dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-974d91301ba44ad1ab30f6b6ace60cf9 | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC>>COC(=O)CC(C)(C)C=CC(Cl)(Br)C(F)(F)F | BrC(C(C=C(C)C)O)(C(F)(F)F)Cl.C(C)(OC)(OC)OC>>BrC(C=CC(CC(=O)OC)(C)C)(C(F)(F)F)Cl | O[CH:10]([CH:9]=[C:6]([CH3:7])[CH3:8])[C:11]([Cl:12])([Br:13])[C:14]([F:15])([F:16])[F:17].CO[C:3]([O:2][CH3:1])([O:4]C)[CH3:5]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]([CH3:7])([CH3:8])[CH:9]=[CH:10][C:11]([Cl:12])([Br:13])[C:14]([F:15])([F:16])[F:17] | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC | COC(=O)CC(C)(C)C=CC(Cl)(Br)C(F)(F)F | null | O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3] | null | Acylation | OtherReaction | 62d15542be43b94a80da01568db53380356499d771ca28bc7e0ff722d34a5863 | 98ff49def7e6e395079390a512d545b9d4d6c593686e816bc1a43a7ae419027a | null | C-O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[#8:3]-[C;D1;H3:4])-[O;H0;D2;+0:5]-C.O-[CH;D3;+0:6](-[CH;D2;+0:7]=[C;H0;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[Br;D1;H0:12])(-[Cl;D1;H0:13])-[C:14](-[F;D1;H0:15])(-[F;D1;H0:16])-[F;D1;H0:17]>>[Br;D1;H0:12]-[C:11](-[Cl;D1;H0:13])(-[CH;D2;+0:6]=[CH;D2;+0:7]-[C;H0;D4;+0:8](-[C;D1... | 65 | [{"value": 59.0, "product": "BrC(C=CC(CC(=O)OC)(C)C)(C(F)(F)F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "BrC(C=CC(CC(=O)OC)(C)C)(C(F)(F)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 111 | CELSIUS | 1 | HOUR | 5-Bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (10.0 g), trimethyl orthoacetate (16.0 g) and Montmorillonite KSF (0.5 g) were charged to a round-bottomed flask fitted with: nitrogen inlet/bubbler, thermometer and still-head. The mixture was heated with agitation, and the methanol-trimethyl orthoacetate di... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary alcohol | Ester | null | null | null | HO- | O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3] | 111 | 1 | CC(C)=CC(O)C(Cl)(Br)C(F)(F)F.COC(C)(OC)OC>O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>COC(=O)CC(C)(C)C=CC(Cl)(Br)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d77e42f5c494f69b479d484b8ed6d48 | CC(C)=CC(O)C(Cl)(Cl)C(F)(F)F.CCOC(C)(OCC)OCC>>CCOC(=O)CC(C)(C)C=CC(Cl)(Cl)C(F)(F)F | C(C)(OCC)(OCC)OCC.ClC(C(C=C(C)C)O)(C(F)(F)F)Cl.C(C(C)C)(=O)O>>ClC(C=CC(CC(=O)OCC)(C)C)(C(F)(F)F)Cl | O[CH:11]([CH:10]=[C:7]([CH3:8])[CH3:9])[C:12]([Cl:13])([Cl:14])[C:15]([F:16])([F:17])[F:18].CCO[C:4]([O:3][CH2:2][CH3:1])([O:5]CC)[CH3:6]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]([CH3:8])([CH3:9])[CH:10]=[CH:11][C:12]([Cl:13])([Cl:14])[C:15]([F:16])([F:17])[F:18] | CC(C)=CC(O)C(Cl)(Cl)C(F)(F)F.CCOC(C)(OCC)OCC | CCOC(=O)CC(C)(C)C=CC(Cl)(Cl)C(F)(F)F | null | null | null | Acylation | OtherReaction | 62d15542be43b94a80da01568db53380356499d771ca28bc7e0ff722d34a5863 | 98ff49def7e6e395079390a512d545b9d4d6c593686e816bc1a43a7ae419027a | null | C-C-O-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[#8:3]-[C:4])-[O;H0;D2;+0:5]-C-C.O-[CH;D3;+0:6](-[CH;D2;+0:7]=[C;H0;D3;+0:8](-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[Cl;D1;H0:12])(-[Cl;D1;H0:13])-[C:14](-[F;D1;H0:15])(-[F;D1;H0:16])-[F;D1;H0:17]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;H0;D1;+0:5])-[CH2;D2;+0:2]-[C;H0;D4;+0:8](-[C;D1;H3:9])... | null | [] | null | null | null | null | A mixture of triethyl orthoacetate (25 ml), 5,5-dichloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (3.5 g), and isobutyric acid (0.11 g) was heated at the reflux temperature. The refluxing volatiles were condensed and collected in a Dean & Stark apparatus containing molecular sieves (4A) to collect the by-product eth... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Secondary alcohol | Ester | null | null | null | HO- | null | null | null | CC(C)=CC(O)C(Cl)(Cl)C(F)(F)F.CCOC(C)(OCC)OCC>>CCOC(=O)CC(C)(C)C=CC(Cl)(Cl)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9878f8a1a69f4990b1191065d489c660 | N#Cc1ccc(O)cc1.O=C([O-])C(F)(F)Cl>>N#Cc1ccc(OC(F)F)cc1 | C(C)(=O)OCC.C(#N)C1=CC=C(C=C1)O.ClC(C(=O)[O-])(F)F.[Na+].[OH-].[Na+]>>FC(OC1=CC=C(C#N)C=C1)F | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:11][cH:12]1.O=C([O-])[C:8](Cl)([F:9])[F:10]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[cH:11][cH:12]1 | N#Cc1ccc(O)cc1.O=C([O-])C(F)(F)Cl | N#Cc1ccc(OC(F)F)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 76f211f5353542c9b838eb8e1b527f9863b90e0b018b98c3cf34f50f16bd6596 | 5bf13e9b56816027718c6488fc8075a60a5c356ea2671f45c1f3f8f299767493 | c1ccccc1 | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-C(=O)-[O-].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 41 | [{"value": 41.0, "product": "FC(OC1=CC=C(C#N)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.8, "product": "FC(OC1=CC=C(C#N)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 4-Cyanophenol (0.50 g, 4.2 mmol, Aldrich), sodium chlorodifluoroacetate (0.77 g, 5 mmol, Alfa Products), and sodium hydroxide (0.20 g, 5 mmol) were combined in dry DMF (2 mL) under an atmosphere of argon. After stirring at 125°-130° C. for 5 h, the mixture was cooled to RT, ethyl acetate (50 mL) was added and the organ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Aromatic alcohol | Secondary halide.Secondary halide.Ether | null | null | c1ccccc1 | Other | CN(C)C=O | null | 5 | N#Cc1ccc(O)cc1.O=C([O-])C(F)(F)Cl>CN(C)C=O>N#Cc1ccc(OC(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b2d252a75b1947e3893ae5090ef4d0e4 | O=C([O-])C(F)(F)Cl.O=[N+]([O-])c1ccc(O)cc1>>O=[N+]([O-])c1ccc(OC(F)F)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)O.ClC(C(=O)[O-])(F)F.[Na+].[OH-].[Na+]>>FC(OC1=CC=C(C=C1)[N+](=O)[O-])F | O=C([O-])[C:9](Cl)([F:10])[F:11].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:12][cH:13]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH:9]([F:10])[F:11])[cH:12][cH:13]1 | O=C([O-])C(F)(F)Cl.O=[N+]([O-])c1ccc(O)cc1 | O=[N+]([O-])c1ccc(OC(F)F)cc1 | null | null | CN(C)C=O.O | Heteroatom Alkylation and Arylation | OtherReaction | 76f211f5353542c9b838eb8e1b527f9863b90e0b018b98c3cf34f50f16bd6596 | 5bf13e9b56816027718c6488fc8075a60a5c356ea2671f45c1f3f8f299767493 | c1ccccc1 | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-C(=O)-[O-].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 73.4 | [{"value": 73.0, "product": "FC(OC1=CC=C(C=C1)[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.4, "product": "FC(OC1=CC=C(C=C1)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | 1 | HOUR | 4-Nitrophenol (0.10 g, 0.72 mmol, Aldrich), sodium chlorodifluoroacetate (0.11 g, 0.72 mmol, Alfa Products) and sodium hydroxide (0.03 g, 0.72 mmol) were combined in dry DMF (1 mL) under an atmosphere of argon. After stirring at 125° C. for 1 h, the mixture was cooled to RT, was diluted with water and was extracted twi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Aromatic alcohol | Secondary halide.Secondary halide.Ether | null | null | c1ccccc1 | Other | CN(C)C=O.O | 125 | 1 | O=C([O-])C(F)(F)Cl.O=[N+]([O-])c1ccc(O)cc1>CN(C)C=O.O>O=[N+]([O-])c1ccc(OC(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4972bb959a7b4018a8ed305bf737462c | COC(=O)C(F)(F)Cl.N#Cc1ccc(O)cc1>>N#Cc1ccc(OC(F)F)cc1 | C(C)(=O)OCC.C(#N)C1=CC=C(C=C1)O.ClC(C(=O)OC)(F)F.C([O-])([O-])=O.[K+].[K+]>>FC(OC1=CC=C(C#N)C=C1)F | COC(=O)[C:8](Cl)([F:9])[F:10].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:11][cH:12]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[cH:11][cH:12]1 | COC(=O)C(F)(F)Cl.N#Cc1ccc(O)cc1 | N#Cc1ccc(OC(F)F)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a71f3c9bdb498e0df7854c01d285462745eacb61fcde4051c28043b77fa1bd37 | 895b1d2fe77d134f12b38f8d837ea80b2e81ef793fb29282c01859f1f67233b7 | c1ccccc1 | C-O-C(=O)-[C;H0;D4;+0:1](-Cl)(-[F;D1;H0:2])-[F;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 53.2 | [{"value": 53.0, "product": "FC(OC1=CC=C(C#N)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "FC(OC1=CC=C(C#N)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.3 | HOUR | 4-Cyanophenol (0.12 G, 1.0 mmol, Aldrich), methyl chlorodifluoroacetate (0.29 g, 2.0 mmol, Aldrich) and potassium carbonate (0.29 g, 2.1 mmol) were combined in dry DMF (0.5 mL) under an argon atmosphere. After stirring at 75°-80° C. for 0.3 h, the mixture was cooled to RT, ethyl acetate (20 mL) was added and the organi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ester.Aromatic alcohol | Secondary halide.Secondary halide.Ether | null | null | c1ccccc1 | HCl | CN(C)C=O | null | 0.3 | COC(=O)C(F)(F)Cl.N#Cc1ccc(O)cc1>CN(C)C=O>N#Cc1ccc(OC(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-78322038f273421dabe49798105b950a | COC(=O)C(F)(F)Cl.O=[N+]([O-])c1ccc(O)cc1>>O=[N+]([O-])c1ccc(OC(F)F)cc1 | C(C)(=O)OCC.[N+](=O)([O-])C1=CC=C(C=C1)O.ClC(C(=O)OC)(F)F.C([O-])([O-])=O.[K+].[K+]>>FC(OC1=CC=C(C=C1)[N+](=O)[O-])F | COC(=O)[C:9](Cl)([F:10])[F:11].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:12][cH:13]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH:9]([F:10])[F:11])[cH:12][cH:13]1 | COC(=O)C(F)(F)Cl.O=[N+]([O-])c1ccc(O)cc1 | O=[N+]([O-])c1ccc(OC(F)F)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a71f3c9bdb498e0df7854c01d285462745eacb61fcde4051c28043b77fa1bd37 | 895b1d2fe77d134f12b38f8d837ea80b2e81ef793fb29282c01859f1f67233b7 | c1ccccc1 | C-O-C(=O)-[C;H0;D4;+0:1](-Cl)(-[F;D1;H0:2])-[F;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 65 | [{"value": 65.0, "product": "FC(OC1=CC=C(C=C1)[N+](=O)[O-])F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.5, "product": "FC(OC1=CC=C(C=C1)[N+](=O)[O-])F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | 4-Nitrophenol (0.14 g, 1.0 mmol, Aldrich), methyl chlorodifluoroacetate (0.29 g, 2.0 mmol, Aldrich) and potassium carbonate (0.29 g, 2.1 mmol) were combined in dry DMF (0.5 mL) under an argon atmosphere. After stirring at 95°-100° C. for 0.5 h, the mixture was cooled to RT, ethyl acetate (20 mL) was added and the organ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ester.Aromatic alcohol | Secondary halide.Secondary halide.Ether | null | null | c1ccccc1 | HCl | CN(C)C=O | null | 0.5 | COC(=O)C(F)(F)Cl.O=[N+]([O-])c1ccc(O)cc1>CN(C)C=O>O=[N+]([O-])c1ccc(OC(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e57e5ba30ba5446d9ef33fda5e7bc0ab | COC(=O)C(F)(F)Cl.O=Cc1ccc(O)c(O)c1>>O=Cc1ccc(OC(F)F)c(O)c1 | OC=1C=C(C=O)C=CC1O.ClC(C(=O)OC)(F)F.C([O-])([O-])=O.[K+].[K+]>>FC(OC1=C(C=C(C=O)C=C1)O)F | COC(=O)[C:8](Cl)([F:9])[F:10].[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:11]([OH:12])[cH:13]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([OH:12])[cH:13]1 | COC(=O)C(F)(F)Cl.O=Cc1ccc(O)c(O)c1 | O=Cc1ccc(OC(F)F)c(O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a71f3c9bdb498e0df7854c01d285462745eacb61fcde4051c28043b77fa1bd37 | 895b1d2fe77d134f12b38f8d837ea80b2e81ef793fb29282c01859f1f67233b7 | c1ccccc1 | C-O-C(=O)-[C;H0;D4;+0:1](-Cl)(-[F;D1;H0:2])-[F;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 38 | [{"value": 38.0, "product": "FC(OC1=C(C=C(C=O)C=C1)O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.4, "product": "FC(OC1=C(C=C(C=O)C=C1)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 3,4-Dihydroxybenzaldehyde (0.50 g, 3.62 mmol, Aldrich), methyl chlorodifluoroacetate (0.52 g, 3.62 mmol, Aldrich) and potassium carbonate (0.50 g, 3.62 mmol) were combined in DMF (5.0 mL) under an argon atmosphere. After stirring at 60°-65° C. for 3 h, DMF was removed in vacuo and the residue was partioned between aque... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ester.Aromatic alcohol | Secondary halide.Secondary halide.Ether | null | null | c1ccccc1 | HCl | CN(C)C=O | null | 3 | COC(=O)C(F)(F)Cl.O=Cc1ccc(O)c(O)c1>CN(C)C=O>O=Cc1ccc(OC(F)F)c(O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-550474a9556d462983b860f2b003f86a | CC(=O)N1CCc2cc(O)c(Br)cc21.COC(=O)C(F)(F)Cl>>CC(=O)N1CCc2cc(OC(F)F)c(Br)cc21 | C(C)(=O)N1CCC2=CC(=C(C=C12)Br)O.ClC(C(=O)OC)(F)F.ClC(C(=O)OC)(F)F.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)N1CCC2=CC(=C(C=C12)Br)OC(F)F | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([OH:10])[c:14]([Br:15])[cH:16][c:17]21.COC(=O)[C:11](Cl)([F:12])[F:13]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][c:9]([O:10][CH:11]([F:12])[F:13])[c:14]([Br:15])[cH:16][c:17]21 | CC(=O)N1CCc2cc(O)c(Br)cc21.COC(=O)C(F)(F)Cl | CC(=O)N1CCc2cc(OC(F)F)c(Br)cc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | a71f3c9bdb498e0df7854c01d285462745eacb61fcde4051c28043b77fa1bd37 | 895b1d2fe77d134f12b38f8d837ea80b2e81ef793fb29282c01859f1f67233b7 | c1ccc2c(c1)CCN2 | C-O-C(=O)-[C;H0;D4;+0:1](-Cl)(-[F;D1;H0:2])-[F;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 3 | HOUR | 1-Acetyl-6-bromo-5-hydroxyindoline (2 g, 7.8 mmol), methyl 2-chloro-2,2-difluoroacetate (0.82 ml, 7.8 mmol) and potassium carbonate (1.08 g, 7.8 mmol) were suspended in N,N-dimethylformamide (20 mL) under an argon atmosphere and placed in a 65° C. oil bath. After 3 hr, additional methyl 2-chloro-2,2-difluoroacetate (0.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ester.Aromatic alcohol | Secondary halide.Secondary halide.Ether | null | null | c1ccc2c(c1)CC[NH]2 | HCl | CN(C=O)C | null | 3 | CC(=O)N1CCc2cc(O)c(Br)cc21.COC(=O)C(F)(F)Cl>CN(C=O)C>CC(=O)N1CCc2cc(OC(F)F)c(Br)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-065831d99277499b89b8f6f92e86ad30 | CCCCCCCCCCCCC.CCOC(=O)CCc1cccc(I)c1.Cc1ccc(N)cc1C.Cc1ccccc1>>CCOC(=O)CCc1cccc(N(c2cccc(CCC(=O)OCC)c2)c2ccc(C)c(C)c2)c1 | CCCCCCCCCCCCC.NC1=CC(=C(C=C1)C)C.IC=1C=C(CCC(=O)OCC)C=CC1.C1(=CC=CC=C1)C.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(=O)CCC=1C=C(C=CC1)N(C1=CC(=C(C=C1)C)C)C1=CC(=CC=C1)CCC(=O)OCC | CCCCCC[CH2:6]CCCC[CH2:2][CH3:1].I[c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][CH2:20][C:21](=[O:22])[O:23][CH2:24][CH3:25])[cH:26]1.[NH2:13][c:27]1[cH:28][cH:29][c:30]([CH3:31])[c:32]([CH3:33])[cH:34]1.[CH3:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:35]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:... | CCCCCCCCCCCCC.CCOC(=O)CCc1cccc(I)c1.Cc1ccc(N)cc1C.Cc1ccccc1 | CCOC(=O)CCc1cccc(N(c2cccc(CCC(=O)OCC)c2)c2ccc(C)c(C)c2)c1 | null | O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2] | null | Acylation | OtherReaction | 54501e10e8da214bc308903d3daa045a3ef2162f00410d5a0b32f2299aacc8c8 | dbb0eb744f989d85895c22aaae807ffdec084fe09a76f7c236614e64944edef6 | c1ccc(N(c2ccccc2)c2ccccc2)cc1 | C-C-C-C-C-C-[CH2;D2;+0:1]-C-C-C-C-[CH2;D2;+0:2]-[C;D1;H3:3].I-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[CH3;D1;+0:9]-[c:10]1:[c:11]:[cH;D2;+0:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17](:[c:18]):[c:19]>>[C;D1;H3:3]-[CH2;D2;+0:2]-[#8:20]-[C:21](=[O;D1;H0:22])-[CH2;D2;+0:1]-[CH2;D2;+0:9]-[c:10]1:[c:11]:[c;H0;D3;+0:1... | null | [] | 230 | CELSIUS | null | null | In a 100 ml-volume flask, 6 g of 3,4-xylidine, 34 g of ethyl 3-iododihydrocinnamate, 19 g of potassium carbonate, 5 g of copper sulfate pentahydrate and 20 ml of n-tridecane were placed, and the mixture was reacted under heating at 230° C. for 10 hours in a nitrogen stream. After the reaction, the system was cooled to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Ester.Tertiary amine | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HI | O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2] | 230 | null | CCCCCCCCCCCCC.CCOC(=O)CCc1cccc(I)c1.Cc1ccc(N)cc1C.Cc1ccccc1>O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2]>CCOC(=O)CCc1cccc(N(c2cccc(CCC(=O)OCC)c2)c2ccc(C)c(C)c2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70576781abfa4a2db8a2ad21736fa5f6 | CCCCCCCCCCCCC.CCOC(=O)CCc1cccc(I)c1.Cc1ccccc1.O=C([O-])[O-].c1ccc(Nc2ccc(-c3ccc(Nc4ccccc4)cc3)cc2)cc1>>CCOC(=O)CCc1cccc(N(c2ccccc2)c2ccc(-c3ccc(N(c4ccccc4)c4cccc(CCC(=O)OCC)c4)cc3)cc2)c1 | CCCCCCCCCCCCC.C1(=CC=CC=C1)NC1=CC=C(C=C1)C1=CC=C(NC2=CC=CC=C2)C=C1.IC=1C=C(CCC(=O)OCC)C=CC1.C1(=CC=CC=C1)C.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC(=CC=C1)CCC(=O)OCC)C1=CC=CC=C1)C1=CC(=CC=C1)CCC(=O)OCC | CCCCCC[CH2:41]CCCC[CH2:45][CH3:46].I[c:12]1[cH:11][cH:10][cH:9][c:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:52]1.[cH:35]1[cH:36][cH:37][cH:38][c:39]([CH3:40])[cH:47]1.[O-][C:42](=[O:43])[O-:44].[NH:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH:21][cH:22][c:23](-[c:24]2[cH:25][cH:26][c:27]([NH:2... | CCCCCCCCCCCCC.CCOC(=O)CCc1cccc(I)c1.Cc1ccccc1.O=C([O-])[O-].c1ccc(Nc2ccc(-c3ccc(Nc4ccccc4)cc3)cc2)cc1 | CCOC(=O)CCc1cccc(N(c2ccccc2)c2ccc(-c3ccc(N(c4ccccc4)c4cccc(CCC(=O)OCC)c4)cc3)cc2)c1 | null | O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2] | null | C-C Coupling | OtherReaction | 497f9e9d1397a0e31d3ddb287447ba2626934ccb58ababaec9ed702cbd7901d6 | 44c1f5b065c6391b4ea52e08552a04f6c348986b4cd4a5d798ee2c633f2c2d31 | c1ccc(N(c2ccccc2)c2ccc(-c3ccc(N(c4ccccc4)c4ccccc4)cc3)cc2)cc1 | C-C-C-C-C-C-[CH2;D2;+0:1]-C-C-C-C-[CH2;D2;+0:2]-[C;D1;H3:3].I-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[CH3;D1;+0:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:[c:15]:1.[O-;H0;D1:16]-[C;H0;D3;+0:17](-[O-])=[O;D1;H0:18].[c:19]:[c:20](-[NH;D2;+0:21]-[c:22](:[c:23]):[c:24]):[c:25].[c:26]:[c:27](-[NH;D2;+0:28]-[c:29](:[c:3... | null | [] | 230 | CELSIUS | null | null | In a 100 ml-volume flask, 10.77 g of N,N'-diphenylbenzidine, 23.0 g of ethyl 3-iododihydrocinnamate, 11.61 g of potassium carbonate, 1.0 g of copper sulfate pentahydrate and 20 ml of n-tridecane were placed, and the mixture was reacted under heating at 230° C. for one hour in a nitrogen stream. After the reaction, the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Secondary amine | Ester.Tertiary amine.Tertiary amine | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HI | O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2] | 230 | null | CCCCCCCCCCCCC.CCOC(=O)CCc1cccc(I)c1.Cc1ccccc1.O=C([O-])[O-].c1ccc(Nc2ccc(-c3ccc(Nc4ccccc4)cc3)cc2)cc1>O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2]>CCOC(=O)CCc1cccc(N(c2ccccc2)c2ccc(-c3ccc(N(c4ccccc4)c4cccc(CCC(=O)OCC)c4)cc3)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db854b27d2914399bbe5f288a9a9adb4 | BrCCCBr.O=Cc1ccc(O)cc1>>O=Cc1ccc(OCCCOc2ccc(C=O)cc2)cc1 | OC1=CC=C(C=O)C=C1.BrCCCBr>>C(=O)C1=CC=C(OCCCOC2=CC=C(C=C2)C=O)C=C1 | Br[CH2:2][CH2:9][CH2:19]Br.[OH:1][c:6]1[cH:5][cH:4][c:15]([CH:16]=[O:17])[cH:18][cH:20]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]([CH:16]=[O:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | BrCCCBr.O=Cc1ccc(O)cc1 | O=Cc1ccc(OCCCOc2ccc(C=O)cc2)cc1 | null | null | C([O-])([O-])=O.[K+].[K+].CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 9ca249d8c990495c198a5173c824a6a22faf7c6f4c2389fbcc6bed0485ec4ce9 | b4c10ccb2388cb913655268bc27e1f9fe5931851a3f009855875eaf96444dbfc | c1ccc(OCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-Br.[O;D1;H0:4]=[C:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[OH;D1;+0:10]):[c:11]:[cH;D2;+0:12]:1>>[O;D1;H0:4]=[C:5]-[c;H0;D3;+0:6]1:[c:13]:[c:14]:[c:15](-[#8:16]-[C:17]-[CH2;D2;+0:2]-[C:18]-[#8:19]-[c;H0;D3;+0:9]2:[c:11]:[cH;D2;+0:12]:[c:20](-[CH;D2;+0:3]... | 76 | [{"value": 76.0, "product": "C(=O)C1=CC=C(OCCCOC2=CC=C(C=C2)C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 10.0 g of 4-hydroxybenzaldehyde and 8.3 g of 1,3-dibromopropane were reacted for 24 hours in 6.2 g of potassium carbonate solution in 100 ml of DMF under reflux. The reaction mixture was poured into cold distilled water to obtain a precipitate. After filtration and vacuum drying the precipitate, the resultant was recry... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aldehyde.Aromatic alcohol | Aldehyde.Aldehyde.Ether.Ether | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | C([O-])([O-])=O.[K+].[K+].CN(C)C=O | null | null | BrCCCBr.O=Cc1ccc(O)cc1>C([O-])([O-])=O.[K+].[K+].CN(C)C=O>O=Cc1ccc(OCCCOc2ccc(C=O)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e22638b8245f48a095b97a9f8f553d18 | CCCCOC1=C(SCCCCCC(=O)OC)[C@@H](/C=C/[C@@H](O)C[C@@H](C)CCCC)[C@H](O)C1>>CCCCOC1=C(SCCCCCC(=O)O)[C@@H](/C=C/[C@@H](O)C[C@@H](C)CCCC)[C@H](O)C1 | Cl.COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@H](CCCC)C)O)O)OCCCC)=O.P(=O)([O-])([O-])[O-].S(=O)(=O)([O-])[O-].[NH4+].