + value: 0.049563017 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21573,7 +21574,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -21582,10 +21583,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 456.32468 + value: 455.9279 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9991304 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -21593,20 +21608,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.03379259 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -21615,24 +21633,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2324.6816 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.094359 + value: 456.32468 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -21640,18 +21644,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.049563017 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -21781,7 +21782,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -21790,10 +21791,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 584.8447 + value: 3198.0068 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21804,10 +21805,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.8603548 + value: 4.7045317 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21819,10 +21820,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.02909892 + value: 0.045770388 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -21831,7 +21832,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -21840,10 +21841,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 679.77155 + value: 584.8447 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8603548 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -21851,20 +21866,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.02909892 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -21873,24 +21891,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 3198.0068 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.7045317 + value: 679.77155 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -21898,18 +21902,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.045770388 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -22036,6 +22037,56 @@ reactions { value: 140.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 2972.5066 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.351969 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.042340305 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -22119,56 +22170,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 2972.5066 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.351969 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.042340305 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -22297,7 +22298,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -22306,10 +22307,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 447.78397 + value: 2815.0942 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22320,10 +22321,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.6369949 + value: 4.004611 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22335,10 +22336,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.021544442 + value: 0.038960863 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22347,7 +22348,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -22356,10 +22357,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 702.9632 + value: 447.78397 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6369949 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -22367,20 +22382,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.021544442 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -22389,24 +22407,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2815.0942 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.004611 + value: 702.9632 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -22414,18 +22418,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.038960863 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -22555,7 +22556,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -22564,10 +22565,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 352.0839 + value: 2405.987 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22578,10 +22579,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5396965 + value: 3.6880496 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22593,10 +22594,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.018253615 + value: 0.035881035 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22605,7 +22606,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -22614,10 +22615,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 652.37384 + value: 352.0839 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5396965 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -22625,20 +22640,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.018253615 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -22647,24 +22665,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2405.987 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.6880496 + value: 652.37384 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -22672,18 +22676,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.035881035 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -22813,7 +22814,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -22822,10 +22823,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 301.3809 + value: 2176.3796 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22836,10 +22837,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.47850642 + value: 3.4554667 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22851,10 +22852,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.016184043 + value: 0.033618234 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -22863,7 +22864,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -22872,10 +22873,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 629.8367 + value: 301.3809 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47850642 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -22883,20 +22898,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.016184043 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -22905,24 +22923,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2176.3796 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.4554667 + value: 629.8367 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -22930,18 +22934,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.033618234 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -23071,7 +23072,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -23080,10 +23081,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 280.38925 + value: 2241.119 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23094,10 +23095,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.40329814 + value: 3.2235153 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23109,10 +23110,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.01364035 + value: 0.03136158 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23121,7 +23122,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -23130,10 +23131,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 695.24066 + value: 280.38925 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.40329814 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -23141,20 +23156,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.01364035 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -23163,24 +23181,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2241.119 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.2235153 + value: 695.24066 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -23188,18 +23192,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.03136158 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -23329,7 +23330,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -23338,10 +23339,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 234.85779 + value: 2095.3333 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23352,10 +23353,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.33848247 + value: 3.0198429 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23367,10 +23368,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.011448154 + value: 0.029380051 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23379,7 +23380,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -23388,10 +23389,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 693.8551 + value: 234.85779 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.33848247 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -23399,20 +23414,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.011448154 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -23421,24 +23439,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2095.3333 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.0198429 + value: 693.8551 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -23446,18 +23450,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.029380051 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -23587,7 +23588,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -23596,10 +23597,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 188.2771 + value: 1912.9745 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23610,10 +23611,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.27893907 + value: 2.8341382 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23625,10 +23626,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.009434276 + value: 0.027573328 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -23637,7 +23638,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -23646,10 +23647,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 674.97577 + value: 188.2771 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.27893907 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -23657,20 +23672,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.009434276 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -23679,24 +23697,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1912.9745 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.8341382 + value: 674.97577 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -23704,18 +23708,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.027573328 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -23842,6 +23843,56 @@ reactions { value: 280.