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-02ee2261663048188cf6d85d2cc96e3f | ord-d0ca2bb5fa8e4a7e9c2ffd5aff410073 | CCO.O=C(O)c1cccnc1O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cccnc1Cl | C(C)O.OC1=C(C(=O)O)C=CC=N1.P(Cl)(Cl)(Cl)(Cl)Cl.P(=O)(Cl)(Cl)Cl>>ClC1=C(C(=O)OCC)C=CC=N1 | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1O.O=P(Cl)(Cl)[Cl:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[Cl:12] | CCO.O=C(O)c1cccnc1O.O=P(Cl)(Cl)Cl | CCOC(=O)c1cccnc1Cl | null | null | null | Protection | OtherReaction | 75789a74555597973d21551267c3e0e83091d9db09905fd888789d98d5f9563f | 4df5c87c1bba9487ca0dac6d5d13d25b2b96819110434b9c385838ee1b983c5e | c1ccncc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c;H0;D3;+0:6](-O):[#7;a:7]:[c:8].[C;D1;H3:9]-[C:10]-[OH;D1;+0:11]>>[C;D1;H3:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c;H0;D3;+0:6](-[Cl;H0;D1;+0:1]):[#7;a:7]:[c:8] | 60 | [{"value": 60.0, "product": "ClC1=C(C(=O)OCC)C=CC=N1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of 2-hydroxynicotinic acid (13.91 g., 0.1 mole) and phosphorus pentachloride (42 g., 0.2 mole) was added phosphorus oxychloride (25 ml., excess) and then stirred at room temperature for 30 minutes. This was then heated at 120° C. for 2 hours. The reaction mixture was then concentrated in vacuo until a red ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Aromatic alcohol | Aromatic halide.Ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | null | null | 0.5 | CCO.O=C(O)c1cccnc1O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cccnc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ca3b6b7778984b1dafee3bcd7b9942eb | CN(C)C=O.c1c[nH]c(-c2cnco2)c1>>O=Cc1ccc(-c2cnco2)[nH]1 | C(C)(=O)[O-].[Na+].N1C(=CC=C1)C1=CN=CO1.CN(C=O)C.P(=O)(Cl)(Cl)Cl>>C(=O)C1=CC=C(N1)C1=CN=CO1 | CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][o:11]2)[nH:12]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][o:11]2)[nH:12]1 | CN(C)C=O.c1c[nH]c(-c2cnco2)c1 | O=Cc1ccc(-c2cnco2)[nH]1 | null | null | C(Cl)(Cl)Cl.ClCCCl | C-C Coupling | OtherReaction | 2b5f756dc741b2c8883ed99aca6ca6cc1773d635791cb1bbe9b51efb615b4170 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1c[nH]c(-c2cnco2)c1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[#7;a:3]1:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:7]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 80 | [{"value": 80.0, "product": "C(=O)C1=CC=C(N1)C1=CN=CO1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To an ice cooled 1 mL dimethylformamide was added 0.82 g (5.4 mmol) of phosphorus oxychloride while stirring under a nitrogen atmosphere. The mixture was stirred 20 minutes and then was added a solution of 0.60 g (4.5 mmol) of 5-(pyrrol-2-yl)oxazole in 15 mL of 1,2-dichloroethane while cooling in an ice bath. The react... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1cocn1 | Other | C(Cl)(Cl)Cl.ClCCCl | null | null | CN(C)C=O.c1c[nH]c(-c2cnco2)c1>C(Cl)(Cl)Cl.ClCCCl>O=Cc1ccc(-c2cnco2)[nH]1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2288569fc3ee4fffb9e3876b2052db84 | Nc1ccccc1O.O=C(O)c1ccc[nH]1>>c1c[nH]c(-c2nc3ccccc3o2)c1 | N1C(=CC=C1)C(=O)O.NC1=C(C=CC=C1)O.B(O)(O)O>>N1C(=CC=C1)C=1OC2=C(N1)C=CC=C2 | [NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[OH:13].O=[C:5](O)[c:4]1[nH:3][cH:2][cH:1][cH:14]1>>[cH:1]1[cH:2][nH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[o:13]2)[cH:14]1 | Nc1ccccc1O.O=C(O)c1ccc[nH]1 | c1c[nH]c(-c2nc3ccccc3o2)c1 | null | null | C(C)(=O)OCC.C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | Benzoxazole formation from ester/carboxylic acid | ab90945f453b9d98729e6912eac27527ccc8f6879f9fc67f913646675914d5f8 | 082415a064525fb5ab1054c8f1a07a8509dc65297c7337b4b21c60d0aec70378 | c1c[nH]c(-c2nc3ccccc3o2)c1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[c:12]:[c:10]1:[o;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]2:[#7;a:3]:[c:4]:[c:5]:[c:6]:2):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | 52 | [{"value": 52.0, "product": "N1C(=CC=C1)C=1OC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.6, "product": "N1C(=CC=C1)C=1OC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(Pyrrol-2-yl)benzoxazole was prepared as follows: A mixture of 5.55 g (0.05 mol) of pyrrole-2-carboxylic acid and 5.46 g (0.05 mol) of o-aminophenol and 3.09 g (0.05 mol) boric acid in 50 mL of xylene was heated under reflux for 3 days while removing water which was generated from reaction using a Dean-Stark trap. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2ocnc2c1 | c1cc[nH]c1.c1ccc2ocnc2c1 | HO- | C(C)(=O)OCC.C=1(C(=CC=CC1)C)C | null | null | Nc1ccccc1O.O=C(O)c1ccc[nH]1>C(C)(=O)OCC.C=1(C(=CC=CC1)C)C>c1c[nH]c(-c2nc3ccccc3o2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-514be903fc7a4ed1b961eb5abfbc5505 | Nc1ccccc1S.O=C(O)c1ccc[nH]1>>c1c[nH]c(-c2nc3ccccc3s2)c1 | N1C(=CC=C1)C(=O)O.NC1=C(C=CC=C1)S.B(O)(O)O>>N1C(=CC=C1)C=1SC2=C(N1)C=CC=C2 | [NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[SH:13].O=[C:5](O)[c:4]1[nH:3][cH:2][cH:1][cH:14]1>>[cH:1]1[cH:2][nH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[s:13]2)[cH:14]1 | Nc1ccccc1S.O=C(O)c1ccc[nH]1 | c1c[nH]c(-c2nc3ccccc3s2)c1 | null | null | C(C)(=O)OCC.C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | Benzothiazole formation from ester/carboxylic acid | 5c56e3620e73de41a8f6dd28e5dfdee2d821cd47d85c852a5166976e26e39b41 | cfddc96fe868437500f756276ee466b3dbb82293a2c1f3605d6b16aab79b3f9d | c1c[nH]c(-c2nc3ccccc3s2)c1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[SH;D1;+0:11]):[c:12]>>[c:12]:[c:10]1:[s;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]2:[#7;a:3]:[c:4]:[c:5]:[c:6]:2):[n;H0;D2;+0:7]:[c:8]:1:[c:9] | 14 | [{"value": 14.0, "product": "N1C(=CC=C1)C=1SC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.0, "product": "N1C(=CC=C1)C=1SC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5.55 g (50 mmol) of pyrrole-2-carboxylic acid, 6.26 g (50 mmol) of 2-aminothiophenol and 3.09 g (50 mmol) of boric acid in 250 mL of xylene was heated under reflux for 3 days while removing water which was generated from reaction using a Dean-Stark trap. the cooled reaction mixture was diluted with 200 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Aromatic thiol | null | c1ccccc1 | c1ccc2scnc2c1 | c1cc[nH]c1.c1ccc2scnc2c1 | HO- | C(C)(=O)OCC.C=1(C(=CC=CC1)C)C | null | null | Nc1ccccc1S.O=C(O)c1ccc[nH]1>C(C)(=O)OCC.C=1(C(=CC=CC1)C)C>c1c[nH]c(-c2nc3ccccc3s2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f133d8b34fb84de6ae33d093fc5b41e4 | Nc1ccccc1N.O=C(O)c1ccc[nH]1>>c1c[nH]c(-c2nc3ccccc3[nH]2)c1 | C1(=C(C=CC=C1)N)N.N1C(=CC=C1)C(=O)O>>N1C(=CC=C1)C=1NC2=C(N1)C=CC=C2 | [NH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[NH2:13].O=[C:5](O)[c:4]1[nH:3][cH:2][cH:1][cH:14]1>>[cH:1]1[cH:2][nH:3][c:4](-[c:5]2[n:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[nH:13]2)[cH:14]1 | Nc1ccccc1N.O=C(O)c1ccc[nH]1 | c1c[nH]c(-c2nc3ccccc3[nH]2)c1 | null | null | C([O-])(O)=O.[Na+] | Aromatic Heterocycle Formation | OtherReaction | 8409c8c0d4e4ea3a5ac4d357a90931cd25bdeaf070f3095e8e16fa38a40808ca | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1c[nH]c(-c2nc3ccccc3[nH]2)c1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[c:9]:[c:8]1:[nH;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]2:[#7;a:3]:[c:4]:[c:5]:[c:6]:2):[n;H0;D2;+0:11]:[c:10]:1:[c:12] | 27.3 | [{"value": 25.0, "product": "N1C(=CC=C1)C=1NC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.3, "product": "N1C(=CC=C1)C=1NC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 30 | MINUTE | A mixture of 1.08 g (10 mmol) of o-phenylenediamine and 20 g of polyophosphate esters was heated gently at 80° C. and was added portionwise 1.11 g (10 mmol) of pyrrole-2-carboxylic acid. After the mixture was stirred at 100° C. for 30 minutes, it was poured into a saturated solution of sodium bicarbonate (500 mL) and s... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1cc[nH]c1.c1ccc2[nH]cnc2c1 | HO- | C([O-])(O)=O.[Na+] | 80 | 0.5 | Nc1ccccc1N.O=C(O)c1ccc[nH]1>C([O-])(O)=O.[Na+]>c1c[nH]c(-c2nc3ccccc3[nH]2)c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7c1e2ef533ec401fb17ad35bd72360ba | COC1O[C@H]2[C@H](OCc3ccccc3)[C@@H]1NC[C@@H]2OCc1ccccc1.O=C(Cl)OCc1ccccc1>>COC1O[C@H]2[C@H](OCc3ccccc3)[C@@H]1N(C(=O)OCc1ccccc1)C[C@@H]2OCc1ccccc1 | C(C1=CC=CC=C1)O[C@@H]1[C@H]2C(OC)O[C@@H]1[C@@H](OCC1=CC=CC=C1)CN2.C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)OC(=O)Cl>>C(C1=CC=CC=C1)OC(=O)N1[C@@H]2C(OC)O[C@@H]([C@@H]2OCC2=CC=CC=C2)[C@@H](OCC2=CC=CC=C2)C1 | [CH3:1][O:2][CH:3]1[O:4][C@H:5]2[C@H:6]([O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[C@@H:15]1[NH:16][CH2:27][C@@H:28]2[O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1.Cl[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][O:2][CH:3]1[O:4][C@H:5]2[C@H:6]([O:7][CH2:8][c:9... | COC1O[C@H]2[C@H](OCc3ccccc3)[C@@H]1NC[C@@H]2OCc1ccccc1.O=C(Cl)OCc1ccccc1 | COC1O[C@H]2[C@H](OCc3ccccc3)[C@@H]1N(C(=O)OCc1ccccc1)C[C@@H]2OCc1ccccc1 | null | null | C(C)OCC | Protection | N-alkylation of secondary amines with alkyl halides | badcf1c4f27013e2481f7ad2e4c9d69ce5bce4dee89060f3a7e5bed4347af601 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)N1C[C@H](OCc2ccccc2)[C@H]2OC[C@@H]1[C@H]2OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[#8:5]-[C:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:10]-[C:11] | null | [] | null | null | 2 | HOUR | To the crude amine (15), in a solution of diethyl ether:saturated sodium bicarbonate (3:2, 20 ml), was added benzylchloroformate (0.2 ml, 1.2 mmol). The reaction was then stirred, at such a rate as to make it one phase, for 2 hours. The aqueous phase was then separated and washed with diethyl ether (3×10 ml). The combi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1C[C@@H]2C[C@@H](CO2)N1 | C1C[C@@H]2C[C@@H](CO2)[NH]1 | c1ccccc1.c1ccccc1.C1C[C@@H]2C[C@@H](CO2)[NH]1.c1ccccc1 | HCl | C(C)OCC | null | 2 | COC1O[C@H]2[C@H](OCc3ccccc3)[C@@H]1NC[C@@H]2OCc1ccccc1.O=C(Cl)OCc1ccccc1>C(C)OCC>COC1O[C@H]2[C@H](OCc3ccccc3)[C@@H]1N(C(=O)OCc1ccccc1)C[C@@H]2OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b687ad6eeb954cfaa22dfb459d6be666 | O=C(OCc1ccccc1)N1C[C@H](OCc2ccccc2)[C@@H](O)[C@H](OCc2ccccc2)[C@H]1CO>>OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O | C(C1=CC=CC=C1)OC(=O)N1C[C@H](OCC2=CC=CC=C2)[C@@H](O)[C@H](OCC2=CC=CC=C2)[C@H]1CO.C(C)OCC>>N1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO | O=C(OCc1ccccc1)[N:4]1[C@H:3]([CH2:2][OH:1])[C@@H:10]([O:11]Cc2ccccc2)[C@H:8]([OH:9])[C@@H:6]([O:7]Cc2ccccc2)[CH2:5]1>>[OH:1][CH2:2][C@H:3]1[NH:4][CH2:5][C@H:6]([OH:7])[C@@H:8]([OH:9])[C@@H:10]1[OH:11] | O=C(OCc1ccccc1)N1C[C@H](OCc2ccccc2)[C@@H](O)[C@H](OCc2ccccc2)[C@H]1CO | OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O | null | [Pd] | C(C)(=O)O | Reduction | OtherReaction | 1dcef89f6803aee8587c37ade3c513b4d9b22ca03377d66f5b09b432cbc37040 | a63a032ebc37eef5f651c3d6a414fd6089bf1618f6929f2e95beb31d07025d65 | C1CCNCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1]1-[C:2]-[C:3](-[O;H0;D2;+0:4]-C-c2:c:c:c:c:c:2)-[C:5]-[C:6](-[O;H0;D2;+0:7]-C-c2:c:c:c:c:c:2)-[C:8]-1-[C:9]>>[C:9]-[C:8]1-[NH;D2;+0:1]-[C:2]-[C:3](-[OH;D1;+0:4])-[C:5]-[C:6]-1-[OH;D1;+0:7] | 96 | [{"value": 95.0, "product": "N1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "N1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The diol (17) (580 mg, 1.2 mmol) was stirred in glacial acetic acid (30 ml) in the presence of palladium black (100 mg) under hydrogen for 3 days, by which time no starting material (Rf 0.2) remained by t.l.c. (diethyl ether). Filtration and removal of the solvent then gave a gum which was purified by ion exchange chro... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether | Secondary alcohol.Secondary alcohol.Secondary amine | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | C1CCNCC1 | C1CCNCC1 | HO- | [Pd].C(C)(=O)O | null | null | O=C(OCc1ccccc1)N1C[C@H](OCc2ccccc2)[C@@H](O)[C@H](OCc2ccccc2)[C@H]1CO>[Pd].C(C)(=O)O>OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8f260ae7aa8349298a8c230f70739320 | C=CCBr.COC(=O)CC(=O)c1cccnc1>>C=CCC(C(=O)OC)C(=O)c1cccnc1 | C(C=C)Br.C(C1=CN=CC=C1)(=O)CC(=O)OC.[Na].C(C=C)Br>>COC(C(CC=C)C(C1=CN=CC=C1)=O)=O | Br[CH2:3][CH:2]=[CH2:1].[CH2:4]([C:5](=[O:6])[O:7][CH3:8])[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[CH2:1]=[CH:2][CH2:3][CH:4]([C:5](=[O:6])[O:7][CH3:8])[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1 | C=CCBr.COC(=O)CC(=O)c1cccnc1 | C=CCC(C(=O)OC)C(=O)c1cccnc1 | null | null | CO | C-C Coupling | OtherReaction | a419f976441b589a3c956c0f129ce3053512f0325f3e460530d895d12d1b751d | c9d64189f02be16d3a7baf78522635b86019231c97f41522f031694d4f90e5ad | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[#7;a:4]:[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13]>>[#7;a:4]:[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13] | null | [] | 25 | CELSIUS | 30 | MINUTE | Methyl 2-(nicotinoyl)acetate (17.9 g, prepared by the method of E. Wenkert el al. J. Org. Chem., 1983, 48, 5006) was added under argon to a solution of sodium metal (2.3 g) in methanol (200 ml) and the resulting mixture was stirred at 25° C. for 30 mins. Allyl bromide (12.0 g) was then added and stirring was continued ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester.Allyl | null | null | c1ccncc1 | HBr | CO | 25 | 0.5 | C=CCBr.COC(=O)CC(=O)c1cccnc1>CO>C=CCC(C(=O)OC)C(=O)c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-db8a01301d8543ea840e78a021d649d8 | CCOC(CBr)OCC.Oc1ccccc1>>CCOC(COc1ccccc1)OCC | [H-].[Na+].C1(=CC=CC=C1)O.C(C)OC(CBr)OCC>>C(C)OC(COC1=CC=CC=C1)OCC | Br[CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:13][CH2:14][CH3:15].[OH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[O:13][CH2:14][CH3:15] | CCOC(CBr)OCC.Oc1ccccc1 | CCOC(COc1ccccc1)OCC | null | null | CN1CCCN(C1=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 110 | CELSIUS | 30 | MINUTE | Sodium hydride (5.83 g of a 55% dispersion in mineral oil) was added to a solution of phenol (12.56 g) in DMPU (25 ml) at 5° C. and the mixture was stirred for 30 minutes. Bromoacetaldehyde diethyl acetal (10.05 ml) was added and the mixture was heated at 110° C. for 5 hours, then allowed to cool. The mixture was parti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CN1CCCN(C1=O)C | 110 | 0.5 | CCOC(CBr)OCC.Oc1ccccc1>CN1CCCN(C1=O)C>CCOC(COc1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-42782490ce0446c8903b1dfab0a8e409 | CCCC[B+]CCCC.O=Cc1cccnc1.O=S(=O)([O-])C(F)(F)F>>C=CCC(CO)C(O)c1cccnc1 | N1=CC(=CC=C1)C=O.[O-]S(=O)(=O)C(F)(F)F.C(CCC)[B+]CCCC.C(C)(C)N(CC)C(C)C>>C(C=C)C(C(O)C=1C=NC=CC1)CO | CCCC[B+][CH2:4][CH2:3][CH2:2][CH3:1].[CH:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1.O=S([O-])(C(F)(F)F)=[O:6]>>[CH2:1]=[CH:2][CH2:3][CH:4]([CH2:5][OH:6])[CH:7]([OH:8])[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1 | CCCC[B+]CCCC.O=Cc1cccnc1.O=S(=O)([O-])C(F)(F)F | C=CCC(CO)C(O)c1cccnc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | e529e8e1b0a2dbb0f2eab56bc1d2a270a57b1a636e658baa7f607f318ac43e7d | fa190e00978154d1e8722264bdac6e8d3f095f9701d0ca8f2dfa2980318c7fc0 | c1ccncc1 | C-C-C-C-[B+]-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[CH3;D1;+0:4].F-C(-F)(-F)-S(=O)(-[O-])=[O;H0;D1;+0:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[CH2;D1;+0:4]=[CH;D2;+0:3]-[C:2]-[CH;D3;+0:1](-[C:13]-[OH;D1;+0:5])-[CH;D3;+0:7](-[OH;D1;+0:6])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12] | null | [] | 5 | CELSIUS | 30 | MINUTE | A 1M solution of dibutylboron triflate in dichloromethane (32.7 ml) was added to a solution of A (6.28 g) in dry dichloromethane (110 ml), cooled to 5° C. under argon, followed by diisopropylethylamine (6.25 ml). The reaction mixture was stirred at 5° C. for 30 minutes and then cooled to -78° C. 3-Pyridinecarboxaldehyd... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Aldehyde.Sulfonic acid | Primary alcohol.Secondary alcohol.Allyl | null | null | c1ccncc1 | HF.B | ClCCl | 5 | 0.5 | CCCC[B+]CCCC.O=Cc1cccnc1.O=S(=O)([O-])C(F)(F)F>ClCCl>C=CCC(CO)C(O)c1cccnc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9ae2160c95854c49add8e88e86c3dc61 | CC(C)(CO)NC(=O)OC(C)(C)C>>CC(C)(C=O)NC(=O)OC(C)(C)C | C(=O)(OC(C)(C)C)NC(CO)(C)C.