[NH4+]>>C(CCC)OC1=C(SCCCCCC(=O)O)[C@H]([C@@H](C1)O)\C=C\[C@H](C[C@H](CCCC)C)O | C[O:16][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][S:8][C:7]1=[C:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:31][C@@H:29]([OH:30])[C@@H:17]1/[CH:18]=[CH:19]/[C@@H:20]([OH:21])[CH2:22][C@@H:23]([CH3:24])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1=[C:7]([S:8][CH2:9][CH2:10][CH2:11][... | CCCCOC1=C(SCCCCCC(=O)OC)[C@@H](/C=C/[C@@H](O)C[C@@H](C)CCCC)[C@H](O)C1 | CCCCOC1=C(SCCCCCC(=O)O)[C@@H](/C=C/[C@@H](O)C[C@@H](C)CCCC)[C@H](O)C1 | null | null | CC(=O)C | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1=CCCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 14 | [{"value": 14.0, "product": "C(CCC)OC1=C(SCCCCCC(=O)O)[C@H]([C@@H](C1)O)\\C=C\\[C@H](C[C@H](CCCC)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.9, "product": "C(CCC)OC1=C(SCCCCCC(=O)O)[C@H]([C@@H](C1)O)\\C=C\\[C@H](C[C@H](CCCC)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Methyl(11R,12S,13E,15S,17S)-9-butyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (51 mg, 0.11 mmol) was dissolved in acetone (1 ml). To this solution was added a pH 8 phosphate buffer (10 ml). Further esterase (from porcine liver made by Sigma Co., 114 μl) was added and the mixture was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1=CCCC1 | Other | CC(=O)C | null | 5 | CCCCOC1=C(SCCCCCC(=O)OC)[C@@H](/C=C/[C@@H](O)C[C@@H](C)CCCC)[C@H](O)C1>CC(=O)C>CCCCOC1=C(SCCCCCC(=O)O)[C@@H](/C=C/[C@@H](O)C[C@@H](C)CCCC)[C@H](O)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f870745fc5f496588a513ddc86e1f2b | CC(C)C(=O)OC(=O)C(C)C.CCCC[C@@H](C)C[C@@H](/C=C/I)O[Si](C)(C)C(C)(C)C.COC(=O)CCCCCSC1=C(O[SiH](C)C)[C@@H](C(C)(C)C)CC1=O>>CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | C(C)(C)(C)[C@@H]1C(=C(C(C1)=O)SCCCCCC(=O)OC)O[SiH](C)C.I\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C.C(C)(C)(C)[Li].C(C(C)C)(=O)OC(C(C)C)=O.C(#CCCCC)[Cu]>>COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C(C)C)=O)=O | CC(C)C(=O)O[C:25](=[O:26])[CH:27]([CH3:28])[CH3:29].I/[CH:10]=[CH:9]/[C@H:8]([CH2:7][C@@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH3:6])[O:40][Si:41]([CH3:42])([CH3:43])[C:44]([CH3:45])([CH3:46])[CH3:47].[C@H:11]1([C:36]([CH3:37])([CH3:38])[CH3:39])[CH2:30][C:23](=[O:24])[C:12]([S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][... | CC(C)C(=O)OC(=O)C(C)C.CCCC[C@@H](C)C[C@@H](/C=C/I)O[Si](C)(C)C(C)(C)C.COC(=O)CCCCCSC1=C(O[SiH](C)C)[C@@H](C(C)(C)C)CC1=O | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | null | null | CN(P(N(C)C)N(C)C)C | Acylation | OtherReaction | 8afc755b548997a6f5fa8fedd78136c9b6506cce35137678927e0ae1199f5198 | 61a9fef0afe1c5bb4f7915b9a6f9c9607c1132c62df54f96cfacb548bb7b17a5 | C1=CCCC1 | C-C(-C)-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].I/[CH;D2;+0:6]=[C:7]/[C:8](-[#8:9])-[C:10].[C:11]-[#16:12]-[C;H0;D3;+0:13]1=[C;H0;D3;+0:14](-[#8:15]-[SiH;D3;+0:16](-[C;D1;H3:17])-[C;D1;H3:18])-[C@@H;D3;+0:19](-[C;H0;D4;+0:20](-[C;D1;H3:21])(-[C;D1;H3:22])-[C;D1;H3:23])-[CH2;D2;+0:24]-[C;H0;... | 65 | [{"value": 65.0, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using as the materials and reagents (1E,3S,5R)-1-iodo-3-(tert-butyldimethylsiloxy)-5-methyl-1-nonene (476 mg, 1.2 mmol), tert-butyllithium (1.54 mol/l, 1.56 ml, 2.4 mmol), 174 mg of 1-hexynylcopper, hexamethylphosphorous triamide (436 μl), (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonylpentylthio)-2-cyclopenten-1-on... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ketone.Monosulfide | Ester.Monosulfide.TMS ether protective group | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | HI | CN(P(N(C)C)N(C)C)C | null | null | CC(C)C(=O)OC(=O)C(C)C.CCCC[C@@H](C)C[C@@H](/C=C/I)O[Si](C)(C)C(C)(C)C.COC(=O)CCCCCSC1=C(O[SiH](C)C)[C@@H](C(C)(C)C)CC1=O>CN(P(N(C)C)N(C)C)C>CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e25048cd0b1a4d4a97c39af9be62f679 | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O | N1=CC=CC=C1.F.COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C(C)C)=O)=O>>COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O)O)OC(C(C)C)=O)=O | CC(C)(C)[Si](C)(C)[O:9][C@@H:8]([CH2:7][C@@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH3:6])/[CH:10]=[CH:11]/[C@@H:12]1[C:13]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[O:22][CH3:23])=[C:24]([O:25][C:26](=[O:27])[CH:28]([CH3:29])[CH3:30])[CH2:31][C@H:32]1[O:33][Si](C)(C)C(C)(C)C>>[CH3:1][CH2:2][CH2:3][CH2:4... | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 64 | [{"value": 64.0, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](C[C@@H](CCCC)C)O)O)OC(C(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.6, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](C[C@@H](CCCC)C)O)O)OC(C(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using as the material and reagent a hydrogen fluoride-pyridine solution (0.6 ml) and methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (466 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1 | Other | null | null | null | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)C)C[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4530e01b498e4c59a4e74ef8002e38f6 | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)(C)C)C[C@H]1O | N1=CC=CC=C1.F.COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C(C)(C)C)=O)=O>>COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O)O)OC(C(C)(C)C)=O)=O | CC(C)(C)[Si](C)(C)[O:9][C@@H:8]([CH2:7][C@@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH3:6])/[CH:10]=[CH:11]/[C@@H:12]1[C:13]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[O:22][CH3:23])=[C:24]([O:25][C:26](=[O:27])[C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32][C@H:33]1[O:34][Si](C)(C)C(C)(C)C>>[CH3:1][CH2:2][CH2... | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)(C)C)C[C@H]1O | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 55 | [{"value": 55.0, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](C[C@@H](CCCC)C)O)O)OC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.6, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](C[C@@H](CCCC)C)O)O)OC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | Using as the material and reagent a hydrogen fluoride-pyridine solution (0.7 ml) and methyl(11R,12S,13E,15S,17R)-9-pivaloyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (564 mg), the same procedure was performed as in Example 2 was performed to obtain methyl(11R,13E,15S,17R)-9-pivalo... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1 | Other | null | null | null | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)C(C)(C)C)C[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-947e00ce913b48258528de610493e045 | CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](C[C@H](C)CCCC)O[Si](C)(C)C(C)(C)C>>CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)C[C@H](C)CCCC | N1=CC=CC=C1.F.C(CCC)(=O)OC1=C(SCCCCCC(=O)OCCCC)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C>>C(CCC)(=O)OC1=C(SCCCCCC(=O)OCCCC)[C@H]([C@@H](C1)O)\C=C\[C@H](C[C@@H](CCCC)C)O | CC(C)(C)[Si](C)(C)[O:24][C@@H:23]1[CH2:22][C:15]([O:16][C:17](=[O:18])[CH2:19][CH2:20][CH3:21])=[C:14]([S:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7])[C@H:25]1/[CH:26]=[CH:27]/[C@@H:28]([O:29][Si](C)(C)C(C)(C)C)[CH2:30][C@H:31]([CH3:32])[CH2:33][CH2:34][CH2:35][CH3:36]>>[CH3:... | CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](C[C@H](C)CCCC)O[Si](C)(C)C(C)(C)C | CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)C[C@H](C)CCCC | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 72 | [{"value": 72.0, "product": "C(CCC)(=O)OC1=C(SCCCCCC(=O)OCCCC)[C@H]([C@@H](C1)O)\\C=C\\[C@H](C[C@@H](CCCC)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.7, "product": "C(CCC)(=O)OC1=C(SCCCCCC(=O)OCCCC)[C@H]([C@@H](C1)O)\\C=C\\[C@H](C[C@@H](CCCC)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | null | null | Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (138 mg), the same procedure as in Example 2 was performed to obtain butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1 | Other | null | null | null | CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](C[C@H](C)CCCC)O[Si](C)(C)C(C)(C)C>>CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)C[C@H](C)CCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76d32aafd0e142d0832c397f95f52a05 | CCCCC[C@@H](/C=C/I)O[Si](C)(C)C(C)(C)C.COC(=O)CCCCCSC1=C(O[SiH](C)C)[C@@H](C(C)(C)C)CC1=O.O=C(OC(=O)c1ccccc1)c1ccccc1.[Li][C](C)(C)C>>CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | C(C)(C)(C)[C@@H]1C(=C(C(C1)=O)SCCCCCC(=O)OC)O[SiH](C)C.I\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C.C(C)(C)(C)[Li].C(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)=O.C(#CCCCC)[Cu]>>COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C1=CC=CC=C1)=O)=O | I/[CH:8]=[CH:7]/[C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:41][Si:42]([CH3:43])([CH3:44])[C:45]([CH3:46])([CH3:47])[CH3:48].CC(C)(C)[C@H:9]1[CH2:31][C:21](=[O:22])[C:10]([S:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[O:19][CH3:20])=[C:32]1[O:33][SiH:34]([CH3:35])[CH3:36].O=C(O[C:23](=[O:24])[c:25]1[c... | CCCCC[C@@H](/C=C/I)O[Si](C)(C)C(C)(C)C.COC(=O)CCCCCSC1=C(O[SiH](C)C)[C@@H](C(C)(C)C)CC1=O.O=C(OC(=O)c1ccccc1)c1ccccc1.[Li][C](C)(C)C | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | null | null | CN(P(N(C)C)N(C)C)C | Acylation | OtherReaction | 46d07187e3b0a5bf5c5a95a7583a8697ecd0d97270c703f53c62a843cfbdb1b4 | 070d9d49bcafdcb794bdb6b71278660ee33eb316daa377ce48b8a62e46ad473d | O=C(OC1=CCCC1)c1ccccc1 | C-C(-C)(-C)-[C@H;D3;+0:1]1-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C;H0;D3;+0:5](-[#16:6]-[C:7])=[C;H0;D3;+0:8]-1-[#8:9]-[SiH;D3;+0:10](-[C;D1;H3:11])-[C;D1;H3:12].I/[CH;D2;+0:13]=[C:14]/[C:15](-[#8:16])-[C:17].O=C(-O-[C;H0;D3;+0:18](=[O;D1;H0:19])-[c:20](:[c:21]):[c:22])-c1:c:c:c:c:c:1.[C;D1;H3:23]-[C;H0;D4;+0:... | 55.4 | [{"value": 33.0, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.4, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C1=CC=CC=C1)... | null | null | null | null | Using as the materials and reagents (1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene (442 mg, 1.2 mmol), tert-butyllithium (1.54 mol/l, 1.56 ml, 2.4 mmol), 1-hexynylcopper (174 mg), hexamethylphosphorous triamide (436 μl), (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonyl-pentylthio)-2-cyclopenten-1-one (373 mg, 1... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ketone.Ester.Ester.Monosulfide.Alkyl lithium | Ester.Monosulfide.TMS ether protective group | C1=CCCC1.c1ccccc1 | C1=CCCC1 | C1=CCCC1.c1ccccc1 | HI.Li | CN(P(N(C)C)N(C)C)C | null | null | CCCCC[C@@H](/C=C/I)O[Si](C)(C)C(C)(C)C.COC(=O)CCCCCSC1=C(O[SiH](C)C)[C@@H](C(C)(C)C)CC1=O.O=C(OC(=O)c1ccccc1)c1ccccc1.[Li][C](C)(C)C>CN(P(N(C)C)N(C)C)C>CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a8c4e36b9c5748c2bdb42724db547b96 | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O | N1=CC=CC=C1.F.COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C1=CC=CC=C1)=O)=O>>C(C1=CC=CC=C1)(=O)OC1=C(SCCCCCC(=O)OC)[C@H]([C@@H](C1)O)\C=C\[C@H](CCCCC)O | CC(C)(C)[Si](C)(C)[O:7][C@@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])/[CH:8]=[CH:9]/[C@@H:10]1[C:11]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH3:21])=[C:22]([O:23][C:24](=[O:25])[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH2:32][C@H:33]1[O:34][Si](C)(C)C(C)(C)C>>[CH3:1][CH2:2][CH2:3][CH2:4]... | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | O=C(OC1=CCCC1)c1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 88.3 | [{"value": 86.0, "product": "C(C1=CC=CC=C1)(=O)OC1=C(SCCCCCC(=O)OC)[C@H]([C@@H](C1)O)\\C=C\\[C@H](CCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.3, "product": "C(C1=CC=CC=C1)(=O)OC1=C(SCCCCCC(=O)OC)[C@H]([C@@H](C1)O)\\C=C\\[C@H](CCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Using as the material and reagent a hydrogen fluoride-pyridine solution (0.3 ml) and methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (239 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,13E,15S)-9-benzoyloxy-11,15-dihydroxy-7-thiaprosta-8,13... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1.c1ccccc1 | Other | null | null | null | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76f66933b8914bb1a7437f5254a0de57 | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCCCSC1=C(OC(=O)CCC)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC | C(CCC)(=O)OC1=C(SCCCCCC(=O)O)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C.C(O)([O-])=O.[Na+].N1=CC=CC=C1.F.C(C)#N>>C(CCC)(=O)OC1=C(SCCCCCC)[C@H]([C@@H](C1)O)\C=C\[C@H](CCCCC)O | CC(C)(C)[Si](C)(C)[O:18][C@@H:17]1[CH2:16][C:9]([O:10][C:11](=[O:12])[CH2:13][CH2:14][CH3:15])=[C:8]([S:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1](=O)O)[C@H:19]1/[CH:20]=[CH:21]/[C@@H:22]([O:23][Si](C)(C)C(C)(C)C)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1=[C:9]([O:10... | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | CCCCCCSC1=C(OC(=O)CCC)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC | null | null | N1=CC=CC=C1.C(C)(=O)OCC | Reduction | OtherReaction | a0e91d17d81c0bb7f1829e6b5b45de64d1a532e1ec02fd5dc124819c438453b0 | 33f60392ace24dc8f1f760d24515776f5bcdb07ae384abcf60bac7667a41c48e | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C.O-[C;H0;D3;+0:12](=O)-[C:13]-[C:14]>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1].[C:14]-[C:13]-[CH3;D1;+0:12] | 35 | [{"value": 33.0, "product": "C(CCC)(=O)OC1=C(SCCCCCC)[C@H]([C@@H](C1)O)\\C=C\\[C@H](CCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.0, "product": "C(CCC)(=O)OC1=C(SCCCCCC)[C@H]([C@@H](C1)O)\\C=C\\[C@H](CCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A hydrogen fluoride-pyridine solution (0.1 ml) was added to a solution of ice-cooled acetonitrile (1 ml) and pyridine (0.1 ml), then a pyridine (0.1 ml) solution of (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid (79 mg) was added. The ice bath was detached, then the so... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1 | HO- | N1=CC=CC=C1.C(C)(=O)OCC | null | 20 | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>N1=CC=CC=C1.C(C)(=O)OCC>CCCCCCSC1=C(OC(=O)CCC)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-22a46d06c9484f61abcb3ba9fcd4507b | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O | N1=CC=CC=C1.F.COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(C1=CC=CC=C1)=O)=O>>COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](C[C@@H](CCCC)C)O)O)OC(C1=CC=CC=C1)=O)=O | CC(C)(C)[Si](C)(C)[O:9][C@@H:8]([CH2:7][C@@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH3:6])/[CH:10]=[CH:11]/[C@@H:12]1[C:13]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[O:22][CH3:23])=[C:24]([O:25][C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[CH2:34][C@H:35]1[O:36][Si](C)(C)C(C)(C)C>>[CH3:1][C... | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | O=C(OC1=CCCC1)c1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 28 | [{"value": 28.0, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](C[C@@H](CCCC)C)O)O)OC(C1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.7, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](C[C@@H](CCCC)C)O)O)OC(C1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | Using as the material and reagent a hydrogen fluoride-pyridine solution (0.7 ml) and methyl(11R,12S,13E,15S,17R)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (734 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,12S,13E,15S,17R)-9-benzoyloxy-11,15-... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1.c1ccccc1 | Other | null | null | null | CCCC[C@@H](C)C[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5c0f98feabe41e293e98aa397fcf97a | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O | N1=CC=CC=C1.F.COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O>>COC(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O)O)OC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O | CC(C)(C)[Si](C)(C)[O:7][C@@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])/[CH:8]=[CH:9]/[C@@H:10]1[C:11]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH3:21])=[C:22]([O:23][C:24](=[O:25])[C@H:26]([CH2:27][c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[NH:34][C:35](=[O:36])[O:37][CH2:38][c:39]2[cH:40][cH:... | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | O=C(N[C@@H](Cc1ccccc1)C(=O)OC1=CCCC1)OCc1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 51 | [{"value": 51.0, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](CCCCC)O)O)OC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.8, "product": "COC(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](CCCCC)O)O)OC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O", "details... | null | null | null | null | Using as the material and reagent a hydrogen fluoride-pyridine solution (0.3 ml) and methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (140 mg), methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-dihydroxy-7-thiaprosta-8,13-di... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e387f53034b342bebeac204bcb29c54a | CCCCCC(C)(C)C(O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C>>CCCCCC(C)(C)C(O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)CCC)C[C@H]1O | N1=CC=CC=C1.F.C(CCC)(=O)OC1=C(SCCCCCC(=O)OC)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\C(C(CCCCC)(C)C)O>>C(CCC)(=O)OC1=C(SCCCCCC(=O)OC)[C@H]([C@@H](C1)O)\C=C\C(C(CCCCC)(C)C)O | CC(C)(C)[Si](C)(C)[O:34][C@H:33]1[C@H:13](/[CH:12]=[CH:11]/[CH:9]([C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([CH3:7])[CH3:8])[OH:10])[C:14]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:22])[O:23][CH3:24])=[C:25]([O:26][C:27](=[O:28])[CH2:29][CH2:30][CH3:31])[CH2:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6... | CCCCCC(C)(C)C(O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C | CCCCCC(C)(C)C(O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)CCC)C[C@H]1O | null | null | null | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]>>[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | null | [] | null | null | null | null | Using as the materials a hydrogen fluoride-pyridine solution (0.25 ml) and methyl(11R,12S,13E)-9-butyryloxy-11-tert-butyldimethylsiloxy-15-hydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate (100 mg), the same procedure as in Example 2 was performed to separately obtain two stereoisomers of methyl(11R,12S,13E)-9-buty... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | C1=CCCC1 | Other | null | null | null | CCCCCC(C)(C)C(O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C>>CCCCCC(C)(C)C(O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)CCC)C[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a3271a594c4451684be2191aa815526 | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C.[NH4+]>>CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | Cl.C(CCC)(=O)OC1=C(SCCCCCC(=O)O)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C.ClC(=O)OCC(C)C.[OH-].[NH4+]>>C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C | O[C:17]([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][C:10]1=[C:20]([O:21][C:22](=[O:23])[CH2:24][CH2:25][CH3:26])[CH2:27][C@@H:28]([O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36])[C@@H:9]1/[CH:8]=[CH:7]/[C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[O:37][Si:38]([CH3:39])([CH3:40])[C:41]([CH3:42])([... | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C.[NH4+] | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | null | null | C(Cl)Cl.C(C)(=O)OCC.C(C)N(CC)CC | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | C1=CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 84 | [{"value": 84.0, "product": "C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\\C=C\\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A methylene chloride (3 ml) solution of (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoic acid (201 mg) was cooled to -40° C., then isobutyl chloroformate (47 μl) and triethylamine (63 μl) were added to the solution which was then stirred as is at -40° C. for 30 minutes. Furth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1=CCCC1 | HO- | C(Cl)Cl.C(C)(=O)OCC.C(C)N(CC)CC | null | 0.5 | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C.[NH4+]>C(Cl)Cl.C(C)(=O)OCC.C(C)N(CC)CC>CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e7a5f5fa47d44c41aa8f5e9d244fb7f5 | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O | N1=CC=CC=C1.F.C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O[Si](C)(C)C(C)(C)C)\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C>>C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O)\C=C\[C@H](CCCCC)O | CC(C)(C)[Si](C)(C)[O:7][C@@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])/[CH:8]=[CH:9]/[C@@H:10]1[C:11]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH2:19])=[O:20])=[C:21]([O:22][C:23](=[O:24])[CH2:25][CH2:26][CH3:27])[CH2:28][C@H:29]1[O:30][Si](C)(C)C(C)(C)C>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:7])/[C... | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 91 | [{"value": 91.0, "product": "C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O)\\C=C\\[C@H](CCCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "C(CCC)(=O)OC1=C(SCCCCCC(=O)N)[C@H]([C@@H](C1)O)\\C=C\\[C@H](CCCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and (11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg), the same procedure was followed as in Example 2 to obtain (11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienami... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1 | Other | null | null | null | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(N)=O)=C(OC(=O)CCC)C[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77b94b1df1cb49efa2184366a550397e | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O | N1=CC=CC=C1.F.C(C)N(C(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(CCC)=O)=O)CC>>C(C)N(C(CCCCCSC1=C(C[C@H]([C@@H]1\C=C\[C@H](CCCCC)O)O)OC(CCC)=O)=O)CC | CC(C)(C)[Si](C)(C)[O:7][C@@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])/[CH:8]=[CH:9]/[C@@H:10]1[C:11]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[N:20]([CH2:21][CH3:22])[CH2:23][CH3:24])=[C:25]([O:26][C:27](=[O:28])[CH2:29][CH2:30][CH3:31])[CH2:32][C@H:33]1[O:34][Si](C)(C)C(C)(C)C>>[CH3:1][CH2:2][CH2:3]... | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O | null | null | null | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4]=[C:5]-[C:6]-1/[C:7]=[C:8]/[C:9](-[C:10])-[O;H0;D2;+0:11]-[Si](-C)(-C)-C(-C)(-C)-C>>[C:10]-[C:9](-[OH;D1;+0:11])/[C:8]=[C:7]/[C:6]1-[C:5]=[C:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 87.2 | [{"value": 78.0, "product": "C(C)N(C(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](CCCCC)O)O)OC(CCC)=O)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.2, "product": "C(C)N(C(CCCCCSC1=C(C[C@H]([C@@H]1\\C=C\\[C@H](CCCCC)O)O)OC(CCC)=O)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg), the same procedure as in Example 2 was performed to obtain N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1=CCCC1 | Other | null | null | null | CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C>>CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db7374af57ba4dcaba7944b782005f33 | CC(C)(C)C(=C(c1ccc([N+](=O)[O-])cc1)C(C)(C)C)c1ccc([N+](=O)[O-])cc1>>CC(C)(C)C(=C(c1ccc([N+](=O)[O-])cc1)C(C)(C)C)c1ccc(N)cc1 | CC(C)(C(=C(C(C)(C)C)C1=CC=C(C=C1)[N+](=O)[O-])C1=CC=C(C=C1)[N+](=O)[O-])C.C1=CCCCC1>>CC(C)(C(=C(C(C)(C)C)C1=CC=C(C=C1)N)C1=CC=C(C=C1)[N+](=O)[O-])C | O=[N+:24]([O-])[c:23]1[cH:22][cH:21][c:20]([C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[C:6]([c:7]2[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]2)[C:16]([CH3:17])([CH3:18])[CH3:19])[cH:26][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[C:6]([c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1)[C:16]([... | CC(C)(C)C(=C(c1ccc([N+](=O)[O-])cc1)C(C)(C)C)c1ccc([N+](=O)[O-])cc1 | CC(C)(C)C(=C(c1ccc([N+](=O)[O-])cc1)C(C)(C)C)c1ccc(N)cc1 | null | [Pd] | C1CCOC1 | Functional Group Interconversion | Reduction of nitro groups to amines | 5c1ea979989295c14f1f65f49e58974d5c524451abca65fc2e6cec44e3d0784f | 10b8579fd1662beac4350d758bc16e1f45ee6ea295ff9572db62110c9e2a77db | C(=Cc1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 50 | [{"value": 50.0, "product": "CC(C)(C(=C(C(C)(C)C)C1=CC=C(C=C1)N)C1=CC=C(C=C1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.9, "product": "CC(C)(C(=C(C(C)(C)C)C1=CC=C(C=C1)N)C1=CC=C(C=C1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.62 g 2,2,5,5-tetramethyl-3,4-di(4-nitrophenyl)hex-3-ene,2.6 g cyclohexene and 1.4 g 10% Pd/C in THF was refluxed for 2 hrs. The Pd/C was removed by filtration and the residue after evaporation of the solvent was purified by chromatography on silica gel (25% CH2Cl2 -hexane) to give 0.285 g (50%) 2,2,5,5-... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].C1CCOC1 | null | null | CC(C)(C)C(=C(c1ccc([N+](=O)[O-])cc1)C(C)(C)C)c1ccc([N+](=O)[O-])cc1>[Pd].C1CCOC1>CC(C)(C)C(=C(c1ccc([N+](=O)[O-])cc1)C(C)(C)C)c1ccc(N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7e4da2f6c23d4c1a8affe98a75ef0117 | CC(=O)NC1(c2ccccc2)CCN(CCC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1 | C(C)(=O)O.C(C)(=O)NC1(CCN(CC1)CCC(CN)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1.FC(C=1C=C(C=O)C=C(C1)C(F)(F)F)(F)F.C(#N)[BH3-].[Na+]>>C(C)(=O)NC1(CCN(CC1)C(CC(CN)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[NH:4][C:5]1([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH2:15][CH2:31][CH:32]([CH2:33][NH2:34])[c:35]2[cH:36][cH:37][c:38]([Cl:39])[c:40]([Cl:41])[cH:42]2)[CH2:43][CH2:44]1.O=[CH:16][c:17]1[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH... | CC(=O)NC1(c2ccccc2)CCN(CCC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1 | null | null | ClCCl.Cl.CO.O | C-C Coupling | OtherReaction | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccc(CCC(Cc2ccccc2)N2CCC(c3ccccc3)CC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[CH2;D2;+0:7]-[C:8]-[C:9])-[C:10]>>[C:5]-[#7:6](-[CH;D3;+0:7](-[C:8]-[C:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10] | null | [] | 0 | CELSIUS | null | null | To a solution of 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)butylamine (0.30 g) in methanol (3 mL) was added 3,5-bis(trifluoromethyl)benzaldehyde (0.088 mL) and the mixture cooled to 0° C. To this stirred mixture was sequentially added acetic acid (0.046 mL) and a solution of sodium cyanoborohydride (0.50... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | Other | ClCCl.Cl.CO.O | 0 | null | CC(=O)NC1(c2ccccc2)CCN(CCC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>ClCCl.Cl.CO.O>CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-615b2ecff1214a958b8e4deec4b08fcd | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=Cc1ccccc1>>CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CNCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1 | C(C)(=O)NC1(CCN(CC1)C(CC(CN)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1.C(C1=CC=CC=C1)=O.ClC=1C=C(C=CC1Cl)CCCCN.FC(C=1C=C(C=O)C=C(C1)C(F)(F)F)(F)F>>C(C)(=O)NC1(CCN(CC1)C(CC(CNCC1=CC=CC=C1)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[NH:4][C:5]1([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH:15]([CH2:16][c:17]2[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[CH2:31][CH:32]([CH2:33][NH2:34])[c:42]2[cH:43][cH:44][c:45]([Cl:46])[c:47]([Cl:48])[cH:49]2)[CH2:50][CH2:... | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=Cc1ccccc1 | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CNCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNCC(CC(Cc2ccccc2)N2CCC(c3ccccc3)CC2)c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Using a procedure similar to that described in Example 1, except replacing the (3,4-dichlorophenyl)butylamine and the 3,5-bis-(trifluoromethyl)benzaldehyde used therein with 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine and benzaldehyde, respectively, the title c... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=Cc1ccccc1>>CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CNCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a37d4b3af3174cb3b9d2b4d6eb76f09a | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.CC(=O)OC(C)=O>>CC(=O)NCC(CC(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1 | C(C)(=O)OC(C)=O.C(C)(=O)NC1(CCN(CC1)C(CC(CN)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1.C(C)(=O)OC(C)=O.C(C)(C)N(CC)C(C)C>>C(C)(=O)NC1(CCN(CC1)C(CC(CNC(C)=O)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1 | [NH2:4][CH2:5][CH:6]([CH2:7][CH:8]([CH2:9][c:10]1[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23]1)[N:24]1[CH2:25][CH2:26][C:27]([NH:28][C:29]([CH3:30])=[O:31])([c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[CH2:38][CH2:39]1)[c:40]1[cH:41][cH:42][c:43]([Cl:44])[c:45]([Cl:46])[... | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.CC(=O)OC(C)=O | CC(=O)NCC(CC(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1 | null | CN(C1=CC=NC=C1)C | ClCCl.Cl.O.O1CCCC1 | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc(CCC(Cc2ccccc2)N2CCC(c3ccccc3)CC2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 8 | HOUR | To a stirred solution of 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine (0.4 g) in tetrahydrofuran (4 mL) was added acetic anhydride (0.085 mL) and diisopropylethylamine (0.32 mL). After 2 hours at room temperature 4-dimethylaminopyridine (7 mg) was added and the ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl.Cl.O.O1CCCC1 | null | 8 | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.CC(=O)OC(C)=O>CN(C1=CC=NC=C1)C.ClCCl.Cl.O.O1CCCC1>CC(=O)NCC(CC(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-be2035c7c1d141fb862b1d083535d3de | C=O.CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1>>CNCC(CC(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1 | C(C)(=O)O.C(C)(=O)NC1(CCN(CC1)C(CC(CN)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1.C=O.C(#N)[BH3-].[Na+]>>C(C)(=O)NC1(CCN(CC1)C(CC(CNC)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1 | O=[CH2:1].[NH2:2][CH2:3][CH:4]([CH2:5][CH:6]([CH2:7][c:8]1[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1)[N:22]1[CH2:23][CH2:24][C:25]([NH:26][C:27]([CH3:28])=[O:29])([c:30]2[cH:31][cH:32][cH:33][cH:34][cH:35]2)[CH2:36][CH2:37]1)[c:38]1[cH:39][cH:40][c:41]([Cl:42])[c:43]([... | C=O.CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1 | CNCC(CC(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1 | null | null | ClCCl.CO.O.C([O-])(O)=O.[Na+] | Heteroatom Alkylation and Arylation | Reductive methylation of primary amine with formaldehyde | 51d235def9103cd7a524cbedb590276839772d481304df37a121e64cb81721f4 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccc(CCC(Cc2ccccc2)N2CCC(c3ccccc3)CC2)cc1 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH2;D1;+0:4]>>[C:2]-[C:3]-[NH;D2;+0:4]-[CH3;D1;+0:1] | null | [] | 0 | CELSIUS | null | null | To a stirred solution of 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine (0.30 g) in methanol (4 mL) was added aqueous formaldehyde (37% w/w, 0.027 mL). The mixture was cooled to 0° C. and acetic acid (0.038 mL) was added followed by a solution of sodium cyanoboroh... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | Other | ClCCl.CO.O.C([O-])(O)=O.[Na+] | 0 | null | C=O.CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1>ClCCl.CO.O.C([O-])(O)=O.[Na+]>CNCC(CC(Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1)N1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0f557f1000674f4b902d975b3b805985 | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=CO>>CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CNC=O)c2ccc(Cl)c(Cl)c2)CC1 | C(=O)O.Cl.CN(CCCN=C=NCC)C.C(C)(=O)NC1(CCN(CC1)C(CC(CN)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1.CN1CCOCC1>>C(C)(=O)NC1(CCN(CC1)C(CC(CNC=O)C1=CC(=C(C=C1)Cl)Cl)CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[NH:4][C:5]1([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH:15]([CH2:16][c:17]2[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]2)[CH2:31][CH:32]([CH2:33][NH2:34])[c:37]2[cH:38][cH:39][c:40]([Cl:41])[c:42]([Cl:43])[cH:44]2)[CH2:45][CH2:... | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=CO | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CNC=O)c2ccc(Cl)c(Cl)c2)CC1 | null | null | ClCCl.Cl.O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(CCC(Cc2ccccc2)N2CCC(c3ccccc3)CC2)cc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]-[C:4]-[NH;D2;+0:5]-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | 15 | MINUTE | To a 0° C. solution of formic acid (0.09 mL) in dichloromethane (3 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.23 g) and the mixture stirred for 15 minutes. To this mixture was added a solution of 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HO- | ClCCl.Cl.O | null | 0.25 | CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CN)c2ccc(Cl)c(Cl)c2)CC1.O=CO>ClCCl.Cl.O>CC(=O)NC1(c2ccccc2)CCN(C(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC(CNC=O)c2ccc(Cl)c(Cl)c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d14267579d347aaab5da8765031fa8d | CC1(N)N=C(O)C=C(O)N1>>Cc1nc(O)cc(O)n1 | OC1=NC(NC(=C1)O)(N)C.[O-]CC.[Na+].[Na].Cl.C(C)(=N)N.C(CC(=O)OCC)(=O)OCC>>OC1=NC(=NC(=C1)O)C | N[C:2]1([CH3:1])[N:3]=[C:4]([OH:5])[CH:6]=[C:7]([OH:8])[NH:9]1>>[CH3:1][c:2]1[n:3][c:4]([OH:5])[cH:6][c:7]([OH:8])[n:9]1 | CC1(N)N=C(O)C=C(O)N1 | Cc1nc(O)cc(O)n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 0874d0075314f074b492eff8e0326b779822212aa8c43b93b315cb0c67e901a6 | 8c3f0b9f773c08a752e3c77dd2b55653809cd7c609bf5f8f068eedde25a3e577 | c1cncnc1 | N-[C;H0;D4;+0:1]1(-[C;D1;H3:2])-[N;H0;D2;+0:3]=[C;H0;D3;+0:4](-[O;D1;H1:5])-[CH;D2;+0:6]=[C;H0;D3;+0:7](-[O;D1;H1:8])-[NH;D2;+0:9]-1>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[O;D1;H1:5]):[cH;D2;+0:6]:[c;H0;D3;+0:7](-[O;D1;H1:8]):[n;H0;D2;+0:9]:1 | null | [] | null | null | 3.5 | HOUR | The first intermediate, 4,6-dihydroxy-2-methylpyrimidinamine, is synthesized by preparing sodium ethoxide in situ from sodium and an hydrous ethanol under a nitrogen blanket. Acetamidine hydrochloride and diethyl malonate are added and the reaction mixture heated to boiling for 2 to 5 hours to afford 4,6-dihydroxy-2-me... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enol.Primary amine | Aromatic alcohol.Aromatic alcohol | C1=CNCN=C1 | c1cncnc1 | c1cncnc1 | Other | C(C)O | null | 3.5 | CC1(N)N=C(O)C=C(O)N1>C(C)O>Cc1nc(O)cc(O)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fc482eaeb84f48f6beade7036825e8ec | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)n1>>Cc1nc(Cl)c(N)c(Cl)n1 | ClC1=NC(=NC(=C1[N+](=O)[O-])Cl)C>>ClC1=NC(=NC(=C1N)Cl)C | O=[N+:7]([O-])[c:6]1[c:4]([Cl:5])[n:3][c:2]([CH3:1])[n:10][c:8]1[Cl:9]>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([NH2:7])[c:8]([Cl:9])[n:10]1 | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)n1 | Cc1nc(Cl)c(N)c(Cl)n1 | null | [Ni] | C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1cncnc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[Cl;D1;H0:9]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c:2]:1-[NH2;D1;+0:1] | null | [] | null | null | null | null | The third intermediate, 4,6-dichloro-2-methyl-5-nitropyrimidine is hydrogenated over Raney-Ni as a 10% to 30% solution in toluene to afford the corresponding compound, 4,6-dichloro-2-methyl-5-aminopyrimidine, as a fourth intermediate.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cncnc1 | Other | [Ni].C1(=CC=CC=C1)C | null | null | Cc1nc(Cl)c([N+](=O)[O-])c(Cl)n1>[Ni].C1(=CC=CC=C1)C>Cc1nc(Cl)c(N)c(Cl)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-034dc9437bee48c3847af5a6f9237cbd | CC(=O)N1CCNC1=Nc1c(Cl)nc(C)nc1Cl.C[O-]>>COc1nc(C)nc(Cl)c1N=C1NCCN1 | C(C)(=O)N1C(NCC1)=NC=1C(=NC(=NC1Cl)C)Cl.C[O-].[Na+].[Na].C[O-].[Na+]>>ClC1=NC(=NC(=C1N=C1NCCN1)OC)C | CC(=O)[N:16]1[C:12](=[N:11][c:10]2[c:3](Cl)[n:4][c:5]([CH3:6])[n:7][c:8]2[Cl:9])[NH:13][CH2:14][CH2:15]1.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[n:4][c:5]([CH3:6])[n:7][c:8]([Cl:9])[c:10]1[N:11]=[C:12]1[NH:13][CH2:14][CH2:15][NH:16]1 | CC(=O)N1CCNC1=Nc1c(Cl)nc(C)nc1Cl.C[O-] | COc1nc(C)nc(Cl)c1N=C1NCCN1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 261cb092c646fb8b95a4c4b3353ba2904f492f41dd6b7d7795ebd05c8fac5a3d | 365bcfafcdf9c10eed012708b51c1f4254f563747f5b31fee043d8c008793122 | c1ncc(N=C2NCCN2)cn1 | C-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-1=[#7:6]-[c:7]1:[c:8](-[Cl;D1;H0:9]):[#7;a:10]:[c:11]:[#7;a:12]:[c;H0;D3;+0:13]:1-Cl.[C;D1;H3:14]-[O-;H0;D1:15]>>[C;D1;H3:14]-[O;H0;D2;+0:15]-[c;H0;D3;+0:13]1:[#7;a:12]:[c:11]:[#7;a:10]:[c:8](-[Cl;D1;H0:9]):[c:7]:1-[#7:6]=[C:5]1-[#7:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | The final product, 4-chloro-N-(imidazolin-2-ylidene)-6-methoxy-2-methyl-5-pyrimidinamine is synthesized by first preparing sodium methoxide in situ from anhydrous methanol and sodium. The fifth intermediate, N-(1-acetylimidazolin-2-ylidene)-4,6-dichloro-2-methyl-5-pyrimidinamine, is added and the reaction mixture broug... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ether.Secondary amine | C1C[NH]CN1.c1cncnc1 | c1cncnc1.C1CNCN1 | c1cncnc1.C1CNCN1 | HCl | CO | null | null | CC(=O)N1CCNC1=Nc1c(Cl)nc(C)nc1Cl.C[O-]>CO>COc1nc(C)nc(Cl)c1N=C1NCCN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0f828e1e7cdc4b0fbb57ab56bd4b3b86 | O=S(=O)(O)O.Oc1ccccc1>>O=S(=O)(O)c1ccc(O)cc1 | OS(=O)(=O)O.O=S(=O)=O.C1(=CC=CC=C1)O>>C1=CC(=CC=C1O)S(=O)(=O)O | O[S:2](=[O:1])(=[O:3])[OH:4].[cH:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | O=S(=O)(O)O.Oc1ccccc1 | O=S(=O)(O)c1ccc(O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4de7a411ca4a8e56f858115b27e6157e074d8465bf6f118cb7ff1cf307084c04 | a824d87b0e6c732faabe155a548de29df954da8631ad9b191cacb2d591bbcaa7 | c1ccccc1 | O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;D1;H1:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[O;D1;H1:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | 1 | HOUR | 440 parts of 66% oleum are added slowly at from 60° to 70° C. to 500 parts of melted phenol, and the mixture is subsequently sulfonated at 100° C. for 1 hour. The phenolsulfonic acid formed is then slowly heated at from 160° to 165° C. in a vacuum of from about 11 to 13 mm, so that only a little phenol distils off, and... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | 1 | O=S(=O)(O)O.Oc1ccccc1>>O=S(=O)(O)c1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-86496e40601a420c9b4fe32d008df94f | O=S(=O)(O)O.Oc1ccccc1>>O=S(=O)(O)c1ccc(O)cc1 | OS(=O)(=O)O.O=S(=O)=O.C1(=CC=CC=C1)O>>C1=CC(=CC=C1O)S(=O)(=O)O | O[S:2](=[O:1])(=[O:3])[OH:4].[cH:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | O=S(=O)(O)O.Oc1ccccc1 | O=S(=O)(O)c1ccc(O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4de7a411ca4a8e56f858115b27e6157e074d8465bf6f118cb7ff1cf307084c04 | a824d87b0e6c732faabe155a548de29df954da8631ad9b191cacb2d591bbcaa7 | c1ccccc1 | O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;D1;H1:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[O;D1;H1:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | 1 | HOUR | 478 parts of 20% oleum are added with stirring to 500 parts of melted phenol, with cooling to ensure that the temperature does not exceed 70° C. The mixture is then sulfonated at 105° C. for 1 hour. The phenolsulfonic acid formed is heated slowly at from 150° to 155° C. under reduced pressure of 11 to 13 torr, and this... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | 1 | O=S(=O)(O)O.Oc1ccccc1>>O=S(=O)(O)c1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-99680520cbc245bc8e09a95648450d19 | C=CC(=O)OC.O=C(O)CNCC(=O)O>>COC(=O)CCN(CC(=O)O)CC(=O)O | C(C=C)(=O)OC.Cl.[OH-].[Na+].C(C=C)(=O)OC.N(CC(=O)O)CC(=O)O>>C(=O)(O)CN(CCC(=O)OC)CC(=O)O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].[NH:7]([CH2:8][C:9](=[O:10])[OH:11])[CH2:12][C:13](=[O:14])[OH:15]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][N:7]([CH2:8][C:9](=[O:10])[OH:11])[CH2:12][C:13](=[O:14])[OH:15] | C=CC(=O)OC.O=C(O)CNCC(=O)O | COC(=O)CCN(CC(=O)O)CC(=O)O | null | null | O | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | 281338207899411a693d475f5874e69a953d9793da7289fa7cfd38421de9c393 | e6898c28c2a6b7f7f5b5322689c9c6b3b6ad3dd52268b1e45ad4c4843df05f7d | null | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[O;D1;H0:7]=[C:8](-[O;D1;H1:9])-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[N;H0;D3;+0:11](-[C:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15])-[C:10]-[C:8](=[O;D1;H0:7])-[O;D... | 96 | [{"value": 96.0, "product": "C(=O)(O)CN(CCC(=O)OC)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | 133 g (1.00 mol) of iminodiacetic acid were dissolved in 530 ml of water, and the solution was adjusted to pH 7.0 with 40.5 g (1.00 mol) of solid NaOH. 86.0 g (1.00 mol) of methyl acrylate were added dropwise to this solution at 20° C., and the mixture was then stirred for 6 h. The methyl acrylate content after this ti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Vinyl | Ester.Tertiary amine | null | null | null | null | O | null | 6 | C=CC(=O)OC.O=C(O)CNCC(=O)O>O>COC(=O)CCN(CC(=O)O)CC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a90868bcdfa84bafb88a66b6d780809a | O=S(=O)(O)O>>O=S(=O)(O)O | [OH-].