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1906.018 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.6608121 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.025887042 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -23925,56 +23976,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 1906.018 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.6608121 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.025887042 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -24103,7 +24104,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -24112,10 +24113,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 133.43137 + value: 1775.5997 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24126,10 +24127,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.1892451 + value: 2.518325 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24141,10 +24142,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0064006476 + value: 0.024500785 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24153,7 +24154,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -24162,10 +24163,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 705.07166 + value: 133.43137 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1892451 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -24173,20 +24188,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0064006476 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -24195,24 +24213,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1775.5997 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.518325 + value: 705.07166 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -24220,18 +24224,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.024500785 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -24361,7 +24362,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -24370,10 +24371,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 108.68061 + value: 1692.2268 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24384,10 +24385,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.15581402 + value: 2.4261243 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24399,10 +24400,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.005269942 + value: 0.023603763 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24411,7 +24412,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -24420,10 +24421,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 697.50214 + value: 108.68061 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15581402 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -24431,20 +24446,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.005269942 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -24453,24 +24471,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1692.2268 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.4261243 + value: 697.50214 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -24478,18 +24482,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.023603763 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -24619,7 +24620,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -24628,10 +24629,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 87.97259 + value: 1617.8046 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24642,10 +24643,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.12535389 + value: 2.3052418 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24657,10 +24658,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.004239719 + value: 0.022427697 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24669,7 +24670,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -24678,10 +24679,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 701.7939 + value: 87.97259 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.12535389 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -24689,20 +24704,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.004239719 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -24711,24 +24729,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1617.8046 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.3052418 + value: 701.7939 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -24736,18 +24740,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.022427697 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -24877,7 +24878,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -24886,10 +24887,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 52.94001 + value: 1588.911 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24900,10 +24901,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.07446365 + value: 2.234909 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24915,10 +24916,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0025185095 + value: 0.02174343 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -24927,7 +24928,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -24936,10 +24937,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 710.95105 + value: 52.94001 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.07446365 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -24947,20 +24962,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0025185095 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -24969,24 +24987,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1588.911 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.234909 + value: 710.95105 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -24994,18 +24998,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.02174343 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -25135,7 +25136,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -25144,10 +25145,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 57.31877 + value: 1451.6746 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25158,10 +25159,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.086056665 + value: 2.1795003 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25173,10 +25174,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0029106087 + value: 0.021204358 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25185,7 +25186,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -25194,10 +25195,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 666.0584 + value: 57.31877 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.086056665 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -25205,20 +25220,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0029106087 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -25227,24 +25245,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1451.6746 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.1795003 + value: 666.0584 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -25252,18 +25256,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.021204358 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -25393,7 +25394,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -25402,10 +25403,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 27.16534 + value: 985.88586 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25416,10 +25417,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.058882028 + value: 2.1369495 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25431,10 +25432,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.001991508 + value: 0.020790381 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25443,7 +25444,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -25452,10 +25453,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 461.35196 + value: 27.16534 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.058882028 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -25463,20 +25478,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.001991508 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -25485,24 +25503,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 985.88586 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.1369495 + value: 461.35196 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -25510,18 +25514,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.020790381 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -25648,6 +25649,56 @@ reactions { value: 420.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 954.605 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.102261 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.020452898 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -25731,56 +25782,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 954.605 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.102261 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.020452898 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -25909,7 +25910,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -25918,10 +25919,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 30.83437 + value: 994.1477 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25932,10 +25933,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.064778596 + value: 2.088562 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25947,10 +25948,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0021909417 + value: 0.02031962 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -25959,7 +25960,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -25968,10 +25969,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 475.99625 + value: 30.83437 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.064778596 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -25979,20 +25994,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0021909417 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -26001,24 +26019,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 994.1477 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.088562 + value: 475.99625 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -26026,18 +26030,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.02031962 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -26167,7 +26168,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -26176,10 +26177,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 30.08823 + value: 985.13983 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -26190,10 +26191,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.06375453 + value: 2.0874317 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -26205,10 +26206,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0021563056 + value: 0.020308623 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -26217,7 +26218,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -26226,10 +26227,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 471.93872 + value: 30.08823 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.06375453 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -26237,20 +26252,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0021563056 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -26259,24 +26277,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 985.13983 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.0874317 + value: 471.93872 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -26284,18 +26288,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.020308623 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -26422,7 +26423,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "07/01/2021, 14:56:43" + value: "07/01/2021, 15:05:35" } person { username: "skearnes" @@ -26713,7 +26714,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -26722,10 +26723,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1534.0931 + value: 5833.023 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -26736,10 +26737,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 2.0300827 + value: 7.718905 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -26751,10 +26752,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.06866146 + value: 0.075097226 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -26763,7 +26764,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -26772,10 +26773,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 755.68005 + value: 1534.0931 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 2.0300827 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -26783,20 +26798,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.06866146 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -26805,24 +26823,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 5833.023 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 7.718905 + value: 755.68005 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -26830,18 +26834,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.075097226 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -26971,7 +26972,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -26980,10 +26981,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 90.9476 + value: 1017.21106 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -26994,10 +26995,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.20505804 + value: 2.293489 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -27009,10 +27010,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.006935473 + value: 0.022313353 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -27021,7 +27022,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -27030,10 +27031,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 443.52127 + value: 90.9476 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.20505804 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -27041,20 +27056,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.006935473 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -27063,24 +27081,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1017.21106 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 2.293489 + value: 443.52127 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -27088,18 +27092,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.022313353 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -27229,7 +27230,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -27238,10 +27239,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 45.96372 + value: 813.1333 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -27252,10 +27253,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.106616 + value: 1.8861184 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -27267,10 +27268,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0036059662 + value: 0.018350046 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -27279,7 +27280,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -27288,10 +27289,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 431.1147 + value: 45.96372 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.106616 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -27299,20 +27314,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0036059662 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -27321,24 +27339,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 813.1333 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.8861184 + value: 431.1147 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -27346,18 +27350,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.018350046 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -27487,7 +27488,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -27496,10 +27497,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 772.1005 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -27510,10 +27511,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.7809473 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -27525,10 +27526,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.017326837 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -27537,7 +27538,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -27546,10 +27547,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 433.5336 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -27557,20 +27572,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -27579,24 +27597,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 772.1005 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.7809473 + value: 433.5336 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -27604,18 +27608,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.017326837 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -27742,6 +27743,56 @@ reactions { value: 100.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1171.0416 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6728189 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.016274856 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -27825,56 +27876,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 1171.0416 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.6728189 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.016274856 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -28003,7 +28004,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -28012,10 +28013,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1130.1597 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28026,10 +28027,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.6621742 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28041,10 +28042,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.016171293 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28053,7 +28054,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -28062,10 +28063,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 679.9285 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -28073,20 +28088,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -28095,24 +28113,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1130.1597 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.6621742 + value: 679.9285 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -28120,18 +28124,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.016171293 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -28261,7 +28262,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -28270,10 +28271,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1124.7384 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28284,10 +28285,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.643217 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28299,10 +28300,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015986858 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28311,7 +28312,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -28320,10 +28321,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 684.47345 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -28331,20 +28346,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -28353,24 +28371,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1124.7384 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.643217 + value: 684.47345 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -28378,18 +28382,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015986858 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -28519,7 +28520,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -28528,10 +28529,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1138.4735 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28542,10 +28543,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.6345782 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28557,10 +28558,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015902812 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28569,7 +28570,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -28578,10 +28579,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 696.4937 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -28589,20 +28604,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -28611,24 +28629,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1138.4735 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.6345782 + value: 696.4937 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -28636,18 +28640,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015902812 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -28777,7 +28778,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -28786,10 +28787,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1105.4827 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28800,10 +28801,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.6076925 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28815,10 +28816,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.01564124 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -28827,7 +28828,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -28836,10 +28837,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 687.6207 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -28847,20 +28862,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -28869,24 +28887,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1105.4827 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.6076925 + value: 687.6207 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -28894,18 +28898,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.01564124 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -29035,7 +29036,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -29044,10 +29045,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1056.302 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29058,10 +29059,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.6113424 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29073,10 +29074,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.01567675 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29085,7 +29086,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -29094,10 +29095,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 655.5416 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -29105,20 +29120,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -29127,24 +29145,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1056.302 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.6113424 + value: 655.5416 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -29152,18 +29156,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.01567675 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -29293,7 +29294,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -29302,10 +29303,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1131.6302 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29316,10 +29317,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5937229 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29331,10 +29332,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015505331 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29343,7 +29344,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -29352,10 +29353,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 710.05457 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -29363,20 +29378,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -29385,24 +29403,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1131.6302 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5937229 + value: 710.05457 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -29410,18 +29414,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015505331 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -29548,6 +29549,56 @@ reactions { value: 240.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 679.06256 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.6182597 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.01574405 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -29631,56 +29682,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 679.06256 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.6182597 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.01574405 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -29809,7 +29810,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -29818,10 +29819,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 736.36505 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29832,10 +29833,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5999928 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29847,10 +29848,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.0155663295 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -29859,7 +29860,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -29868,10 +29869,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 460.23026 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -29879,20 +29894,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -29901,24 +29919,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 736.36505 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5999928 + value: 460.23026 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -29926,18 +29930,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0155663295 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -30067,7 +30068,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -30076,10 +30077,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1115.1511 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30090,10 +30091,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.6001036 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30105,10 +30106,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015567408 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30117,7 +30118,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -30126,10 +30127,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 696.9243 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -30137,20 +30152,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -30159,24 +30177,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1115.1511 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.6001036 + value: 696.9243 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -30184,18 +30188,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015567408 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -30325,7 +30326,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -30334,10 +30335,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1088.0696 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30348,10 +30349,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5991116 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30363,10 +30364,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015557757 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30375,7 +30376,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -30384,10 +30385,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 680.42126 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -30395,20 +30410,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -30417,24 +30435,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1088.0696 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5991116 + value: 680.42126 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -30442,18 +30446,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015557757 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -30583,7 +30584,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -30592,10 +30593,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1108.9601 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30606,10 +30607,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5983974 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30621,10 +30622,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015550807 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30633,7 +30634,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -30642,10 +30643,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 693.795 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -30653,20 +30668,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -30675,24 +30693,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1108.9601 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5983974 + value: 693.795 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -30700,18 +30704,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015550807 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -30841,7 +30842,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -30850,10 +30851,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1114.72 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30864,10 +30865,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.592292 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30879,10 +30880,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015491408 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -30891,7 +30892,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -30900,10 +30901,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 700.07263 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -30911,20 +30926,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -30933,24 +30951,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1114.72 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.592292 + value: 700.07263 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -30958,18 +30962,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015491408 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -31099,7 +31100,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -31108,10 +31109,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1063.2148 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31122,10 +31123,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5700895 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31137,10 +31138,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.0152754 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31149,7 +31150,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -31158,10 +31159,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 677.1683 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -31169,20 +31184,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -31191,24 +31209,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1063.2148 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5700895 + value: 677.1683 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -31216,18 +31220,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.0152754 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -31354,6 +31355,56 @@ reactions { value: 380.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 971.79895 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5802133 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.015373895 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -31437,56 +31488,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 971.79895 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5802133 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.015373895 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -31615,7 +31616,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -31624,10 +31625,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 1109.1903 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31638,10 +31639,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5891726 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31653,10 +31654,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.01546106 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31665,7 +31666,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -31674,10 +31675,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 697.96716 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -31685,20 +31700,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -31707,24 +31725,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1109.1903 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5891726 + value: 697.96716 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -31732,18 +31736,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.01546106 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -31873,7 +31874,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -31882,10 +31883,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 793.6947 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31896,10 +31897,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.567419 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31911,10 +31912,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015249421 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -31923,7 +31924,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -31932,10 +31933,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 506.37045 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -31943,20 +31958,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -31965,24 +31983,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 793.6947 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.567419 + value: 506.37045 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -31990,18 +31994,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015249421 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -32131,7 +32132,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -32140,10 +32141,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 707.43713 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -32154,10 +32155,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5168102 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -32169,10 +32170,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.014757046 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -32181,7 +32182,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -32190,10 +32191,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 466.39795 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -32201,20 +32216,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -32223,24 +32241,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 707.43713 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5168102 + value: 466.39795 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -32248,18 +32252,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.014757046 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -32389,7 +32390,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -32398,10 +32399,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 0.0 + value: 707.4815 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -32412,10 +32413,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.0 + value: 1.5624777 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -32427,10 +32428,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.0 + value: 0.015201346 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -32439,7 +32440,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -32448,10 +32449,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 452.79462 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.0 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -32459,20 +32474,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.0 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -32481,24 +32499,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 707.4815 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 1.5624777 + value: 452.79462 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -32506,18 +32510,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.015201346 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -32644,7 +32645,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "07/01/2021, 14:56:43" + value: "07/01/2021, 15:05:35" } person { username: "skearnes" @@ -32978,7 +32979,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -32987,10 +32988,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 460.132 + value: 2325.931 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33001,10 +33002,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.8322558 + value: 9.261909 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33016,10 +33017,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33028,7 +33029,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -33037,10 +33038,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 251.12868 + value: 460.132 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.8322558 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -33048,20 +33063,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -33070,24 +33088,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 2325.931 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 9.261909 + value: 251.12868 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -33095,18 +33099,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -33236,7 +33237,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -33245,10 +33246,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 343.407 + value: 1882.4817 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33259,10 +33260,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.5309289 + value: 8.392216 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33274,10 +33275,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33286,7 +33287,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -33295,10 +33296,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.31285 + value: 343.407 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.5309289 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -33306,20 +33321,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -33328,24 +33346,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1882.4817 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 8.392216 + value: 224.31285 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -33353,18 +33357,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -33491,6 +33492,56 @@ reactions { value: 10.