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C.[OH-].[Na+]>>C(=O)(OC(C)(C)C)NC(C=O)(C)C | [CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13]>>[CH3:1][C:2]([CH3:3])([CH:4]=[O:5])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13] | CC(C)(CO)NC(=O)OC(C)(C)C | CC(C)(C=O)NC(=O)OC(C)(C)C | null | null | C(Cl)Cl.C(C)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | null | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[CH2;D2;+0:12]-[OH;D1;+0:13]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[CH;D2;+0:12]=[O;H0;D1;+0:13] | 87.9 | [{"value": 87.9, "product": "C(=O)(OC(C)(C)C)NC(C=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | The resulting N-BOC-2-amino-2-methyl-1-propanol (3.69 g, 19.5 mmol) was dissolved in methylene chloride (74 ml) and added to a stirred suspension of Dess-Martin periodinane (10.75 g, 25.35 mmol; Aldrich Chemical Company, Milwaukee, Wis.) in methylene chloride (89 ml). After stirring for 20 minutes under nitrogen, the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | null | null | C(Cl)Cl.C(C)OCC | null | 0.333333 | CC(C)(CO)NC(=O)OC(C)(C)C>C(Cl)Cl.C(C)OCC>CC(C)(C=O)NC(=O)OC(C)(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-478badbfe80b4ba79d32c3a102b14cc6 | CC(=O)Cc1ccccc1.NCCC(=O)O>>CC(Cc1ccccc1)NCCC(=O)O | C1(=CC=CC=C1)CC(C)=O.NCCC(=O)O.C(#N)[BH3-].[Na+]>>C(=O)(O)CCNC(C)CC1=CC=CC=C1 | O=[C:2]([CH3:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[NH2:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15] | CC(=O)Cc1ccccc1.NCCC(=O)O | CC(Cc1ccccc1)NCCC(=O)O | null | null | CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[C:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[C:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | 60.2 | [{"value": 60.2, "product": "C(=O)(O)CCNC(C)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Phenylacetone (100 mg, 0.745 mmol) was dissolved in anhydrous methanol (2.0 ml). Beta-alanine (398 mg, 4.47 mmol) was added, followed by sodium cyanoborohydride (94 mg, 1.49 mmol). After 18 hours of stirring under nitrogen, the reaction mixture was filtered, and the filtrate solvent was removed in vacuo. The resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | CO.C(C)(=O)OCC | null | 18 | CC(=O)Cc1ccccc1.NCCC(=O)O>CO.C(C)(=O)OCC>CC(Cc1ccccc1)NCCC(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2356c1ff19bd4e029e4fdd495659ed04 | CC(=O)Nc1ccc(O)cc1.CC(C)(Oc1ccc(N)cc1)C(=O)O>>CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1 | NC1=CC=C(OC(C(=O)O)(C)C)C=C1.C(Cl)(Cl)Cl.[OH-].[Na+].N(C(=O)C)C1=CC=C(C=C1)O.CC(=O)C>>N(C(=O)C)C1=CC=C(OC(C(=O)O)(C)C)C=C1 | Oc1ccc(N[C:2]([CH3:1])=[O:3])cc1.[NH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([CH3:11])([CH3:12])[C:13](=[O:14])[OH:15])[cH:16][cH:17]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([CH3:11])([CH3:12])[C:13](=[O:14])[OH:15])[cH:16][cH:17]1 | CC(=O)Nc1ccc(O)cc1.CC(C)(Oc1ccc(N)cc1)C(=O)O | CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1 | null | null | null | Acylation | OtherReaction | f0587316dec6322bc8536bc1554a2dcfb19ea5ea59546c16f81f49f5f2fb7d70 | 07fa0d1f4d8418421a4320317c5bccf00c4e081ec51f5368bcd2c8236c65866e | c1ccccc1 | O-c1:c:c:c(-N-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):c:c:1.[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 60 | [{"value": 60.0, "product": "N(C(=O)C)C1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | FIG. 2A illustrates a reaction scheme for preparing 2-(4-aminophenoxy)-2-methyl propionic acid, a compound that is useful as a precursor in the preparation of Group I compounds. In accordance with the scheme of FIG. 2A, 8 grams (g) (0.2 mol) of pulverized sodium hydroxide is added to a suspension of 5.28 g (0.035 mol) ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Aromatic alcohol.Primary amine | Secondary amide | c1ccccc1 | null | c1ccccc1 | HO- | null | null | 0.5 | CC(=O)Nc1ccc(O)cc1.CC(C)(Oc1ccc(N)cc1)C(=O)O>>CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-13b9f603fcc84708924f96e5ef9dda01 | CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1>>CC(C)(Oc1ccc(N)cc1)C(=O)O | N(C(=O)C)C1=CC=C(OC(C(=O)O)(C)C)C=C1.C(C)(=O)O>>NC1=CC=C(OC(C(=O)O)(C)C)C=C1 | CC(=O)[NH:9][c:8]1[cH:7][cH:6][c:5]([O:4][C:2]([CH3:1])([CH3:3])[C:12](=[O:13])[OH:14])[cH:11][cH:10]1>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][cH:11]1)[C:12](=[O:13])[OH:14] | CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1 | CC(C)(Oc1ccc(N)cc1)C(=O)O | null | null | [OH-].[K+] | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 62 | [{"value": 62.0, "product": "NC1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.5, "product": "NC1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.18 g (0.005 mol) of the 2-(4-acetaminophenoxy)-2-methyl propionic acid is boiled in 10% KOH (60 ml) for 1/2 hour. The solution is then cooled and acidified with acetic acid to yield 0.6 g (62% yield) of 2-(4-aminophenoxy)-2-methyl propionic acid as a yellowish white powder, mp 214°-16° C.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | [OH-].[K+] | null | null | CC(=O)Nc1ccc(OC(C)(C)C(=O)O)cc1>[OH-].[K+]>CC(C)(Oc1ccc(N)cc1)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2138dfdaab5f4ec785968d0e14338622 | CC(C)(Oc1ccc(N)cc1)C(=O)O.O=C(Cl)Cc1ccccc1>>CC(C)(Oc1ccc(NC(=O)Cc2ccccc2)cc1)C(=O)O | NC1=CC=C(OC(C(=O)O)(C)C)C=C1.C1(=CC=CC=C1)CC(=O)Cl.O.[OH-].[Na+]>>C1(=CC=CC=C1)CC(=O)NC1=CC=C(OC(C(=O)O)(C)C)C=C1 | [CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:19][cH:20]1)[C:21](=[O:22])[OH:23].Cl[C:10](=[O:11])[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1)[C:21](=[O:2... | CC(C)(Oc1ccc(N)cc1)C(=O)O.O=C(Cl)Cc1ccccc1 | CC(C)(Oc1ccc(NC(=O)Cc2ccccc2)cc1)C(=O)O | null | [OH-].[Na+] | CCOCC.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)Nc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 57.4 | [{"value": 56.0, "product": "C1(=CC=CC=C1)CC(=O)NC1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "C1(=CC=CC=C1)CC(=O)NC1=CC=C(OC(C(=O)O)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | FIG. 2C illustrates a general reaction scheme for preparing the Group I 2-[4-(arylacetamido)phenoxy]-2-methyl propionic acids. In accordance with the illustrated scheme, 1 g (0.005 mol) of 2-(4-aminophenoxy)-2-methyl propionic acid is dissolved with stirring in 10 ml of water containing 0.41 g (0.1 mol) of NaOH. To thi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | [OH-].[Na+].CCOCC.O1CCCC1 | null | 1 | CC(C)(Oc1ccc(N)cc1)C(=O)O.O=C(Cl)Cc1ccccc1>[OH-].[Na+].CCOCC.O1CCCC1>CC(C)(Oc1ccc(NC(=O)Cc2ccccc2)cc1)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-70204c4fc8114c65865ea0d378637a4f | Nc1ccc(Cl)cc1.O=C(O)Cc1ccc(O)cc1>>O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1 | CC(=O)C.P(Cl)(Cl)(Cl)(Cl)Cl.OC1=CC=C(C=C1)CC(=O)O.ClC1=CC=C(N)C=C1>>ClC1=CC=C(NC(=O)CC=2C=C(C=CC2)O)C=C1 | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:10][c:8]([OH:9])[cH:7][cH:6]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]1 | Nc1ccc(Cl)cc1.O=C(O)Cc1ccc(O)cc1 | O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1 | null | null | C(C)C(=O)CC.C1(=CC(=CC(=C1)C)C)C | Acylation | OtherReaction | 4d66d758b08f9f828e782c8e08171e18b46fe11b590da48a7f0ca692ffa62bad | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:7](-[O;D1;H1:8]):[c:9]:[cH;D2;+0:10]:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:6]:[c:7](-[O;D1;H1:8]):[c:9]:[cH;D2;+0:10]:[cH;D2;+0:5]:1)-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14] | 90 | [{"value": 90.0, "product": "ClC1=CC=C(NC(=O)CC=2C=C(C=CC2)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | FIG. 6b presents a similar reaction scheme to FIG. 6a, except that 3- rather than 4-hydroxyphenylacetic acid (HPAA) is used as the precursor material so that the final compound has a meta rather than a para substitution. In addition, rather than reacting with acetone (dimethyl ketone) a diethyl ketone is used to positi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C(C)C(=O)CC.C1(=CC(=CC(=C1)C)C)C | null | 2 | Nc1ccc(Cl)cc1.O=C(O)Cc1ccc(O)cc1>C(C)C(=O)CC.C1(=CC(=CC(=C1)C)C)C>O=C(Cc1cccc(O)c1)Nc1ccc(Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c5f43a80403f4b4babc1305c8508f598 | CN(C)C1C(=O)C(C(N)=O)=C(O)C2(O)C(=O)C3=C(O)c4c(O)cccc4CC3CC12.O=C1CCC(=O)N1Br>>CN(C)C1C(O)=C(C(N)=O)C(=O)C2(O)C(O)=C3C(=O)c4c(O)ccc(Br)c4CC3CC12 | S(O)(O)(=O)=O.CN(C)C1C2CC3CC4=C(C(=CC=C4)O)C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O.BrN1C(CCC1=O)=O.C(C)OCC>>S(=O)(=O)(O)O.BrC1=C2CC3CC4C(C(=C(C(C4(C(=C3C(C2=C(C=C1)O)=O)O)O)=O)C(=O)N)O)N(C)C | [CH3:1][N:2]([CH3:3])[CH:4]1[C:5](=[O:6])[C:7]([C:8]([NH2:9])=[O:10])=[C:11]([OH:12])[C:13]2([OH:14])[C:15](=[O:16])[C:17]3=[C:18]([OH:19])[c:20]4[c:21]([OH:22])[cH:23][cH:24][cH:25][c:27]4[CH2:28][CH:29]3[CH2:30][CH:31]12.O=C1CCC(=O)N1[Br:26]>>[CH3:1][N:2]([CH3:3])[CH:4]1[C:5]([OH:6])=[C:7]([C:8]([NH2:9])=[O:10])[C:11... | CN(C)C1C(=O)C(C(N)=O)=C(O)C2(O)C(=O)C3=C(O)c4c(O)cccc4CC3CC12.O=C1CCC(=O)N1Br | CN(C)C1C(O)=C(C(N)=O)C(=O)C2(O)C(O)=C3C(=O)c4c(O)ccc(Br)c4CC3CC12 | null | null | null | Acylation | OtherReaction | 067f4bf724c6e44fe372eb2fec6145982ef9256ce32da29996886b4531327f93 | fe885760af681fc3d379e2235d0034d8359ce2474dcf96974b27a7acba880032 | O=C1C2=CC3C(=O)C=CCC3CC2Cc2ccccc21 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7:2]-[C:3]1-[C:4]2-[C:5]-[C:6]3-[C:7]-[c:8]4:[cH;D2;+0:9]:[c:10]:[c:11]:[c:12]:[c:13]:4-[C;H0;D3;+0:14](-[OH;D1;+0:15])=[C;H0;D3;+0:16]-3-[C;H0;D3;+0:17](=[O;H0;D1;+0:18])-[C:19]-2(-[O;D1;H1:20])-[C;H0;D3;+0:21](-[OH;D1;+0:22])=[C;H0;D3;+0:23](-[C:24](-[N;D1;H2:25])=[O;D1;H0:26])-[C... | null | [] | 0 | CELSIUS | 45 | MINUTE | A solution of 4.14. g of 6-demethyl-6-deoxytetracycline, prepared by the described literature procedure, and 1.99 g of N-bromosuccinimide dissolved in 50 ml of concentrated sulfuric acid is stirred at 0° C. for 45 minutes or until solution occurs. The reaction mixture is added dropwise to 2 L of cold diethyl ether. The... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Tertiary amide.Tertiary amide.Enol.Enol | Aromatic halide.Ketone.Ketone.Enol.Enol | C1=CC2CC3=Cc4ccccc4CC3CC2CC1.C1CCNC1 | C1=CCC2CC3Cc4ccccc4CC3=CC2C1 | C1=CCC2CC3Cc4ccccc4CC3=CC2C1 | HO- | null | 0 | 0.75 | CN(C)C1C(=O)C(C(N)=O)=C(O)C2(O)C(=O)C3=C(O)c4c(O)cccc4CC3CC12.O=C1CCC(=O)N1Br>>CN(C)C1C(O)=C(C(N)=O)C(=O)C2(O)C(O)=C3C(=O)c4c(O)ccc(Br)c4CC3CC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bbaa095270804d84806076369776a1e2 | C1=CCCC1.Cl[SiH](Cl)Cl>>Cl[Si](Cl)(Cl)C1CCCC1 | C1=CCCC1.Cl[SiH](Cl)Cl.C(C)(C)O>>C1(CCCC1)[Si](Cl)(Cl)Cl | [CH:5]1=[CH:9][CH2:8][CH2:7][CH2:6]1.[Cl:1][SiH:2]([Cl:3])[Cl:4]>>[Cl:1][Si:2]([Cl:3])([Cl:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1 | C1=CCCC1.Cl[SiH](Cl)Cl | Cl[Si](Cl)(Cl)C1CCCC1 | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | null | Miscellaneous | OtherReaction | 973dc51cc8732bf0bda1491fded43c0890bf4aedb1728cf351a967b36f591bfa | ebe950a4f1214ee7787c0782c7e3e1a5d4a0740c23df8283e2cc604317625e61 | C1CCCC1 | [C:1]1-[C:2]-[C:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-1.[Cl;D1;H0:6]-[SiH;D3;+0:7](-[Cl;D1;H0:8])-[Cl;D1;H0:9]>>[Cl;D1;H0:6]-[Si;H0;D4;+0:7](-[Cl;D1;H0:8])(-[Cl;D1;H0:9])-[CH;D3;+0:5]1-[C:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1 | null | [] | 150 | CELSIUS | 30 | MINUTE | In a 100 ml autoclave were charged 16.7 g (0.245 mole) of cyclopentene, 30.1 g (0.222 mole) of trichlorosilane and 25 μl of a 0.077 m mole/ml chloroplatinic acid solution in isopropyl alcohol (platinum content 1.92×10-6 mole), which were then stirred at 150° C. for 30 minutes. Cyclopentyl trichlorosilane was obtained q... | 10.6084/m9.figshare.5104873.v1 | null | null | Silyl protective group | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | 150 | 0.5 | C1=CCCC1.Cl[SiH](Cl)Cl>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>Cl[Si](Cl)(Cl)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-10db705dac8b406da8c9efae3471dda0 | CCC(C)O.CO[Si](OC)(OC)C1CCCC1>>CCC(C)O[Si](OC)(OC)C1CCCC1 | C1(CCCC1)[Si](OC)(OC)OC.C(C)(CC)O.C[Si](Cl)(C)C>>C(C)(CC)O[Si](OC)(OC)C1CCCC1 | [CH3:1][CH2:2][CH:3]([CH3:4])[OH:5].CO[Si:6]([O:7][CH3:8])([O:9][CH3:10])[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[O:5][Si:6]([O:7][CH3:8])([O:9][CH3:10])[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1 | CCC(C)O.CO[Si](OC)(OC)C1CCCC1 | CCC(C)O[Si](OC)(OC)C1CCCC1 | null | C[O-].[Na+] | null | Protection | OtherReaction | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | C1CCCC1 | C-O-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6](-[C:7])-[C:8].[C:9]-[C:10](-[C;D1;H3:11])-[OH;D1;+0:12]>>[C:7]-[C:6](-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[O;H0;D2;+0:12]-[C:10](-[C:9])-[C;D1;H3:11])-[C:8] | 84.3 | [{"value": 84.0, "product": "C(C)(CC)O[Si](OC)(OC)C1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.3, "product": "C(C)(CC)O[Si](OC)(OC)C1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 100 ml three-neck flask provided with a magnetic stirrer were charged 10.3 g (0.0542 mole) of cyclopentyl trimethoxysilane, 40.3 g (0.543 mole) of sec-butyl alcohol and 33.7 mg (0.625 m mole) of sodium methoxide, which were then reacted with each other at room temperature for 2 hours under stirring. Then, trimethy... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | C1CCCC1 | HO- | C[O-].[Na+] | null | null | CCC(C)O.CO[Si](OC)(OC)C1CCCC1>C[O-].[Na+]>CCC(C)O[Si](OC)(OC)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dfdccf328d594417823f1d891b869737 | CO[Si](OC)(OC)C1CCCC1.OC1CCCCC1>>CO[Si](OC)(OC1CCCCC1)C1CCCC1 | C1(CCCC1)[Si](OC)(OC)OC.C1(CCCCC1)O>>C1(CCCCC1)O[Si](OC)(OC)C1CCCC1 | CO[Si:3]([O:2][CH3:1])([O:4][CH3:5])[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1.[OH:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1>>[CH3:1][O:2][Si:3]([O:4][CH3:5])([O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1 | CO[Si](OC)(OC)C1CCCC1.OC1CCCCC1 | CO[Si](OC)(OC1CCCCC1)C1CCCC1 | null | C[O-].[Na+] | null | Protection | OtherReaction | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | C1CCC(O[SiH2]C2CCCC2)CC1 | C-O-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6](-[C:7])-[C:8].[C:9]-[C:10](-[OH;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[O;H0;D2;+0:11]-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6](-[C:7])-[C:8])-[C:12] | 83.3 | [{"value": 83.0, "product": "C1(CCCCC1)O[Si](OC)(OC)C1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.3, "product": "C1(CCCCC1)O[Si](OC)(OC)C1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedures of Example 2 were repeated with the exception that 10.0 g (0.0526 mole) of cyclopentyl trimethoxysilane, 85.1 mg (1.58 m mole) of sodium methoxide, and 52.7 g (0.526 mole) of cyclohexanol in place of sec-butyl alcohol were used and the reaction time was one and a half hours. Then, 11.3 g (0.0438 mole) of... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | C1CCCCC1.C1CCCC1 | HO- | C[O-].[Na+] | null | null | CO[Si](OC)(OC)C1CCCC1.OC1CCCCC1>C[O-].[Na+]>CO[Si](OC)(OC1CCCCC1)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-db48ca45905a4ffa943827bd251f129c | C1=CCCC1.Cl[SiH](Cl)Cl>>Cl[Si](Cl)(Cl)C1CCCC1 | C1=CCCC1.Cl[SiH](Cl)Cl.C(C)(C)O>>C1(CCCC1)[Si](Cl)(Cl)Cl | [CH:5]1=[CH:9][CH2:8][CH2:7][CH2:6]1.[Cl:1][SiH:2]([Cl:3])[Cl:4]>>[Cl:1][Si:2]([Cl:3])([Cl:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1 | C1=CCCC1.Cl[SiH](Cl)Cl | Cl[Si](Cl)(Cl)C1CCCC1 | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | null | Miscellaneous | OtherReaction | 973dc51cc8732bf0bda1491fded43c0890bf4aedb1728cf351a967b36f591bfa | ebe950a4f1214ee7787c0782c7e3e1a5d4a0740c23df8283e2cc604317625e61 | C1CCCC1 | [C:1]1-[C:2]-[C:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-1.