[Na+].S(O)(O)(=O)=O.NC(=O)N>>S(O)(O)(=O)=O.NC(=O)N | [O:5]=[S:6](=[O:7])([OH:8])[OH:9]>>[O:5]=[S:6](=[O:7])([OH:8])[OH:9] | O=S(=O)(O)O | O=S(=O)(O)O | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | Prilled urea (17.5 grams, 0.29 moles) was dissolved in 53.5 grams water. To this solution was slowly added sulfuric acid (29.0 grams, 0.26 moles, 89.3%) at 66° C. The temperature was maintained below 50° C. in a cooling bath during the addition. The final solution on titration with 0.5N NaOH (phenolphthalein indicator)... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | O=S(=O)(O)O>O>O=S(=O)(O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-889d3fb76dc4464094f72ea8e4bc1474 | C=CC(N)=O.CC(C)(N=NC(C)(C)C1=NCCN1)C1=NCCN1.Cl>>C=CC(N)=O.CCl | C(C=C)(=O)N.[Cl-].C(C=C)(=O)OCC.C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O.Cl.Cl.N(=NC(C)(C)C=1NCCN1)C(C)(C)C=1NCCN1>>C(C=C)(=O)N.CCl.C(C=C)(=O)OCC | [CH2:8]=[CH:9][C:10]([NH2:11])=[O:12].CC(C)(N=NC(C)(C1=NCCN1)[CH3:13])C1=NCCN1.[ClH:14]>>[CH2:8]=[CH:9][C:10]([NH2:11])=[O:12].[CH3:13][Cl:14] | C=CC(N)=O.CC(C)(N=NC(C)(C)C1=NCCN1)C1=NCCN1.Cl | C=CC(N)=O.CCl | null | null | O | Miscellaneous | OtherReaction | 785bce4c0acb75870b3148764a843e343dc0cf0c38ae2dfc11375d60a1898def | f031920ffd7a64c0e3bc8da8b6bdfc5c52af5440f2051d430a793359451db646 | null | C-C(-C)(-N=N-C(-C)(-[CH3;D1;+0:1])-C1=N-C-C-N-1)-C1=N-C-C-N-1.[ClH;D0;+0:2]>>[CH3;D1;+0:1]-[Cl;H0;D1;+0:2] | 10 | [{"value": 10.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A 10% solution of poly(AMD/DMAEA.MeCl/EA) was prepared as follows: 13.87 parts of 53.58% aqueous acrylamide (AMD), 25.31 parts of a 80% aqueous solution of ethacryloxyethyltrimethylammonium chloride (DMAEA.MeCl), 2.33 parts of ethyl acrylate (EA), 0.3 part EDTA, 258.16 parts of deionized water and 0.030 parts of VA-044... | 10.6084/m9.figshare.5104873.v1 | null | Diazene.Secondary amine.Secondary amine | null | C1=NCCN1.C1=NCCN1 | null | null | Other | O | null | 1 | C=CC(N)=O.CC(C)(N=NC(C)(C)C1=NCCN1)C1=NCCN1.Cl>O>C=CC(N)=O.CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-174ccccc38a64a6887d340e17eeb43b4 | O=[N+]([O-])c1ccc(F)cc1.OCC(F)(F)F>>O=[N+]([O-])c1ccc(OCC(F)(F)F)cc1 | O.[Na].FC1=CC=C(C=C1)[N+](=O)[O-].FC(CO)(F)F>>FC(COC1=CC=C(C=C1)[N+](=O)[O-])(F)F | F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:15][cH:14]1.[OH:8][CH2:9][C:10]([F:11])([F:12])[F:13]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1 | O=[N+]([O-])c1ccc(F)cc1.OCC(F)(F)F | O=[N+]([O-])c1ccc(OCC(F)(F)F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C:10]-[OH;D1;+0:11]>>[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 62 | [{"value": 62.0, "product": "FC(COC1=CC=C(C=C1)[N+](=O)[O-])(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under a nitrogen atmosphere, 10.1 g (0.44 mol) of sodium was dissolved in 200 ml of 2,2,2-trifluoro ethanol in 300 ml of a three-necked flask, to which 40 ml (0.38 mol) of p-fluoronitro benzene was dropped and refluxed for 4 hours. After cooling to a room temperature, water was poured (about 1 liter), and precipitated ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | null | null | null | O=[N+]([O-])c1ccc(F)cc1.OCC(F)(F)F>>O=[N+]([O-])c1ccc(OCC(F)(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-785e0a0408f94a47b06e9ceee5b1cfa9 | O=[N+]([O-])c1ccc(OCC(F)(F)F)cc1>>Nc1ccc(OCC(F)(F)F)cc1 | FC(COC1=CC=C(C=C1)[N+](=O)[O-])(F)F.C(C)O.Cl>>FC(COC1=CC=C(N)C=C1)(F)F | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]1 | O=[N+]([O-])c1ccc(OCC(F)(F)F)cc1 | Nc1ccc(OCC(F)(F)F)cc1 | null | null | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 94 | [{"value": 94.0, "product": "FC(COC1=CC=C(N)C=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "FC(COC1=CC=C(N)C=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a nitrogen atmosphere, 30.1 g (0.14 mol) of p-(2,2,2-trifluroethoxy) nitrobenzene, 82.1 g (1.47 mol) of reduced iron, 120 ml of ethanol and 40 ml of water were placed in a three-necked flask, to which 1.4 ml of concentrated hydrochloric acid was dropped under stirring and then refluxed for one hour. After cooling to... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | O | null | null | O=[N+]([O-])c1ccc(OCC(F)(F)F)cc1>O>Nc1ccc(OCC(F)(F)F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9102e88c394640fc8efd773b9c3e0835 | O=P(O)(O)O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>O=P([O-])([O-])OP(=O)([O-])[O-] | [O-2].[O-2].[Ti+4].[O-2].[O-2].[Ti+4].O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.[O-2].[O-2].[Ti+4].P(O)(O)(O)=O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>[O-]P([O-])(=O)OP(=O)([O-])[O-].[Ti+4] | [O:1]=[P:2]([OH:3])([OH:4])[OH:5].O=P12OP3(=O)OP(=O)(O1)[O:9][P:6](=[O:7])(O2)[O:8]3>>[O:1]=[P:2]([O-:3])([O-:4])[O:5][P:6](=[O:7])([O-:8])[O-:9] | O=P(O)(O)O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | O=P([O-])([O-])OP(=O)([O-])[O-] | null | null | null | Functional Group Interconversion | OtherReaction | 984d7e95798f9d2c581130f421f542f9bc9ee9e6dd52cb07273abd9cc125b05b | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | O=P12-O-P3(=O)-O-P(=O)(-O-1)-[O;H0;D2;+0:1]-[P;H0;D4;+0:2](=[O;D1;H0:3])(-O-2)-[O;H0;D2;+0:4]-3.[O;D1;H0:5]=[#15:6](-[OH;D1;+0:7])(-[OH;D1;+0:8])-[OH;D1;+0:9]>>[O-;H0;D1:7]-[#15:6](-[O-;H0;D1:8])(=[O;D1;H0:5])-[O;H0;D2;+0:9]-[P;H0;D4;+0:2](-[O-;H0;D1:4])(-[O-;H0;D1:1])=[O;D1;H0:3] | null | [] | null | null | null | null | The method of the present invention generally involves the mixture of titanium dioxide and hot concentrated phosphoric acid in a reaction vessel. The reaction mixture has a phosphorus pentoxide to titanium dioxide mole ratio greater than one. Preferably, the phosphorus pentoxide to titanium dioxide mole ratio is about ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | O1P2OP3OP1OP(O2)O3 | null | null | HO- | null | null | null | O=P(O)(O)O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>O=P([O-])([O-])OP(=O)([O-])[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36aa7f1e188145b59bcac8eea2adfe61 | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>O=P([O-])([O-])OP(=O)([O-])[O-] | [O-2].[O-2].[Ti+4].[O-2].[O-2].[Ti+4].P(O)(O)(O)=O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>[O-]P([O-])(=O)OP(=O)([O-])[O-].[Ti+4] | O=P12OP3(=O)[O:3][P:2](=[O:1])([O:4]1)[O:5][P:6](=[O:7])([O:8]2)[O:9]3>>[O:1]=[P:2]([O-:3])([O-:4])[O:5][P:6](=[O:7])([O-:8])[O-:9] | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3 | O=P([O-])([O-])OP(=O)([O-])[O-] | null | null | null | Functional Group Interconversion | OtherReaction | 984d7e95798f9d2c581130f421f542f9bc9ee9e6dd52cb07273abd9cc125b05b | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | O=P12-O-P3(=O)-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[#8:4]-[#15:5](=[O;D1;H0:6])(-[O;H0;D2;+0:7]-1)-[O;H0;D2;+0:8]-3)-[O;H0;D2;+0:9]-2>>[O-;H0;D1:1]-[#15:2](-[O-;H0;D1:9])(=[O;D1;H0:3])-[#8:4]-[#15:5](-[O-;H0;D1:7])(-[O-;H0;D1:8])=[O;D1;H0:6] | 90 | [{"value": 90.0, "product": "[O-]P([O-])(=O)OP(=O)([O-])[O-].[Ti+4]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | thermally reacting titanium dioxide and phosphoric acid at a temperature of about 400° C. to about 500° C. in a reaction mixture having a phosphorus pentoxide to titanium dioxide mole ratio of about 1.20 to about 1.25 to form a fine titanium pyrophosphate powder with greater than 90% of said fine titanium pyrophosphate... | 10.6084/m9.figshare.5104873.v1 | null | null | null | O1P2OP3OP1OP(O2)O3 | null | null | Other | null | null | null | O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3>>O=P([O-])([O-])OP(=O)([O-])[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dba6f3dde0664944932faac3af102356 | CI.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OCc1ccccc1>>COC(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)OCc1ccccc1 | IC.COC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=C(C=C1)O)=O.C([O-])([O-])=O.[K+].[K+]>>COC([C@@H](NC(=O)OCC1=CC=CC=C1)CC1=CC=C(C=C1)OC)=O | I[CH3:12].[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:13][cH:14]1)[NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14]1)[NH:15][C:16](=[O:17])[O:18][CH2:19][c:20]1[... | CI.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OCc1ccccc1 | COC(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | O=C(NCCc1ccccc1)OCc1ccccc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | 32.94 g (100 mmol) of N-benzyloxycarbonyl-tyrosine methyl ester is mixed in 200 ml of DMF with 27.64 g (200 mmol) of ground potassium carbonate. 15.6 g (110 mmol) of iodomethane is instilled in this suspension and stirred overnight at room temperature. The solution is concentrated by evaporation, dispersed between ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HI | CN(C)C=O | null | 8 | CI.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OCc1ccccc1>CN(C)C=O>COC(=O)[C@H](Cc1ccc(OC)cc1)NC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2219c1d1d75847559c21756e148ff10b | CC(=O)c1ccc2c(c1)CC(C)O2.OBr>>CC1Cc2cc(C(=O)O)ccc2O1 | Cl.BrBr.[OH-].[Na+].C(C)(=O)C=1C=C2CC(OC2=CC1)C.BrO>>C(=O)(O)C=1C=C2CC(OC2=CC1)C | C[C:7]([c:6]1[cH:5][c:4]2[c:12]([cH:11][cH:10]1)[O:13][CH:2]([CH3:1])[CH2:3]2)=[O:8].Br[OH:9]>>[CH3:1][CH:2]1[CH2:3][c:4]2[cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][cH:11][c:12]2[O:13]1 | CC(=O)c1ccc2c(c1)CC(C)O2.OBr | CC1Cc2cc(C(=O)O)ccc2O1 | null | null | O.O1CCOCC1 | Acylation | OtherReaction | e1d216f9ec5d1e0ab04cbd7e284acaaebe679828044d718ad57104584ff5302e | 7b5bc8122b5027b4d965c982eed9443b26b90bd801407eec9b2b367c037fc8de | c1ccc2c(c1)CCO2 | Br-[OH;D1;+0:1].C-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[O;D1;H0:3]=[C;H0;D3;+0:2](-[OH;D1;+0:1])-[c:4](:[c:5]):[c:6] | 57.4 | [{"value": 57.4, "product": "C(=O)(O)C=1C=C2CC(OC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "C(=O)(O)C=1C=C2CC(OC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | On an ice-common salt bath, 6.25 ml of bromine was added dropwise to a solution of 15.1 g of sodium hydroxide in 100 ml of water under stirring and cooling. To a solution of 6.50 g of 5-acetyl-2-methyl coumaran (Ml) in 100 ml of dioxane, the above mixture (i.e., hypobromous acid solution) was added dropwise at 3°-8° C.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Carboxylic acid | null | null | c1ccc2c(c1)CCO2 | HBr | O.O1CCOCC1 | null | null | CC(=O)c1ccc2c(c1)CC(C)O2.OBr>O.O1CCOCC1>CC1Cc2cc(C(=O)O)ccc2O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-74043014bdd746ff9751b62ff8d91839 | CC1Cc2cc(C(=N)N)ccc2O1.CC1Cc2cc(C(=O)O)ccc2O1>>CCCCCCCCc1ccc(-c2cnc(-c3ccc4c(c3)CC(C)O4)nc2)cc1 | C[O-].[Na+].Cl.C(N)(=N)C=1C=C2CC(OC2=CC1)C.C(=O)(O)C=1C=C2CC(OC2=CC1)C>>CC1OC2=CC=C(C=C2C1)C1=NC=C(C=N1)C1=CC=C(C=C1)CCCCCCCC | [NH2:15][C:16]([c:17]1[cH:18][cH:19][c:20]2[c:21]([cH:22]1)[CH2:23][CH:24]([CH3:25])[O:26]2)=[NH:27].O=[C:13](O)[c:12]1[cH:5][c:4]2[c:9]([cH:30][cH:29]1)O[CH:2]([CH3:1])[CH2:3]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][n:15][c:16](-[c:17]3[cH:18][cH:19][c:20]4[... | CC1Cc2cc(C(=N)N)ccc2O1.CC1Cc2cc(C(=O)O)ccc2O1 | CCCCCCCCc1ccc(-c2cnc(-c3ccc4c(c3)CC(C)O4)nc2)cc1 | null | null | CO | C-C Coupling | OtherReaction | 32ea512a0b0c0a08f0b1a65f4ed6194340dc244897306482934e9b45d932f117 | 8c413d7c50ade1af88c69e9a2a3bf780b58b3c8c53f942b06480db8d8f10a730 | c1ccc(-c2cnc(-c3ccc4c(c3)CCO4)nc2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5]2:[c;H0;D3;+0:6](:[cH;D2;+0:7]:1)-[C:8]-[CH;D3;+0:9](-[C;D1;H3:10])-O-2.[NH2;D1;+0:11]-[C;H0;D3;+0:12](=[NH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[C;D1;H3:10]-[CH2;D2;+0:9]-[C:8]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C:19]-[C:20]-[C:21]-[c;H0;D3;... | 58.4 | [{"value": 58.4, "product": "CC1OC2=CC=C(C=C2C1)C1=NC=C(C=N1)C1=CC=C(C=C1)CCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.40 g (1.88 mM) of 5-amidino-2-methylcoumaran hydrochloride (M5) as an intermediate product prepared in Example 1, 0.79 g (1.90 mM) of 3-dimethylamino-2-(4-octylphenyl)-N,N-dimethylpropene-(2)-ammonium perchlorate 0.41 g (7.59 mM) of sodium methylate and 15 ml of methanol were placed in a 50 ml-round bottomed flask an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | null | c1ccc2c(c1)CCO2 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccc2c(c1)CCO2 | null | CO | null | null | CC1Cc2cc(C(=N)N)ccc2O1.CC1Cc2cc(C(=O)O)ccc2O1>CO>CCCCCCCCc1ccc(-c2cnc(-c3ccc4c(c3)CC(C)O4)nc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7cfb9a4aa79d4897a5745b991d796205 | CCCCCCCCC(=O)OC(=O)CCCCCCCC.Oc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCCCc1cc2ccccc2o1 | C(C)N(CC)CC.[Br-].OC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1.C(CCCCCCCC)(=O)OC(CCCCCCCC)=O>>C(CCCCCCC)C=1OC2=C(C1)C=CC=C2 | CCCCCCCCC(=O)O[C:9](=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[OH:17])cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[o:17]1 | CCCCCCCCC(=O)OC(=O)CCCCCCCC.Oc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCCCc1cc2ccccc2o1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 06e94a6dcd746736c6cf6cc292284b9776b898eaa1042b8cc777d98ad50eab2b | 6720b0fe7909c5c14b6890f35a7242cac504e521ec14a785321a1fee7a7aa3da | c1ccc2occc2c1 | C-C-C-C-C-C-C-C-C(=O)-O-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7](-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:9]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:8]:[c:7](:[c:9]):[c:5](:[c:6]):[o;H0;D2;+0:4]:1 | 76.6 | [{"value": 76.6, "product": "C(CCCCCCC)C=1OC2=C(C1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 112 g (249 mM) of (2-hydroxybenzyl)triphenylphosphonium bromide, 83 g (278 mM) of nonanoic anhydride, 104 g (1.03 mM) of triethylamine and 800 ml of toluene were placed in a 3 1-three-necked flask, followed by refluxing for 4.5 hours under stirring. After the reaction, the reaction mixture was left standing at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2occc2c1 | c1ccc2occc2c1 | HO- | C1(=CC=CC=C1)C | null | null | CCCCCCCCC(=O)OC(=O)CCCCCCCC.Oc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>CCCCCCCCc1cc2ccccc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f28ffd070d2241e988f52b5c36d20b5d | CCCCCCCCc1cc2ccccc2o1>>CCCCCCCCC1Cc2ccccc2O1 | C(CCCCCCC)C=1OC2=C(C1)C=CC=C2>>C(CCCCCCC)C1OC2=CC=CC=C2C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[o:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17]1 | CCCCCCCCc1cc2ccccc2o1 | CCCCCCCCC1Cc2ccccc2O1 | null | [C].[Pd] | C(C)O | Reduction | OtherReaction | b86bd3f15ad056b18f24f98e80df6dc8108bba5322ef4250b69a51408c14b3cb | 7ece147c6909fe307632f67c21e1517a1747c8ff389dff4b19e644c711d1d84d | c1ccc2c(c1)CCO2 | [C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:8]):[o;H0;D2;+0:9]:1>>[C:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8])-[O;H0;D2;+0:9]-1 | 94.6 | [{"value": 94.6, "product": "C(CCCCCCC)C1OC2=CC=CC=C2C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Then, 44 g of 2-octylbenzofuran was dissolved in 440 ml of ethanol. To the solution 35 g of 10%-palladium-carbon was added to effect catalytic reduction for 3 hours sunder normal pressure. After the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a res... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccc2occc2c1 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | null | [C].[Pd].C(C)O | null | null | CCCCCCCCc1cc2ccccc2o1>[C].[Pd].C(C)O>CCCCCCCCC1Cc2ccccc2O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0e0dacda86084c48b46139c9f6c1c731 | BrBr.CCCCCCCCC1Cc2ccccc2O1>>CCCCCCCCC1Cc2cc(Br)ccc2O1 | C(CCCCCCC)C1OC2=CC=CC=C2C1.BrBr.C(=O)(O)[O-].[Na+].O>>BrC=1C=C2CC(OC2=CC1)CCCCCCCC | Br[Br:14].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][c:11]2[cH:12][cH:13][cH:15][cH:16][c:17]2[O:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[O:18]1 | BrBr.CCCCCCCCC1Cc2ccccc2O1 | CCCCCCCCC1Cc2cc(Br)ccc2O1 | null | null | ClCCl | Functional Group Interconversion | Bromination | 8a5899f39c577ae2f5dbb7e89484f9814910050aa00e810b5c8bafb1acd06dbc | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2c(c1)CCO2 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | 96.3 | [{"value": 96.3, "product": "BrC=1C=C2CC(OC2=CC1)CCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 50 ml-three-necked flask, 2.00 g (8.61 mM) of 2-octylcoumaran and 3.2 ml of dichloremethane were placed and mixed to obtain a solution. To the solution, 0.73 (8.69 mM) of NaHCO3 and 3.2 ml of water were added. To the mixture, a solution of 0.44 ml (0.54 mM) of bromine in 1 ml of dichloromethane were added dropwise... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HBr | ClCCl | null | null | BrBr.CCCCCCCCC1Cc2ccccc2O1>ClCCl>CCCCCCCCC1Cc2cc(Br)ccc2O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bcf47efb084b407da3df0c21bd581e1b | CC(C)OB(OC(C)C)OC(C)C.CCCCCCC(Br)CC1Cc2ccccc2O1>>CCCCCCCCC1Cc2cc(B(O)O)ccc2O1 | O.C(C)(C)OB(OC(C)C)OC(C)C.BrC(CC1OC2=CC=CC=C2C1)CCCCCC.C(CCC)[Li]>>C(CCCCCCC)C1OC2=CC=C(C=C2C1)B(O)O | CC(C)O[B:14]([O:15]C(C)C)[O:16]C(C)C.Br[CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:8][CH:9]1[CH2:10][c:11]2[cH:12][cH:13][cH:17][cH:18][c:19]2[O:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][c:11]2[cH:12][c:13]([B:14]([OH:15])[OH:16])[cH:17][cH:18][c:19]2[O:20]1 | CC(C)OB(OC(C)C)OC(C)C.CCCCCCC(Br)CC1Cc2ccccc2O1 | CCCCCCCCC1Cc2cc(B(O)O)ccc2O1 | null | null | C1CCOC1.CCCCCC | Miscellaneous | OtherReaction | 04f258477ada574ec7deb70066f24e9226c81b4144647bddc16f35f3ab7f443f | 439f75838a365ac96edb92157a4b914b608bcaa4f1e95debd26b1d95d818cefc | c1ccc2c(c1)CCO2 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]-[#8:6].[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11].C-C(-C)-O-[B;H0;D3;+0:12](-[O;H0;D2;+0:13]-C(-C)-C)-[O;H0;D2;+0:14]-C(-C)-C>>[#8:6]-[C:5]-[C:4]-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:13]-[B;H0;D3;+0:12](-[OH;D1;+0:14])-[c;H0;D3;+0:9](:[c:8]:[c:7]):[c:10]:[c:11] | 67.1 | [{"value": 67.1, "product": "C(CCCCCCC)C1OC2=CC=C(C=C2C1)B(O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Then, 2.00 g (6.43 mM) of b-bromo-2-octylcoumaran and 28 ml of dry THF were placed in a 100 ml-three-necked flask. To the mixture, 4.5 ml (7.20 mM) of a 1.6M solution of butyllithium in hexane was added dropwise under stirring and nitrogen atmosphere on a dry ice-acetone bath at an inner temperature of -70° to -68° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Boronic acid | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HBr | C1CCOC1.CCCCCC | null | null | CC(C)OB(OC(C)C)OC(C)C.CCCCCCC(Br)CC1Cc2ccccc2O1>C1CCOC1.CCCCCC>CCCCCCCCC1Cc2cc(B(O)O)ccc2O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-03e5f7ccfb154de09af0ec7af5397bc8 | CCCCCCCCC1Cc2cc(B(O)O)ccc2O1.CCCCCCCCCCc1cnc(Cl)nc1>>CCCCCCCCCCc1cnc(-c2ccc3c(c2)CC(CCCCCCCC)O3)nc1 | C([O-])([O-])=O.[Na+].[Na+].C(CCCCCCC)C1OC2=CC=C(C=C2C1)B(O)O.ClC1=NC=C(C=N1)CCCCCCCCCC.C1=CC=CC=C1>>C(CCCCCCCCC)C=1C=NC(=NC1)C=1C=C2CC(OC2=CC1)CCCCCCCC | OB(O)[c:15]1[cH:16][cH:17][c:18]2[c:19]([cH:20]1)[CH2:21][CH:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[O:31]2.Cl[c:14]1[n:13][cH:12][c:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:33][n:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C... | CCCCCCCCC1Cc2cc(B(O)O)ccc2O1.CCCCCCCCCCc1cnc(Cl)nc1 | CCCCCCCCCCc1cnc(-c2ccc3c(c2)CC(CCCCCCCC)O3)nc1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O | C-C Coupling | Suzuki coupling with boronic acids | 651f57f47af816cdb773c531ed2942d02c6e268aa0360db28cee44bddd1a0cfe | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cnc(-c2ccc3c(c2)CCO3)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[#7;a:4]:[c:5] | 23.9 | [{"value": 22.5, "product": "C(CCCCCCCCC)C=1C=NC(=NC1)C=1C=C2CC(OC2=CC1)CCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.9, "product": "C(CCCCCCCCC)C=1C=NC(=NC1)C=1C=C2CC(OC2=CC1)CCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under nitrogen atmosphere, 0.30 g (1.09 mM) of 2-octylcoumaran-5-boronic acid, 0.26 g (1.02 mM) of 2-chloro-5-decylpyrimidine and 1.5 ml of benzene were placed in a 20 ml-round-bottomed flask. Under stirring, 0.06 g of tetrakis(triphenylphosphine) palladium (0) and 1.5 ml of a 2M-sodium carbonate aqueous solution were ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1cncnc1 | c1cncnc1.c1ccc2c(c1)CCO2 | c1cncnc1.c1ccc2c(c1)CCO2 | HCl.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O | null | null | CCCCCCCCC1Cc2cc(B(O)O)ccc2O1.CCCCCCCCCCc1cnc(Cl)nc1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O>CCCCCCCCCCc1cnc(-c2ccc3c(c2)CC(CCCCCCCC)O3)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-37d8555154644a60ab7cecfd4db2ff16 | CCCCCCCCC1Cc2cc(B(O)O)ccc2O1.CCCCCCCCCCc1cnc(-c2cccc(Br)c2)nc1>>CCCCCCCCCCc1cnc(-c2ccc(-c3ccc4c(c3)CC(CCCCCCCC)O4)cc2)nc1 | C([O-])([O-])=O.