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1742.1005 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 7.5630627 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -33574,56 +33625,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 1742.1005 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 7.5630627 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.1 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -33752,7 +33753,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -33761,10 +33762,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 287.48743 + value: 1756.9401 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33775,10 +33776,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.1350102 + value: 6.93646 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33790,10 +33791,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -33802,7 +33803,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -33811,10 +33812,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 253.29059 + value: 287.48743 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.1350102 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -33822,20 +33837,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -33844,24 +33862,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1756.9401 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.93646 + value: 253.29059 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -33869,18 +33873,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -34010,7 +34011,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -34019,10 +34020,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 228.26155 + value: 1441.8502 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34033,10 +34034,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.0776374 + value: 6.807067 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34048,10 +34049,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34060,7 +34061,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -34069,10 +34070,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 211.81667 + value: 228.26155 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0776374 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -34080,20 +34095,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -34102,24 +34120,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1441.8502 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.807067 + value: 211.81667 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -34127,18 +34131,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -34268,7 +34269,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -34277,10 +34278,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 220.16705 + value: 1428.4741 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34291,10 +34292,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.0243027 + value: 6.645817 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34306,10 +34307,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34318,7 +34319,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -34327,10 +34328,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 214.94334 + value: 220.16705 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.0243027 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -34338,20 +34353,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -34360,24 +34378,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1428.4741 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.645817 + value: 214.94334 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -34385,18 +34389,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -34526,7 +34527,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -34535,10 +34536,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 206.6496 + value: 1392.3435 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34549,10 +34550,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.9300487 + value: 6.2663918 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34564,10 +34565,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34576,7 +34577,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -34585,10 +34586,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 222.19221 + value: 206.6496 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9300487 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -34596,20 +34611,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -34618,24 +34636,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1392.3435 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.2663918 + value: 222.19221 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -34643,18 +34647,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -34784,7 +34785,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -34793,10 +34794,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 190.25092 + value: 1330.5581 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34807,10 +34808,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.8852116 + value: 6.190906 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34822,10 +34823,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -34834,7 +34835,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -34843,10 +34844,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 214.92139 + value: 190.25092 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.8852116 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -34854,20 +34869,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -34876,24 +34894,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1330.5581 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.190906 + value: 214.92139 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -34901,18 +34905,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -35042,7 +35043,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -35051,10 +35052,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 178.89474 + value: 1298.4664 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35065,10 +35066,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.7958401 + value: 5.776422 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35080,10 +35081,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35092,7 +35093,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -35101,10 +35102,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.78731 + value: 178.89474 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7958401 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -35112,20 +35127,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -35134,24 +35152,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1298.4664 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.776422 + value: 224.78731 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -35159,18 +35163,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -35297,6 +35298,56 @@ reactions { value: 45.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1338.8685 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.691218 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -35380,56 +35431,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 1338.8685 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.691218 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.1 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -35558,7 +35559,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -35567,10 +35568,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 164.8724 + value: 1265.1046 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35581,10 +35582,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.73829603 + value: 5.665119 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35596,10 +35597,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35608,7 +35609,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -35617,10 +35618,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 223.31474 + value: 164.8724 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.73829603 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -35628,20 +35643,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -35650,24 +35668,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1265.1046 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.665119 + value: 223.31474 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -35675,18 +35679,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -35816,7 +35817,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -35825,10 +35826,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 151.15038 + value: 1197.0447 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35839,10 +35840,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.69674647 + value: 5.5179267 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35854,10 +35855,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -35866,7 +35867,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -35875,10 +35876,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 216.93741 + value: 151.15038 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.69674647 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -35886,20 +35901,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -35908,24 +35926,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1197.0447 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.5179267 + value: 216.93741 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -35933,18 +35937,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -36074,7 +36075,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -36083,10 +36084,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 161.63391 + value: 1322.7485 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36097,10 +36098,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.6556496 + value: 5.365579 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36112,10 +36113,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36124,7 +36125,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -36133,10 +36134,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 246.52484 + value: 161.63391 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6556496 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -36144,20 +36159,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -36166,24 +36184,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1322.7485 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.365579 + value: 246.52484 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -36191,18 +36195,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -36332,7 +36333,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -36341,10 +36342,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 145.09882 + value: 1236.9221 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36355,10 +36356,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.64060265 + value: 5.4609385 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36370,10 +36371,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36382,7 +36383,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -36391,10 +36392,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 226.5036 + value: 145.09882 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.64060265 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -36402,20 +36417,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -36424,24 +36442,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1236.9221 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.4609385 + value: 226.5036 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -36449,18 +36453,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -36590,7 +36591,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -36599,10 +36600,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 131.73769 + value: 1143.7059 