[Cl;D1;H0:6]-[SiH;D3;+0:7](-[Cl;D1;H0:8])-[Cl;D1;H0:9]>>[Cl;D1;H0:6]-[Si;H0;D4;+0:7](-[Cl;D1;H0:8])(-[Cl;D1;H0:9])-[CH;D3;+0:5]1-[C:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1 | null | [] | 150 | CELSIUS | 30 | MINUTE | In a 100 ml autoclave were charged 13.5 g (0.198 mole) of cyclopentene, 24.4 g (0.180 mole) of trichlorosilane and 25 μl of a 0.077 m mole/ml chloroplatinic acid solution in isopropyl alcohol (platinum content 1.92×10-6 mole), which were then stirred at 150° C. for 30 minutes. Cyclopentyl trichlorosilane was obtained q... | 10.6084/m9.figshare.5104873.v1 | null | null | Silyl protective group | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | 150 | 0.5 | C1=CCCC1.Cl[SiH](Cl)Cl>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>Cl[Si](Cl)(Cl)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-44523718c32f4f8db78be90afe1a804e | CCC(C)(C)O.CO[Si](OC)(OC)C1CCCC1>>CCC(C)(C)O[Si](OC)(OC)C1CCCC1 | C1(CCCC1)[Si](OC)(OC)OC.C(C)(C)(CC)O.C[Si](Cl)(C)C>>C(C)(C)(CC)O[Si](OC)(OC)C1CCCC1 | [CH3:1][CH2:2][C:3]([CH3:4])([CH3:5])[OH:6].CO[Si:7]([O:8][CH3:9])([O:10][CH3:11])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][CH2:2][C:3]([CH3:4])([CH3:5])[O:6][Si:7]([O:8][CH3:9])([O:10][CH3:11])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | CCC(C)(C)O.CO[Si](OC)(OC)C1CCCC1 | CCC(C)(C)O[Si](OC)(OC)C1CCCC1 | null | C[O-].[Na+] | null | Protection | OtherReaction | 9769bfd0e2301823e43c8e03cbd04c370095023efd8ba0f40deaf2a30665c67c | d4f7fc2e4845ce90b51777d3c64652d4a3aab88a89713e59aada938381b9c2e3 | C1CCCC1 | C-O-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6](-[C:7])-[C:8].[C:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[OH;D1;+0:13]>>[C:7]-[C:6](-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[O;H0;D2;+0:13]-[C:10](-[C:9])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:8] | 82 | [{"value": 82.0, "product": "C(C)(C)(CC)O[Si](OC)(OC)C1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "C(C)(C)(CC)O[Si](OC)(OC)C1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 100 ml three-neck flask provided with a magnetic stirrer and a reflux condenser were charged 10.1 g (0.0531 mole) of cyclopentyl trimethoxysilane, 30.6 g (0.347 mole) of tert-amyl alcohol and 86.4 mg (1.6 m mole) of sodium methoxide, which were then reacted with each other in an oil bath of 105° C. for 4 hours und... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Silyl protective group | Silyl protective group | null | null | C1CCCC1 | HO- | C[O-].[Na+] | null | null | CCC(C)(C)O.CO[Si](OC)(OC)C1CCCC1>C[O-].[Na+]>CCC(C)(C)O[Si](OC)(OC)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e4a11d3163094ac6b8aeb21c55a2d94d | C1=CCCC1.Cl[SiH](Cl)Cl>>Cl[Si](Cl)(Cl)C1CCCC1 | C1=CCCC1.Cl[SiH](Cl)Cl.C(C)(C)O>>C1(CCCC1)[Si](Cl)(Cl)Cl | [CH:5]1=[CH:9][CH2:8][CH2:7][CH2:6]1.[Cl:1][SiH:2]([Cl:3])[Cl:4]>>[Cl:1][Si:2]([Cl:3])([Cl:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1 | C1=CCCC1.Cl[SiH](Cl)Cl | Cl[Si](Cl)(Cl)C1CCCC1 | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | null | Miscellaneous | OtherReaction | 973dc51cc8732bf0bda1491fded43c0890bf4aedb1728cf351a967b36f591bfa | ebe950a4f1214ee7787c0782c7e3e1a5d4a0740c23df8283e2cc604317625e61 | C1CCCC1 | [C:1]1-[C:2]-[C:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-1.[Cl;D1;H0:6]-[SiH;D3;+0:7](-[Cl;D1;H0:8])-[Cl;D1;H0:9]>>[Cl;D1;H0:6]-[Si;H0;D4;+0:7](-[Cl;D1;H0:8])(-[Cl;D1;H0:9])-[CH;D3;+0:5]1-[C:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1 | null | [] | 150 | CELSIUS | 30 | MINUTE | In a 100 ml autoclave were charged 13.9 g (0.204 mole) of cyclopentene, 25.1 g (0.185 mole) of trichlorosilane and 25 μl of a 0.077 m mole/ml chloroplatinic acid solution in isopropyl alcohol (platinum content 1.92×10-6 mole), which were then stirred at 150° C. for 30 minutes. Cyclopentyl trichlorosilane was obtained q... | 10.6084/m9.figshare.5104873.v1 | null | null | Silyl protective group | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | 150 | 0.5 | C1=CCCC1.Cl[SiH](Cl)Cl>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>Cl[Si](Cl)(Cl)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-26d59802162f454b919e6a3c67915737 | CO[Si](OC)(OC)C1CCCC1.OC1CCCC1>>CO[Si](OC)(OC1CCCC1)C1CCCC1 | C1(CCCC1)[Si](OC)(OC)OC.C1(CCCC1)O.C[Si](Cl)(C)C>>C1(CCCC1)O[Si](OC)(OC)C1CCCC1 | CO[Si:3]([O:2][CH3:1])([O:4][CH3:5])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.[OH:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][O:2][Si:3]([O:4][CH3:5])([O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | CO[Si](OC)(OC)C1CCCC1.OC1CCCC1 | CO[Si](OC)(OC1CCCC1)C1CCCC1 | null | C[O-].[Na+] | null | Protection | OtherReaction | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | C1CCC(O[SiH2]C2CCCC2)C1 | C-O-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6](-[C:7])-[C:8].[C:9]-[C:10](-[OH;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[O;H0;D2;+0:11]-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6](-[C:7])-[C:8])-[C:12] | 85.1 | [{"value": 85.0, "product": "C1(CCCC1)O[Si](OC)(OC)C1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "C1(CCCC1)O[Si](OC)(OC)C1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 50 ml three-neck flask provided with a magnetic stirrer and a reflux condenser were charged 5.0 g (0.0262 mole) of cyclopentyl trimethoxysilane, 22.5 g (0.262 mole) of cyclopentyl alcohol and 18.6 mg (0.34 m mole) of sodium methoxide, which were then reacted with each other at room temperature for 2 hours under st... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | C1CCCC1.C1CCCC1 | HO- | C[O-].[Na+] | null | null | CO[Si](OC)(OC)C1CCCC1.OC1CCCC1>C[O-].[Na+]>CO[Si](OC)(OC1CCCC1)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9bcc3d835c564b278f0acc655903f697 | C1=CCCC1.Cl[SiH](Cl)Cl>>Cl[Si](Cl)(Cl)C1CCCC1 | C1=CCCC1.Cl[SiH](Cl)Cl.C(C)(C)O>>C1(CCCC1)[Si](Cl)(Cl)Cl | [CH:5]1=[CH:9][CH2:8][CH2:7][CH2:6]1.[Cl:1][SiH:2]([Cl:3])[Cl:4]>>[Cl:1][Si:2]([Cl:3])([Cl:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1 | C1=CCCC1.Cl[SiH](Cl)Cl | Cl[Si](Cl)(Cl)C1CCCC1 | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | null | Miscellaneous | OtherReaction | 973dc51cc8732bf0bda1491fded43c0890bf4aedb1728cf351a967b36f591bfa | ebe950a4f1214ee7787c0782c7e3e1a5d4a0740c23df8283e2cc604317625e61 | C1CCCC1 | [C:1]1-[C:2]-[C:3]-[CH;D2;+0:4]=[CH;D2;+0:5]-1.[Cl;D1;H0:6]-[SiH;D3;+0:7](-[Cl;D1;H0:8])-[Cl;D1;H0:9]>>[Cl;D1;H0:6]-[Si;H0;D4;+0:7](-[Cl;D1;H0:8])(-[Cl;D1;H0:9])-[CH;D3;+0:5]1-[C:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1 | null | [] | 150 | CELSIUS | 30 | MINUTE | In a 100 ml autoclave were charged 13.7 g (0.201 mole) of cyclopentene, 24.8 g (0.183 mole) of trichlorosilane and 25 μl of a 0.077 m mole/ml chloroplatinic acid solution in isopropyl alcohol (platinum content 1.92×10-6 mole), which were then stirred at 150° C. for 30 minutes. Cyclopentyl trichlorosilane was obtained q... | 10.6084/m9.figshare.5104873.v1 | null | null | Silyl protective group | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | [H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl | 150 | 0.5 | C1=CCCC1.Cl[SiH](Cl)Cl>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>Cl[Si](Cl)(Cl)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4f67e89866a749378b2de7b9b7e24fbf | CO[Si](OC)(OC)C1CCCC1.OC1CCOC1>>CO[Si](OC)(OC1CCOC1)C1CCCC1 | C1(CCCC1)[Si](OC)(OC)OC.OC1COCC1.C[Si](Cl)(C)C>>C1(CCCC1)[Si](OC1COCC1)(OC)OC | CO[Si:3]([O:2][CH3:1])([O:4][CH3:5])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.[OH:6][CH:7]1[CH2:8][CH2:9][O:10][CH2:11]1>>[CH3:1][O:2][Si:3]([O:4][CH3:5])([O:6][CH:7]1[CH2:8][CH2:9][O:10][CH2:11]1)[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | CO[Si](OC)(OC)C1CCCC1.OC1CCOC1 | CO[Si](OC)(OC1CCOC1)C1CCCC1 | null | C[O-].[Na+] | null | Protection | OtherReaction | ea139b3cb6171a748fbc881d815cc598a14c6b8245b87168b4a15a10e325f24c | 1e2a25dd539d267852f3b05b92dd4080ece1d4c7abb9db1b6fd2b64d2b33a864 | C1CCC([SiH2]OC2CCOC2)C1 | C-O-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6](-[C:7])-[C:8].[#8:9]-[C:10]-[C:11](-[OH;D1;+0:12])-[C:13]>>[#8:9]-[C:10]-[C:11](-[O;H0;D2;+0:12]-[Si;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6](-[C:7])-[C:8])-[C:13] | 54 | [{"value": 54.0, "product": "C1(CCCC1)[Si](OC1COCC1)(OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.0, "product": "C1(CCCC1)[Si](OC1COCC1)(OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a 100 ml three-neck flask provided with a magnetic stirrer and a reflux condenser were charged 7.7 g (0.0404 mole) of cyclopentyl trimethoxysilane, 35.7 g (0.405 mole) of 3-hydroxy tetrahydrofurane and 53.0 mg (0.98 m mole) of sodium methoxide, which were then reacted with each other in an oil bath of 80° C. for 2 h... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | Silyl protective group | null | null | C1CCOC1.C1CCCC1 | HO- | C[O-].[Na+] | null | null | CO[Si](OC)(OC)C1CCCC1.OC1CCOC1>C[O-].[Na+]>CO[Si](OC)(OC1CCOC1)C1CCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a09f60cece474e8a9b8d9edbc056d2df | O=C(Cl)Cl.O=C(c1ccccc1)c1ccc(O)cc1>>O=C(Cl)c1ccc(C(=O)c2ccccc2)cc1 | C(=O)(Cl)Cl.C(=O)(Cl)Cl.C(=O)(Cl)Cl.OC1=CC=C(C(=O)C2=CC=CC=C2)C=C1>>ClC(=O)C1=CC=C(C(=O)C2=CC=CC=C2)C=C1 | Cl[C:2](=[O:1])[Cl:3].O[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | O=C(Cl)Cl.O=C(c1ccccc1)c1ccc(O)cc1 | O=C(Cl)c1ccc(C(=O)c2ccccc2)cc1 | null | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C | CC=1C=CC=CC1C | C-C Coupling | OtherReaction | 1a9a73072b79f12d8d265f2cb995c58c1597c5e5abba004b3080381ef79885e5 | ef72d272f34893178d8f33792eb77b63ee817d1a04f49561ae829111b8207762 | O=C(c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](-[Cl;D1;H0:2])=[O;D1;H0:3].O-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8] | 99.2 | [{"value": 93.0, "product": "ClC(=O)C1=CC=C(C(=O)C2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "ClC(=O)C1=CC=C(C(=O)C2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A total of 3.4 kg of phosgene were passed in the course of 5 hours into a solution of 4 kg of 4-hydroxybenzophenone and 190 g of benzyltrimethylammonium chloride in 11.4 kg of o-xylene. During this time, the internal temperature was increased from 95° to 1200° C. After the end of the introduction of phosgene, stirring ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Aromatic alcohol | Acyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.CC=1C=CC=CC1C | null | 0.5 | O=C(Cl)Cl.O=C(c1ccccc1)c1ccc(O)cc1>[Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.CC=1C=CC=CC1C>O=C(Cl)c1ccc(C(=O)c2ccccc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-acde304896214d548673d4710d7c0098 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Br)cc1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Br)cc2)OC(C)(C)O1 | O.BrC1=CC=C(C=C1)S(=O)(=O)Cl.OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.C(C)N(CC)CC>>BrC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][OH:13])[O:24][C:25]([CH3:26])([CH3:27])[O:28]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([Br:21])[cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][S:14](=[... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Br)cc1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Br)cc2)OC(C)(C)O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | O=S(=O)(OC[C@@H]1CCOCO1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 144.4 | [{"value": 144.4, "product": "BrC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a stirring, 20°-25° C. solution of the (4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2 dimethyl-1,3- dioxane-4-acetate (European Patent Application 0319,847) (10 g, 38 mmol) in methylene chloride) (250 mL) containing triethylamine (10 mL, 72 mmol) is added 4-bromobenzenesulfonyl chloride (15 g, 57.5 mmol). Stirring i... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | C1COCOC1.c1ccccc1 | HCl | C(Cl)Cl | null | 20 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Br)cc1>C(Cl)Cl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Br)cc2)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2023d8b66fd14bfc92a109f8fab6f737 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Cl)cc1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Cl)cc2)OC(C)(C)O1 | O.ClC1=CC=C(C=C1)S(=O)(=O)Cl.OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.C(C)N(CC)CC>>ClC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][OH:13])[O:24][C:25]([CH3:26])([CH3:27])[O:28]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][S:14](=[... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Cl)cc1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Cl)cc2)OC(C)(C)O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | O=S(=O)(OC[C@@H]1CCOCO1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 130.1 | [{"value": 130.1, "product": "ClC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a stirring, 0°-5° C. solution of the (4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (European Patent Application 0319,847) (10 g, 38 mmol) in methylene chloride (250 mL) containing triethylamine (10 mL, 72 mmol) is added 4-chlorobenzenesulfonyl chloride (12.7 g, 60 mmol). Stirring is c... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | C1COCOC1.c1ccccc1 | HCl | C(Cl)Cl | null | 2.5 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Cl)cc1>C(Cl)Cl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Cl)cc2)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1a1f349b82e5444490349d675368ebff | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2cc(Cl)ccc2Cl)OC(C)(C)O1 | O.ClC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl.OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.C(C)N(CC)CC>>ClC1=C(C=C(C=C1)Cl)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][OH:13])[O:25][C:26]([CH3:27])([CH3:28])[O:29]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]1[Cl:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][S:... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2cc(Cl)ccc2Cl)OC(C)(C)O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | O=S(=O)(OC[C@@H]1CCOCO1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 137.9 | [{"value": 137.9, "product": "ClC1=C(C=C(C=C1)Cl)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a stirring 0°-5° C. solution of the (4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (European Patent Application 0319,847) (10 g, 38 mmol) in methylene chloride (250 mL) containing triethylamine (10 mL, 72 mmol) is added 2,5-dichlorobenzenesulfonyl chloride (14.7 g, 57.5 mmol). Stirring... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | C1COCOC1.c1ccccc1 | HCl | C(Cl)Cl | null | 3.5 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl>C(Cl)Cl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2cc(Cl)ccc2Cl)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f0db01e0d32e4cd2b57589e37275a000 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccccc2[N+](=O)[O-])OC(C)(C)O1 | [N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl.OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.C(C)N(CC)CC.O.[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl>>[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][OH:13])[O:26][C:27]([CH3:28])([CH3:29])[O:30]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[N+:23](=[O:24])[O-:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccccc2[N+](=O)[O-])OC(C)(C)O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | O=S(=O)(OC[C@@H]1CCOCO1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 122.9 | [{"value": 122.9, "product": "[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a stirring 20°-25° C. solution of the (4R cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl -1,3-dioxane-4-acetate (European Patent Application 0319,847) (10 g, 0.038 mol) in methylene chloride (250 mL) containing triethylamine (7 mL, 0.05 mol) is added 2-nitrobenzenesulfonyl chloride (9.8 g, 0.043 mol). Stirring ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | C1COCOC1.c1ccccc1 | HCl | C(Cl)Cl | null | 24 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccccc2[N+](=O)[O-])OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a12e310df1644252937b6e4ef4818172 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc([N+](=O)[O-])cc2)OC(C)(C)O1 | O.