[Na+].[Na+].C(CCCCCCC)C1OC2=CC=C(C=C2C1)B(O)O.C(C)O.BrC=1C=C(C=CC1)C1=NC=C(C=N1)CCCCCCCCCC>>C(CCCCCCCCC)C=1C=NC(=NC1)C1=CC=C(C=C1)C=1C=C2CC(OC2=CC1)CCCCCCCC | OB(O)[c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24]1)[CH2:25][CH:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[O:35]2.Br[c:36]1[cH:18][cH:17][cH:16][c:15](-[c:14]2[n:13][cH:12][c:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:39][n:38]2)[cH:37]1>>[CH3:1][CH2:2][CH2:3... | CCCCCCCCC1Cc2cc(B(O)O)ccc2O1.CCCCCCCCCCc1cnc(-c2cccc(Br)c2)nc1 | CCCCCCCCCCc1cnc(-c2ccc(-c3ccc4c(c3)CC(CCCCCCCC)O4)cc2)nc1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1=CC=CC=C1 | C-C Coupling | OtherReaction | 56c93a2f9806908798c499807b17d3f0e66e3ff1161f180dd511ec545b7e9634 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cnc(-c2ccc(-c3ccc4c(c3)CCO4)cc2)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1):[c:10]:[c:11] | 66.5 | [{"value": 66.5, "product": "C(CCCCCCCCC)C=1C=NC(=NC1)C1=CC=C(C=C1)C=1C=C2CC(OC2=CC1)CCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.5, "product": "C(CCCCCCCCC)C=1C=NC(=NC1)C1=CC=C(C=C1)C=1C=C2CC(OC2=CC1)CCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under nitrogen atmosphere, 0.25 g (0.91 mM) of 2-octylcoumaran-5-boronic acid, 0.7 ml of ethanol, 0.30 g (0.80 mM) of 2-(3-bromophenyl)-5-decylpyrimidine and 1.3 ml of benzene were placed in a 20 ml-round-bottomed flask. Under stirring, 0.05 g of tetrakis(triphenylphosphine) palladium (0) and 1.3 ml of a 2M-sodium carb... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1cncnc1.c1ccccc1.c1ccc2c(c1)CCO2 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=CC=C1 | null | null | CCCCCCCCC1Cc2cc(B(O)O)ccc2O1.CCCCCCCCCCc1cnc(-c2cccc(Br)c2)nc1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=CC=C1>CCCCCCCCCCc1cnc(-c2ccc(-c3ccc4c(c3)CC(CCCCCCCC)O4)cc2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81a231be09734e50823c3b6abac323f1 | C=CC(=O)Cl.OCCOc1ccccc1O>>C=CC(=O)Oc1ccccc1 | OCCOC1=C(C=CC=C1)O.C(C)N(CC)CC.O1CCCC1.C(C=C)(=O)Cl>>C(C=C)(=O)OC1=CC=CC=C1 | Cl[C:3]([CH:2]=[CH2:1])=[O:4].OCCO[c:11]1[c:6]([OH:5])[cH:7][cH:8][cH:9][cH:10]1>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | C=CC(=O)Cl.OCCOc1ccccc1O | C=CC(=O)Oc1ccccc1 | null | C1=CC=CC=2SC3=CC=CC=C3NC12 | null | Acylation | OtherReaction | a688b942154e6a847b3c1f63e2609740d90a3a21e5c3293f44fc051e2ce89f3e | fb24c4440c0fbc7ace4fff55268919df3e2b4365d542ebdb85cd4b96d977c435 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].O-C-C-O-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](-[OH;D1;+0:9]):[c:10]>>[C;D1;H2:4]=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[c:8](:[c:10]):[cH;D2;+0:5]:[c:6]:[c:7] | 62 | [{"value": 62.0, "product": "C(C=C)(=O)OC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500-ml, two necked flask was equipped with magnetic stirring bar, nitrogen atmosphere and an addition funnel. The flask was charged with 25 g of 2-(2-hydroxyethoxy)phenol (0.16 mol.), 33 g of triethylamine (0.32 mol.), 250 ml of tetrahydrofuran and 1 g of phenothiazine. Next, 30 g of acryloyl chloride (0.18 mol.) was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol.Aromatic alcohol | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C1=CC=CC=2SC3=CC=CC=C3NC12 | null | null | C=CC(=O)Cl.OCCOc1ccccc1O>C1=CC=CC=2SC3=CC=CC=C3NC12>C=CC(=O)Oc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a1e984cbfd144cd8fa2cccd3f2e67f2 | NCCOCCO.O=C1OC(=O)C2CCCCC12>>O=C1C2CCCCC2C(=O)N1CCOCCO | NCCOCCO.C1(C2C(C(=O)O1)CCCC2)=O>>OCCOCCN1C(C2C(C1=O)CCCC2)=O | [NH2:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17].O1[C:2](=[O:1])[CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]2[C:9]1=[O:10]>>[O:1]=[C:2]1[CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17] | NCCOCCO.O=C1OC(=O)C2CCCCC12 | O=C1C2CCCCC2C(=O)N1CCOCCO | null | null | C(C)O | Acylation | OtherReaction | fd4ebb9664b8f1fa0723d696f691dbe0d733549ae6e429af7ea144f47ba2e4b4 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1NC(=O)C2CCCCC12 | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[C:6](-[C:7])-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-[C;H0;D3;+0:10]-1=[O;D1;H0:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:10](=[O;D1;H0:11])-[C:5](-[C:4])-[C:6](-[C:7])-[C;H0;D3;+0:8]-1=[O;D1;H0:9] | 96 | [{"value": 96.0, "product": "OCCOCCN1C(C2C(C1=O)CCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "OCCOCCN1C(C2C(C1=O)CCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500-ml, two necked flask was equipped with a magnetic stirring bar, heating mantle and condenser. The flask was charged with 51 g of 2-(aminoethoxy) ethanol (0.49 mol.) and 250 ml of ethanol. Next, 75 g of hexahydrophthalic anhydride (0.49 mol.) was slowly added to the flask. After the addition was complete the react... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CCC2COCC2C1 | C1CCC2C[NH]CC2C1 | C1CCC2C[NH]CC2C1 | HO- | C(C)O | null | null | NCCOCCO.O=C1OC(=O)C2CCCCC12>C(C)O>O=C1C2CCCCC2C(=O)N1CCOCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-af9dc50fe19f475a8fbd4e36870e7ec5 | C=CC(=O)Cl.O=C1C2CCCCC2C(=O)N1CCOCCO>>C=CC(=O)OCCOCCN1C(=O)C2CCCCC2C1=O | OCCOCCN1C(C2C(C1=O)CCCC2)=O.C(C)N(CC)CC.C(C=C)(=O)Cl>>C(C=C)(=O)OCCOCCN1C(C2C(C1=O)CCCC2)=O | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[OH:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N:11]1[C:12](=[O:13])[CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]2[C:20]1=[O:21]>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N:11]1[C:12](=[O:13])[CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]2[C:20]1=[O:21] | C=CC(=O)Cl.O=C1C2CCCCC2C(=O)N1CCOCCO | C=CC(=O)OCCOCCN1C(=O)C2CCCCC2C1=O | null | C1=CC=CC=2SC3=CC=CC=C3NC12 | CC(=O)C | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | O=C1NC(=O)C2CCCCC12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4] | 59.5 | [{"value": 59.0, "product": "C(C=C)(=O)OCCOCCN1C(C2C(C1=O)CCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.5, "product": "C(C=C)(=O)OCCOCCN1C(C2C(C1=O)CCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A one liter, three necked flask was equipped with overhead stirrer, nitrogen atmosphere and an addition funnel. The flask was charged with 100 g of N-(2-hydroxyethoxyethyl)hexahydrophthalimide (0.41 mol.), 42 g of triethylamine (0.41 mol.), 1 g of phenothiazine and 400 ml of acetone. Next, 38 g of acryloyl chloride (0.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1CCC2C[NH]CC2C1 | HCl | C1=CC=CC=2SC3=CC=CC=C3NC12.CC(=O)C | null | 12 | C=CC(=O)Cl.O=C1C2CCCCC2C(=O)N1CCOCCO>C1=CC=CC=2SC3=CC=CC=C3NC12.CC(=O)C>C=CC(=O)OCCOCCN1C(=O)C2CCCCC2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ebb2fd6722bb446b8b566d5f8733e3f7 | NCC(O)CO.O=C1OC(=O)C2CCCCC12>>C=CC(=O)OCC(CN1C(=O)C2CCCCC2C1=O)OC(=O)C=C | NCC(CO)O.C1(C2C(C(=O)O1)CCCC2)=O>>C(C=C)(=O)OC(CN1C(C2C(C1=O)CCCC2)=O)COC(C=C)=O | [OH:5][CH2:6][CH:7]([CH2:8][NH2:9])[OH:20].[CH2:1]1[CH2:13][CH:12]2[C:10](=[O:11])[O:19][C:3](=[O:4])[CH:17]2[CH2:16][CH2:15]1>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH:7]([CH2:8][N:9]1[C:10](=[O:11])[CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]2[C:18]1=[O:19])[O:20][C:21](=[O:22])[CH:23]=[CH2:24] | NCC(O)CO.O=C1OC(=O)C2CCCCC12 | C=CC(=O)OCC(CN1C(=O)C2CCCCC2C1=O)OC(=O)C=C | null | null | C(C)O | Acylation | OtherReaction | 37aad88ec273d256158b0f4cb1f2443a40d4edb4bca01dc8259cc5a878baf5b6 | 32b0947c632de63f555f97f544b66ccd6cc5dfd855d370241eba47f794e22b4d | O=C1NC(=O)C2CCCCC12 | [NH2;D1;+0:1]-[C:2]-[C:3](-[OH;D1;+0:4])-[C:5]-[OH;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-[O;H0;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[CH;D3;+0:12]2-[C:13]-[CH2;D2;+0:14]-[CH2;D2;+0:15]-[CH2;D2;+0:16]-[C:17]-1-2>>[C:18]-[C:19](=[O;D1;H0:20])-[O;H0;D2;+0:4]-[C:3](-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[C:2... | 109.7 | [{"value": 81.0, "product": "C(C=C)(=O)OC(CN1C(C2C(C1=O)CCCC2)=O)COC(C=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 109.7, "product": "C(C=C)(=O)OC(CN1C(C2C(C1=O)CCCC2)=O)COC(C=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A 500-ml, two necked flask was equipped a magnetic stirring bar, heating mantle and condenser. The flask was charged with 46 g of 3-amino-1,2-propanediol (0.50 mol.) and 300 ml of ethanol. Next, 77 g of hexahydrophthalic anhydride (0.50 mol.) was slowly added to the flask after which the reaction was refluxed for 12 ho... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol.Secondary alcohol.Primary amine | Ester.Ester.Substituted dicarboximide.Vinyl.Vinyl | C1CCC2COCC2C1 | C1CCC2C[NH]CC2C1 | C1CCC2C[NH]CC2C1 | Other | C(C)O | null | null | NCC(O)CO.O=C1OC(=O)C2CCCCC12>C(C)O>C=CC(=O)OCC(CN1C(=O)C2CCCCC2C1=O)OC(=O)C=C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-89e65a3dba8b4753baf97d14535ec204 | CNCCO.O=C(Cl)c1ccco1>>CN(CCO)C(=O)c1ccco1 | CNCCO.O1C(=CC=C1)C(=O)Cl>>OCCN(C(=O)C=1OC=CC1)C | [CH3:1][NH:2][CH2:3][CH2:4][OH:5].Cl[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][o:12]1>>[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][o:12]1 | CNCCO.O=C(Cl)c1ccco1 | CN(CCO)C(=O)c1ccco1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccoc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C;D1;H3:10]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C;D1;H3:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#8;a:5]:[c:6] | 57.6 | [{"value": 44.0, "product": "OCCN(C(=O)C=1OC=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "OCCN(C(=O)C=1OC=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A one liter, three necked flask was equipped with overhead stirrer, nitrogen atmosphere and an addition funnel. The flask was charged with 115 g of 2-(methylamino)ethanol (1.53 mol.) and 500 ml of dichloromethane. The reaction flask was cooled with an ice bath. Next, 100 g of furoyl chloride (0.77 mol.) was slowly adde... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccoc1 | HCl | ClCCl | null | null | CNCCO.O=C(Cl)c1ccco1>ClCCl>CN(CCO)C(=O)c1ccco1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77519deec78d44d89cdc131b10b54df8 | C=CC(=O)Cl.O=C1NCC(CO)O1>>C=CC(=O)OCC1CNC(=O)O1 | C(C=C)(=O)Cl.OCC1CNC(O1)=O.C(C)N(CC)CC.C1=CC=CC=2SC3=CC=CC=C3NC12>>C(C=C)(=O)OCC1CNC(O1)=O | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][NH:9][C:10](=[O:11])[O:12]1>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][NH:9][C:10](=[O:11])[O:12]1 | C=CC(=O)Cl.O=C1NCC(CO)O1 | C=CC(=O)OCC1CNC(=O)O1 | null | null | O1CCCC1 | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | O=C1NCCO1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4] | null | [] | null | null | null | null | 105 g (0.90 mol.) of 5-hydroxymethyl-oxazolidin-2-one were placed into a one liter, three necked, round bottomed flask equipped with a paddle stirrer and thermometer. This was followed by 500 ml of tetrahydrofuran, 101 g (1.0 mol.) of triethylamine and 0.5 g of phenothiazine. Stirring was started as 90 g (1.0 mol.) of ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1COCN1 | HCl | O1CCCC1 | null | null | C=CC(=O)Cl.O=C1NCC(CO)O1>O1CCCC1>C=CC(=O)OCC1CNC(=O)O1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bd858f048833400792f09a0d07c7449f | Brc1ccsc1.Fc1cc(Br)cc(F)c1F>>Fc1cc(-c2ccsc2)cc(F)c1F | BrC1=CSC=C1.[Mg].[Mg].BrC1=CC(=C(C(=C1)F)F)F>>FC=1C=C(C=C(C1F)F)C1=CSC=C1 | Br[c:5]1[cH:6][cH:7][s:8][cH:9]1.Br[c:4]1[cH:3][c:2]([F:1])[c:13]([F:14])[c:11]([F:12])[cH:10]1>>[F:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][s:8][cH:9]2)[cH:10][c:11]([F:12])[c:13]1[F:14] | Brc1ccsc1.Fc1cc(Br)cc(F)c1F | Fc1cc(-c2ccsc2)cc(F)c1F | null | [Cl-].[Zn+2].[Cl-].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | null | C-C Coupling | Negishi | 465b747680a8e5c8f91311f4e5462c5cd984c0085c515df27dc91db7d0c5b083 | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccsc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1):[c:4]:[c:5] | null | [] | 40 | CELSIUS | null | null | In a first three-necked round-bottom flask (100 ml), metallic magnesium (52 mmol) (product #25411-8, manufactured by Aldrich Chemical) was flame dried in an argon atmosphere for 3 to 4 minutes. Upon cooling under the argon atmosphere, 50 ml of freshly dried tetrahydrofuran (product #T 397-4, manufactured by Fisher Scie... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccsc1.c1ccccc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | Br- | [Cl-].[Zn+2].[Cl-].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | 40 | null | Brc1ccsc1.Fc1cc(Br)cc(F)c1F>[Cl-].[Zn+2].[Cl-].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2]>Fc1cc(-c2ccsc2)cc(F)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d67d9c65c42044a99182159ada0d0d78 | Fc1cc(-c2ccsc2)cc(F)c1F>>Fc1ccc(-c2ccsc2)cc1F | FC=1C=C(C=C(C1F)F)C1=CSC=C1.BrC1=CC(=C(C=C1)F)F.BrC1=CC(=C(C(=C1)F)F)F>>FC=1C=C(C=CC1F)C1=CSC=C1 | F[c:3]1[c:2]([F:1])[c:12]([F:13])[cH:11][c:5](-[c:6]2[cH:7][cH:8][s:9][cH:10]2)[cH:4]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][s:9][cH:10]2)[cH:11][c:12]1[F:13] | Fc1cc(-c2ccsc2)cc(F)c1F | Fc1ccc(-c2ccsc2)cc1F | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccsc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6]>>[F;D1;H0:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | The same procedures set forth above in Example (1)(a) for synthesizing 3(3,4,5-trifluorophenyl)thiophene were followed, with the exception that 1-bromo-3,4-difluorobenzene was substituted for 1-bromo-3,4,5-trifluorobenzene as the 1-bromo-substituted fluorobenzene.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1 | Other | null | null | null | Fc1cc(-c2ccsc2)cc(F)c1F>>Fc1ccc(-c2ccsc2)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1353d03acc334b3781453676e9c404d0 | Fc1cc(-c2ccsc2)cc(F)c1F>>Fc1cc(F)cc(-c2ccsc2)c1 | FC=1C=C(C=C(C1F)F)C1=CSC=C1.BrC1=CC(=CC(=C1)F)F.BrC1=CC(=C(C(=C1)F)F)F>>FC=1C=C(C=C(C1)F)C1=CSC=C1 | F[c:3]1[c:2]([F:1])[cH:13][c:7](-[c:8]2[cH:9][cH:10][s:11][cH:12]2)[cH:6][c:4]1[F:5]>>[F:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7](-[c:8]2[cH:9][cH:10][s:11][cH:12]2)[cH:13]1 | Fc1cc(-c2ccsc2)cc(F)c1F | Fc1cc(F)cc(-c2ccsc2)c1 | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccsc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7]>>[F;D1;H0:3]-[c:2](:[c:4]):[cH;D2;+0:1]:[c:5](-[F;D1;H0:6]):[c:7] | null | [] | null | null | null | null | The same procedures set forth above in Example (1)(a) for synthesizing 3(3,4,5-trifluorophenyl)thiophene were followed, with the exception that 1-bromo-3,5-difluorobenzene was substituted for 1-bromo-3,4,5-trifluorobenzene as the 1-bromo-substituted fluorobenzene.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1 | Other | null | null | null | Fc1cc(-c2ccsc2)cc(F)c1F>>Fc1cc(F)cc(-c2ccsc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84962d33083243bb8070accd1465b529 | Fc1cc(-c2ccsc2)cc(F)c1F.Fc1ccc(Br)c(F)c1>>Fc1ccc(-c2ccsc2)c(F)c1 | FC=1C=C(C=C(C1F)F)C1=CSC=C1.BrC1=C(C=C(C=C1)F)F.BrC1=CC(=C(C(=C1)F)F)F>>FC1=C(C=CC(=C1)F)C1=CSC=C1 | Fc1c[c:5](-[c:6]2[cH:7][cH:8][s:9][cH:10]2)cc(F)c1F.Brc1[cH:4][cH:3][c:2]([F:1])[cH:13][c:11]1[F:12]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][s:9][cH:10]2)[c:11]([F:12])[cH:13]1 | Fc1cc(-c2ccsc2)cc(F)c1F.Fc1ccc(Br)c(F)c1 | Fc1ccc(-c2ccsc2)c(F)c1 | null | null | null | Miscellaneous | OtherReaction | 8b9e24f975dd591e39ba8138d18457a38e7be5393a85a11a540dd0516aef781f | dbb6583364c59bca8c7508ce4061692996dd4e8a899e1de1dcdf405af3c96d3c | c1ccc(-c2ccsc2)cc1 | Br-c1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[c;H0;D3;+0:5]:1-[F;D1;H0:6].F-c1:c:[c;H0;D3;+0:7](-[c:8]2:[c:9]:[#16;a:10]:[c:11]:[c:12]:2):c:c(-F):c:1-F>>[F;D1;H0:6]-[c;H0;D3;+0:5]1:[c:4]:[c:3]:[c:2]:[cH;D2;+0:1]:[c;H0;D3;+0:7]:1-[c:8]1:[c:9]:[#16;a:10]:[c:11]:[c:12]:1 | 97 | [{"value": 97.0, "product": "FC1=C(C=CC(=C1)F)C1=CSC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | The same procedures set forth above in Example (1)(a) for synthesizing 3(3,4,5-trifluorophenyl)thiophene were followed, with the exception that 1-bromo-2,4-difluorobenzene was substituted for 1-bromo-3,4,5-trifluorobenzene as the 1-bromo-substituted fluorobenzene, and the coupling reaction mixture was heated to reflux ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide | Aromatic halide | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1 | HF.Br- | null | 80 | null | Fc1cc(-c2ccsc2)cc(F)c1F.Fc1ccc(Br)c(F)c1>>Fc1ccc(-c2ccsc2)c(F)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-921b325d103d4c73b989008641f1fd3d | C=C(C)C(=O)OCCN=C=O.OCc1ccccc1>>C=C(C)C(=O)OCCNC(=O)OCc1ccccc1 | C(C(=C)C)(=O)OCCN=C=O.C(C1=CC=CC=C1)O>>C(C(=C)C)(=O)OCCNC(=O)OCC1=CC=CC=C1 | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11].[OH:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | C=C(C)C(=O)OCCN=C=O.OCc1ccccc1 | C=C(C)C(=O)OCCNC(=O)OCc1ccccc1 | null | C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC | O1CCOCC1 | Protection | OtherReaction | 8d2aa5da7fec498749aba98cc9467e8d82c146f343570568bec74a92b10e0ae2 | e505c5de73b3f9ad0414c141c59109424d376f26a728bbd154d3edfd03d2f50a | c1ccccc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[OH;D1;+0:6]-[C:7]-[c:8]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[C:7]-[c:8] | 80.6 | [{"value": 80.6, "product": "C(C(=C)C)(=O)OCCNC(=O)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 77.5 g of methacryloyloxyethyl isocyanate (Karenzu MOI, available from Showa Denko K.K.) and 60 g of benzyl alcohol were dissolved in 260 g of dioxane. To the solution were then added 5 drops of di-n-butyltin dilaurate. The reaction mixture was then allowed to undergo reaction at a temperature of 65° C. for 3 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary alcohol | Carbamic ester | null | null | c1ccccc1 | null | C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC.O1CCOCC1 | null | null | C=C(C)C(=O)OCCN=C=O.OCc1ccccc1>C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCC)[Sn+2]CCCC.O1CCOCC1>C=C(C)C(=O)OCCNC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7f1fb53c79494e0b8520d17b81fa2775 | C=C(C)C(=O)Cl.CC(C)COC(=O)Nc1ccc(S(N)(=O)=O)cc1>>C=C(C)C(=O)NS(=O)(=O)c1ccc(NC(=O)OCC(C)C)cc1 | C(C(C)C)OC(=O)NC1=CC=C(C=C1)S(=O)(=O)N.C(C)N(CC)CC.CN(C(C)=O)C.C(C(=C)C)(=O)Cl>>C(C(C)C)OC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC(C(=C)C)=O | Cl[C:4]([C:2](=[CH2:1])[CH3:3])=[O:5].[NH2:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][CH:19]([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][CH:19]([CH3:20])[CH3... | C=C(C)C(=O)Cl.CC(C)COC(=O)Nc1ccc(S(N)(=O)=O)cc1 | C=C(C)C(=O)NS(=O)(=O)c1ccc(NC(=O)OCC(C)C)cc1 | null | null | O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 403eb34e708e50f7077a9da490b1654c837258ce901614ddd1204eb6f2a10a27 | 37dfa12f19cd8cec29206fb8a18b7504935d92bc326a2084e9ef8a13076d3b87 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]>>[C;D1;H2:4]=[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10] | 58.8 | [{"value": 58.8, "product": "C(C(C)C)OC(=O)NC1=CC=C(C=C1)S(=O)(=O)NC(C(=C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of 54.4 g of p-isobutyloxycarbonylaminophenyl sulfonamide, 40 g of triethylamine, 2 g of N,N-dimethylaminopyridine and 150 ml of N,N-dimethylacetamide was then added dropwise 22.8 g of methacrylic chloride under cooling with ice. After the completion of the dropwise addition, the reaction mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide | Sulfonamide.Secondary amide | null | null | c1ccccc1 | HCl | O | null | 2 | C=C(C)C(=O)Cl.CC(C)COC(=O)Nc1ccc(S(N)(=O)=O)cc1>O>C=C(C)C(=O)NS(=O)(=O)c1ccc(NC(=O)OCC(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2d4f64dd7b0a4a1ab9ebcd6c62f6820c | O=C(O)CCC(=O)c1ccc(C(=O)C2(O)CCCCC2)cc1.O=S(Cl)Cl>>O=C(Cl)CCC(=O)c1ccc(C(=O)C2(O)CCCCC2)cc1 | C(=O)(O)CCC(=O)C1=CC=C(C=C1)C(=O)C1(CCCCC1)O.S(=O)(Cl)Cl>>ClC(=O)CCC(=O)C1=CC=C(C=C1)C(=O)C1(CCCCC1)O | O[C:2](=[O:1])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[C:14]2([OH:15])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21][cH:22]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[C:14]2([OH:15])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:... | O=C(O)CCC(=O)c1ccc(C(=O)C2(O)CCCCC2)cc1.O=S(Cl)Cl | O=C(Cl)CCC(=O)c1ccc(C(=O)C2(O)CCCCC2)cc1 | null | null | C(C)OCC | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C(c1ccccc1)C1CCCCC1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C:6]=[O;D1;H0:7]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C:6]=[O;D1;H0:7] | 94 | [{"value": 94.0, "product": "ClC(=O)CCC(=O)C1=CC=C(C=C1)C(=O)C1(CCCCC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "ClC(=O)CCC(=O)C1=CC=C(C=C1)C(=O)C1(CCCCC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 30 | MINUTE | A 250-ml round-bottomed flask fitted with a condenser was charged with 12.0 g of 1-hydroxycyclohexyl 4-(2-carboxyethyl)carbonylphenyl ketone (0.04 mole), 5.95 g (0.05 mole) of thionyl chloride (Aldrich), and 50 ml of diethyl ether. The resulting reaction mixture was stirred at 30° C. for 30 minutes, after which time th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1.C1CCCCC1 | HCl | C(C)OCC | 30 | 0.5 | O=C(O)CCC(=O)c1ccc(C(=O)C2(O)CCCCC2)cc1.O=S(Cl)Cl>C(C)OCC>O=C(Cl)CCC(=O)c1ccc(C(=O)C2(O)CCCCC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e6001659ddac4b01bf370c708fa8cdd0 | CC(=O)O[C@H]1COC[C@H]1O.CC(Cl)C(=O)Cl>>CC(=O)O[C@H]1COC[C@H]1OC(=O)C(C)Cl | O[C@@H]1COC[C@@H]1OC(=O)C.N1=CC=CC=C1.ClCCl.ClC(C(=O)Cl)C>>C(C)(=O)O[C@@H]1[C@@H](COC1)OC(C(C)Cl)=O | [CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][O:7][CH2:8][C@H:9]1[OH:10].Cl[C:11](=[O:12])[CH:13]([CH3:14])[Cl:15]>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][O:7][CH2:8][C@H:9]1[O:10][C:11](=[O:12])[CH:13]([CH3:14])[Cl:15] | CC(=O)O[C@H]1COC[C@H]1O.CC(Cl)C(=O)Cl | CC(=O)O[C@H]1COC[C@H]1OC(=O)C(C)Cl | null | null | O | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | C1CCOC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[Cl;D1;H0:5].