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36613,10 +36614,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5857351 + value: 5.085171 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36628,10 +36629,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36640,7 +36641,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -36649,10 +36650,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.91002 + value: 131.73769 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5857351 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -36660,20 +36675,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -36682,24 +36700,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1143.7059 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.085171 + value: 224.91002 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -36707,18 +36711,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -36848,7 +36849,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -36857,10 +36858,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 123.58422 + value: 1108.5471 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36871,10 +36872,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5595545 + value: 5.019189 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36886,10 +36887,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -36898,7 +36899,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -36907,10 +36908,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 220.8618 + value: 123.58422 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5595545 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -36918,20 +36933,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -36940,24 +36958,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1108.5471 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.019189 + value: 220.8618 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -36965,18 +36969,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -37103,6 +37104,56 @@ reactions { value: 80.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1046.921 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.012879 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -37186,56 +37237,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 1046.921 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.012879 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.1 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -37364,7 +37365,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -37373,10 +37374,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 108.40001 + value: 1031.2479 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37387,10 +37388,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5066475 + value: 4.8199186 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37402,10 +37403,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37414,7 +37415,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -37423,10 +37424,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 213.95546 + value: 108.40001 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5066475 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -37434,20 +37449,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -37456,24 +37474,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1031.2479 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.8199186 + value: 213.95546 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -37481,18 +37485,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -37622,7 +37623,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -37631,10 +37632,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 105.88336 + value: 1051.4462 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37645,10 +37646,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.47973463 + value: 4.7638755 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37660,10 +37661,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37672,7 +37673,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -37681,10 +37682,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 220.71236 + value: 105.88336 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47973463 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -37692,20 +37707,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -37714,24 +37732,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1051.4462 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.7638755 + value: 220.71236 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -37739,18 +37743,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -37880,7 +37881,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -37889,10 +37890,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 106.96274 + value: 1074.9697 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37903,10 +37904,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.47515005 + value: 4.7752323 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37918,10 +37919,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -37930,7 +37931,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -37939,10 +37940,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 225.1136 + value: 106.96274 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.47515005 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -37950,20 +37965,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -37972,24 +37990,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1074.9697 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.7752323 + value: 225.1136 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -37997,18 +38001,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -38138,7 +38139,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -38147,10 +38148,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 96.94833 + value: 1003.8419 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38161,10 +38162,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.4592564 + value: 4.755325 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38176,10 +38177,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38188,7 +38189,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -38197,10 +38198,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 211.09848 + value: 96.94833 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4592564 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -38208,20 +38223,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -38230,24 +38248,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1003.8419 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.755325 + value: 211.09848 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -38255,18 +38259,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -38396,7 +38397,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -38405,10 +38406,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 90.7617 + value: 975.63495 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38419,10 +38420,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.43025428 + value: 4.624981 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38434,10 +38435,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38446,7 +38447,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -38455,10 +38456,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 210.94897 + value: 90.7617 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.43025428 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -38466,20 +38481,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -38488,24 +38506,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 975.63495 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.624981 + value: 210.94897 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -38513,18 +38517,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -38654,7 +38655,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -38663,10 +38664,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 83.65161 + value: 892.4936 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38677,10 +38678,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.42352614 + value: 4.518674 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38692,10 +38693,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -38704,7 +38705,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -38713,10 +38714,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 197.51227 + value: 83.65161 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.42352614 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -38724,20 +38739,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -38746,24 +38764,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 892.4936 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.518674 + value: 197.51227 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -38771,18 +38775,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -38909,6 +38910,56 @@ reactions { value: 115.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 950.13464 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 4.512458 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -38992,56 +39043,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 950.13464 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.512458 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.1 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -39167,7 +39168,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "07/01/2021, 14:56:43" + value: "07/01/2021, 15:05:35" } person { username: "skearnes" @@ -39501,7 +39502,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -39510,10 +39511,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 366.40317 + value: 1959.6674 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -39524,10 +39525,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.7086594 + value: 9.138578 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -39539,10 +39540,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -39551,7 +39552,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -39560,10 +39561,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 214.43896 + value: 366.40317 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.7086594 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -39571,20 +39586,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -39593,24 +39611,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1959.6674 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 9.138578 + value: 214.43896 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -39618,18 +39622,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -39759,7 +39760,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -39768,10 +39769,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 230.27904 + value: 1391.4832 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -39782,10 +39783,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 1.2495995 + value: 7.550825 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -39797,10 +39798,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -39809,7 +39810,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -39818,10 +39819,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 184.28227 + value: 230.27904 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 1.2495995 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -39829,20 +39844,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -39851,24 +39869,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1391.4832 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 7.550825 + value: 184.28227 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -39876,18 +39880,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -40017,7 +40018,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -40026,10 +40027,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 204.6626 + value: 1339.4518 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40040,10 +40041,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.9693906 + value: 6.3443537 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40055,10 +40056,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40067,7 +40068,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -40076,10 +40077,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 211.12502 + value: 204.6626 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.9693906 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -40087,20 +40102,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -40109,24 +40127,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1339.4518 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.3443537 + value: 211.12502 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -40134,18 +40138,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -40275,7 +40276,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -40284,10 +40285,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 189.95229 + value: 1322.0558 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40298,10 +40299,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.870995 + value: 6.06207 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40313,10 +40314,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40325,7 +40326,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -40334,10 +40335,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 218.08653 + value: 189.95229 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.870995 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -40345,20 +40360,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -40367,24 +40385,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1322.0558 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 6.06207 + value: 218.08653 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -40392,18 +40396,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -40533,7 +40534,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -40542,10 +40543,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 195.8778 + value: 1440.2578 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40556,10 +40557,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.7621141 + value: 5.603702 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40571,10 +40572,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40583,7 +40584,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -40592,10 +40593,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 257.01898 + value: 195.8778 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.7621141 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -40603,20 +40618,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -40625,24 +40643,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1440.2578 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.603702 + value: 257.01898 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -40650,18 +40654,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -40791,7 +40792,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -40800,10 +40801,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 129.99352 + value: 1039.9495 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40814,10 +40815,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.6560164 + value: 5.2481384 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40829,10 +40830,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -40841,7 +40842,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -40850,10 +40851,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 198.15588 + value: 129.99352 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.6560164 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -40861,20 +40876,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -40883,24 +40901,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1039.9495 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.2481384 + value: 198.15588 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -40908,18 +40912,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -41046,6 +41047,56 @@ reactions { value: 30.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 1028.6123 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 5.135779 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -41129,56 +41180,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 1028.6123 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 5.135779 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.1 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -41307,7 +41308,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -41316,10 +41317,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 110.84234 + value: 1024.5057 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41330,10 +41331,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.5097206 + value: 4.711302 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41345,10 +41346,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41357,7 +41358,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -41366,10 +41367,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 217.45705 + value: 110.84234 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.5097206 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -41377,20 +41392,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -41399,24 +41417,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1024.5057 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.711302 + value: 217.45705 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -41424,18 +41428,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -41565,7 +41566,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -41574,10 +41575,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 100.09444 + value: 1006.9278 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41588,10 +41589,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.4628293 + value: 4.6559596 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41603,10 +41604,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41615,7 +41616,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -41624,10 +41625,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 216.26643 + value: 100.09444 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.4628293 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -41635,20 +41650,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -41657,24 +41675,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 1006.9278 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.6559596 + value: 216.26643 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -41682,18 +41686,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -41823,7 +41824,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -41832,10 +41833,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 86.94685 + value: 951.93884 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41846,10 +41847,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.40530694 + value: 4.437509 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41861,10 +41862,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -41873,7 +41874,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -41882,10 +41883,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 214.521 + value: 86.94685 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.40530694 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -41893,20 +41908,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -41915,24 +41933,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 951.93884 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.437509 + value: 214.521 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -41940,18 +41944,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -42081,7 +42082,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -42090,10 +42091,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 82.16212 + value: 954.34174 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42104,10 +42105,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.36706245 + value: 4.263559 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42119,10 +42120,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42131,7 +42132,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -42140,10 +42141,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 223.83688 + value: 82.16212 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.36706245 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -42151,20 +42166,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -42173,24 +42191,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 954.34174 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.263559 + value: 223.83688 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -42198,18 +42202,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -42339,7 +42340,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -42348,10 +42349,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 71.93629 + value: 849.9856 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42362,10 +42363,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.35624695 + value: 4.209347 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42377,10 +42378,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42389,7 +42390,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -42398,10 +42399,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 201.92815 + value: 71.93629 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.35624695 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -42409,20 +42424,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -42431,24 +42449,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 849.9856 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.209347 + value: 201.92815 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -42456,18 +42460,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -42597,7 +42598,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -42606,10 +42607,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 66.21473 + value: 882.4792 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42620,10 +42621,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.3105963 + value: 4.1394835 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42635,10 +42636,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -42647,7 +42648,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -42656,10 +42657,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 213.18584 + value: 66.21473 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.3105963 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -42667,20 +42682,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -42689,24 +42707,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 882.4792 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 4.1394835 + value: 213.18584 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -42714,18 +42718,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -42852,6 +42853,56 @@ reactions { value: 65.