[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)Cl.OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.C(C)N(CC)CC>>[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][OH:13])[O:26][C:27]([CH3:28])([CH3:29])[O:30]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc([N+](=O)[O-])cc2)OC(C)(C)O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | O=S(=O)(OC[C@@H]1CCOCO1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 110.5 | [{"value": 110.5, "product": "[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | To a stirring 20°-25° C. solution of the (4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3- dioxane-4-acetate (European Patent Application 0319,847) (10 g, 0.038 mol) in methylene chloride (250 mL) containing triethylamine (7 mL, 0.05 mol) is added 4-nitrobenzenesulfonyl chloride (10.5 g, 43 mmol). Stirring i... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | C1COCOC1.c1ccccc1 | HCl | C(Cl)Cl | null | 22 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1>C(Cl)Cl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc([N+](=O)[O-])cc2)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-25c2d201df154c4a8596ac428de335f8 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Cl)cc1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Cl)cc2)OC(C)(C)O1 | O.ClC1=CC=C(C=C1)S(=O)(=O)Cl.OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.C(C)N(CC)CC>>ClC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][OH:13])[O:24][C:25]([CH3:26])([CH3:27])[O:28]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][O:13][S:14](=[... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Cl)cc1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Cl)cc2)OC(C)(C)O1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 76a2f1ce13fb019af608455a0d79fe83b29c455d623b278b739d67e5b567ea89 | e7708aa65b3d8696add9aec26cae169160bb027d6d2772db2030dd9c0b07b540 | O=S(=O)(OC[C@@H]1CCOCO1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 130.1 | [{"value": 130.1, "product": "ClC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a stirring, 0°-5° C. solution of the (4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (European Patent Application 0319,847) (10 g, 38 mmol) in methylene chloride (250 mL) containing triethylamine (10 mL, 72 mmol) is added 4-chlorobenzenesulfonyl chloride (12.7 g, 60 mmol). Stirring is c... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfonate | null | null | C1COCOC1.c1ccccc1 | HCl | C(Cl)Cl | null | 2.5 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CO)OC(C)(C)O1.O=S(=O)(Cl)c1ccc(Cl)cc1>C(Cl)Cl>CC(C)(C)OC(=O)C[C@H]1C[C@@H](COS(=O)(=O)c2ccc(Cl)cc2)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4431975f4b2f4be985331eb77f3e56b1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1>>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 | C(#N)C[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.N.[H][H]>>NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][C:13]#[N:14])[O:15][C:16]([CH3:17])([CH3:18])[O:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C@H:9]1[CH2:10][C@@H:11]([CH2:12][CH2:13][NH2:14])[O:15][C:16]([CH3:17])([CH3:18])[O:19]1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 | null | [Ni] | CO | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1COCOC1 | [#8:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#8:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | null | null | 16 | HOUR | A solution of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, (Example 1) 5.63 g (0.048 mol), in 100 mL of methanol saturated with gaseous ammonia is treated with 0.5 g of Raney nickel #30 and hydrogen gas in a shaker at 50 pounds per square inch (psi) and 40° C. After 16 hours, thin layer ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1COCOC1 | null | [Ni].CO | null | 16 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CC#N)OC(C)(C)O1>[Ni].CO>CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-274e1321147e44d895be1b035e36de0f | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1 | NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.CC(C)O>>FC1=CC=C(C=C1)C=1N(C(=C(C1C1=CC=CC=C1)C(=O)NC1=CC=CC=C1)C(C)C)CC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C | [NH2:30][CH2:31][CH2:32][C@@H:33]1[CH2:34][C@H:35]([CH2:36][C:37](=[O:38])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43])[O:44][C:45]([CH3:46])([CH3:47])[O:48]1.O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1 | null | null | CCCCCCC.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | Paal-Knorr pyrrole synthesis | 0cb7b72300a2af7a2e4398a0e1226bb84c0d31edad76ec86c7b51828dc8686b6 | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | O=C(Nc1ccccc1)c1cn(CC[C@@H]2CCOCO2)c(-c2ccccc2)c1-c1ccccc1 | O=[C;H0;D3;+0:1](-[CH;D3;+0:2](-[CH;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7])-[C;H0;D3;+0:8](=O)-[C:9](-[C;D1;H3:10])-[C;D1;H3:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16])-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:20]:[c:21].[C:22]-[C:23]-[NH2;D1;+0:24]>>[C:22]-[C:23]-[n;H0;D3;+0:24]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:17](... | null | [] | 25 | CELSIUS | null | null | A solution of (4R-cis)-1,1-dimethylethyl 6-(2-aminoethyl) -2,2-dimethyl-1,3-dioxane-4-acetate, (Example 2) 1.36 g (4.97 mmol), and (±)-4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)], and [S-R*,S*)] isomers, (Example 3) 1.60 g (3.83 mmol), in 50 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1COCOC1 | HO- | CCCCCCC.C1(=CC=CC=C1)C | 25 | null | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>CCCCCCC.C1(=CC=CC=C1)C>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@H](CC(=O)OC(C)(C)C)OC(C)(C)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-abee60ee9b184c41888df66883fa9eae | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 | NCC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C.FC1=CC=C(C=C1)C(C(C(C(=O)NC1=CC=CC=C1)C(C(C)C)=O)C1=CC=CC=C1)=O.O1CCCC1.[Cl-].[NH4+]>>FC1=CC=C(C=C1)C1=C(C(=C(N1CC[C@H]1OC(C[C@@H](C1)O)=O)C(C)C)C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 | CC(C)(C)O[C:38]([CH2:37][C@H:35]1[CH2:34][C@@H:33]([CH2:32][CH2:31][NH2:30])[O:40]C(C)(C)[O:36]1)=[O:39].O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]([C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=O)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[... | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1 | CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 | null | null | O.CCCCCCC.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 8e30b51508dc6a589cdd4f06c85afddd9a01bb1823227fed405ef8a23d32c02e | c5a8056bd33aab4597438c284a5d6d5fc73a7560d573a9ac4f0b77bcc8496ccc | O=C1CCC[C@@H](CCn2cc(C(=O)Nc3ccccc3)c(-c3ccccc3)c2-c2ccccc2)O1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]1-[C:5]-[C:6](-[C:7]-[C:8]-[NH2;D1;+0:9])-[O;H0;D2;+0:10]-C(-C)(-C)-[O;H0;D2;+0:11]-1.O=[C;H0;D3;+0:12](-[CH;D3;+0:13](-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#7:17]-[c:18])-[C;H0;D3;+0:19](=O)-[C:20](-[C;D1;H3:21])-[C;D1;H3:22])-[c;H0;D3;+0:23](:[c:24]:[c:25]):[c:26... | null | [] | null | null | 15 | HOUR | A solution of (4R-cis)-1,1-dimethylethyl 6-(2-aminoethyl) -2,2-dimethyl-1,3-dioxane-4-acetate, (Example 2) 2.56 g (9.36 mmol), and (±)-4-fluoroα-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenylbenzenebutaneamide mixture of [R-(R*,R*)], [R-(R*,S*)], [S-(R*,R*)], and [S (R*,S*)] isomers (Example 3), 3.00 g (7.20 mmol), in 60 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Ether.Ether.Primary amine.Boc | Ester.Secondary alcohol | C1COCOC1 | c1cc[nH]c1.C1CCOCC1 | c1cc[nH]c1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | O.CCCCCCC.C1(=CC=CC=C1)C | null | 15 | CC(C)(C)OC(=O)C[C@H]1C[C@@H](CCN)OC(C)(C)O1.CC(C)C(=O)C(C(=O)Nc1ccccc1)C(C(=O)c1ccc(F)cc1)c1ccccc1>O.CCCCCCC.C1(=CC=CC=C1)C>CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H]1C[C@@H](O)CC(=O)O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-da4df0e2a9804ff7a23ad117f2bc5cf7 | COC(=O)CC(=O)C(C)C.Nc1ccccc1>>CC(C)C(=O)CC(=O)Nc1ccccc1 | NC1=CC=CC=C1.C1(=CC=CC=C1)C.CC(C(CC(=O)OC)=O)C.C(CN)N>>CC(C(CC(=O)NC1=CC=CC=C1)=O)C | CO[C:7]([CH2:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[CH2:6][C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | COC(=O)CC(=O)C(C)C.Nc1ccccc1 | CC(C)C(=O)CC(=O)Nc1ccccc1 | null | null | O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](-[C:5])=[O;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 157.4 | [{"value": 157.4, "product": "CC(C(CC(=O)NC1=CC=CC=C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | A three-necked, 12-L round-bottom flask equipped with a mechanical stirrer, a thermometer, and set up for distillation is charged with 2.6 L of toluene, 1.73 kg (12 mol) of methyl 4-methyl-3-oxopentanoate and 72 g (1.18 mol) of ethylenediamine. The mixture is heated to 80° C. and charged with 0.49 kg of aniline. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O | 80 | 16 | COC(=O)CC(=O)C(C)C.Nc1ccccc1>O>CC(C)C(=O)CC(=O)Nc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bac2e5d16cf345c093dab45174ba84b2 | O=CC(=O)O.Oc1ccccc1>>O=C(O)C(O)c1ccccc1O | C1(=CC=CC=C1)O.C(C=O)(=O)O>>OC1=C(C(C(=O)O)O)C=CC=C1 | [O:1]=[C:2]([OH:3])[CH:4]=[O:5].[cH:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]>>[O:1]=[C:2]([OH:3])[CH:4]([OH:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12] | O=CC(=O)O.Oc1ccccc1 | O=C(O)C(O)c1ccccc1O | null | null | null | C-C Coupling | OtherReaction | 236dc10d6be2d7527fb96a5b91492b698c2d2e32974acf29ee0457d6cf74bb4a | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[O;H0;D1;+0:5].[O;D1;H1:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4](-[OH;D1;+0:5])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7](-[O;D1;H1:6]):[c:8] | null | [] | null | null | null | null | reacting glyoxylic acid with a boric acid ester of a phenol of the formula: ##STR9## under acid conditions to form a boric acid ester of a 2-hydroxymandelic acid;
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | null | null | null | O=CC(=O)O.Oc1ccccc1>>O=C(O)C(O)c1ccccc1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4d1ae81964184c9cac35555f802dc7dc | CC1(C)C(=O)N(Br)C(=O)N1Br.COc1cc(C(=O)O)cc(OC)c1OC>>COc1cc(C(=O)O)c(Br)c(OC)c1OC | COC=1C=C(C(=O)O)C=C(C1OC)OC.CC1(C(=O)N(C(=O)N1Br)Br)C>>BrC1=C(C(=O)O)C=C(C(=C1OC)OC)OC | CC1(C)C(=O)N(Br)C(=O)N1[Br:10].[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:11]([O:12][CH3:13])[c:14]1[O:15][CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9]([Br:10])[c:11]([O:12][CH3:13])[c:14]1[O:15][CH3:16] | CC1(C)C(=O)N(Br)C(=O)N1Br.COc1cc(C(=O)O)cc(OC)c1OC | COc1cc(C(=O)O)c(Br)c(OC)c1OC | null | null | null | Functional Group Interconversion | Bromination | e7196acac6d3571a6f057a0662dc983b0dda8f4f322e529a27cdf589fdea1d97 | 704bb5e37b3db6e189ba45e819fbdaa9822cc38202dae736860ec5273d025324 | c1ccccc1 | Br-N1-C(=O)-N(-[Br;H0;D1;+0:1])-C(-C)(-C)-C-1=O.[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[c:10]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[c:10] | null | [] | null | null | 25 | HOUR | Using the procedure described herein above in Example 1, Method E, 3,4,5-trimethoxybenzoic acid was brominated with DBDMH to provide the following results (assay yields) after reacting for 25 hours at 20°-25° C.:
Conditions: See reaction.notes.procedure_details.
Workup: to provide the; following results; (assay yields) | 10.6084/m9.figshare.5104873.v1 | null | Urea.Tertiary amide | Aromatic halide | C1CNCN1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | null | null | 25 | CC1(C)C(=O)N(Br)C(=O)N1Br.COc1cc(C(=O)O)cc(OC)c1OC>>COc1cc(C(=O)O)c(Br)c(OC)c1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4583e7f0d868404ea0bdbff4012d8e64 | CC1(C)C(=O)N(Br)C(=O)N1Br.COc1cccc(C(=O)O)c1OC>>COc1ccc(Br)c(C(=O)O)c1OC | COC1=C(C(=O)O)C=CC=C1OC.CC1(C(=O)N(C(=O)N1Br)Br)C>>BrC1=CC=C(C(=C1C(=O)O)OC)OC | CC1(C)C(=O)N(Br)C(=O)N1[Br:7].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:8]([C:9](=[O:10])[OH:11])[c:12]1[O:13][CH3:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([C:9](=[O:10])[OH:11])[c:12]1[O:13][CH3:14] | CC1(C)C(=O)N(Br)C(=O)N1Br.COc1cccc(C(=O)O)c1OC | COc1ccc(Br)c(C(=O)O)c1OC | null | null | null | Functional Group Interconversion | Bromination | e7196acac6d3571a6f057a0662dc983b0dda8f4f322e529a27cdf589fdea1d97 | 704bb5e37b3db6e189ba45e819fbdaa9822cc38202dae736860ec5273d025324 | c1ccccc1 | Br-N1-C(=O)-N(-[Br;H0;D1;+0:1])-C(-C)(-C)-C-1=O.[O;D1;H0:2]=[C:3](-[O;D1;H1:4])-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](-[C:3](=[O;D1;H0:2])-[O;D1;H1:4]):[c:6] | null | [] | null | null | 22 | HOUR | Using the procedure described herein above in Example 1, Method E, 2,3-dimethoxybenzoic acid was brominated with DBDMH to provide the following results (assay yields) after reacting for 22 hours at 20°-25° C:
Conditions: See reaction.notes.procedure_details.
Workup: to provide the; following results; (assay yields) | 10.6084/m9.figshare.5104873.v1 | null | Urea.Tertiary amide | Aromatic halide | C1CNCN1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | null | null | 22 | CC1(C)C(=O)N(Br)C(=O)N1Br.COc1cccc(C(=O)O)c1OC>>COc1ccc(Br)c(C(=O)O)c1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e9daf0d13fb242e8a2f100e9a0e8682e | CC(=O)Nc1cc(S)c(Cl)cc1F>>Nc1cc(S)c(Cl)cc1F | N(C(=O)C)C=1C(=CC(=C(C1)S)Cl)F.[OH-].[Na+].Cl>>NC=1C(=CC(=C(C1)S)Cl)F | CC(=O)[NH:1][c:2]1[cH:3][c:4]([SH:5])[c:6]([Cl:7])[cH:8][c:9]1[F:10]>>[NH2:1][c:2]1[cH:3][c:4]([SH:5])[c:6]([Cl:7])[cH:8][c:9]1[F:10] | CC(=O)Nc1cc(S)c(Cl)cc1F | Nc1cc(S)c(Cl)cc1F | null | null | O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97.9 | [{"value": 97.9, "product": "NC=1C(=CC(=C(C1)S)Cl)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.2, "product": "NC=1C(=CC(=C(C1)S)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a 100 ml reaction flask, 4.8 g (0.022 mol) of 5-acetamino-2-chloro-4-fluoro-thiophenol, 2.55 g (0.064 mol) of sodium hydroxide and 25.5 cc of water were added and stirred under reflux for 4 hours to obtain a uniform solution. The solution was cooled to room temperature and neutralized with 10% hydrochloric acid. T... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | O | null | null | CC(=O)Nc1cc(S)c(Cl)cc1F>O>Nc1cc(S)c(Cl)cc1F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7f55e0a2549a42539e09fd9289ec2f3a | CC(=O)CCCC(=O)OCc1ccccc1.FC(F)(Br)Br>>CC(CCCC(=O)OCc1ccccc1)=C(F)F | CN(C)P(N(C)C)N(C)C.BrC(F)(F)Br.O=C(CCCC(=O)OCC1=CC=CC=C1)C>>FC(=C(CCCC(=O)OCC1=CC=CC=C1)C)F | O=[C:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.Br[C:16](Br)([F:17])[F:18]>>[CH3:1][C:2]([CH2:3][CH2:4][CH2:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[C:16]([F:17])[F:18] | CC(=O)CCCC(=O)OCc1ccccc1.FC(F)(Br)Br | CC(CCCC(=O)OCc1ccccc1)=C(F)F | null | null | COCCOCCOC | C-C Coupling | OtherReaction | 063e2488dc04a2778c8d9e640fba2ecd94fd30d914823aeb4af5739622133a94 | d6a105150c2ffb7f6f5aff908de6bf6312362b4e5f748d12674ad40b306aec9d | c1ccccc1 | Br-[C;H0;D4;+0:1](-Br)(-[F;D1;H0:2])-[F;D1;H0:3].O=[C;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[C:7]>>[C:7]-[C:6]-[C;H0;D3;+0:4](-[C;D1;H3:5])=[C;H0;D3;+0:1](-[F;D1;H0:2])-[F;D1;H0:3] | null | [] | null | null | 3 | HOUR | 27.85 g Tris(dimethylamino)phosphine was added dropwise to a solution of 17.90 g dibromodifluoromethane in 130 ml diglyme, maintained under a nitrogen atmosphere and ice bath cooling. After stirring for one hour on the ice bath, 8.82 g benzyl 5-oxohexanoate in 70 ml diglyme was added slowly, dropwise. The ice bath was ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ketone | Alkenyl halide.Alkenyl halide | null | null | c1ccccc1 | Br- | COCCOCCOC | null | 3 | CC(=O)CCCC(=O)OCc1ccccc1.FC(F)(Br)Br>COCCOCCOC>CC(CCCC(=O)OCc1ccccc1)=C(F)F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d30cf53005b044ea9db9fca6b67dce41 | O=C(O)CCCC=C(F)F.O=S(Cl)Cl>>O=C(Cl)CCCC=C(F)F | S(=O)(Cl)Cl.FC(=CCCCC(=O)O)F>>FC(=CCCCC(=O)Cl)F | O[C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH:7]=[C:8]([F:9])[F:10].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[CH2:4][CH2:5][CH2:6][CH:7]=[C:8]([F:9])[F:10] | O=C(O)CCCC=C(F)F.O=S(Cl)Cl | O=C(Cl)CCCC=C(F)F | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=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 | null | null | 10.23 ml (140.68 mmol) Thionyl chloride was added dropwise to 8.0 g (52.29 mmol) of the product of Example 9 at room temperature. A drop of dimethylformamide was added and the mixture heated under reflux for 6 hours. It was then distilled under reduced pressure.