[#8:6]-[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[#8:6]-[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[Cl;D1;H0:5])-[C:10] | null | [] | 23 | CELSIUS | 4 | HOUR | 12.4 g of (±)-2-chloropropionyl chloride were added dropwise at 0°-5° C. to an ice-cooled mixture of 15.0 g of (±)-(3R,4S)-3-hydroxy-4-methylcarbonyloxytetrahydrofuran, 8.1 g of anhydrous pyridine and 200 ml of anhydrous dichloromethane. After addition was complete, the reaction mixture was stirred at 23° C. for a furt... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | C1CCOC1 | HCl | O | 23 | 4 | CC(=O)O[C@H]1COC[C@H]1O.CC(Cl)C(=O)Cl>O>CC(=O)O[C@H]1COC[C@H]1OC(=O)C(C)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-854b8b53d833423eaf0208d0354bd8e9 | NC1C(=O)N(CC23CC4CC(CC(C4)C2)C3)c2ccccc2N(c2ccccc2)C1=O.O=C=Nc1cccc([N+](=O)[O-])c1>>O=C(Nc1cccc([N+](=O)[O-])c1)NC1C(=O)N(CC23CC4CC(CC(C4)C2)C3)c2ccccc2N(c2ccccc2)C1=O | [N+](=O)([O-])C=1C=C(C=CC1)N=C=O.C12(CC3CC(CC(C1)C3)C2)CN2C(C(C(N(C3=C2C=CC=C3)C3=CC=CC=C3)=O)N)=O>>C12(CC3CC(CC(C1)C3)C2)CN2C(C(C(N(C3=C2C=CC=C3)C3=CC=CC=C3)=O)NC(=O)NC3=CC(=CC=C3)[N+](=O)[O-])=O | [NH2:13][CH:14]1[C:15](=[O:16])[N:17]([CH2:18][C:19]23[CH2:20][CH:21]4[CH2:22][CH:23]([CH2:24][CH:25]([CH2:26]4)[CH2:27]2)[CH2:28]3)[c:29]2[cH:30][cH:31][cH:32][cH:33][c:34]2[N:35]([c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[C:42]1=[O:43].[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1>>... | NC1C(=O)N(CC23CC4CC(CC(C4)C2)C3)c2ccccc2N(c2ccccc2)C1=O.O=C=Nc1cccc([N+](=O)[O-])c1 | O=C(Nc1cccc([N+](=O)[O-])c1)NC1C(=O)N(CC23CC4CC(CC(C4)C2)C3)c2ccccc2N(c2ccccc2)C1=O | null | null | C(C)#N.ClCCl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)NC1C(=O)N(CC23CC4CC(CC(C4)C2)C3)c2ccccc2N(c2ccccc2)C1=O | [C:1]-[#7:2]1-[c:3]:[c:4]-[#7:5](-[c:6])-[C:7](=[O;D1;H0:8])-[C:9](-[NH2;D1;+0:10])-[C:11]-1=[O;D1;H0:12].[O;D1;H0:13]=[C;H0;D2;+0:14]=[N;H0;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:1]-[#7:2]1-[c:3]:[c:4]-[#7:5](-[c:6])-[C:7](=[O;D1;H0:8])-[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:14](=[O;D1;H0:13])-[NH;D2;+0:15]-[c:16](:[c:17]):[c... | 82.1 | [{"value": 82.1, "product": "C12(CC3CC(CC(C1)C3)C2)CN2C(C(C(N(C3=C2C=CC=C3)C3=CC=CC=C3)=O)NC(=O)NC3=CC(=CC=C3)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 3-nitrophenyl isocyanate (0.082 g) in dry acetonitrile (8 ml) was added to a solution of the 1-(1-Adamantylmethyl-3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (0.2 g) in dry acetonitrile (10 ml) under a nitrogen atmosphere. The mixture was stirred at 23° for 2 h, then diluted with d... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)[NH]CCC[NH]2.C1C2CC3CC1CC(C2)C3 | null | C(C)#N.ClCCl | null | 2 | NC1C(=O)N(CC23CC4CC(CC(C4)C2)C3)c2ccccc2N(c2ccccc2)C1=O.O=C=Nc1cccc([N+](=O)[O-])c1>C(C)#N.ClCCl>O=C(Nc1cccc([N+](=O)[O-])c1)NC1C(=O)N(CC23CC4CC(CC(C4)C2)C3)c2ccccc2N(c2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-888b842697c24f2abdd0a5f6ef3eaa40 | C[C@H](NC(=O)OC(C)(C)C)C(=O)O.NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O>>C[C@H](N)C(=O)NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O | C(C)(C)(C)OC(=O)NCC(=O)O.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.NCCCNC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)NCCCN.C(C)(C)(C)OC(=O)N[C@@H](C)C(=O)O>>NCCCNC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)NCCCNC([C@@H](N)C)=O | CC(C)(C)OC(=O)[NH:3][C@@H:2]([CH3:1])[C:4](O)=[O:5].[NH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[cH:12][cH:13][c:14]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])[c:20]2[c:21]1[C:22](=[O:23])[c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1[C:30]2=[O:31]>>[CH3:1][C@H:2]([NH2:3])[C:4](=[O:5])[NH:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[... | C[C@H](NC(=O)OC(C)(C)C)C(=O)O.NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O | C[C@H](N)C(=O)NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O | null | null | null | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | O=C1c2ccccc2C(=O)c2ccccc21 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;H0;D3;+0:4](-O)=[O;D1;H0:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:1] | null | [] | null | null | null | null | Example 28 was prepared by an equivalent procedure to that described for Example 24 except that the starting anthraquinone was 1,4-bis[(3-aminopropyl)amino]-anthracene-9,10-dione and N-tertiarybutoxycarbonyl-L-alanine replaced N-tertiarybutoxycarbonylglycine.
Conditions: See reaction.notes.procedure_details.
Workup: Ex... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccc2c(c1)Cc1ccccc1C2 | HO- | null | null | null | C[C@H](NC(=O)OC(C)(C)C)C(=O)O.NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O>>C[C@H](N)C(=O)NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5825bb94a6c044969c60477a29132a82 | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O>>NCCCNc1ccc(NCCCNC(=O)[C@@H](N)Cc2ccccc2)c2c1C(=O)c1ccccc1C2=O | C(C)(C)(C)OC(=O)NCC(=O)O.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.NCCCNC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)NCCCN.C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O>>NCCCNC1=CC=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)NCCCNC([C@@H](N)CC1=CC=CC=C1)=O | CC(C)(C)OC(=O)[NH:18][C@H:17]([C:15](O)=[O:16])[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])[c:26]2[c:27]1[C:28](=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][c:35]1[C:36]2=[O:37]>>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][c... | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O | NCCCNc1ccc(NCCCNC(=O)[C@@H](N)Cc2ccccc2)c2c1C(=O)c1ccccc1C2=O | null | null | null | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | O=C(CCc1ccccc1)NCCCNc1cccc2c1C(=O)c1ccccc1C2=O | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C;H0;D3;+0:4](-O)=[O;D1;H0:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | null | [] | null | null | null | null | Example 29 was prepared by an equivalent procedure to that described for Example 24 except that the starting anthraquinone was 1,4-bis[(3-aminopropyl)amino]-anthracene-9,10-dione and N-tertiarybutoxycarbonyl-L-phenylalanine replaced N-tertiarybutoxycarbonylglycine.
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccccc1.c1ccc2c(c1)Cc1ccccc1C2 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O.NCCCNc1ccc(NCCCN)c2c1C(=O)c1ccccc1C2=O>>NCCCNc1ccc(NCCCNC(=O)[C@@H](N)Cc2ccccc2)c2c1C(=O)c1ccccc1C2=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bbab05d627554b729c0070280001d3e6 | CCOP(=O)(CCOCn1cnc2c(OC)ncnc21)OCC.N>>CCOP(=O)([O-])CCOCn1cnc2c(N)ncnc21.[NH4+] | COC1=C2N=CN(C2=NC=N1)COCCP(OCC)(OCC)=O.N>>N1=CN=C2N(C=NC2=C1N)COCCP(OCC)([O-])=O.[NH4+] | CC[O:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[CH2:7][CH2:8][O:9][CH2:10][n:11]1[cH:12][n:13][c:14]2[c:15](OC)[n:17][cH:18][n:19][c:20]12.[NH3:16]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O-:6])[CH2:7][CH2:8][O:9][CH2:10][n:11]1[cH:12][n:13][c:14]2[c:15]([NH2:16])[n:17][cH:18][n:19][c:20]12.[NH4+:21] | CCOP(=O)(CCOCn1cnc2c(OC)ncnc21)OCC.N | CCOP(=O)([O-])CCOCn1cnc2c(N)ncnc21.[NH4+] | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 0cd510195a6b358a413cf3d0ba916c1a77eb59b88b58776aeaefdb0f23cd4d52 | 4764b8d6a7ad8d9253070fdb827f95d720ac9a4f642f3b03b75fe3f308c3d0a7 | c1ncc2nc[nH]c2n1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[#8:3])(-[C:4])=[O;D1;H0:5].C-O-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11](-[C:12]):[c:13]:[#7;a:14]:[c:15]:2:1.[NH3;D0;+0:16]>>[#8:3]-[#15:2](-[C:4])(-[O-;H0;D1:1])=[O;D1;H0:5].[C:12]-[#7;a:11]1:[c:13]:[#7;a:14]:[c:15]2:[c:10]:1:[#7;a:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:2-[NH2;D... | 40 | [{"value": 40.0, "product": "N1=CN=C2N(C=NC2=C1N)COCCP(OCC)([O-])=O.[NH4+]", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 11 (3.44 g, 10.0 mmol) in MeOH (40 mL) was added a saturated methanolic NH3 solution (100 mL). The solution was heated in a sealed flask at 100° C. for 30 h. The solvent was evaporated and the residue was crystallized from EtOH to give 12 (1.20 g) in 40% yield: mp 190°-193° C.; TLC Rf 0.37 (AcOEt/MeOH=... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary amine | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | HO- | CO | 100 | null | CCOP(=O)(CCOCn1cnc2c(OC)ncnc21)OCC.N>CO>CCOP(=O)([O-])CCOCn1cnc2c(N)ncnc21.[NH4+] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-665b5ee29c834289ad987373eaa9f519 | CCOP(=O)([O-])CCOCn1cnc2c(N)ncnc21>>Nc1ncnc2c1ncn2COCCP(=O)(O)O | N1=CN=C2N(C=NC2=C1N)COCCP(OCC)([O-])=O.[NH4+].CO.O>>N1=CN=C2N(C=NC2=C1N)COCCP(O)(O)=O | CC[O:18][P:15]([CH2:14][CH2:13][O:12][CH2:11][n:10]1[c:6]2[n:5][cH:4][n:3][c:2]([NH2:1])[c:7]2[n:8][cH:9]1)(=[O:16])[O-:17]>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[CH2:11][O:12][CH2:13][CH2:14][P:15](=[O:16])([OH:17])[OH:18] | CCOP(=O)([O-])CCOCn1cnc2c(N)ncnc21 | Nc1ncnc2c1ncn2COCCP(=O)(O)O | null | null | CN(C)C=O | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ncc2nc[nH]c2n1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(-[O-;H0;D1:4])=[O;D1;H0:5]>>[C:3]-[#15:2](=[O;D1;H0:5])(-[OH;D1;+0:4])-[OH;D1;+0:1] | 45 | [{"value": 45.0, "product": "N1=CN=C2N(C=NC2=C1N)COCCP(O)(O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.9, "product": "N1=CN=C2N(C=NC2=C1N)COCCP(O)(O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 6 | HOUR | To a solution of 12 (0.32 g, 1.0 mmol) in DMF (7.0 mL) was added Me3 SiBr (1.07 g, 7.01 mmol). After the solution was stirred at 40° C. for 6 h, a mixture of MeOH and H2O(5:1, 20 mL) was added and the solvents were evaporated. The crude residue was purified by use of column chromatography (resin XAD-4, H2O) to afford 1... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncnc2nc[nH]c12 | Other | CN(C)C=O | 40 | 6 | CCOP(=O)([O-])CCOCn1cnc2c(N)ncnc21>CN(C)C=O>Nc1ncnc2c1ncn2COCCP(=O)(O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-04b5894104d743daa3447f348afad5c1 | CCC(=O)N[C@@H]1CCc2cc3c(cc2[C@H]1O)SCC3>>CCCN[C@@H]1CCc2cc3c(cc2[C@H]1O)SCC3 | O[C@H]1[C@@H](CCC2=CC3=C(SCC3)C=C12)NC(CC)=O.[OH-].[Na+]>>O[C@H]1[C@@H](CCC2=CC3=C(SCC3)C=C12)NCCC | O=[C:3]([CH2:2][CH3:1])[NH:4][C@@H:5]1[CH2:6][CH2:7][c:8]2[cH:9][c:10]3[c:11]([cH:12][c:13]2[C@H:14]1[OH:15])[S:16][CH2:17][CH2:18]3>>[CH3:1][CH2:2][CH2:3][NH:4][C@@H:5]1[CH2:6][CH2:7][c:8]2[cH:9][c:10]3[c:11]([cH:12][c:13]2[C@H:14]1[OH:15])[S:16][CH2:17][CH2:18]3 | CCC(=O)N[C@@H]1CCc2cc3c(cc2[C@H]1O)SCC3 | CCCN[C@@H]1CCc2cc3c(cc2[C@H]1O)SCC3 | null | null | O.O1CCCC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1c2c(cc3c1CCS3)CCCC2 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4]-[C;D1;H3:5]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4]-[C;D1;H3:5] | 97 | [{"value": 97.0, "product": "O[C@H]1[C@@H](CCC2=CC3=C(SCC3)C=C12)NCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.2, "product": "O[C@H]1[C@@H](CCC2=CC3=C(SCC3)C=C12)NCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | In a 500 ml three-necked flask fitted with a magnetic stirrer and a nitrogen inlet, 2.3 g (61 mmol) of AILiH4 are suspended in 75 ml of dry tetrahydrofuran. 6.2 g (24.5 mmol) of the product obtained in Step 2 dissolved in 97 ml of dry tetrahydrofuran are slowly added at room temperature. After 18 hours' stirring at roo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1c2c(cc3c1CCS3)CCCC2 | Other | O.O1CCCC1 | null | 18 | CCC(=O)N[C@@H]1CCc2cc3c(cc2[C@H]1O)SCC3>O.O1CCCC1>CCCN[C@@H]1CCc2cc3c(cc2[C@H]1O)SCC3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84edcdeb710843f298afe85eff4bc91e | C=CC#N.CN(C)CCCCN>>CN(C)CCCCNCCC#N | C(C=C)#N.CN(CCCCN)C>>C(#N)CCNCCCCN(C)C | [CH2:9]=[CH:10][C:11]#[N:12].[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:11]#[N:12] | C=CC#N.CN(C)CCCCN | CN(C)CCCCNCCC#N | null | null | CO | Heteroatom Alkylation and Arylation | aza-Michael addition primary | b45dd075b7e75caee6dc0a68cb402266c75e0848f7502f06a5dbd8a34863aae2 | 2e45960e6468a140db4162555f247a2535630c23e1aa16e082b84ce22691ebbf | null | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]#[N;D1;H0:4] | 80 | [{"value": 80.0, "product": "C(#N)CCNCCCCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of acrylonitrile (1.17 g, 22.07 mmol) in methanol (1.0 ml) was added dropwise to a solution of N,N-dimethyl-1,4-diaminobutane 322 (2.1 g, 18.42 mmol) in methanol (1.0 ml) at 0° C., and the mixture was stirred at 0° C. for sixteen hours. Evaporation of the solvent in vacuo afforded almost pure N-(2-cyanoethyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Vinyl | Secondary amine | null | null | null | null | CO | 0 | null | C=CC#N.CN(C)CCCCN>CO>CN(C)CCCCNCCC#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9d5cb107bd0146788c6f94e9866436c0 | CN(C)CCCCN(CCC#N)C(=O)OC(C)(C)C>>CN(C)CCCCN(CCCN)C(=O)OC(C)(C)C | [H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)(C)(C)OC(=O)N(CCCCN(C)C)CCC#N>>NCCCN(CCCCN(C)C)C(=O)OC(C)(C)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][C:11]#[N:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][CH2:11][NH2:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | CN(C)CCCCN(CCC#N)C(=O)OC(C)(C)C | CN(C)CCCCN(CCCN)C(=O)OC(C)(C)C | null | null | CCOCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 59 | [{"value": 59.0, "product": "NCCCN(CCCCN(C)C)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.7, "product": "NCCCN(CCCCN(C)C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a solution of LAH (0.62 mg, 16.30 mmol) in anhydrous ether (100 ml) was added N-(tert-butoxycarbonyl)--N-(2-cyanoethyl)-N',N'-dimethyl-1,4-diaminobutane 324 (2.22 g, 8.10 mmol) in anhydrous ether (50 ml) at 0° C. The mixture was stirred at 0° C. for thirty minutes. The excess LAH was quenched with 1N NaOH at 0° C., ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | CCOCC | 0 | null | CN(C)CCCCN(CCC#N)C(=O)OC(C)(C)C>CCOCC>CN(C)CCCCN(CCCN)C(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-78b65606c5ee45768c20fb14a7e7de91 | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)O)[C@@]4(C)CC[C@@H]32)C1.O=C(Cl)C(=O)Cl>>CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)Cl)[C@@]4(C)CC[C@@H]32)C1 | C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(=O)O)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C.C(C(=O)Cl)(=O)Cl>>C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(=O)Cl)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C | O[C:22]([CH2:21][CH2:20][C@H:18]([C@H:17]1[CH2:16][CH2:15][C@H:14]2[C@@H:13]3[CH2:12][CH:11]=[C:10]4[C@:8]([CH3:9])([CH2:7][CH2:6][C@H:5]([O:4][C:2]([CH3:1])=[O:3])[CH2:30]4)[C@H:29]3[CH2:28][CH2:27][C@@:25]21[CH3:26])[CH3:19])=[O:23].O=C(Cl)C(=O)[Cl:24]>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][CH2:7][C@@:8]2([CH3:9])... | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)O)[C@@]4(C)CC[C@@H]32)C1.O=C(Cl)C(=O)Cl | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)Cl)[C@@]4(C)CC[C@@H]32)C1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3[C@@H]2C1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | 1 | HOUR | To a solution of 3β-acetoxy-5-cholenic acid (50.0 g, 118 mmole) in dry dichloromethane (200 ml) was added dropwise oxalyl chloride (30 ml, 448 mmole). The solution was stirred at room temperature for one hour and then concentrated in vacuo to obtain 3β-acetoxy-5-cholenic acid chloride 331. 1H NMR (400 MHz, CDCl3) δ: 0.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | HCl | ClCCl | null | 1 | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)O)[C@@]4(C)CC[C@@H]32)C1.O=C(Cl)C(=O)Cl>ClCCl>CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)Cl)[C@@]4(C)CC[C@@H]32)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b098fde08ae9480bb834d7a3afe28656 | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)Cl)[C@@]4(C)CC[C@@H]32)C1.CC(C)Br>>CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)C(C)C)[C@@]4(C)CC[C@@H]32)C1 | C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(=O)Cl)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C.Cl.BrC(C)C.C(C)(C)[Mg]Br.[Mg]>>C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(C(C)C)=O)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C | Cl[C:22]([CH2:21][CH2:20][C@H:18]([C@H:17]1[CH2:16][CH2:15][C@H:14]2[C@@H:13]3[CH2:12][CH:11]=[C:10]4[C@:8]([CH3:9])([CH2:7][CH2:6][C@H:5]([O:4][C:2]([CH3:1])=[O:3])[CH2:32]4)[C@H:31]3[CH2:30][CH2:29][C@@:27]21[CH3:28])[CH3:19])=[O:23].Br[CH:24]([CH3:25])[CH3:26]>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][CH2:7][C@@:8]2... | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)Cl)[C@@]4(C)CC[C@@H]32)C1.CC(C)Br | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)C(C)C)[C@@]4(C)CC[C@@H]32)C1 | null | [Br-].[Cd+2].[Br-] | CCOCC.C1=CC=CC=C1 | C-C Coupling | OtherReaction | 1a82298ae4aa4f3a471f136807b8bb5808cc2b5f42cb51ba765c73e0855ddfc3 | 9d8d90537f36b9d149b91de6298c1feb746b621c63a1437522f2775cb55320fe | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3[C@@H]2C1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].Cl-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[C:7]>>[C:7]-[C:6]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | 70 | [{"value": 70.0, "product": "C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(C(C)C)=O)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "C(C)(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(C(C)C)=O)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C", "details": "CALCULATED... | null | null | null | null | To a mixture of magnesium (24 g, 1.00 mole) in dry ether (500 ml) was added dropwise 2-bromopropane (60 ml, 639 mmole) while stirring. After the addition was completed, the reaction mixture was stirred for thirty minutes. The ethereal solution was transferred to another flask. Then to the resulting isopropyl-magnesium ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide | Ketone | null | null | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | Br- | [Br-].[Cd+2].[Br-].CCOCC.C1=CC=CC=C1 | null | null | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)Cl)[C@@]4(C)CC[C@@H]32)C1.CC(C)Br>[Br-].[Cd+2].[Br-].CCOCC.C1=CC=CC=C1>CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)C(C)C)[C@@]4(C)CC[C@@H]32)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a9146312177a4f9b96171064a8052dc6 | C=CC#N.NCCCCN>>N#CCCNCCCCN | NCCCCN.C(C=C)#N>>C(#N)CCNCCCCN | [N:1]#[C:2][CH:3]=[CH2:4].[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:10]>>[N:1]#[C:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:10] | C=CC#N.NCCCCN | N#CCCNCCCCN | null | null | CO | Heteroatom Alkylation and Arylation | aza-Michael addition primary | b45dd075b7e75caee6dc0a68cb402266c75e0848f7502f06a5dbd8a34863aae2 | 2e45960e6468a140db4162555f247a2535630c23e1aa16e082b84ce22691ebbf | null | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]#[N;D1;H0:4] | 80 | [{"value": 80.0, "product": "C(#N)CCNCCCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "C(#N)CCNCCCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1,4-diaminobutane (4.3 g, 48.8 mmole) in methanol (1.5 ml) was added a solution of acrylonitrile (3.1 g, 58.4 mmole) in methanol (1.5 ml) at 0° C., and the mixture was stirred for twelve hours. Evaporation of the solvent in vacuo afforded N-(2'-cyanoethyl)-1,4-diaminobutane as a colorless oil (5.5 g, 8... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Vinyl | Secondary amine | null | null | null | null | CO | null | null | C=CC#N.NCCCCN>CO>N#CCCNCCCCN |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-26714608e58f4c188b984bcbdffd717d | CN(C)C=O.On1nnc2ccccc21>>C(=NC1CCCCC1)=NC1CCCCC1 | O.CN(C=O)C.C=1C=CC2=C(C1)N=NN2O>>C1CCC(CC1)N=C=NC2CCCCC2 | O=[CH:1][N:2]([CH3:10])[CH3:13].O[n:9]1nn[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]21>>[C:1](=[N:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)=[N:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | CN(C)C=O.On1nnc2ccccc21 | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 114f3155f1ca7cd07407db85b051f50fc4a6d62987a3a4d615a136aa5a7fbbfd | 8023798407645490f6e731ea699842ac34c1c05388635bc82dc9a964e1bf68d5 | C(=NC1CCCCC1)=NC1CCCCC1 | O-[n;H0;D3;+0:1]1:n:n:[c;H0;D3;+0:2]2:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7]:2:1.O=[CH;D2;+0:8]-[N;H0;D3;+0:9](-[CH3;D1;+0:10])-[CH3;D1;+0:11]>>[C:12]1-[C:13]-[CH2;D2;+0:11]-[C:14]-[C:15]-[CH;D3;+0:10]-1-[N;H0;D2;+0:1]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[... | 100 | [{"value": 100.0, "product": "C1CCC(CC1)N=C=NC2CCCCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The subtitled compound was prepared substantially in accordance with the procedure detailed in Example 33, using 0.17 g (0.55 mmol) of S-2-N(t-butoxycarbonyl)amino-3-p-fluoro-phenylthio propanoic acid, 0.22 g (0.55 mmol) of the subtitled intermediate of Preparation 3B and 0.07 g (0.55 mmol) of HOBT.H2O, and 0.11 g (0.5... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | c1ccc2[nH]nnc2c1 | C1CCCCC1.C1CCCCC1 | C1CCCCC1.C1CCCCC1 | null | O1CCCC1 | null | null | CN(C)C=O.On1nnc2ccccc21>O1CCCC1>C(=NC1CCCCC1)=NC1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7eea098e740f49b1bcfabe60ca2ecee0 | CN(C)C=O.On1nnc2ccccc21>>C(=NC1CCCCC1)=NC1CCCCC1 | C=1C=CC2=C(C1)N=NN2O.O.CN(C=O)C>>C1CCC(CC1)N=C=NC2CCCCC2 | O=[CH:1][N:2]([CH3:10])[CH3:13].O[n:9]1nn[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]21>>[C:1](=[N:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1)=[N:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | CN(C)C=O.On1nnc2ccccc21 | C(=NC1CCCCC1)=NC1CCCCC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 114f3155f1ca7cd07407db85b051f50fc4a6d62987a3a4d615a136aa5a7fbbfd | 8023798407645490f6e731ea699842ac34c1c05388635bc82dc9a964e1bf68d5 | C(=NC1CCCCC1)=NC1CCCCC1 | O-[n;H0;D3;+0:1]1:n:n:[c;H0;D3;+0:2]2:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7]:2:1.O=[CH;D2;+0:8]-[N;H0;D3;+0:9](-[CH3;D1;+0:10])-[CH3;D1;+0:11]>>[C:12]1-[C:13]-[CH2;D2;+0:11]-[C:14]-[C:15]-[CH;D3;+0:10]-1-[N;H0;D2;+0:1]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[... | null | [] | null | null | null | null | The subtitled compound was prepared substantially in accordance with the procedure detailed in Example 33, using 0.41 g (0.12 mmol) of S-2-N(t-butoxycarbonyl)amino-3-naphth-2-ylthio propanoic acid, 0.47 g (0.12 mmol) of the subtitled intermediate of Preparation 3B and 0.16 g (0.12 mmol) of HOBT.H2O, and 0.24 g (0.12 mm... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | c1ccc2[nH]nnc2c1 | C1CCCCC1.C1CCCCC1 | C1CCCCC1.C1CCCCC1 | null | O1CCCC1 | null | null | CN(C)C=O.On1nnc2ccccc21>O1CCCC1>C(=NC1CCCCC1)=NC1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-83eb8c4f8a924307bcc393ec98b1dc0e | CCc1c(COC(C)=O)[nH]c(C(=O)OCc2ccccc2)c1C.CCc1c[nH]cc1CC.Cc1ccc(S(=O)(=O)O)cc1>>CCc1c(Cc2[nH]c(Cc3[nH]c(C(=O)OCc4ccccc4)c(C)c3CC)c(CC)c2CC)[nH]c(C(=O)OCc2ccccc2)c1C | C(C)C1=CNC=C1CC.C(C)(=O)OCC1=C(C(=C(N1)C(=O)OCC1=CC=CC=C1)C)CC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C1=CC=CC=C1)OC(=O)C1=C(C(=C(N1)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CC)C)C(=O)OCC1=CC=CC=C1)CC)C | O([CH2:5][c:4]1[c:3]([CH2:2][CH3:1])[c:46]([CH3:47])[c:35]([C:36](=[O:37])[O:38][CH2:39][c:40]2[cH:41][cH:42][cH:43][cH:44][cH:45]2)[nH:34]1)[C:8](=[O:14])[CH3:24].[cH:6]1[nH:7][cH:10][c:25]([CH2:26][CH3:27])[c:31]1[CH2:32][CH3:33].O=S(=O)([OH:15])[c:20]1[cH:19][cH:18][c:17]([CH3:16])[cH:22][cH:21]1>>[CH3:1][CH2:2][c:3... | CCc1c(COC(C)=O)[nH]c(C(=O)OCc2ccccc2)c1C.CCc1c[nH]cc1CC.Cc1ccc(S(=O)(=O)O)cc1 | CCc1c(Cc2[nH]c(Cc3[nH]c(C(=O)OCc4ccccc4)c(C)c3CC)c(CC)c2CC)[nH]c(C(=O)OCc2ccccc2)c1C | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 600aaf398f929c1262936e200da881e7793fedc5e27f3fc1a58785791ed628e0 | 65cad71a238f9f57a0a754682b9dac8d4198c0621de1552964f93c5ea2fe28f4 | O=C(OCc1ccccc1)c1ccc(Cc2ccc(Cc3ccc(C(=O)OCc4ccccc4)[nH]3)[nH]2)[nH]1 | O=S(=O)(-[OH;D1;+0:1])-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5](-[CH3;D1;+0:6]):[c:7]:[c:8]:1.[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]:[#7;a:13]:[c:14](-[CH2;D2;+0:15]-O-[C;H0;D3;+0:16](-[CH3;D1;+0:17])=[O;H0;D1;+0:18]):[c:19].[C;D1;H3:20]-[C:21]-[c;H0;D3;+0:22]1:[cH;D2;+0:23]:[nH;D2;+0:24]:[cH;D2;+0:25]:[c;H0;D3;+0:26]:1-[C:27]-[... | 82 | [{"value": 82.0, "product": "C(C1=CC=CC=C1)OC(=O)C1=C(C(=C(N1)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CC)C)C(=O)OCC1=CC=CC=C1)CC)C", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 3,4-Diethylpyrrole (2A, FIG. 2)28 (0.6, 4.9 mmol), benzyl 5-(acetoxymethyl)-3-methyl-4-ethyl-pyrrole-2-carboxylate (2B, FIG. 2)29 (2.5 g, 7.9 mmol), and p-toluenesulfonic acid (0.15 g) were dissolved in 60 mL of absolute ethanol and heated at 60° C. for 8 h under nitrogen. The resulting suspension was reduced in volume... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ester | Ester | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1cc[nH]c1.c1cc[nH]c1.c1ccccc1.c1ccccc1 | null | C(C)O | 60 | null | CCc1c(COC(C)=O)[nH]c(C(=O)OCc2ccccc2)c1C.CCc1c[nH]cc1CC.Cc1ccc(S(=O)(=O)O)cc1>C(C)O>CCc1c(Cc2[nH]c(Cc3[nH]c(C(=O)OCc4ccccc4)c(C)c3CC)c(CC)c2CC)[nH]c(C(=O)OCc2ccccc2)c1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-faa1480b90664caba1f4a00882c01709 | CCc1c[nH]cc1CC.COC(=O)CCc1c(COC(C)=O)[nH]c(C(=O)OCc2ccccc2)c1C.Cc1ccc(S(=O)(=O)O)cc1>>CCc1c(Cc2[nH]c(C(=O)OCc3ccccc3)c(C)c2CCC(=O)OC)[nH]c(Cc2[nH]c(C(=O)OCc3ccccc3)c(C)c2CCC(=O)OC)c1CC | C(C)C1=CNC=C1CC.C(C)(=O)OCC=1NC(=C(C1CCC(=O)OC)C)C(=O)OCC1=CC=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C1=CC=CC=C1)OC(=O)C1=C(C(=C(N1)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CCC(=O)OC)C)C(=O)OCC1=CC=CC=C1)CCC(=O)OC)C | [CH3:1][CH2:2][c:3]1[cH:4][nH:7][cH:29][c:53]1[CH2:54][CH3:55].[O:11]([C:24]([CH3:23])=[O:25])[CH2:30][c:31]1[nH:32][c:33]([C:34](=[O:35])[O:36][CH2:37][c:38]2[cH:39][cH:40][cH:41][cH:42][cH:43]2)[c:44]([CH3:45])[c:46]1[CH2:47][CH2:48][C:49]([O:26][CH3:27])=[O:50].O=S([c:9]1[cH:5][cH:52][c:13]([CH3:12])[cH:14][cH:15]1)... | CCc1c[nH]cc1CC.COC(=O)CCc1c(COC(C)=O)[nH]c(C(=O)OCc2ccccc2)c1C.Cc1ccc(S(=O)(=O)O)cc1 | CCc1c(Cc2[nH]c(C(=O)OCc3ccccc3)c(C)c2CCC(=O)OC)[nH]c(Cc2[nH]c(C(=O)OCc3ccccc3)c(C)c2CCC(=O)OC)c1CC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41c704c9268eecf128b8ec15576492d38d32af8d1b98e647657336d6d17e7795 | a62d3e14dc3e686bbba664c7702698a10196425b96dfa226dc079bfa87919be9 | O=C(OCc1ccccc1)c1ccc(Cc2ccc(Cc3ccc(C(=O)OCc4ccccc4)[nH]3)[nH]2)[nH]1 | O=S(=[O;H0;D1;+0:1])(-[OH;D1;+0:2])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5]:[c;H0;D3;+0:6](-[CH3;D1;+0:7]):[cH;D2;+0:8]:[cH;D2;+0:9]:1.[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]:[#7;a:14]:[c:15](-[CH2;D2;+0:16]-[O;H0;D2;+0:17]-[C;H0;D3;+0:18](-[CH3;D1;+0:19])=[O;D1;H0:20]):[c:21]-[C:22]-[C:23]-[C;H0;D3;+0:24](=[O;D1;H0:25])-[O;H0... | 61 | [{"value": 61.0, "product": "C(C1=CC=CC=C1)OC(=O)C1=C(C(=C(N1)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CCC(=O)OC)C)C(=O)OCC1=CC=CC=C1)CCC(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 7C, FIG. 7. In a 500 mL round bottom flask was placed 250 mL of ethanol from an unopened bottle and this was then purged with dry nitrogen for ten minutes. 3,4-Diethylpyrrole 7B (1.29 g, 0.01 mol) and 2-acetoxymethyl-5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrole 7A (7.83 g, 0.02 mol) were added and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ester.Ester | Ester.Ester.Ester | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1cc[nH]c1.c1ccccc1.c1cc[nH]c1.c1ccccc1 | null | null | 60 | null | CCc1c[nH]cc1CC.COC(=O)CCc1c(COC(C)=O)[nH]c(C(=O)OCc2ccccc2)c1C.Cc1ccc(S(=O)(=O)O)cc1>>CCc1c(Cc2[nH]c(C(=O)OCc3ccccc3)c(C)c2CCC(=O)OC)[nH]c(Cc2[nH]c(C(=O)OCc3ccccc3)c(C)c2CCC(=O)OC)c1CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-712078ea7b614a19ba70e3fd5bf416de | CCc1c(Cc2[nH]c(C=O)c(C)c2CCCOC(C)=O)[nH]c(Cc2[nH]c(C=O)c(C)c2CCCOC(C)=O)c1CC>>CCc1c(Cc2[nH]c(C=O)c(C)c2CCCO)[nH]c(Cc2[nH]c(C=O)c(C)c2CCCO)c1CC | C(C)(=O)OCCCC1=C(NC(=C1C)C=O)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CCCOC(C)=O)C)C=O.[Li+].[OH-]>>C(=O)C1=C(C(=C(N1)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CCCO)C)C=O)CCCO)C | CC(=O)[O:17][CH2:16][CH2:15][CH2:14][c:13]1[c:6]([CH2:5][c:4]2[c:3]([CH2:2][CH3:1])[c:33]([CH2:34][CH3:35])[c:19]([CH2:20][c:21]3[nH:22][c:23]([CH:24]=[O:25])[c:26]([CH3:27])[c:28]3[CH2:29][CH2:30][CH2:31][O:32]C(C)=O)[nH:18]2)[nH:7][c:8]([CH:9]=[O:10])[c:11]1[CH3:12]>>[CH3:1][CH2:2][c:3]1[c:4]([CH2:5][c:6]2[nH:7][c:8]... | CCc1c(Cc2[nH]c(C=O)c(C)c2CCCOC(C)=O)[nH]c(Cc2[nH]c(C=O)c(C)c2CCCOC(C)=O)c1CC | CCc1c(Cc2[nH]c(C=O)c(C)c2CCCO)[nH]c(Cc2[nH]c(C=O)c(C)c2CCCO)c1CC | null | null | CO | Reduction | OtherReaction | 8eb0b0948ba02d6bff2e6dcc47886480a262869f201923801796429d5f921f16 | 3906c52a610c5241bd14656b0a46d01a4c70864c3b16d9b6e34a49708e61df8d | c1c[nH]c(Cc2ccc(Cc3ccc[nH]3)[nH]2)c1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3].C-C(=O)-[O;H0;D2;+0:4]-[C:5]-[C:6]>>[C:3]-[C:2]-[OH;D1;+0:1].[C:6]-[C:5]-[OH;D1;+0:4] | 94 | [{"value": 94.0, "product": "C(=O)C1=C(C(=C(N1)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CCCO)C)C=O)CCCO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "C(=O)C1=C(C(=C(N1)CC=1NC(=C(C1CC)CC)CC=1NC(=C(C1CCCO)C)C=O)CCCO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7H, FIG. 7. 2,5-Bis[(3-acetoxypropyl-5-formyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole 7G (5.98 g, 0.011 mol) and LiOH (1.76 g, 0.042 mol) were added to 400 mL of 95% methanol, which had been degassed with nitrogen prior to use, add the mixture heated to reflux under a nitrogen atmosphere. The reaction became hom... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Primary alcohol.Primary alcohol | null | null | c1cc[nH]c1.c1cc[nH]c1.c1cc[nH]c1 | HO- | CO | null | null | CCc1c(Cc2[nH]c(C=O)c(C)c2CCCOC(C)=O)[nH]c(Cc2[nH]c(C=O)c(C)c2CCCOC(C)=O)c1CC>CO>CCc1c(Cc2[nH]c(C=O)c(C)c2CCCO)[nH]c(Cc2[nH]c(C=O)c(C)c2CCCO)c1CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-61d7db87905c47f9b370b8d2340da826 | COc1cc([N+](=O)[O-])c([N+](=O)[O-])cc1OC>>O=[N+]([O-])c1cc(O)c(O)cc1[N+](=O)[O-] | Br.COC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])OC>>OC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])O | C[O:7][c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:11]([N+:12](=[O:13])[O-:14])[cH:10][c:8]1[O:9]C>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([OH:7])[c:8]([OH:9])[cH:10][c:11]1[N+:12](=[O:13])[O-:14] | COc1cc([N+](=O)[O-])c([N+](=O)[O-])cc1OC | O=[N+]([O-])c1cc(O)c(O)cc1[N+](=O)[O-] | null | null | C(C)(=O)O | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | 9,869.8 | [{"value": 84.0, "product": "OC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9869.8, "product": "OC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 8B, FIG. 8. In a dry 500 mL round bottom flask, 1,2-dimethoxy-4,5-dinitrobenzene (3.2 g, 0.12 mmol) 8A was stirred vigorously in 40 mL of glacial acetic acid at 30° C. Once a homogeneous solution 200 mL of 48% HBr was added to the flask and the reaction was slowly heated to reflux. The reaction was complete as indicate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | C(C)(=O)O | null | 4 | COc1cc([N+](=O)[O-])c([N+](=O)[O-])cc1OC>C(C)(=O)O>O=[N+]([O-])c1cc(O)c(O)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-158b075907054ab39ba581443375f769 | O=[N+]([O-])c1cc(O)c(O)cc1[N+](=O)[O-].OCC(O)CCl.[OH-]>>O=[N+]([O-])c1cc(OCC(O)CO)c(OCC(O)CO)cc1[N+](=O)[O-] | OC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])O.ClCC(CO)O.[OH-].[K+]>>OC(COC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])OCC(CO)O)CO | [O-:1][N+:2]([c:4]1[cH:5][c:6]([OH:7])[c:13]([OH:14])[cH:20][c:11]1[N+:22](=[O:23])[O-:24])=[O:12].Cl[CH2:8][CH:9]([OH:10])[CH2:18][OH:19].[OH-:17]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][CH:9]([OH:10])[CH2:11][OH:12])[c:13]([O:14][CH2:15][CH:16]([OH:17])[CH2:18][OH:19])[cH:20][c:21]1[N+:22](=[O:23])[O-:24] | O=[N+]([O-])c1cc(O)c(O)cc1[N+](=O)[O-].OCC(O)CCl.[OH-] | O=[N+]([O-])c1cc(OCC(O)CO)c(OCC(O)CO)cc1[N+](=O)[O-] | null | null | C(CCC)O | C-C Coupling | OtherReaction | 77234debcd7382bb96dee1071914678bc9622b5773ffb5986defbec6cbdb1be6 | 6231048ecbe0ac7045ba507e078985495fd6b43d9ee9f2401519f1f270735cc4 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[CH;D3;+0:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[O;D1;H1:5].[O-;H0;D1:6]-[N+;H0;D3:7](=[O;H0;D1;+0:8])-[c;H0;D3;+0:9]1:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13](-[OH;D1;+0:14]):[cH;D2;+0:15]:[c;H0;D3;+0:16]:1-[N+;H0;D3:17](-[O;-;D1;H0:18])=[O;D1;H0:19].[OH-;D0:20]>>[O;-;D1;H0:18]-[N+;H0;D3:17](=[O;D1;H0:19])-[c:21... | 67.9 | [{"value": 30.0, "product": "OC(COC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])OCC(CO)O)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "OC(COC1=C(C=C(C(=C1)[N+](=O)[O-])[N+](=O)[O-])OCC(CO)O)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 8C, FIG. 8. 1,2-Dihydroxy-4,5-dinitrobenzene 8B (5.0 g, 22 mmol) and 1-chloro-2,3-dihydroxypropane (12.1 g, 110 mmol) were refluxed for 48 hours in a solution of potassium hydroxide (4.4 g) in 1-butanol (100 mL) under a nitrogen atmosphere. The resulting mixture was concentrated under reduced pressure, and the dark res... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitro group.Nitro group.Primary alcohol.Secondary alcohol.Aromatic alcohol.Aromatic alcohol | Ether.Ether.Nitro group.Nitro group.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C(CCC)O | null | 0.25 | O=[N+]([O-])c1cc(O)c(O)cc1[N+](=O)[O-].OCC(O)CCl.[OH-]>C(CCC)O>O=[N+]([O-])c1cc(OCC(O)CO)c(OCC(O)CO)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1df0841ea5aa4fe28c1d99da441ccf1a | COC(=O)c1nc2ccccc2c(O)c1C(=O)OC.NN>>O=c1[nH][nH]c(=O)c2c(O)c3ccccc3nc12 | OC1=C(C(=NC2=CC=CC=C12)C(=O)OC)C(=O)OC.O.NN>>OC1=C2C(=NC=3C=CC=CC13)C(NNC2=O)=O | CO[C:2](=[O:1])[c:17]1[c:7]([C:5](OC)=[O:6])[c:8]([OH:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[n:16]1.[NH2:3][NH2:4]>>[O:1]=[c:2]1[nH:3][nH:4][c:5](=[O:6])[c:7]2[c:8]([OH:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[n:16][c:17]12 | COC(=O)c1nc2ccccc2c(O)c1C(=O)OC.NN | O=c1[nH][nH]c(=O)c2c(O)c3ccccc3nc12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | ec1917a0188259fb1d502a40ed3d9aad8b3b567f28677d868775be5ee838e719 | 1775b7eba35fc46eaa0b0ad39cde9e207db465168e4fe5d9832db816e257be74 | O=c1[nH][nH]c(=O)c2nc3ccccc3cc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[#7;a:4]:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-O-C):[c:9].[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:10]:[nH;D2;+0:11]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[c:6](:[c:9]):[c:3]:1:[#7;a:4]:[c:5] | 112.8 | [{"value": 112.8, "product": "OC1=C2C(=NC=3C=CC=CC13)C(NNC2=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of dimethyl 4-hydroxyquinoline-2,3-dicarboxylate (1.00 g, 3.83 mM, prepared as described by H. Biere and W. Seelen, Liebigs Ann. Chem. 1976, 1972) in ethanol (15 mL) was added hydrazine hydrate (9.64 g, 193 mM) whereupon the solids dissolved. The resulting solution was refluxed for 3 hr during w... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester.Ester | null | c1ccc2ncccc2c1 | C1=c2cc3ccccc3nc2=CNN1 | C1=c2cc3ccccc3nc2=CNN1 | HO- | C(C)O | null | null | COC(=O)c1nc2ccccc2c(O)c1C(=O)OC.NN>C(C)O>O=c1[nH][nH]c(=O)c2c(O)c3ccccc3nc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d09058163d114c2aaa3e06a2b0426827 | COC(=O)C#CC(=O)OC.COC(=O)c1ccc(Cl)cc1N>>COC(=O)c1nc2cc(Cl)ccc2c(O)c1C(=O)OC | CC(C)([O-])C.[K+].NC1=C(C(=O)OC)C=CC(=C1)Cl.C(#CC(=O)OC)C(=O)OC.C(#CC(=O)OC)C(=O)OC>>ClC1=CC=C2C(=C(C(=NC2=C1)C(=O)OC)C(=O)OC)O | [CH3:1][O:2][C:3](=[O:4])[C:5]#[C:16][C:17](=[O:18])[O:19][CH3:20].CO[C:14]([c:13]1[c:7]([NH2:6])[cH:8][c:9]([Cl:10])[cH:11][cH:12]1)=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][cH:12][c:13]2[c:14]([OH:15])[c:16]1[C:17](=[O:18])[O:19][CH3:20] | COC(=O)C#CC(=O)OC.COC(=O)c1ccc(Cl)cc1N | COC(=O)c1nc2cc(Cl)ccc2c(O)c1C(=O)OC | null | null | C(C)(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | f5368757c96521e83619cf21dfc52b28c31825e0516659832aaa47488ac6716c | bbcf1c85e1dbdba58f5fefc8b60992ba8e370d006abd0aa7780d40fd3f3dc3a2 | c1ccc2ncccc2c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D2;+0:12]#[C;H0;D2;+0:13]-[C:14](=[O;D1;H0:15])-[#8:16]-[C;D1;H3:17]>>[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:12]1:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3](:[c:4]):[c;H0;D3;+0:1](-[OH;D1;+... | 28.9 | [{"value": 28.9, "product": "ClC1=CC=C2C(=C(C(=NC2=C1)C(=O)OC)C(=O)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.9, "product": "ClC1=CC=C2C(=C(C(=NC2=C1)C(=O)OC)C(=O)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of methyl 2-amino-4-chlorobenzoate (2.50 g, 13.5 mM) and dimethyl acetylenedicarboxylate (2.05 g, 14.4 mM) in t-butanol (22 mL) was refluxed for 7 hr under a nitrogen atmosphere. After adding additional dimethyl acetylenedicarboxylate (1.16 g, 8.13 mM) and refluxing another 2.5 hr, the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Primary amine | Ester.Ester.Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C(C)(C)(C)O | null | null | COC(=O)C#CC(=O)OC.COC(=O)c1ccc(Cl)cc1N>C(C)(C)(C)O>COC(=O)c1nc2cc(Cl)ccc2c(O)c1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-11cb73d43db14970822d1f7987ae94cd | Nc1cccc(Cl)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=c1[nH]c2cccc(Cl)c2c(=O)o1 | NC1=C(C(=O)O)C(=CC=C1)Cl.ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O>>ClC1=CC=CC2=C1C(OC(N2)=O)=O | [NH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Cl:9])[c:10]1[C:11](=[O:12])[OH:13].ClC(Cl)(Cl)O[C:2](OC(Cl)(Cl)Cl)=[O:1]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([Cl:9])[c:10]2[c:11](=[O:12])[o:13]1 | Nc1cccc(Cl)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=c1[nH]c2cccc(Cl)c2c(=O)o1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 28a53b633dce43f36b75fb909640acd87a8c845fa916e16156b098b24210c80e | 978aee14c5a6c161c15b14d8af7d43f564770f634ab8a62eec842fdff80e6ac1 | O=c1[nH]c2ccccc2c(=O)o1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:8]=[c;H0;D3;+0:7]1:[o;H0;D2;+0:9]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:3]:[c:4](:[c:5]):[c:6]:1:[c:10] | 250.3 | [{"value": 87.0, "product": "ClC1=CC=CC2=C1C(OC(N2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 250.3, "product": "ClC1=CC=CC2=C1C(OC(N2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred warm (50° C.) solution of 2-amino-6-chlorobenzoic acid (2.00 g, 11.7 mM) in tetrahydrofuran (20 mL) was added bis(trichloromethyl)carbonate (1.20 g, 4.10 mM). A vigorous gas evolution ensued along with the formation of a precipitate. The reaction mixture was allowed to cool to room temperature and the prec... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Carboxylic acid.Primary amine | null | c1ccccc1 | c1nc2ccccc2co1 | c1nc2ccccc2co1 | HCl | O1CCCC1 | null | null | Nc1cccc(Cl)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O1CCCC1>O=c1[nH]c2cccc(Cl)c2c(=O)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-36369dc8420f49d692dad33fc33db94f | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cccc1Cl>>COC(=O)c1nc2cccc(Cl)c2c(O)c1C(=O)OC | NC1=C(C(=O)OC)C(=CC=C1)Cl.C(#CC(=O)OC)C(=O)OC.CC(C)([O-])C.