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 816.761 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.9738708 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -42935,56 +42986,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 816.761 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.9738708 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.1 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -43113,7 +43114,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -43122,10 +43123,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 58.0082 + value: 858.04517 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43136,10 +43137,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.26291758 + value: 3.8890219 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43151,10 +43152,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43163,7 +43164,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -43172,10 +43173,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 220.63264 + value: 58.0082 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.26291758 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -43183,20 +43198,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -43205,24 +43223,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 858.04517 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.8890219 + value: 220.63264 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -43230,18 +43234,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -43371,7 +43372,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -43380,10 +43381,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 56.16369 + value: 865.7765 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43394,10 +43395,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.24998306 + value: 3.8535476 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43409,10 +43410,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43421,7 +43422,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -43430,10 +43431,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.66998 + value: 56.16369 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.24998306 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -43441,20 +43456,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -43463,24 +43481,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 865.7765 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.8535476 + value: 224.66998 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -43488,18 +43492,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -43629,7 +43630,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -43638,10 +43639,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 51.75714 + value: 808.3491 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43652,10 +43653,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.24204662 + value: 3.7803128 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43667,10 +43668,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43679,7 +43680,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -43688,10 +43689,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 213.83128 + value: 51.75714 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.24204662 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -43699,20 +43714,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -43721,24 +43739,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 808.3491 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.7803128 + value: 213.83128 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -43746,18 +43750,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -43887,7 +43888,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -43896,10 +43897,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 44.61722 + value: 773.153 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43910,10 +43911,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.2224432 + value: 3.8546245 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43925,10 +43926,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -43937,7 +43938,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -43946,10 +43947,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 200.57803 + value: 44.61722 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2224432 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -43957,20 +43972,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -43979,24 +43997,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 773.153 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.8546245 + value: 200.57803 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -44004,18 +44008,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -44145,7 +44146,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -44154,10 +44155,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 38.9466 + value: 737.7882 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44168,10 +44169,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.1971873 + value: 3.7354343 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44183,10 +44184,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44195,7 +44196,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -44204,10 +44205,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 197.5107 + value: 38.9466 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.1971873 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -44215,20 +44230,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -44237,24 +44255,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 737.7882 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.7354343 + value: 197.5107 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -44262,18 +44266,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -44403,7 +44404,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -44412,10 +44413,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 37.24174 + value: 660.9548 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44426,10 +44427,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.2076118 + value: 3.6846297 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44441,10 +44442,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44453,7 +44454,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -44462,10 +44463,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 179.3816 + value: 37.24174 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.2076118 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -44473,20 +44488,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -44495,24 +44513,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 660.9548 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.6846297 + value: 179.3816 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -44520,18 +44524,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -44658,6 +44659,56 @@ reactions { value: 100.0 units: MINUTE } + products { + identifiers { + type: SMILES + value: "OB(O)c1cc(OCc2ccccc2)ccc1" + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: false + is_normalized: false + uses_authentic_standard: false + float_value { + value: 783.1327 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 3.599438 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: CUSTOM + details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true + float_value { + value: 0.1 + } + retention_time { + value: 1.83 + units: MINUTE + } + } + reaction_role: REACTANT + } products { identifiers { type: SMILES @@ -44741,56 +44792,6 @@ reactions { } reaction_role: INTERNAL_STANDARD } - products { - identifiers { - type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: false - is_normalized: false - uses_authentic_standard: false - float_value { - value: 783.1327 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.599438 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: CUSTOM - details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true - float_value { - value: 0.1 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - reaction_role: REACTANT - } products { identifiers { type: SMILES @@ -44919,7 +44920,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -44928,10 +44929,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 38.10116 + value: 816.08594 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44942,10 +44943,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16998385 + value: 3.6408715 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44957,10 +44958,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -44969,7 +44970,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -44978,10 +44979,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 224.14577 + value: 38.10116 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16998385 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -44989,20 +45004,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -45011,24 +45029,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 816.08594 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.6408715 + value: 224.14577 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -45036,18 +45040,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -45177,7 +45178,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -45186,10 +45187,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 35.46846 + value: 775.35864 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -45200,10 +45201,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.16307606 + value: 3.5649257 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -45215,10 +45216,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -45227,7 +45228,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -45236,10 +45237,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 217.49643 + value: 35.46846 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.16307606 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -45247,20 +45262,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -45269,24 +45287,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 775.35864 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.5649257 + value: 217.49643 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -45294,18 +45298,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -45435,7 +45436,7 @@ reactions { products { identifiers { type: SMILES - value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" + value: "OB(O)c1cc(OCc2ccccc2)ccc1" } measurements { analysis_key: "Online HPLC-UV" @@ -45444,10 +45445,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 29.09146 + value: 694.42114 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -45458,10 +45459,10 @@ reactions { is_normalized: true uses_authentic_standard: false float_value { - value: 0.15090774 + value: 3.602209 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -45473,10 +45474,10 @@ reactions { is_normalized: true uses_authentic_standard: true float_value { - value: 0.09 + value: 0.1 } retention_time { - value: 2.4 + value: 1.83 units: MINUTE } } @@ -45485,7 +45486,7 @@ reactions { products { identifiers { type: SMILES - value: "COc1cc(OC)cc(OC)c1" + value: "COC(=O)/C(C)=C(/OS(=O)(=O)c1ccc(C)cc1)C1CC1" } measurements { analysis_key: "Online HPLC-UV" @@ -45494,10 +45495,24 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 192.77646 + value: 29.09146 } retention_time { - value: 1.65 + value: 2.4 + units: MINUTE + } + } + measurements { + analysis_key: "Online HPLC-UV" + type: AREA + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: false + float_value { + value: 0.15090774 + } + retention_time { + value: 2.4 units: MINUTE } } @@ -45505,20 +45520,23 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" + uses_internal_standard: true + is_normalized: true + uses_authentic_standard: true float_value { - value: 0.009 + value: 0.09 } retention_time { - value: 1.65 + value: 2.4 units: MINUTE } } - reaction_role: INTERNAL_STANDARD + reaction_role: REACTANT } products { identifiers { type: SMILES - value: "OB(O)c1cc(OCc2ccccc2)ccc1" + value: "COc1cc(OC)cc(OC)c1" } measurements { analysis_key: "Online HPLC-UV" @@ -45527,24 +45545,10 @@ reactions { is_normalized: false uses_authentic_standard: false float_value { - value: 694.42114 - } - retention_time { - value: 1.83 - units: MINUTE - } - } - measurements { - analysis_key: "Online HPLC-UV" - type: AREA - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: false - float_value { - value: 3.602209 + value: 192.77646 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } @@ -45552,18 +45556,15 @@ reactions { analysis_key: "Online HPLC-UV" type: CUSTOM details: "Concentration (M)" - uses_internal_standard: true - is_normalized: true - uses_authentic_standard: true float_value { - value: 0.1 + value: 0.009 } retention_time { - value: 1.83 + value: 1.65 units: MINUTE } } - reaction_role: REACTANT + reaction_role: INTERNAL_STANDARD } products { identifiers { @@ -45690,7 +45691,7 @@ reactions { publication_url: "https://pubs.rsc.org/en/content/articlelanding/2019/re/c9re00086k" record_created { time { - value: "07/01/2021, 14:56:43" + value: "07/01/2021, 15:05:35" } person { username: "skearnes"