Conditions: See reaction.notes.procedure_details.
Workup:... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | CN(C=O)C | null | null | O=C(O)CCCC=C(F)F.O=S(Cl)Cl>CN(C=O)C>O=C(Cl)CCCC=C(F)F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-10fea42bec564443a9bc5ae1ea51daad | O=C(OCc1ccccc1)C(CCC(F)=C(F)F)C(=O)OCc1ccccc1>>O=C(O)C(CCC(F)=C(F)F)C(=O)O | [OH-].[K+].C(C)O.FC(CCC(C(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=C(F)F>>FC(CCC(C(=O)O)C(=O)O)=C(F)F | c1ccc(C[O:3][C:2](=[O:1])[CH:4]([CH2:5][CH2:6][C:7]([F:8])=[C:9]([F:10])[F:11])[C:12](=[O:13])[O:14]Cc2ccccc2)cc1>>[O:1]=[C:2]([OH:3])[CH:4]([CH2:5][CH2:6][C:7]([F:8])=[C:9]([F:10])[F:11])[C:12](=[O:13])[OH:14] | O=C(OCc1ccccc1)C(CCC(F)=C(F)F)C(=O)OCc1ccccc1 | O=C(O)C(CCC(F)=C(F)F)C(=O)O | null | null | O | Deprotection | OtherReaction | c3cedf6fcf01bee6478da3bdaea2e9c7140af795b9e8421ed6d8cc9c9f58df51 | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | null | [O;D1;H0:1]=[C:2](-[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1)-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6] | null | [] | null | null | null | null | 5.56 g (99 mmol) KOH flakes were dissolved in 6.82 ml water and 13.65 ml ethanol and then treated with 11.12 g (28.34 mmol) of dibenzyl 2-(3,4,4-trifluoro-3-butenyl)-malonate. After heating under reflux for 4 hours, the reaction mixture was poured into 30 ml water and washed with ether. The aqueous phase was acidified ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | c1ccccc1.c1ccccc1 | null | null | Other | O | null | null | O=C(OCc1ccccc1)C(CCC(F)=C(F)F)C(=O)OCc1ccccc1>O>O=C(O)C(CCC(F)=C(F)F)C(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-790e2a778f77438c9b5e15011df151a3 | CC(C)(C)[SiH2]OCCCCC(=C(F)F)C(F)(F)F>>OCCCCC(=C(F)F)C(F)(F)F | FC(=C(CCCCO[SiH2]C(C)(C)C)C(F)(F)F)F>>FC(=C(CCCCO)C(F)(F)F)F | CC(C)(C)[SiH2][O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[C:7]([F:8])[F:9])[C:10]([F:11])([F:12])[F:13]>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[C:7]([F:8])[F:9])[C:10]([F:11])([F:12])[F:13] | CC(C)(C)[SiH2]OCCCCC(=C(F)F)C(F)(F)F | OCCCCC(=C(F)F)C(F)(F)F | null | null | CO | Deprotection | OtherReaction | d7487e9652d81f9226fa8fb90bf02725deb1441d4abc97ee4fdbe439e00122e0 | ff9889ffd40f59bd281424811967f384d29acb01a2d54e10590c5a677f81d17a | null | C-C(-C)(-C)-[SiH2]-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | 3 | HOUR | A solution of 3.59 g (11.28 mmol) 6,6-difluoro-5-trifluoromethyl-1-tert-butylsilyloxy-5-hexene in 50 ml methanol was treated with a teaspoon full of ion exchange resin and the mixture stirred for 3 hours at room temperature. The ion exchange resin was then filtered off and washed with methanol. The filtrate was careful... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | null | Other | CO | null | 3 | CC(C)(C)[SiH2]OCCCCC(=C(F)F)C(F)(F)F>CO>OCCCCC(=C(F)F)C(F)(F)F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6a9f947d18fd4b718325c2f1fee21eab | CC(=O)CCCCCC(=O)OCc1ccccc1.FC(F)(Br)Br>>CC(CCCCCC(=O)OCc1ccccc1)=C(F)F | CN(C)P(N(C)C)N(C)C.BrC(F)(F)Br.O=C(CCCCCC(=O)OCC1=CC=CC=C1)C>>FC(=C(CCCCCC(=O)OCC1=CC=CC=C1)C)F | O=[C:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.Br[C:18](Br)([F:19])[F:20]>>[CH3:1][C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[C:18]([F:19])[F:20] | CC(=O)CCCCCC(=O)OCc1ccccc1.FC(F)(Br)Br | CC(CCCCCC(=O)OCc1ccccc1)=C(F)F | null | null | COCCOCCOC | C-C Coupling | OtherReaction | 063e2488dc04a2778c8d9e640fba2ecd94fd30d914823aeb4af5739622133a94 | d6a105150c2ffb7f6f5aff908de6bf6312362b4e5f748d12674ad40b306aec9d | c1ccccc1 | Br-[C;H0;D4;+0:1](-Br)(-[F;D1;H0:2])-[F;D1;H0:3].O=[C;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[C:7]>>[C:7]-[C:6]-[C;H0;D3;+0:4](-[C;D1;H3:5])=[C;H0;D3;+0:1](-[F;D1;H0:2])-[F;D1;H0:3] | null | [] | null | null | 1 | HOUR | 123 ml (0.68 mol) Tris(dimethylamino)phosphine in 100 ml diglyme was added slowly dropwise to a solution of 26.3 ml (0.34 mol) dibromodifluoromethane in 800 ml diglyme. After stirring for one hour on an ice bath, 43 g (0.17 mol}benzyl 7-oxooctanoate in 100 ml diglyme was slowly added dropwise. The ice bath was removed ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ketone | Alkenyl halide.Alkenyl halide | null | null | c1ccccc1 | Br- | COCCOCCOC | null | 1 | CC(=O)CCCCCC(=O)OCc1ccccc1.FC(F)(Br)Br>COCCOCCOC>CC(CCCCCC(=O)OCc1ccccc1)=C(F)F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c4bb80abbe704cb6b9de76dd9722654e | BrCc1ccccc1.CC(=O)CCCCCC(=O)O>>CC(=O)CCCCCC(=O)OCc1ccccc1 | O=C(CCCCCC(=O)O)C.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>O=C(CCCCCC(=O)OCC1=CC=CC=C1)C | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[OH:11]>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | BrCc1ccccc1.CC(=O)CCCCCC(=O)O | CC(=O)CCCCCC(=O)OCc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Benzyl 7-oxooctanoate was prepared by benzylation of 7-oxooctanoic acid with benzyl bromide and potassium carbonate in dimethyl formamide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HBr | CN(C=O)C | null | null | BrCc1ccccc1.CC(=O)CCCCCC(=O)O>CN(C=O)C>CC(=O)CCCCCC(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e1b1a95009504cf9bff9d61402140b73 | CC(=O)C1CCCCC1=O.[OH-]>>CC(=O)CCCCCC(=O)O | C(C)(=O)C1C(CCCC1)=O.[OH-].[K+]>>O=C(CCCCCC(=O)O)C | [CH3:1][C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1=[O:10].[OH-:11]>>[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[OH:11] | CC(=O)C1CCCCC1=O.[OH-] | CC(=O)CCCCCC(=O)O | null | null | null | Acylation | OtherReaction | d6e01e4bce9376c221bbc59d2280a136e5c257de567a453a205d7a0c9331cfc1 | 553e3366df9577c6f76b744a1617173162a370f5ca95b87c9cc38060deb2e92e | null | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]-[C:8]-[C;H0;D3;+0:9]-1=[O;D1;H0:10].[OH-;D0:11]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C:5]-[C:6]-[C:7]-[C:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[OH;D1;+0:11] | null | [] | null | null | null | null | 7-Oxooctanoic acid was prepared by treatment of 2-acetyl cyclohexanone with aqueous potassium hydroxide (S. Hunig et al; Chem Ber 91, 129-133 (1958)).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Carboxylic acid.Ketone | C1CCCCC1 | null | null | null | null | null | null | CC(=O)C1CCCCC1=O.[OH-]>>CC(=O)CCCCCC(=O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-de601d7504a04544afaf93084d42b5be | ClCCOCCCl.Oc1ccc(I)cc1.[OH-]>>Ic1ccc(OCCOCCOc2ccc(I)cc2)cc1 | ClCCOCCCl.[OH-].[Na+].IC1=CC=C(C=C1)O>>IC1=CC=C(OCCOCCOC2=CC=C(C=C2)I)C=C1 | Cl[CH2:3][CH2:5][O:9][CH2:8][CH2:7]Cl.[I:1][c:2]1[cH:15][cH:14][c:13]([OH:12])[cH:19][cH:18]1.[OH-:6]>>[I:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][c:16]([I:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | ClCCOCCCl.Oc1ccc(I)cc1.[OH-] | Ic1ccc(OCCOCCOc2ccc(I)cc2)cc1 | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | e7f830160b182d96fee8d6f0fdedd44f07771178446e1b5ed644fdfd9fa19d6a | 0c5376f97e025bc1b8def6abd84e300900d8c12e37bed566d9fb7dca2bf71d25 | c1ccc(OCCOCCOc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[C:4]-[CH2;D2;+0:5]-Cl.[I;D1;H0:6]-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]:[cH;D2;+0:13]:1.[OH-;D0:14]>>[I;D1;H0:15]-[c:16]1:[cH;D2;+0:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[C:17]-[C:18]-[O;H0;D2;+0:3]-[C:4]-[CH2;D2;+0:5]-[O;H0;D2;+0:14]-[c;H0;D3;+0:2]2:... | null | [] | null | null | null | null | A mixture prepared by adding 3.08 g of sodium hydroxide and 40 ml of n-butanol to 15.4 g of 4-iodophenol was refluxed. 2 ml of n-butanol solution of 5.01 g of 1,5-dichloro-3-oxapentane was added dropwise to the above prepared mixture over a period of 5 minutes.
Conditions: See reaction.notes.procedure_details.
Workup: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary halide.Ether.Aromatic alcohol | Aromatic halide.Aromatic halide.Ether.Ether.Ether | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | C(CCC)O | null | null | ClCCOCCCl.Oc1ccc(I)cc1.[OH-]>C(CCC)O>Ic1ccc(OCCOCCOc2ccc(I)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f4cc62040f7c42ea8b1be3806e91e5ff | CC(C)(C)OC(=O)NCC(=O)O.C[C@@H](N)C(=O)OCc1ccccc1.ClCCl>>C[C@@H](NC(=O)CN)C(=O)OCc1ccccc1.Cl | C1(CCCCC1)N=C=NC1CCCCC1.C(C)(C)(C)OC(=O)NCC(=O)O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)OC([C@H](N)C)=O.C(Cl)Cl.C(C)N(CC)CC>>Cl.C(C1=CC=CC=C1)OC([C@H](NC(CN)=O)C)=O | CC(C)(C)OC(=O)[NH:7][CH2:6][C:4](O)=[O:5].[CH3:1][C@@H:2]([NH2:3])[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.ClC[Cl:18]>>[CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[CH2:6][NH2:7])[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[ClH:18] | CC(C)(C)OC(=O)NCC(=O)O.C[C@@H](N)C(=O)OCc1ccccc1.ClCCl | C[C@@H](NC(=O)CN)C(=O)OCc1ccccc1.Cl | null | null | null | Acylation | OtherReaction | c4b6ff1c5a86405f86fe4a3d689987915e1ddb8ecb5b8ab8c4aa3d729fe0ceef | c73530b43160ba59e35b2ca368dd7f9e092fe1309aabd3f94299d7158bc36c97 | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](-O)=[O;D1;H0:4].Cl-C-[Cl;H0;D1;+0:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])-[NH2;D1;+0:12]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:2]-[NH2;D1;+0:1].[ClH;D0;+0:5] | 70 | [{"value": 70.0, "product": "Cl.C(C1=CC=CC=C1)OC([C@H](NC(CN)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a cold (0° C.) solution of 100 ml. methylene chloride containing 10 g. (57 mmol) of N-t-butyloxycarbonylglycine, 20 g. (57 mmol) of D-alanine benzyl ester p-toluene sulfonic acid salt and 5.77 g. (57 mmol) of triethylamine was added 12.3 g. (60 mmol) of dicyclohexylcarbodiimide and the resulting action mixture allow... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccccc1 | HCl | null | null | 0.5 | CC(C)(C)OC(=O)NCC(=O)O.C[C@@H](N)C(=O)OCc1ccccc1.ClCCl>>C[C@@H](NC(=O)CN)C(=O)OCc1ccccc1.Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e18ec41772ca4d5fa1f5d0902ef672de | CCCCc1ncc(C=N[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl.CI>>CCCCc1ncc(C=N[C@@](C)(Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | C(C)(C)NC(C)C.C(CCC)[Li].COC([C@@H](N=CC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O.CI>>COC([C@@](N=CC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)(CC1=CC=CC=C1)C)=O | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH:9]=[N:10][C@@H:11]([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:20](=[O:21])[O:22][CH3:23])[n:24]1[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[Cl:32].I[CH3:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH:9]=[N:10][C@@:11]([CH3:12])([CH2:... | CCCCc1ncc(C=N[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl.CI | CCCCc1ncc(C=N[C@@](C)(Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | null | null | O1CCCC1 | C-C Coupling | Methylation with MeI_tertiary | 0570231f487a8ed6f750cd320473f7dbaf49269e0dc5684a4c7ab99270540147 | 14e59a0462685ab029a3f096b6ab1b088ab82a473dbad968017fbb67b5b8465e | C(=NCCc1ccccc1)c1cncn1Cc1ccccc1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3](-[C:4]=[#7:5]-[C@@H;D3;+0:6](-[C:7]-[c:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]):[c:13]:[#7;a:14]>>[#7;a:2]:[c:3](-[C:4]=[#7:5]-[C@@;H0;D4;+0:6](-[CH3;D1;+0:1])(-[C:7]-[c:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]):[c:13]:[#7;a:14] | null | [] | 0 | CELSIUS | 15 | MINUTE | To a solution of diisopropylamine (1.27 g, 12.6 mmol) in tetrahydrofuran (50 ml) was added n-butyl lithium (5 ml of 2.5M in hexane, 12.6 mmol) at 0° C. After being stirred at 0° C. for 15 minutes, the solution was cooled to -78° C. and a solution of the imine, N [{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Substituted imine | Ester.Substituted imine | null | null | c1c[nH]cn1.c1ccccc1.c1ccccc1 | HI | O1CCCC1 | 0 | 0.25 | CCCCc1ncc(C=N[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl.CI>O1CCCC1>CCCCc1ncc(C=N[C@@](C)(Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7b25920dfe6144a1a723eec9437b7937 | CCCCc1ncc(C=O)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1cccs1>>CCCCc1ncc(C=N[C@@H](Cc2cccs2)C(=O)OC)n1Cc1ccccc1Cl | C(CCC)C=1N(C(=CN1)C=O)CC1=C(C=CC=C1)Cl.COC([C@@H](N)CC=1SC=CC1)=O.C1(=CC=CC=C1)C>>COC([C@@H](N=CC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC=1SC=CC1)=O | O=[CH:9][c:8]1[cH:7][n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:22]1[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1[Cl:30].[NH2:10][C@@H:11]([CH2:12][c:13]1[cH:14][cH:15][cH:16][s:17]1)[C:18](=[O:19])[O:20][CH3:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH:9]=[N:10][C@@H:11]([CH2:12][c:13]2[cH:14][cH:15... | CCCCc1ncc(C=O)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1cccs1 | CCCCc1ncc(C=N[C@@H](Cc2cccs2)C(=O)OC)n1Cc1ccccc1Cl | null | null | O | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | C(=NCCc1cccs1)c1cncn1Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[C:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C:8]-[C:9](-[N;H0;D2;+0:10]=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[C:7])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14] | null | [] | null | null | 8 | HOUR | A solution of 2-n-butyl-1-[(2-chlorophenyl)methyl]-1H-imidazol-5-carboxaldehyde (0.6 g, 2.12 mmol), β-(2-thienyl)alanine methyl ester (0.4 g, 2.16 mmol) and toluene (25 ml) was refluxed under argon with a Dean-Stark water separator for 8 hours. The solvent was evaporated to an orange-red oil (1.1 g) of the title imine ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1c[nH]cn1.c1ccsc1.c1ccccc1 | HO- | O | null | 8 | CCCCc1ncc(C=O)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1cccs1>O>CCCCc1ncc(C=N[C@@H](Cc2cccs2)C(=O)OC)n1Cc1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-50dfb916fc1b4933aac44bd6fca31f18 | CCCCc1ncc(CCO)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1ccccc1>>CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | COC([C@@H](N)CC1=CC=CC=C1)=O.FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F.C(CCC)C=1N(C(=CN1)CCO)CC1=C(C=CC=C1)Cl.C(C)(C)N(CC)C(C)C>>COC([C@@H](NCCC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O | O[CH2:10][CH2:9][c:8]1[cH:7][n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:24]1[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[Cl:32].[NH2:11][C@@H:12]([CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C:20](=[O:21])[O:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][C@@H:12]([CH... | CCCCc1ncc(CCO)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1ccccc1 | CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 80c5fffb5a6cd9bcf0b3d20ee51fe5f6574f02d4cb5ea6a4d33b4a9098b0e672 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1ccc(CCNCCc2cncn2Cc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[c:3](:[#7;a:4]):[c:5]:[#7;a:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13]>>[#7;a:4]:[c:3](-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C:8](-[C:7])-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13]):[c:5]:[#7;a:6] | 65 | [{"value": 65.0, "product": "COC([C@@H](NCCC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.6, "product": "COC([C@@H](NCCC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | MINUTE | A solution of trifluoromethanesulfonic anhydride (0.954 g, 3.38 mmol) in methylene chloride (5 ml) was cooled to -78° C. under nitrogen, and a solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-(2-hydroxyethyl)-1H-imidazole (0.9 g, 3.07 mmol), diisopropylethylamine (0.44 g. 3.38 mmol) and methylene chloride (10 ml) was a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | null | c1c[nH]cn1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | -78 | 0.25 | CCCCc1ncc(CCO)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1ccccc1>C(Cl)Cl>CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0938af2f3f7e40ac8becd6f17afdc7e9 | CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl>>CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)O)n1Cc1ccccc1Cl | O.COC([C@@H](NCCC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O.COC([C@@H](NCCC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O.C(C)O.