[K+]>>ClC1=C2C(=C(C(=NC2=CC=C1)C(=O)OC)C(=O)OC)O | [CH3:1][O:2][C:3](=[O:4])[C:5]#[C:16][C:17](=[O:18])[O:19][CH3:20].CO[C:14]([c:13]1[c:7]([NH2:6])[cH:8][cH:9][cH:10][c:11]1[Cl:12])=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][c:11]([Cl:12])[c:13]2[c:14]([OH:15])[c:16]1[C:17](=[O:18])[O:19][CH3:20] | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cccc1Cl | COC(=O)c1nc2cccc(Cl)c2c(O)c1C(=O)OC | null | null | C(C)(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | f5368757c96521e83619cf21dfc52b28c31825e0516659832aaa47488ac6716c | bbcf1c85e1dbdba58f5fefc8b60992ba8e370d006abd0aa7780d40fd3f3dc3a2 | c1ccc2ncccc2c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D2;+0:12]#[C;H0;D2;+0:13]-[C:14](=[O;D1;H0:15])-[#8:16]-[C;D1;H3:17]>>[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:12]1:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3](:[c:4]):[c;H0;D3;+0:1](-[OH;D1;+... | 80.4 | [{"value": 80.2, "product": "ClC1=C2C(=C(C(=NC2=CC=C1)C(=O)OC)C(=O)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "ClC1=C2C(=C(C(=NC2=CC=C1)C(=O)OC)C(=O)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 2-amino-6-chlorobenzoate (3.00 g, 16.2 mM) and dimethyl acetylenedicarboxylate (2.64 g, 18.6 mM) in t-butanol (25 mL) was refluxed under a nitrogen atmosphere for 18 hr. The reaction mixture was cooled to room temperature and potassium t-butoxide (2.09 g, 18.6 mM) was added in one portion whereupon... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Primary amine | Ester.Ester.Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C(C)(C)(C)O | null | null | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cccc1Cl>C(C)(C)(C)O>COC(=O)c1nc2cccc(Cl)c2c(O)c1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-62f911c33ec34c2dbe633593e1d5ee82 | CC(=O)O.O=C1Nc2cc(Cl)cc(Cl)c2C1=O>>O=c1[nH]c2cc(Cl)cc(Cl)c2c(=O)o1 | ClC1=C2C(C(NC2=CC(=C1)Cl)=O)=O.C(C)(=O)O>>ClC1=CC(=CC2=C1C(OC(N2)=O)=O)Cl | CC(=O)[OH:14].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][c:9]([Cl:10])[c:11]2[C:12]1=[O:13]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([Cl:7])[cH:8][c:9]([Cl:10])[c:11]2[c:12](=[O:13])[o:14]1 | CC(=O)O.O=C1Nc2cc(Cl)cc(Cl)c2C1=O | O=c1[nH]c2cc(Cl)cc(Cl)c2c(=O)o1 | null | [O-2].[O-2].[O-2].[Cr+6].[O-2].[O-2].[O-2].[Cr+6] | C(C)(=O)OC(C)=O.O | Miscellaneous | OtherReaction | 0f840b75ec018dc5052ca8f2adcc7010a68835c9436e293d8f842301d50cb013 | 60d059b579be791b3a253c788440e1c71f340c489355625c4d000c8e8143e816 | O=c1[nH]c2ccccc2c(=O)o1 | C-C(=O)-[OH;D1;+0:1].[O;D1;H0:2]=[C;H0;D3;+0:3]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]-1:[c:10]>>[O;D1;H0:2]=[c;H0;D3;+0:3]1:[o;H0;D2;+0:1]:[c;H0;D3;+0:4](=[O;D1;H0:5]):[nH;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10] | 72 | [{"value": 72.0, "product": "ClC1=CC(=CC2=C1C(OC(N2)=O)=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 4,6-dichloro-1H-indole-2,3-dione (5.00 g, 23.2 mM) in acetic acid (21 mL) and acetic anhydride (21 mL) at 80° C. was added in small portions chromium trioxide (4.12 g, 41.3 mM). The temperature of the reaction mixture was maintained between 80°-90° C. during the addition of the chromium trioxid... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Secondary amide | null | c1ccc2c(c1)CCN2 | c1ccc2cocnc2c1 | c1ccc2cocnc2c1 | HO- | [O-2].[O-2].[O-2].[Cr+6].[O-2].[O-2].[O-2].[Cr+6].C(C)(=O)OC(C)=O.O | null | null | CC(=O)O.O=C1Nc2cc(Cl)cc(Cl)c2C1=O>[O-2].[O-2].[O-2].[Cr+6].[O-2].[O-2].[O-2].[Cr+6].C(C)(=O)OC(C)=O.O>O=c1[nH]c2cc(Cl)cc(Cl)c2c(=O)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-739ac2ee85f042ce86c3862c763ac88d | O=c1[nH]c2cc(Cl)cc(Cl)c2c(=O)o1>>COC(=O)c1c(N)cc(Cl)cc1Cl | [OH-].[Na+].ClC1=CC(=CC2=C1C(OC(N2)=O)=O)Cl>>NC1=C(C(=O)OC)C(=CC(=C1)Cl)Cl | O=[c:1]1[o:2][c:3](=[O:4])[c:5]2[c:6]([nH:7]1)[cH:8][c:9]([Cl:10])[cH:11][c:12]2[Cl:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[Cl:13] | O=c1[nH]c2cc(Cl)cc(Cl)c2c(=O)o1 | COC(=O)c1c(N)cc(Cl)cc1Cl | null | null | CO | Reduction | OtherReaction | fb3a8999d982d1c42a150fbbeb96fa0db2838a9c48a5140f183de4d3421c8ad6 | 9f87be38aa9793f80b3cef223629015a04ccba30a9633b313486e0a6edc9c43d | c1ccccc1 | O=[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](=[O;D1;H0:8]):[o;H0;D2;+0:9]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:5](:[c:6]):[c:3](-[NH2;D1;+0:2]):[c:4] | 92.2 | [{"value": 92.1, "product": "NC1=C(C(=O)OC)C(=CC(=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "NC1=C(C(=O)OC)C(=CC(=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 2 | HOUR | To a stirred solution of sodium hydroxide (0.070 g, 1.8 mM) in methanol (8.5 mL) was added 5,7-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione (4.13 g, 17.8 mM). The reaction mixture was stirred at 55° C. for 2 hr, allowed to cool to room temperature and concentrated. The residue was diluted with water and the resulting mixt... | 10.6084/m9.figshare.5104873.v1 | null | null | Ester.Primary amine | c1ccc2cocnc2c1 | c1ccccc1 | c1ccccc1 | Other | CO | 55 | 2 | O=c1[nH]c2cc(Cl)cc(Cl)c2c(=O)o1>CO>COC(=O)c1c(N)cc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-80b7e4ba59954100866003a993d7b735 | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cc(Cl)cc1Cl>>COC(=O)c1nc2cc(Cl)cc(Cl)c2c(O)c1C(=O)OC | NC1=C(C(=O)OC)C(=CC(=C1)Cl)Cl.C(#CC(=O)OC)C(=O)OC.CC(C)([O-])C.[K+]>>ClC1=C2C(=C(C(=NC2=CC(=C1)Cl)C(=O)OC)C(=O)OC)O | [CH3:1][O:2][C:3](=[O:4])[C:5]#[C:17][C:18](=[O:19])[O:20][CH3:21].CO[C:15]([c:14]1[c:7]([NH2:6])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[Cl:13])=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]2[cH:8][c:9]([Cl:10])[cH:11][c:12]([Cl:13])[c:14]2[c:15]([OH:16])[c:17]1[C:18](=[O:19])[O:20][CH3:21] | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cc(Cl)cc1Cl | COC(=O)c1nc2cc(Cl)cc(Cl)c2c(O)c1C(=O)OC | null | null | C(C)(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | f5368757c96521e83619cf21dfc52b28c31825e0516659832aaa47488ac6716c | bbcf1c85e1dbdba58f5fefc8b60992ba8e370d006abd0aa7780d40fd3f3dc3a2 | c1ccc2ncccc2c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D2;+0:12]#[C;H0;D2;+0:13]-[C:14](=[O;D1;H0:15])-[#8:16]-[C;D1;H3:17]>>[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:12]1:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3](:[c:4]):[c;H0;D3;+0:1](-[OH;D1;+... | 59 | [{"value": 59.0, "product": "ClC1=C2C(=C(C(=NC2=CC(=C1)Cl)C(=O)OC)C(=O)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.0, "product": "ClC1=C2C(=C(C(=NC2=CC(=C1)Cl)C(=O)OC)C(=O)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 2-amino-4,6-dichlorobenzoate (1.30 g, 5.91 mM) and dimethyl acetylenedicarboxylate (0.96 g, 6.78 mM) in t-butanol (14 mL) was refluxed for 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (0.76 g, 6.8 mM) was added to the stirred mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Primary amine | Ester.Ester.Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C(C)(C)(C)O | null | null | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cc(Cl)cc1Cl>C(C)(C)(C)O>COC(=O)c1nc2cc(Cl)cc(Cl)c2c(O)c1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3dda300c17224ab9a94f5d53c331760a | COC(=O)C#CC(=O)OC.COC(=O)c1c(C)cccc1N>>COC(=O)c1nc2cccc(C)c2c(O)c1C(=O)OC | NC1=C(C(=O)OC)C(=CC=C1)C.C(#CC(=O)OC)C(=O)OC.CC(C)([O-])C.[K+]>>OC1=C(C(=NC2=CC=CC(=C12)C)C(=O)OC)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C:5]#[C:16][C:17](=[O:18])[O:19][CH3:20].CO[C:14]([c:13]1[c:7]([NH2:6])[cH:8][cH:9][cH:10][c:11]1[CH3:12])=[O:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][c:11]([CH3:12])[c:13]2[c:14]([OH:15])[c:16]1[C:17](=[O:18])[O:19][CH3:20] | COC(=O)C#CC(=O)OC.COC(=O)c1c(C)cccc1N | COC(=O)c1nc2cccc(C)c2c(O)c1C(=O)OC | null | null | C(C)(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | f5368757c96521e83619cf21dfc52b28c31825e0516659832aaa47488ac6716c | bbcf1c85e1dbdba58f5fefc8b60992ba8e370d006abd0aa7780d40fd3f3dc3a2 | c1ccc2ncccc2c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D2;+0:12]#[C;H0;D2;+0:13]-[C:14](=[O;D1;H0:15])-[#8:16]-[C;D1;H3:17]>>[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:12]1:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3](:[c:4]):[c;H0;D3;+0:1](-[OH;D1;+... | 66.4 | [{"value": 66.4, "product": "OC1=C(C(=NC2=CC=CC(=C12)C)C(=O)OC)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.4, "product": "OC1=C(C(=NC2=CC=CC(=C12)C)C(=O)OC)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of methyl 2-amino-6-methylbenzoate (1.50 g, 9.08 mM) and dimethyl acetylenedicarboxylate (1.40 g, 9.82 mM) in t-butanol (20 mL) was refluxed fpr 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (1.10 g, 9.82 mM) was added in one portion wh... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Primary amine | Ester.Ester.Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C(C)(C)(C)O | null | null | COC(=O)C#CC(=O)OC.COC(=O)c1c(C)cccc1N>C(C)(C)(C)O>COC(=O)c1nc2cccc(C)c2c(O)c1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5139598c1f4b45d2b198d2ebd6c62ba7 | Cc1cc(C)cc(N)c1.NO.OC(O)C(Cl)(Cl)Cl>>Cc1cc(C)cc(NC(=O)C=NO)c1 | ClC(C(O)O)(Cl)Cl.S(=O)(=O)([O-])[O-].[Na+].[Na+].CC=1C=C(N)C=C(C1)C.Cl.Cl.NO>>CC=1C=C(C=C(C1)C)NC(C=NO)=O | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([NH2:8])[cH:14]1.[NH2:12][OH:13].O[CH:11]([C:9](Cl)(Cl)Cl)[OH:10]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([NH:8][C:9](=[O:10])[CH:11]=[N:12][OH:13])[cH:14]1 | Cc1cc(C)cc(N)c1.NO.OC(O)C(Cl)(Cl)Cl | Cc1cc(C)cc(NC(=O)C=NO)c1 | null | null | O | Acylation | OtherReaction | 945b0c41a86c791948d53e53b6060216294cdbc727563e10d955fcd0adda1c96 | ed66e3eedfeda41282995a3fcf8794b82675627b3c0201c4e47ec301ec6a89a1 | c1ccccc1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[CH;D3;+0:2](-O)-[OH;D1;+0:3].[NH2;D1;+0:4]-[O;D1;H1:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H1:5]-[N;H0;D2;+0:4]=[CH;D2;+0:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:3])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 95 | [{"value": 95.0, "product": "CC=1C=C(C=C(C1)C)NC(C=NO)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of chloral hydrate (14.1 g, 85.24 mM) and sodium sulfate (88.2g, 7.53 eq.) in 270 mL of water was added a solution of 3,5-dimethylaniline in a solution of concentrated HCl (16 mL) and water (51 mL), whereupon an off-white precipitate formed. The mixture was stirred for 10 min prior to adding an aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary alcohol.Secondary alcohol.Primary amine.Primary amine | Secondary amide.Oxime | null | null | c1ccccc1 | HCl | O | null | 0.166667 | Cc1cc(C)cc(N)c1.NO.OC(O)C(Cl)(Cl)Cl>O>Cc1cc(C)cc(NC(=O)C=NO)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d8484403e58847a9996f4809780dd83c | Cc1cc(C)cc(NC(=O)C=NO)c1>>Cc1cc(C)c2c(c1)NC(=O)C2=O | OS(=O)(=O)O.CC=1C=C(C=C(C1)C)NC(C=NO)=O>>CC1=C2C(C(NC2=CC(=C1)C)=O)=O | N(=[CH:12][C:10]([NH:9][c:7]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:8]1)=[O:11])[OH:13]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7]([cH:8]1)[NH:9][C:10](=[O:11])[C:12]2=[O:13] | Cc1cc(C)cc(NC(=O)C=NO)c1 | Cc1cc(C)c2c(c1)NC(=O)C2=O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 03e26bd863db1451489ee0f1368908e688e08d7fcfd1b579498bc95cc4edfd9e | ab4bf08516e66cf6fd8670ac9e8d4ecd074b35f40b66b51c2d0c9c0d98ab1c51 | O=C1Nc2ccccc2C1=O | [C;D1;H3:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[#7:6]-[C:7](=[O;D1;H0:8])-[CH;D2;+0:9]=N-[OH;D1;+0:10]):[c:11]>>[C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[c:5](:[c:11])-[#7:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10] | 72.6 | [{"value": 72.6, "product": "CC1=C2C(C(NC2=CC(=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a stirred warm (60°-70° C.) solution of concentrated H2SO4 (60 mL) and water (6 mL) was added in small portions N-(3,5-dimethylphenyl)-2-(hydroxyimino)acetamide (15.0 g, 78 mM) so that the temperature of the reaction mixture did not exceed 70° C. After the addition was completed, the reaction mixture was heated at 8... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Ketone | c1ccccc1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | O | 80 | null | Cc1cc(C)cc(NC(=O)C=NO)c1>O>Cc1cc(C)c2c(c1)NC(=O)C2=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ed246c15161e44ccb5ed8c113f70f2e4 | Cc1cc(C)c2c(c1)NC(=O)C2=O.O>>Cc1cc(C)c2c(=O)oc(=O)[nH]c2c1 | CC1=C2C(C(NC2=CC(=C1)C)=O)=O.O>>CC1=CC(=CC2=C1C(OC(N2)=O)=O)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:13]([cH:14]1)[NH:12][C:10](=[O:11])[C:7]2=[O:8].[OH2:9]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]2[c:7](=[O:8])[o:9][c:10](=[O:11])[nH:12][c:13]2[cH:14]1 | Cc1cc(C)c2c(c1)NC(=O)C2=O.O | Cc1cc(C)c2c(=O)oc(=O)[nH]c2c1 | null | [O-2].[O-2].[O-2].[Cr+6] | C(C)(=O)O | Miscellaneous | OtherReaction | 5d9736fd05de108b71c591acfae61cb6af4635bfbe20446a56c7b74a3d5953af | 8242b1e5e71ebd9e44538af93284e3a1145dd4183387fabf58d37d4a04b884a5 | O=c1[nH]c2ccccc2c(=O)o1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;D1;H0:9].[OH2;D0;+0:10]>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8](=[O;D1;H0:9]):[o;H0;D2;+0:10]:1 | 31 | [{"value": 31.0, "product": "CC1=CC(=CC2=C1C(OC(N2)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a stirred warm (60° C.) solution of 4,6-dimethyl-1H-indole-2,3-dione (2.0 g, 11.4 mM) in acetic acid (20 mL) was added in small portions chromium trioxide (6.6 g, 66 mM) while maintaining the temperature of the reaction mixture at 65°-70° C. The reaction mixture was then heated at 80° C. for one hour, cooled, poured... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide | null | c1ccc2c(c1)CCN2 | c1ccc2cocnc2c1 | c1ccc2cocnc2c1 | null | [O-2].[O-2].[O-2].[Cr+6].C(C)(=O)O | 80 | null | Cc1cc(C)c2c(c1)NC(=O)C2=O.O>[O-2].[O-2].[O-2].[Cr+6].C(C)(=O)O>Cc1cc(C)c2c(=O)oc(=O)[nH]c2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a81f6348ff444b79db47e60e3184959 | Cc1cc(C)c2c(=O)oc(=O)[nH]c2c1>>COC(=O)c1c(C)cc(C)cc1N | [OH-].[Na+].CC1=CC(=CC2=C1C(OC(N2)=O)=O)C>>NC1=C(C(=O)OC)C(=CC(=C1)C)C | O=[c:1]1[o:2][c:3](=[O:4])[c:5]2[c:6]([CH3:7])[cH:8][c:9]([CH3:10])[cH:11][c:12]2[nH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[cH:8][c:9]([CH3:10])[cH:11][c:12]1[NH2:13] | Cc1cc(C)c2c(=O)oc(=O)[nH]c2c1 | COC(=O)c1c(C)cc(C)cc1N | null | null | CO | Reduction | OtherReaction | fb3a8999d982d1c42a150fbbeb96fa0db2838a9c48a5140f183de4d3421c8ad6 | 9f87be38aa9793f80b3cef223629015a04ccba30a9633b313486e0a6edc9c43d | c1ccccc1 | O=[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](=[O;D1;H0:8]):[o;H0;D2;+0:9]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:5](:[c:6]):[c:3](-[NH2;D1;+0:2]):[c:4] | 86 | [{"value": 86.0, "product": "NC1=C(C(=O)OC)C(=CC(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "NC1=C(C(=O)OC)C(=CC(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a stirred solution of sodium hydroxide (0.013 g, 0.33 mM) in methanol (1.7 mL) was added 5,7-dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione (0.67 g, 3.5 mM). The mixture was heated to 60° C. and maintained at that temperature for 45 min during which vigorous gas evolution ensued and all solids dissolved completely. The s... | 10.6084/m9.figshare.5104873.v1 | null | null | Ester.Primary amine | c1ccc2cocnc2c1 | c1ccccc1 | c1ccccc1 | Other | CO | 60 | null | Cc1cc(C)c2c(=O)oc(=O)[nH]c2c1>CO>COC(=O)c1c(C)cc(C)cc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-25ba7dfa0f824982b8c2a5e57de886c1 | CC(=O)O.COc1ccc(C#N)c([N+](=O)[O-])c1.O=S(=O)(O)O>>COc1ccc(C(=O)O)c([N+](=O)[O-])c1 | [N+](=O)([O-])C1=C(C#N)C=CC(=C1)OC.C(C)(=O)O.S(O)(O)(=O)=O>>[N+](=O)([O-])C1=C(C(=O)O)C=CC(=C1)OC | CC(O)=[O:8].N#[C:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][c:10]1[N+:11](=[O:12])[O-:13].O=S(=O)(O)[OH:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | CC(=O)O.COc1ccc(C#N)c([N+](=O)[O-])c1.O=S(=O)(O)O | COc1ccc(C(=O)O)c([N+](=O)[O-])c1 | null | null | O | Acylation | OtherReaction | f768caf13c17ba0cc87c566c3e05dbc3f4c74e5e896689cebac8385f7f67f9cd | 1db0fabeaac9f8265574309fafb4f2e7a5658521945038cfd32008ac3c3325d4 | c1ccccc1 | C-C(-O)=[O;H0;D1;+0:1].N#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].O-S(=O)(=O)-[OH;D1;+0:6]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[OH;D1;+0:6])-[c:3](:[c:4]):[c:5] | 91.8 | [{"value": 91.8, "product": "[N+](=O)([O-])C1=C(C(=O)O)C=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-nitro-4-methoxybenzonitrile (14.0 g, 78.6 mM) in a solution of acetic acid (28 mL), sulfuric acid (28 mL) and water (28 mL) was refluxed for 11 hr, allowed to cool and diluted with water (200 mL). The resulting precipitate which formed was collected, washed with water and dried to give the title benzoic ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitrile | Carboxylic acid | null | null | c1ccccc1 | HO- | O | null | null | CC(=O)O.COc1ccc(C#N)c([N+](=O)[O-])c1.O=S(=O)(O)O>O>COc1ccc(C(=O)O)c([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-49d860bfec704ababf3ed788e3799c62 | COc1cccc([N+](=O)[O-])c1C(=O)O>>COc1cccc(N)c1C(=O)O | COC1=CC=CC(=C1C(=O)O)[N+](=O)[O-]>>NC1=C(C(=O)O)C(=CC=C1)OC | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:9]1[C:10](=[O:11])[OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[c:9]1[C:10](=[O:11])[OH:12] | COc1cccc([N+](=O)[O-])c1C(=O)O | COc1cccc(N)c1C(=O)O | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | 100.2 | [{"value": 100.0, "product": "NC1=C(C(=O)O)C(=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.2, "product": "NC1=C(C(=O)O)C(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-methoxy-2-nitrobenzoic acid (3.25 g, 16.5 mM) in ethanol (180 mL) containing 10% palladium-on-carbon catalyst (0.30g) was hydrogenated using a Parr apparatus. When hydrogen consumption ceased, the resulting mixture was filtered through diatomaceous earth and the filtrate concentrated to provide the titl... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | null | null | COc1cccc([N+](=O)[O-])c1C(=O)O>[Pd].C(C)O>COc1cccc(N)c1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-566fc546dbbd4317ba914612b55bdb28 | COc1cccc(N)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>COc1cccc2[nH]c(=O)oc(=O)c12 | NC1=C(C(=O)O)C(=CC=C1)OC.ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O>>COC1=CC=CC2=C1C(OC(N2)=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[c:14]1[C:12]([OH:11])=[O:13].ClC(Cl)(Cl)O[C:9](OC(Cl)(Cl)Cl)=[O:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][c:9](=[O:10])[o:11][c:12](=[O:13])[c:14]12 | COc1cccc(N)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | COc1cccc2[nH]c(=O)oc(=O)c12 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 28a53b633dce43f36b75fb909640acd87a8c845fa916e16156b098b24210c80e | 978aee14c5a6c161c15b14d8af7d43f564770f634ab8a62eec842fdff80e6ac1 | O=c1[nH]c2ccccc2c(=O)o1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:10]):[c;H0;D3;+0:7](=[O;D1;H0:8]):[o;H0;D2;+0:9]:1 | 283.3 | [{"value": 94.6, "product": "COC1=CC=CC2=C1C(OC(N2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 283.3, "product": "COC1=CC=CC2=C1C(OC(N2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To a stirred warm (50° C.) solution of 2-amino-6-methoxybenzoic acid (2.70 g, 16.2 mM) in tetrahydrofuran (25 mL) under a nitrogen atmosphere was added bis(trichloromethyl)carbonate (1.60 g, 5.38 mM), whereupon a tan precipitate formed. The reaction mixture was maintained at 50° C. for 30 min, cooled, rewarmed to 50° C... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Carboxylic acid.Primary amine | null | c1ccccc1 | c1nc2ccccc2co1 | c1nc2ccccc2co1 | HCl | O1CCCC1 | 50 | 0.5 | COc1cccc(N)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O1CCCC1>COc1cccc2[nH]c(=O)oc(=O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6710997eb6b640a184d2ce252b03ace7 | COc1cccc2[nH]c(=O)oc(=O)c12>>COC(=O)c1c(N)cccc1OC | O.[OH-].[Na+].COC1=CC=CC2=C1C(OC(N2)=O)=O>>NC1=C(C(=O)OC)C(=CC=C1)OC | O=[c:1]1[o:2][c:3](=[O:4])[c:5]2[c:6]([nH:7]1)[cH:8][cH:9][cH:10][c:11]2[O:12][CH3:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][cH:9][cH:10][c:11]1[O:12][CH3:13] | COc1cccc2[nH]c(=O)oc(=O)c12 | COC(=O)c1c(N)cccc1OC | null | null | CO | Reduction | OtherReaction | 4a877ce7f9d8b0e05ec6ae8c859c09c08e7f1fd55a56b7ca38718591b6593140 | 9f87be38aa9793f80b3cef223629015a04ccba30a9633b313486e0a6edc9c43d | c1ccccc1 | O=[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](=[O;D1;H0:8]):[o;H0;D2;+0:9]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:5](:[c:6]):[c:3](-[NH2;D1;+0:2]):[c:4] | 94 | [{"value": 94.0, "product": "NC1=C(C(=O)OC)C(=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "NC1=C(C(=O)OC)C(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 14.5 | HOUR | To a stirred solution of sodium hydroxide (0.06 g, 1.5 mM) in methanol (7 mL) under a nitrogen atmosphere was added 5-methoxy-2H-3,1-benzoxazine-2,4(1H)-dione (2.90 g, 15.0 mM). The reaction mixture was stirred at 65° C. for 14.5 hr, cooled to room temperature and poured into water. The resulting solution was extracted... | 10.6084/m9.figshare.5104873.v1 | null | null | Ester.Primary amine | c1nc2ccccc2co1 | c1ccccc1 | c1ccccc1 | Other | CO | 65 | 14.5 | COc1cccc2[nH]c(=O)oc(=O)c12>CO>COC(=O)c1c(N)cccc1OC |
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