[OH-].[K+]>>ClC1=C(C=CC=C1)CN1C(=NC=C1CCN[C@@H](CC1=CC=CC=C1)C(=O)O)CCCC | C[O:22][C:20]([C@@H:12]([NH:11][CH2:10][CH2:9][c:8]1[cH:7][n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:23]1[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][c:30]1[Cl:31])[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)=[O:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][C@@H:12]([CH2:13][c:14... | CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)O)n1Cc1ccccc1Cl | null | null | CCOCC | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CCNCCc2cncn2Cc2ccccc2)cc1 | 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] | null | [] | null | null | null | null | The procedure of Example 2 (ii) was followed using 0.9 g (1.99 mmol) of N-[2-{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol -5-yl}ethyl]phenylalanine methyl ester, 0.33 g of potassium hydroxide, 15 ml of water and 25 ml of ethanol to afford after workup 0.54 q of product. Trituration with ether provided the title co... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1c[nH]cn1.c1ccccc1.c1ccccc1 | Other | CCOCC | null | null | CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl>CCOCC>CCCCc1ncc(CCN[C@@H](Cc2ccccc2)C(=O)O)n1Cc1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2ee5331ec52c4b96954c2cbc8e4bbd96 | CCCCc1ncc(CO)n1Cc1ccccc1Cl.O=C1CCC(=O)N1Cl>>CCCCc1nc(Cl)c(CO)n1Cc1ccccc1Cl | ClN1C(CCC1=O)=O.C(CCC)C=1N(C(=CN1)CO)CC1=C(C=CC=C1)Cl.ClN1C(CCC1=O)=O>>C(CCC)C=1N(C(=C(N1)Cl)CO)CC1=C(C=CC=C1)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:9]([CH2:10][OH:11])[n:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[Cl:20].O=C1CCC(=O)N1[Cl:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH2:10][OH:11])[n:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[Cl:20] | CCCCc1ncc(CO)n1Cc1ccccc1Cl.O=C1CCC(=O)N1Cl | CCCCc1nc(Cl)c(CO)n1Cc1ccccc1Cl | null | null | O1CCCC1 | Functional Group Interconversion | Chlorination | 339179e6c50945dd3ac07a96a57059a7154e475073d7636ad2fc68e36469c54f | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(Cn2ccnc2)cc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[C:2]-[c:3]1:[cH;D2;+0:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[C:8]>>[C:2]-[c:3]1:[#7;a:7](-[C:8]):[c:6]:[#7;a:5]:[c;H0;D3;+0:4]:1-[Cl;H0;D1;+0:1] | 44.2 | [{"value": 44.0, "product": "C(CCC)C=1N(C(=C(N1)Cl)CO)CC1=C(C=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.2, "product": "C(CCC)C=1N(C(=C(N1)Cl)CO)CC1=C(C=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 3 | HOUR | A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole (Example 3(i) Method A) (10.2 g. 0.0368 mol) in tetrahydrofuran (100 ml) was treated portionwise with N-chlorosuccinimide (NCS) (4.92 g, 0.0368 mol) and stirred at 45° C. for a total of 3 hours after the addition of the NCS. The tetrahydrofur... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1c[nH]cn1.C1CCNC1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | HO- | O1CCCC1 | 45 | 3 | CCCCc1ncc(CO)n1Cc1ccccc1Cl.O=C1CCC(=O)N1Cl>O1CCCC1>CCCCc1nc(Cl)c(CO)n1Cc1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bc86844699a84905a340fdf779a0e7ca | CCCCc1ncc[nH]1.Fc1cccc(Cl)c1CCl>>CCCCc1nccn1Cc1c(F)cccc1Cl | C(CCC)C=1NC=CN1.[H-].[Na+].ClC1=C(CCl)C(=CC=C1)F>>C(CCC)C=1N(C=CN1)CC1=C(C=CC=C1F)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][cH:8][nH:9]1.Cl[CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][cH:8][n:9]1[CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18] | CCCCc1ncc[nH]1.Fc1cccc(Cl)c1CCl | CCCCc1nccn1Cc1c(F)cccc1Cl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5118ce9eea46859cccf16d01cf8151757afd816de0c93fe6fcb74a0ee15c5a67 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccnc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[n;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 95.3 | [{"value": 94.0, "product": "C(CCC)C=1N(C=CN1)CC1=C(C=CC=C1F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "C(CCC)C=1N(C=CN1)CC1=C(C=CC=C1F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 2 n-butylimidazole (3.75 g, 0.03 mol) in dry dimethylformamide (4 ml) was added to sodium hydride (0.95 g) in dimethylformamide (18 ml). After the gas evolution subsided, the mixture was stirred one hour under argon and 2-chloro-6-fluorobenzylchloride (5.5 q, 0.031 mol) in dimethylformamide (7 ml) was add... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccccc1 | HCl | CN(C=O)C | null | 1 | CCCCc1ncc[nH]1.Fc1cccc(Cl)c1CCl>CN(C=O)C>CCCCc1nccn1Cc1c(F)cccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d2c9533997c74d79a948283e529ded3f | CCCCc1ncc(CO)n1Cc1c(F)cccc1Cl>>CCCCc1nccn1Cc1c(F)cccc1Cl | C(CCC)C=1N(C(=CN1)CO)CC1=C(C=CC=C1F)Cl.ClC1=C(C=CC=C1)CN1C(=NC=C1CCN[C@@H](CC1=CC=CC=C1)C(=O)O)CCCC>>C(CCC)C=1N(C=CN1)CC1=C(C=CC=C1F)Cl | OC[c:8]1[cH:7][n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:9]1[CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][cH:8][n:9]1[CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18] | CCCCc1ncc(CO)n1Cc1c(F)cccc1Cl | CCCCc1nccn1Cc1c(F)cccc1Cl | null | null | null | Reduction | OtherReaction | 0bfcf9be29de871a8a1dc7820346d1be2cd5fe407ee81265651f772633ca02be | 0a2c8330040d049ae67653e1474aff520bf8a2d8c908ffd7076f536576936945 | c1ccc(Cn2ccnc2)cc1 | O-C-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5]):[#7;a:6]:1-[C:7]>>[C:7]-[#7;a:6]1:[cH;D2;+0:1]:[c:2]:[#7;a:3]:[c:4]:1-[C:5] | null | [] | null | null | null | null | The procedures of Example 1(ii iii) were used. From 7.63 g of crude 2-n-butyl-1-(2-chloro-6-fluorophenyl)methyl-1H-imidazole was obtained 2.8 q of 2-n-butyl-1-(2-chloro-6-fluorophenyl)methyl-5-hydroxymethyl-1H-imidazo le; mp 106°-108° C. (from ethyl acetate). This material was oxidized with manganese dioxide and worked... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccccc1 | HO- | null | null | null | CCCCc1ncc(CO)n1Cc1c(F)cccc1Cl>>CCCCc1nccn1Cc1c(F)cccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-36b3c2ed1dbc482aa4b7a196ab5747d7 | CCCCc1nc(Cl)c(CO)n1Cc1ccccc1Cl.CC[C@](N)(Cc1ccccc1)C(=O)OC>>CCCCc1ncc(CN[C@@](CC)(Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | C(CCC)C=1N(C(=C(N1)Cl)CO)CC1=C(C=CC=C1)Cl.COC([C@@](N)(CC1=CC=CC=C1)CC)=O>>COC([C@@](NCC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)(CC1=CC=CC=C1)CC)=O | O[CH2:9][c:8]1[c:7](Cl)[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:25]1[CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][c:32]1[Cl:33].[NH2:10][C@@:11]([CH2:12][CH3:13])([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:21](=[O:22])[O:23][CH3:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH2:9][NH:10][C@@:11](... | CCCCc1nc(Cl)c(CO)n1Cc1ccccc1Cl.CC[C@](N)(Cc1ccccc1)C(=O)OC | CCCCc1ncc(CN[C@@](CC)(Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 381acdd477743c8db4aee37f977438acfb7d2e431e8c4efe7996dd0ebaf534d9 | ef8b457f33bb2e8764dcedaad5d616341ac6cab05b3d6d88254b664261093078 | c1ccc(CCNCc2cncn2Cc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4](-[C:5]):[c:6]:1-[CH2;D2;+0:7]-O.[C:8]-[C:9](-[C:10])(-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[C:8]-[C:9](-[C:10])(-[NH;D2;+0:11]-[CH2;D2;+0:7]-[c:6]1:[cH;D2;+0:1]:[#7;a:2]:[c:3]:[#7;a:4]:1-[C:5])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15] | null | [] | null | null | null | null | The procedure of Example 4 (i), Method A, was followed using a-ethylphenylalanine methyl ester in place of α-methyl-phenylalanine methyl ester to give N-[{1-(2-chlorophenyl)methyl-2-n butyl-1H-imidazol-5-yl}methyl-α-ethylphenylalanine methyl ester. Hydrolysis of the ester using the procedure of Example 2 (ii), followed... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.Primary amine | Secondary amine | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCCCc1nc(Cl)c(CO)n1Cc1ccccc1Cl.CC[C@](N)(Cc1ccccc1)C(=O)OC>>CCCCc1ncc(CN[C@@](CC)(Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-88e25dc0a82b4570b0c9e6e0b265c717 | C=O.CCCCc1ncc(CN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl>>CCCCc1ncc(CN(C)[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | Cl.COC([C@@H](NCC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O.C=O>>COC([C@@H](N(C)CC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O | O=[CH2:11].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH2:9][NH:10][C@@H:12]([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[C:20](=[O:21])[O:22][CH3:23])[n:24]1[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[Cl:32]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH2:9][N:10]([CH3:11])[C@@H:12]([C... | C=O.CCCCc1ncc(CN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | CCCCc1ncc(CN(C)[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl | null | null | C(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | deb0f39510ff32c3bd75ceaf7ece4070b1f686ff120d798ccd640765025dab3c | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(CCNCc2cncn2Cc2ccccc2)cc1 | O=[CH2;D1;+0:1].[#7;a:2]:[c:3](-[C:4]-[NH;D2;+0:5]-[C:6](-[C:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]):[c:12]:[#7;a:13]>>[#7;a:2]:[c:3](-[C:4]-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[C:6](-[C:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]):[c:12]:[#7;a:13] | 70.4 | [{"value": 70.0, "product": "COC([C@@H](N(C)CC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "COC([C@@H](N(C)CC1=CN=C(N1CC1=C(C=CC=C1)Cl)CCCC)CC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[{1-[(2-Chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}methyl]phenylalanine methyl ester (prepared in Example 3(i) method B) (o.52 g, 1.18 mmol), 88% formic acid (0.31 g), and 37% aqueous formaldehyde (o.44 g) were heated over a steam bath for 18 hours. The reaction mixture was poured into 10% hydrochloric acid solu... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | null | null | c1c[nH]cn1.c1ccccc1.c1ccccc1 | Other | C(=O)O | null | null | C=O.CCCCc1ncc(CN[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl>C(=O)O>CCCCc1ncc(CN(C)[C@@H](Cc2ccccc2)C(=O)OC)n1Cc1ccccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4abdcb5f4ce64f6f9dc993a5b72d5eb7 | CCCCc1ncc(COC(C)=O)n1C(C)=O.OCCC12CC3CC(CC(C3)C1)C2>>CCCCc1ncc(COC(C)=O)n1CCC12CC3CC(CC(C3)C1)C2 | C12(CC3CC(CC(C1)C3)C2)CCO.C(C)(C)N(CC)C(C)C.C(C)(=O)N1C(=NC=C1COC(C)=O)CCCC.S(=O)(=O)(C(F)(F)F)OS(=O)(=O)C(F)(F)F>>C(C)(=O)OCC1=CN=C(N1CCC12CC3CC(CC(C1)C3)C2)CCCC | CC(=O)[n:14]1[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][cH:7][c:8]1[CH2:9][O:10][C:11]([CH3:12])=[O:13].O[CH2:15][CH2:16][C:17]12[CH2:18][CH:19]3[CH2:20][CH:21]([CH2:22][CH:23]([CH2:24]3)[CH2:25]1)[CH2:26]2>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([CH2:9][O:10][C:11]([CH3:12])=[O:13])[n:14]1[CH2:15][CH2:16][C:... | CCCCc1ncc(COC(C)=O)n1C(C)=O.OCCC12CC3CC(CC(C3)C1)C2 | CCCCc1ncc(COC(C)=O)n1CCC12CC3CC(CC(C3)C1)C2 | null | null | C(Cl)Cl.CO.C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | c9c7310a5bc60da55b1f395ba76d921b3153fead201d0dda950cbe942da07ef7 | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | c1cn(CCC23CC4CC(CC(C4)C2)C3)cn1 | C-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]):[#7;a:4]:[c:5]:[c:6]:1-[C:7].O-[CH2;D2;+0:8]-[C:9]-[C:10]>>[C:10]-[C:9]-[CH2;D2;+0:8]-[n;H0;D3;+0:1]1:[c:2](-[C:3]):[#7;a:4]:[c:5]:[c:6]:1-[C:7] | null | [] | null | null | 4 | DAY | A mixture of 2-(1-adamantyl)ethanol (10.7 g) and diisopropylethylamine (11 ml) in methylene chloride (70 ml) was added to triflic anhydride (16.75 g) in 70 ml of methylene chloride at -78° C. for 45 minutes, 1-acetyl-2-n-butyl 5-acetoxymethyl imidazole in 50 ml of methylene chloride was added and the mixture was allowe... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.C1C2CC3CC1CC(C2)C3 | HO- | C(Cl)Cl.CO.C(Cl)(Cl)Cl | null | 96 | CCCCc1ncc(COC(C)=O)n1C(C)=O.OCCC12CC3CC(CC(C3)C1)C2>C(Cl)Cl.CO.C(Cl)(Cl)Cl>CCCCc1ncc(COC(C)=O)n1CCC12CC3CC(CC(C3)C1)C2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7b615b850a714ed28667ec5cac687e9c | CCCCc1nc(Cl)c(CN[C@@H](Cc2ccccc2)C(=O)O)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1cccs1.COC(=O)c1ccc(CBr)cc1>>CCCCc1ncc(CN[C@@H](Cc2cccs2)C(=O)O)n1Cc1ccc(C(=O)O)cc1 | C(CCC)C=1N(C(=C(N1)Cl)CO)CC1=C(C=CC=C1)Cl.COC([C@@H](N)CC=1SC=CC1)=O.C(=O)(OC)C1=CC=C(CBr)C=C1.COC([C@@H](N)CC1=CC=CC=C1)=O.C(#N)[BH3-].[Na+].[BH4-].[Na+].ClC1=C(C=CC=C1)CN1C(=NC(=C1CN[C@@H](CC1=CC=CC=C1)C(=O)O)Cl)CCCC>>C(=O)(O)C1=CC=C(C=C1)CN1C(=NC=C1CN[C@@H](CC=1SC=CC1)C(=O)O)CCCC | O=C(O)[C@H](Cc1ccccc1)N[CH2:9][c:8]1[c:7](Cl)[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:21]1Cc1ccccc1Cl.C[O:20][C:18]([C@@H:11]([NH2:10])[CH2:12][c:13]1[cH:14][cH:15][cH:16][s:17]1)=[O:19].C[O:29][C:27]([c:26]1[cH:25][cH:24][c:23]([CH2:22]Br)[cH:31][cH:30]1)=[O:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([C... | CCCCc1nc(Cl)c(CN[C@@H](Cc2ccccc2)C(=O)O)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1cccs1.COC(=O)c1ccc(CBr)cc1 | CCCCc1ncc(CN[C@@H](Cc2cccs2)C(=O)O)n1Cc1ccc(C(=O)O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | abbcf6d4fbda0f95f8d47a1eea51d1d5ab4b6319e2f4833399a3a30ee465bd65 | 7bbdf5a711431b9eda0cebdcd4441ee7870943efe7023c11bfcc3df4436fe9ae | c1ccc(Cn2cncc2CNCCc2cccs2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8].C-[O;H0;D2;+0:9]-[C:10](=[O;D1;H0:11])-[C:12](-[C:13])-[NH2;D1;+0:14].Cl-[c;H0;D3;+0:15]1:[#7;a:16]:[c:17](-[C:18]):[n;H0;D3;+0:19](-C-c2:c:c:c:c:c:2-Cl):[c:20]:1-[CH2;D2;+0:21]-N-[C@H](-C-c1:c:c:c:c:c:1)-C(-O)=O>>[C:13]-[C:12](-[NH;D2;+0:1... | null | [] | null | null | null | null | The title compound was prepared following the procedure of Example 3 [(i) method B and (ii)] replacing 2-chlorobenzyl bromide with 4-carbomethoxybenzyl bromide, phenylalanine methyl ester with β-(2-thienyl)alanine methyl ester and sodium cyanoborohydride with sodium borohydride; mp 151°-152° C.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary halide.Carboxylic acid.Ester.Ester.Primary amine.Secondary amine | Carboxylic acid.Carboxylic acid.Secondary amine | c1ccccc1.c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccsc1.c1ccccc1 | HCl.Br- | null | null | null | CCCCc1nc(Cl)c(CN[C@@H](Cc2ccccc2)C(=O)O)n1Cc1ccccc1Cl.COC(=O)[C@@H](N)Cc1cccs1.COC(=O)c1ccc(CBr)cc1>>CCCCc1ncc(CN[C@@H](Cc2cccs2)C(=O)O)n1Cc1ccc(C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d099e8b2015d49a88b10fcd0cbfb9273 | C#Cc1cccc(OCc2ccc(OC)cc2)c1.CON(C)C(=O)c1ccccc1>>COc1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 | CON(C(C1=CC=CC=C1)=O)C.C[Si](N[Si](C)(C)C)(C)C.[Li].COC1=CC=C(COC=2C=C(C=CC2)C#C)C=C1>>C1(=CC=CC=C1)C(C#CC1=CC(=CC=C1)OCC1=CC=C(C=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]#[CH:15])[cH:24]2)[cH:25][cH:26]1.CON(C)[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]#[C:15][C:16](=[O:17])[c:18]3[cH:19][cH:20][... | C#Cc1cccc(OCc2ccc(OC)cc2)c1.CON(C)C(=O)c1ccccc1 | COc1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 70300835c4109ac6dd5d70878496806f120b832b4507de4dfe0bbdc19bbdd827 | 67d51335ef436619c1a58767ff7244203654d1fbbffcdb7f79bf5d30a9071b21 | O=C(C#Cc1cccc(OCc2ccccc2)c1)c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 45 | MINUTE | Place lithium hexamethyldisilazane (2 mL of a 1M solution in tetrahydrofuran, 2 mmol) and tetrahydrofuran (8 mL) under an argon atmosphere and cool to 0° C. Add a solution of 3-(4-methoxybenzyloxy)phenylacetylene (0.48 g, 2 mmol) in tetrahydrofuran and stir the brown solution for 45 minutes at 0° C. Add N-methoxy-N-met... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Alkyne | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.75 | C#Cc1cccc(OCc2ccc(OC)cc2)c1.CON(C)C(=O)c1ccccc1>O1CCCC1>COc1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b6c9f2f23d2345ee9bd3354a56c32325 | CNOC.COc1cc(C(=O)Cl)cc(OC)c1OC>>COc1cc(C(=O)N(C)OC)cc(OC)c1OC | COC=1C=C(C(=O)Cl)C=C(C1OC)OC.Cl.CNOC.N1=CC=CC=C1>>CON(C(C1=CC(=C(C(=C1)OC)OC)OC)=O)C | [NH:8]([CH3:9])[O:10][CH3:11].Cl[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:16]([O:17][CH3:18])[c:13]([O:14][CH3:15])[cH:12]1)=[O:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[N:8]([CH3:9])[O:10][CH3:11])[cH:12][c:13]([O:14][CH3:15])[c:16]1[O:17][CH3:18] | CNOC.COc1cc(C(=O)Cl)cc(OC)c1OC | COc1cc(C(=O)N(C)OC)cc(OC)c1OC | null | null | C(C)O | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#8:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:6]-[#8:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 97.9 | [{"value": 97.9, "product": "CON(C(C1=CC(=C(C(=C1)OC)OC)OC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | Dissolve 3,4,5-trimethoxybenzoyl chloride (2.3 g, 10 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.10 g, 11 mmol) in ethanol-free chloroform at room temperature. Cool the solution to 0° C. and add pyridine (1.85 g, 22 mmol). Stir at ambient temperature for 1 hour and evaporate the solvent in vacuo. Partition the... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HCl | C(C)O | 0 | 1 | CNOC.COc1cc(C(=O)Cl)cc(OC)c1OC>C(C)O>COc1cc(C(=O)N(C)OC)cc(OC)c1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-49f779f24ab24cde9206b27accb4fa10 | C#Cc1ccccc1.COc1cc(C(=O)N(C)OC)cc(OC)c1OC>>COc1cc(C(=O)C#Cc2ccccc2)cc(OC)c1OC | CON(C(C1=CC(=C(C(=C1)OC)OC)OC)=O)C.C[Si](N[Si](C)(C)C)(C)C.[Li].C1(=CC=CC=C1)C#C>>COC=1C=C(C=C(C1OC)OC)C(C#CC1=CC=CC=C1)=O | [CH:8]#[C:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.CON(C)[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:20]([O:21][CH3:22])[c:17]([O:18][CH3:19])[cH:16]1)=[O:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[C:8]#[C:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][c:17]([O:18][CH3:19])[c:20]1[O:21][CH3:22] | C#Cc1ccccc1.COc1cc(C(=O)N(C)OC)cc(OC)c1OC | COc1cc(C(=O)C#Cc2ccccc2)cc(OC)c1OC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 70300835c4109ac6dd5d70878496806f120b832b4507de4dfe0bbdc19bbdd827 | 67d51335ef436619c1a58767ff7244203654d1fbbffcdb7f79bf5d30a9071b21 | O=C(C#Cc1ccccc1)c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | 34.9 | [{"value": 34.9, "product": "COC=1C=C(C=C(C1OC)OC)C(C#CC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Place lithium hexamethyldisilazane (3 mL of a 1M solution in tetrahydrofuran, 3 mmol) and tetrahydrofuran (10 mL) under an argon atmosphere and cool to 0° C. Add phenylacetylene (0.33 mL, 3 mmol) and stir at 0° C. for 30 minutes. Add N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide (0.76 g, 3 mmol), remove the cooling ba... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Alkyne | Ketone | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 1 | C#Cc1ccccc1.COc1cc(C(=O)N(C)OC)cc(OC)c1OC>O1CCCC1>COc1cc(C(=O)C#Cc2ccccc2)cc(OC)c1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2aabad6285ab40aaa1f0ffe29c00c7a8 | C#Cc1ccccc1.CON(C)C(=O)c1ccccc1>>O=C(C#Cc1ccccc1)c1ccccc1 | C1(=CC=CC=C1)C#C.CON(C(C1=CC=CC=C1)=O)C.C(C)(C)[N-]C(C)C.[Li+].O1CCCC1>>C1(=CC=CC=C1)C(C#CC1=CC=CC=C1)=O | [CH:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.CON(C)[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([C:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C#Cc1ccccc1.CON(C)C(=O)c1ccccc1 | O=C(C#Cc1ccccc1)c1ccccc1 | null | null | C1CCCCC1 | C-C Coupling | OtherReaction | 70300835c4109ac6dd5d70878496806f120b832b4507de4dfe0bbdc19bbdd827 | 67d51335ef436619c1a58767ff7244203654d1fbbffcdb7f79bf5d30a9071b21 | O=C(C#Cc1ccccc1)c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | 61.4 | [{"value": 61.4, "product": "C1(=CC=CC=C1)C(C#CC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Place lithium diisopropylamide (10 mL of a 1.5M solution in cyclohexane) and tetrahydrofuran (40 mL) under an argon atmosphere and cool to 0° C. Add, by dropwise addition, phenylacetylene (1.65 mL, 15 mmol). Remove the cooling bath and stir for 30 minutes as room temperature. Cool the yellow solution to 0° C. and add, ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Alkyne | Ketone | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCCCC1 | null | 0.5 | C#Cc1ccccc1.CON(C)C(=O)c1ccccc1>C1CCCCC1>O=C(C#Cc1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8b7ba583998740be987368a88e5eb0cd | C#Cc1cccc(OCc2ccccc2)c1.CON(C)C(=O)c1ccccc1>>O=C(C#Cc1cccc(OCc2ccccc2)c1)c1ccccc1 | CON(C(C1=CC=CC=C1)=O)C.C[Si](N[Si](C)(C)C)(C)C.[Li].C(C1=CC=CC=C1)OC=1C=C(C=CC1)C#C>>C1(=CC=CC=C1)C(C#CC1=CC(=CC=C1)OCC1=CC=CC=C1)=O | [CH:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1.CON(C)[C:2](=[O:1])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[O:1]=[C:2]([C:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1)[c:19]1[cH:20][cH:21][cH:22... | C#Cc1cccc(OCc2ccccc2)c1.CON(C)C(=O)c1ccccc1 | O=C(C#Cc1cccc(OCc2ccccc2)c1)c1ccccc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 70300835c4109ac6dd5d70878496806f120b832b4507de4dfe0bbdc19bbdd827 | 67d51335ef436619c1a58767ff7244203654d1fbbffcdb7f79bf5d30a9071b21 | O=C(C#Cc1cccc(OCc2ccccc2)c1)c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | 57 | [{"value": 57.0, "product": "C1(=CC=CC=C1)C(C#CC1=CC(=CC=C1)OCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.0, "product": "C1(=CC=CC=C1)C(C#CC1=CC(=CC=C1)OCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | Place lithium hexamethyldisilazane (15 mL of a 1M solution in tetrahydrofuran, 15 mmol) and tetrahydrofuran (75 mL) under an argon atmosphere and cool with an ice-water bath. Add, by dropwise addition, a solution of 3-benzyloxyphenylacetylene (3.13 g, 15 mmol) in tetrahydrofuran. Stir at 0° C. for 45 minutes, then add,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Alkyne | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.75 | C#Cc1cccc(OCc2ccccc2)c1.CON(C)C(=O)c1ccccc1>O1CCCC1>O=C(C#Cc1cccc(OCc2ccccc2)c1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ebb9a025acde4ca7b55929f332170217 | CCOc1ccc(C=O)cc1>>CCOc1ccc(CO)cc1 | C(C)OC1=CC=C(C=O)C=C1.[BH4-].[Na+].Cl>>C(C)OC1=CC=C(CO)C=C1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH:8]=[O:9])[cH:10][cH:11]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][OH:9])[cH:10][cH:11]1 | CCOc1ccc(C=O)cc1 | CCOc1ccc(CO)cc1 | null | null | C(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Mix 4-ethoxybenzaldehyde (3.3 g, 22 mmol), sodium borohydride (830 mg, 22 mmol) and absolute ethanol (25 mL). Stir at room temperature until the reaction is complete, pour onto dilute hydrochloric acid and extract into ethyl acetate. Separate the organic phase and extract the aqueous phase with ethyl acetate (2×). Comb... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | C(C)O | null | null | CCOc1ccc(C=O)cc1>C(C)O>CCOc1ccc(CO)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-43a0aaa7336a47c9a189d7a4c5585e94 | CCOc1ccc(CO)cc1.O=Cc1cccc(O)c1>>CCOc1ccc(COc2cccc(C=O)c2)cc1 | C(C)OC1=CC=C(CO)C=C1.OC=1C=C(C=O)C=CC1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)OC1=CC=C(COC=2C=C(C=O)C=CC2)C=C1 | O[CH2:8][c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:19][cH:18]1.[OH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([CH:15]=[O:16])[cH:17]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH:15]=[O:16])[cH:17]2)[cH:18][cH:19]1 | CCOc1ccc(CO)cc1.O=Cc1cccc(O)c1 | CCOc1ccc(COc2cccc(C=O)c2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(COc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Mix 4-ethoxybenzyl alcohol (3.35 g. 22 mmol), 3-hydroxybenzaldehyde (2.69 g, 22 mmol), triphenylphosphine (5.8 g, 22 mmol) and diethylazadicarboxylate (3.83 g, 22 mmol) in tetrahydrofuran (25 mL). Stir at room temperature under anhydrous atmosphere until the reaction is done. Concentrate the solution in vacuo and dilut... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | null | CCOc1ccc(CO)cc1.O=Cc1cccc(O)c1>O1CCCC1>CCOc1ccc(COc2cccc(C=O)c2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6297d7b87210484783ae1ce1e663fd0f | C#Cc1cccc(OCc2ccc(OCC)cc2)c1.CON(C)C(=O)c1ccccc1>>CCOc1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 | CON(C(C1=CC=CC=C1)=O)C.C[Si](N[Si](C)(C)C)(C)C.[Li].C(C)OC1=CC=C(COC=2C=C(C=CC2)C#C)C=C1>>C1(=CC=CC=C1)C(C#CC1=CC(=CC=C1)OCC1=CC=C(C=C1)OCC)=O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[CH:16])[cH:25]2)[cH:26][cH:27]1.CON(C)[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[C:16][C:17](=[O:18])[c:19]... | C#Cc1cccc(OCc2ccc(OCC)cc2)c1.CON(C)C(=O)c1ccccc1 | CCOc1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 70300835c4109ac6dd5d70878496806f120b832b4507de4dfe0bbdc19bbdd827 | 67d51335ef436619c1a58767ff7244203654d1fbbffcdb7f79bf5d30a9071b21 | O=C(C#Cc1cccc(OCc2ccccc2)c1)c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 45 | MINUTE | Place lithium hexamethyldisilazane (2 mL of a 1M solution in tetrahydrofuran, 2 mmol) and tetrahydrofuran (8 mL) under an argon atmosphere and cool to 0° C. Add a solution of 3-(4-ethoxybenzyloxy)phenylacetylene (0.51 g, 2 mmol) in tetrahydrofuran and stir the solution for 45 minutes at 0° C. Add N-methoxy-N-methylbenz... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Alkyne | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.75 | C#Cc1cccc(OCc2ccc(OCC)cc2)c1.CON(C)C(=O)c1ccccc1>O1CCCC1>CCOc1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d66256aab42c4645ba01c94ac4791f03 | CN(C)c1ccc(C=O)cc1>>CN(C)c1ccc(CO)cc1 | CN(C1=CC=C(C=O)C=C1)C.[BH4-].[Na+].Cl>>CN(C1=CC=C(CO)C=C1)C | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]=[O:9])[cH:10][cH:11]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][OH:9])[cH:10][cH:11]1 | CN(C)c1ccc(C=O)cc1 | CN(C)c1ccc(CO)cc1 | null | null | C(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Mix 4-dimethylaminobenzaldehyde (3.3 g, 22 mmol), sodium borohydride (830 mg, 22 mmol) and absolute ethanol (25 mL). Stir at room temperature until the reaction is complete, pour onto dilute hydrochloric acid and extract into ethyl acetate. Separate the organic phase and extract the aqueous phase with ethyl acetate (2×... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | C(C)O | null | null | CN(C)c1ccc(C=O)cc1>C(C)O>CN(C)c1ccc(CO)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7100e9edbf604a50bcb345884fc1b480 | CN(C)c1ccc(CO)cc1.O=Cc1cccc(O)c1>>CN(C)c1ccc(COc2cccc(C=O)c2)cc1 | CN(C1=CC=C(CO)C=C1)C.OC=1C=C(C=O)C=CC1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CN(C1=CC=C(COC=2C=C(C=O)C=CC2)C=C1)C | O[CH2:8][c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:19][cH:18]1.[OH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([CH:15]=[O:16])[cH:17]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([CH:15]=[O:16])[cH:17]2)[cH:18][cH:19]1 | CN(C)c1ccc(CO)cc1.O=Cc1cccc(O)c1 | CN(C)c1ccc(COc2cccc(C=O)c2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(COc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Mix 4-(dimethylamino)benzyl alcohol (3.35 g. 22 mmol), 3-hydroxybenzaldehyde (2.69 g, 22 mmol), triphenylphosphine (5.8 g, 22 mmol) and diethylazadicarboxylate (3.83 g, 22 mmol) in tetrahydrofuran (25 mL). Stir at room temperature under anhydrous atmosphere until the reaction is done. Concentrate the solution in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | null | CN(C)c1ccc(CO)cc1.O=Cc1cccc(O)c1>O1CCCC1>CN(C)c1ccc(COc2cccc(C=O)c2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1dcbf41e8a1e4ec0990437ca83de30a4 | C#Cc1cccc(OCc2ccc(N(C)C)cc2)c1.CON(C)C(=O)c1ccccc1>>CN(C)c1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 | CON(C(C1=CC=CC=C1)=O)C.C[Si](N[Si](C)(C)C)(C)C.[Li].CN(C1=CC=C(COC=2C=C(C=CC2)C#C)C=C1)C>>C1(=CC=CC=C1)C(C#CC1=CC(=CC=C1)OCC1=CC=C(C=C1)N(C)C)=O | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[CH:16])[cH:25]2)[cH:26][cH:27]1.CON(C)[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][c:14]([C:15]#[C:16][C:17](=[O:18])[c... | C#Cc1cccc(OCc2ccc(N(C)C)cc2)c1.CON(C)C(=O)c1ccccc1 | CN(C)c1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 70300835c4109ac6dd5d70878496806f120b832b4507de4dfe0bbdc19bbdd827 | 67d51335ef436619c1a58767ff7244203654d1fbbffcdb7f79bf5d30a9071b21 | O=C(C#Cc1cccc(OCc2ccccc2)c1)c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 45 | MINUTE | Place lithium hexamethyldisilazane (2 mL of a 1M solution in tetrahydrofuran, 2 mmol) and tetrahydrofuran (8 mL) under an argon atmosphere and cool to 0° C. Add a solution of 3-(4-(dimethylamino)benzyloxy)phenylacetylene (0.51 g, 2 mmol) in tetrahydrofuran and stir the solution for 45 minutes at 0° C. Add N-methoxy-N-m... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Alkyne | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.75 | C#Cc1cccc(OCc2ccc(N(C)C)cc2)c1.CON(C)C(=O)c1ccccc1>O1CCCC1>CN(C)c1ccc(COc2cccc(C#CC(=O)c3ccccc3)c2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c746273d17404f66b6613167aa8be31a | C=CCBr.CCOC(=O)CC(=O)COC1CCCCC1>>C=CCC(C(=O)COC1CCCCC1)C(=O)OCC | [Na].C(C=C)Br.C1(CCCCC1)OCC(CC(=O)OCC)=O>>C1(CCCCC1)OCC(=O)C(C(=O)OCC)CC=C | Br[CH2:3][CH:2]=[CH2:1].[CH2:4]([C:5](=[O:6])[CH2:7][O:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)[C:15](=[O:16])[O:17][CH2:18][CH3:19]>>[CH2:1]=[CH:2][CH2:3][CH:4]([C:5](=[O:6])[CH2:7][O:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)[C:15](=[O:16])[O:17][CH2:18][CH3:19] | C=CCBr.CCOC(=O)CC(=O)COC1CCCCC1 | C=CCC(C(=O)COC1CCCCC1)C(=O)OCC | null | null | C(C)O | C-C Coupling | OtherReaction | a419f976441b589a3c956c0f129ce3053512f0325f3e460530d895d12d1b751d | c9d64189f02be16d3a7baf78522635b86019231c97f41522f031694d4f90e5ad | C1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](-[C:10])=[O;D1;H0:11]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:9](-[C:10])=[O;D1;H0:11] | null | [] | 50 | CELSIUS | 2 | HOUR | 320 g of ethyl 4-cyclohexyloxy-acetoacetate (1.4 mol) are initially introduced into a threenecked flask fitted with a stirrer, dropping funnel, drying tube and reflux condenser, and an Na ethanolate solution prepared from 32 g of sodium (1.4 mol) and 475 g of ethanol is added at 50° C. in the course of 30 minutes. 170 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester.Allyl | null | null | C1CCCCC1 | HBr | C(C)O | 50 | 2 | C=CCBr.CCOC(=O)CC(=O)COC1CCCCC1>C(C)O>C=CCC(C(=O)COC1CCCCC1)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-65ad894ecf63452786d85d75967b1990 | C=CCC(C(=O)COC1CCCCC1)C(=O)OCC>>C=CCCC(=O)COC1CCCCC1 | C1(CCCCC1)OCC(=O)C(C(=O)OCC)CC=C.[OH-].[Na+]>>C1(CCCCC1)OCC(CCC=C)=O | CCOC(=O)[CH:4]([CH2:3][CH:2]=[CH2:1])[C:5](=[O:6])[CH2:7][O:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][C:5](=[O:6])[CH2:7][O:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1 | C=CCC(C(=O)COC1CCCCC1)C(=O)OCC | C=CCCC(=O)COC1CCCCC1 | null | null | CCOCC | Reduction | Decarboxylation | fdc964bea6eaeadfb2309e01318abba99b151c57fdaf3760a2830a6479750a9b | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | C1CCCCC1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2]-[C:3]=[C;D1;H2:4])-[C:5](-[C:6])=[O;D1;H0:7]>>[C:6]-[C:5](=[O;D1;H0:7])-[CH2;D2;+0:1]-[C:2]-[C:3]=[C;D1;H2:4] | 58.6 | [{"value": 58.6, "product": "C1(CCCCC1)OCC(CCC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 140 g of ethyl 2-(cyclohexyloxyacetyl)-4-pentenoate are heated under reflux in 650 g of 5% strength aqueous sodium hydroxide solution for 4 hours. 500 ml of ether are added to the reaction mixture. The organic phase is separated off and concentrated and the residue is distilled. About 60 g of 1-cyclohexyloxy-hex-5-en-2... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | null | null | C1CCCCC1 | HO- | CCOCC | null | null | C=CCC(C(=O)COC1CCCCC1)C(=O)OCC>CCOCC>C=CCCC(=O)COC1CCCCC1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-24c621edc5884c249b64914319a77e74 | CCOC(=O)C1(c2ccc(OCC)cc2)CC1(F)F>>CCOc1ccc(C2(CO)CC2(F)F)cc1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)OC(=O)C1(C(C1)(F)F)C1=CC=C(C=C1)OCC.O.[OH-].[Na+].O>>C(C)OC1=CC=C(C=C1)C1(C(C1)(F)F)CO | CCO[C:9]([C:8]1([c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:16][cH:15]2)[CH2:11][C:12]1([F:13])[F:14])=[O:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8]2([CH2:9][OH:10])[CH2:11][C:12]2([F:13])[F:14])[cH:15][cH:16]1 | CCOC(=O)C1(c2ccc(OCC)cc2)CC1(F)F | CCOc1ccc(C2(CO)CC2(F)F)cc1 | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(C2CC2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]1(-[c:4])-[C:5]-[C:6]-1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[C:3]1(-[c:4])-[C:5]-[C:6]-1 | 92 | [{"value": 92.0, "product": "C(C)OC1=CC=C(C=C1)C1(C(C1)(F)F)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 1.0 g of lithium aluminium hydride in 120 ml of dry ether, at room temperature is added dropwise 5.4 g (0.02 moles) of ethyl-1-(4-ethoxyphenyl)-2,2-difluorocyclopropane-1-carboxylate in 20 ml of ether. The reaction mixture is stirred for 1 hr after which 1.0 ml of water 1.0 ml of 15% NaOH, followed by 3.0 ml of wate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.C1CC1 | HO- | CCOCC | null | null | CCOC(=O)C1(c2ccc(OCC)cc2)CC1(F)F>CCOCC>CCOc1ccc(C2(CO)CC2(F)F)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4fe44030a62b460f8a5604dcd68ea078 | CCOc1ccc(CC#N)cc1>>CCOc1ccc(C2(C#N)CC2)cc1 | Cl.C(CCC)[Li].ClCCCl.C(C)OC1=CC=C(C=C1)CC#N>>C(#N)C1(CC1)C1=CC=C(C=C1)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9]#[N:10])[cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8]2([C:9]#[N:10])[CH2:11][CH2:12]2)[cH:13][cH:14]1 | CCOc1ccc(CC#N)cc1 | CCOc1ccc(C2(C#N)CC2)cc1 | null | null | CCOCC.CCCCCC.O1CCCC1 | C-C Coupling | OtherReaction | ac91075a06a8cce8890c40dac805065f8c8b8f1e346a2fcf9830e69753a8b680 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc(C2CC2)cc1 | [N;D1;H0:1]#[C:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[N;D1;H0:1]#[C:2]-[C;H0;D4;+0:3]1(-[c:4](:[c:5]):[c:6])-[C:7]-[C:8]-1 | null | [] | null | null | 1 | HOUR | To 7.5 ml (0.012 mol) of 1.7M n-butyllithium in hexane, at room temperature, under an atmosphere of nitrogen, is added rapidly 10 ml of anhydrous tetrahydrofuran, followed by a solution of 4-ethoxyphenyl acetonitrile (0.8 g 0.005 mol) in 4 ml of tetrahydrofuran, during 5 minutes. The reaction mixture is stirred magneti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | C1CC1 | c1ccccc1.C1CC1 | Other | CCOCC.CCCCCC.O1CCCC1 | null | 1 | CCOc1ccc(CC#N)cc1>CCOCC.CCCCCC.O1CCCC1>CCOc1ccc(C2(C#N)CC2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ab56fa56606c42aa84ddab96051d6371 | CO.Oc1ccccc1O>>COc1ccccc1O.Oc1ccccc1O | CO.C=1(O)C(O)=CC=CC1>>C=1(O)C(O)=CC=CC1.C=1(C(O)=CC=CC1)OC | [CH3:1][OH:2].[cH:3]1[cH:13][cH:12][c:11]([OH:9])[c:16]([OH:17])[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].[OH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[OH:17] | CO.Oc1ccccc1O | COc1ccccc1O.Oc1ccccc1O | null | null | null | Aromatic Heterocycle Formation | Mitsunobu aryl ether | 9a57d4c07a5f6d2cf92579430cfc733994c27a45d88e5ebd02a1e499ac5e35ef | 67125d0d97ed0786028bd231bca324496f85d82449ddec65b9084d96e2533ec5 | c1ccccc1.c1ccccc1 | [C;D1;H3:1]-[OH;D1;+0:2].[O;D1;H1:3]-[c:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:[c;H0;D3;+0:9]:1-[OH;D1;+0:10]>>[C;D1;H3:1]-[O;H0;D2;+0:2]-[c;H0;D3;+0:6](:[c:11]:[c:12]):[c:13](-[OH;D1;+0:10]):[c:14].[O;D1;H1:15]-[c;H0;D3;+0:9]1:[c:8]:[cH;D2;+0:7]:[c:16]:[cH;D2;+0:5]:[c:4]:1-[O;D1;H1:3] | null | [] | null | null | 14 | HOUR | The catalyst stratum was heated and when the temperature of the catalyst stratum reached 280° C., a starting compound mixture gas consisting of catechol and methyl alcohol in a molar mixing ratio of 1:3.44 and evaporated in an evaporator was fed, at a feeding rate of 10.5 g/min, together with nitrogen gas, into the rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Methanol | Ether.Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | 14 | CO.Oc1ccccc1O>>COc1ccccc1O.Oc1ccccc1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bef22d2b530d42b096e5b7de282c4ca6 | CO.Oc1ccccc1O>>COc1ccccc1O.Oc1ccccc1 | C=1(O)C(O)=CC=CC1.CO>>C1(=CC=CC=C1)O.C=1(C(O)=CC=CC1)OC | [CH3:1][OH:2].[c:3]1([OH:10])[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].[OH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CO.Oc1ccccc1O | COc1ccccc1O.Oc1ccccc1 | null | null | null | Aromatic Heterocycle Formation | Mitsunobu aryl ether | 1c408c593650ad66b08f11ab8cf58e8474f9926d90b8b8d7d3991fc69c445d7c | 18d36c13c0c32581070c190f4159cf9b3c3365b00512bcecf63fdb4006ec2a66 | c1ccccc1.c1ccccc1 | [C;D1;H3:1]-[OH;D1;+0:2].[O;D1;H1:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[OH;D1;+0:7]):[c:8]:[c:9]>>[C;D1;H3:1]-[O;H0;D2;+0:2]-[c;H0;D3;+0:6](:[c:8]:[c:9]):[c:4](-[O;D1;H1:3]):[c:5].[OH;D1;+0:7]-[c:10](:[c:11]):[c:12] | null | [] | null | null | 14 | HOUR | When the temperature of the catalyst stratum reached 280° C., a starting compound mixture consisting of catechol and methyl alcohol in a molar mixing ratio of 1:3.44 was evaporated in a evaporator, and the resultant starting compound mixture gas was fed in a feeding rate of 10.5 g/min. together with a nitrogen gas into... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Methanol | Ether.Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | 14 | CO.Oc1ccccc1O>>COc1ccccc1O.Oc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bc1049bbac104ae6857eeaa65fae9134 | CO.Oc1ccccc1O>>COc1ccccc1O.Oc1ccccc1 | C=1(O)C(O)=CC=CC1.CO>>C1(=CC=CC=C1)O.C=1(C(O)=CC=CC1)OC | [CH3:1][OH:2].[c:3]1([OH:10])[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].[OH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CO.Oc1ccccc1O | COc1ccccc1O.Oc1ccccc1 | null | null | null | Aromatic Heterocycle Formation | Mitsunobu aryl ether | 1c408c593650ad66b08f11ab8cf58e8474f9926d90b8b8d7d3991fc69c445d7c | 18d36c13c0c32581070c190f4159cf9b3c3365b00512bcecf63fdb4006ec2a66 | c1ccccc1.c1ccccc1 | [C;D1;H3:1]-[OH;D1;+0:2].[O;D1;H1:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[OH;D1;+0:7]):[c:8]:[c:9]>>[C;D1;H3:1]-[O;H0;D2;+0:2]-[c;H0;D3;+0:6](:[c:8]:[c:9]):[c:4](-[O;D1;H1:3]):[c:5].[OH;D1;+0:7]-[c:10](:[c:11]):[c:12] | null | [] | null | null | 14 | HOUR | When the temperature of the catalyst stratum reached 260° C. in Example 43 and 300° C. in Example 44, a starting compound mixture consisting of catechol and methyl alcohol in a mixing molar ratio of 1:3.44 was evaporated in an evaporator, and the resultant starting compound mixture gas was fed in a feeding rate of 10.5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Methanol | Ether.Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | 14 | CO.Oc1ccccc1O>>COc1ccccc1O.Oc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-37aaff7b9d20449697e2d1307179b739 | CC(C)(Cl)CCC(C)(C)Cl.Oc1ccccc1>>CC1(C)CCC(C)(C)c2cc(O)ccc21 | [Cl-].[Al+3].[Cl-].[Cl-].C1(=CC=CC=C1)O.ClC(C)(CCC(C)(C)Cl)C>>CC1(C=2C=CC(=CC2C(CC1)(C)C)O)C | Cl[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6](Cl)([CH3:7])[CH3:8].[cH:9]1[cH:10][c:11]([OH:12])[cH:13][cH:14][cH:15]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]21 | CC(C)(Cl)CCC(C)(C)Cl.Oc1ccccc1 | CC1(C)CCC(C)(C)c2cc(O)ccc21 | null | null | null | C-C Coupling | OtherReaction | faa48b683da39df7e0e9cf4df3d89478446096416db2d6e2d979384c88ae8eca | 950e3556c1b5e86d9a0ad65231c6585f2d3e11c0ea678211dde9bdb559a1f623 | c1ccc2c(c1)CCCC2 | Cl-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4]-[C:5]-[C;H0;D4;+0:6](-Cl)(-[C;D1;H3:7])-[C;D1;H3:8].[c:9]1:[c:10]:[c:11]:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:1>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[c;H0;D3;+0:14]2:[c:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:... | 32.1 | [{"value": 32.1, "product": "CC1(C=2C=CC(=CC2C(CC1)(C)C)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 27.5 g (0.2 mol) of anhydrous aluminum chloride were added by spatula to 250.0 g (2.65 mol) of phenol plus 414.5 g (2.27 mol) of 2,5-dichloro-2,5-dimethylhexane in 500 ml of petroleum ether at room temperature while stirring. After 48 hours, the reaction mixture was poured into ice-water and extracted with ether, and t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | null | c1ccccc1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HCl | null | null | 48 | CC(C)(Cl)CCC(C)(C)Cl.Oc1ccccc1>>CC1(C)CCC(C)(C)c2cc(O)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4f2ef7e7bc5d48b9b8a54d0213b449e8 | CC1(C)CCC(C)(C)c2ccccc21.O=[N+]([O-])O>>CC1(C)CCC(C)(C)c2cc([N+](=O)[O-])ccc21 | [N+](=O)(O)[O-].CC1(CCC(C2=CC=CC=C12)(C)C)C>>[N+](=O)([O-])C1=CC=2C(CCC(C2C=C1)(C)C)(C)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][cH:11][cH:15][cH:16][c:17]21.O[N+:12](=[O:13])[O-:14]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][c:17]21 | CC1(C)CCC(C)(C)c2ccccc21.O=[N+]([O-])O | CC1(C)CCC(C)(C)c2cc([N+](=O)[O-])ccc21 | null | null | C(C)(=O)O.C(C)(=O)OC(C)=O | Functional Group Addition | Aromatic nitration with HNO3 | 5993c528ef8bcdffbf8c0a893a552b598272f75e0f1825b53fb570da12e0cd5d | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2c(c1)CCCC2 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:5]:[c:4] | null | [] | null | null | 8 | HOUR | 77.2 ml of glacial acetic acid and 20.8 ml of nitric acid (98% strength) were mixed while cooling and then added dropwise within 2 hours to a solution of 65.8 g (0.35 mol) of 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene in 154 ml of glacial acetic acid and 257 ml of acetic anhydride in a salt/ice bath. After the a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | C(C)(=O)O.C(C)(=O)OC(C)=O | null | 8 | CC1(C)CCC(C)(C)c2ccccc21.O=[N+]([O-])O>C(C)(=O)O.C(C)(=O)OC(C)=O>CC1(C)CCC(C)(C)c2cc([N+](=O)[O-])ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-870f165d08ed449088d95aa4882d0671 | CC1(C)CCC(C)(C)c2ccccc21.O=S(=O)(O)Cl>>CC1(C)CCC(C)(C)c2cc(S(=O)(=O)Cl)ccc21 | CC1(CCC(C2=CC=CC=C12)(C)C)C.ClS(=O)(=O)O>>CC1(C=2C=CC(=CC2C(CC1)(C)C)S(=O)(=O)Cl)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][cH:11][cH:16][cH:17][c:18]21.O=[S:12]([OH:13])(=[O:14])[Cl:15]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([S:12](=[O:13])(=[O:14])[Cl:15])[cH:16][cH:17][c:18]21 | CC1(C)CCC(C)(C)c2ccccc21.O=S(=O)(O)Cl | CC1(C)CCC(C)(C)c2cc(S(=O)(=O)Cl)ccc21 | null | null | null | Protection | Aromatic sulfonyl chlorination | 8571fb317e67ad387a94c9ed0cf7dddce67335d5f8173100c517d9514fb0d882 | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1ccc2c(c1)CCCC2 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:6]:[c:5] | null | [] | 60 | CELSIUS | null | null | 94.0 g (0.5 mol) of 1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene were stirred into 100 ml of chlorosulfonic acid at 20° C. within 30 min. The reaction solution was maintained at 60° C. for 1 hour, cooled to room temperature and then poured into 1.5 l of ice and extracted with ether. The organic phase was washed to... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HO- | null | 60 | null | CC1(C)CCC(C)(C)c2ccccc21.O=S(=O)(O)Cl>>CC1(C)CCC(C)(C)c2cc(S(=O)(=O)Cl)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2312dd61119e4794b7fcad57c714dd9a | CC1(C)CCC(C)(C)c2cc(O)ccc21.N#Cc1ccc(CCl)cc1>>CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21 | CC1(C=2C=CC(=CC2C(CC1)(C)C)O)C.C(#N)C1=CC=C(CCl)C=C1.C([O-])([O-])=O.[K+].[K+].O>>CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C#N)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([OH:12])[cH:22][cH:23][c:24]21.Cl[CH2:13][c:14]1[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20... | CC1(C)CCC(C)(C)c2cc(O)ccc21.N#Cc1ccc(CCl)cc1 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21 | null | null | CC(CC)=O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccc3c(c2)CCCC3)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 98.6 | [{"value": 98.6, "product": "CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C#N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 40.8 g (0.2 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol, 30.4 g (0.2 mol) of 4-cyanobenzyl chloride and 80 g (1.2 mol) of anhydrous potassium carbonate in 400 ml of butanone and 300 ml of dimethylformamide were refluxed for 9 h. The mixture was cooled and then poured into 1.5 l of water, and the solid was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | HCl | CC(CC)=O.CN(C=O)C | null | null | CC1(C)CCC(C)(C)c2cc(O)ccc21.N#Cc1ccc(CCl)cc1>CC(CC)=O.CN(C=O)C>CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-db4c527265944cbe953069fef82d126e | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21.O.[OH-]>>CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21 | Cl.CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C#N)C.[OH-].[Na+].O>>CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C(=O)O)C | N#[C:18][c:17]1[cH:16][cH:15][c:14]([CH2:13][O:12][c:11]2[cH:10][c:9]3[c:25]([cH:24][cH:23]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]3([CH3:7])[CH3:8])[cH:22][cH:21]1.[OH2:20].[OH-:19]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:... | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21.O.[OH-] | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21 | null | null | C(C)O | Acylation | OtherReaction | e05c34ebe51fe654c61f91bb118ee544dcd0a035df9f073c07f2e1b77a1f299a | e722778fc7d66899e0f2f256942c8c213a77617f32bb1410d97747833c62e260 | c1ccc(COc2ccc3c(c2)CCCC3)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH-;D0:5].[OH2;D0;+0:6]>>[O;H0;D1;+0:5]=[C;H0;D3;+0:1](-[OH;D1;+0:6])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 20 g (0.063 mol) of 4-cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether were refluxed with 163 ml of 10N sodium hydroxide solution in 245 ml of ethanol for 2 h. The mixture was cooled and then poured into water, which was then acidified with hydrochloric acid, and the precipitate was filtered off with... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Carboxylic acid | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | Other | C(C)O | null | null | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21.O.[OH-]>C(C)O>CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-29b56e7bfb744771ab87ed2781bf6d17 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21>>CC1(C)CCC(C)(C)c2cc(OCc3ccc(C=O)cc3)ccc21 | S(=O)(=O)([O-])[O-].[Na+].[Na+].[H-].C(C(C)C)[Al+]CC(C)C.CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C#N)C.C(C(O)C(O)C(=O)O)(=O)O>>CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C=O)C | N#[C:18][c:17]1[cH:16][cH:15][c:14]([CH2:13][O:12][c:11]2[cH:10][c:9]3[c:24]([cH:23][cH:22]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]3([CH3:7])[CH3:8])[cH:21][cH:20]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]... | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C=O)cc3)ccc21 | null | null | CCOCC | Functional Group Interconversion | OtherReaction | aa5d6273be01dadb1e5fec75e16ca9b6066d03aa195b40fe3322b26fa6d0b811 | 9f36587406d4620bb1f6625b2c5b8279180c3bebdc2492867ca9e2e72e879d2d | c1ccc(COc2ccc3c(c2)CCCC3)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[O;D1;H0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 25 | CELSIUS | 40 | MINUTE | 15.5 ml (19.7 mmol) of diisobutylaluminum hydride solution (20% in hexane) were added dropwise under nitrogen to a solution of 3 g (9.4 mmol) of 4-cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether in 40 ml of dry ether at 25° C. The mixture was stirred at 25° C. for 40 min and then 250 ml of saturated... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | null | CCOCC | 25 | 0.666667 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21>CCOCC>CC1(C)CCC(C)(C)c2cc(OCc3ccc(C=O)cc3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8d935727faf84d70b9ee58a54f250c2e | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21>>CC1(C)CCC(C)(C)c2cc(OCc3ccc(CN)cc3)ccc21 | S(=O)(=O)([O-])[O-].[Na+].[Na+].CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C#N)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)CN)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20][cH:21]3)[cH:22][cH:23][c:24]21>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][NH2:19])[cH:20]... | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(CN)cc3)ccc21 | null | null | CCOCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(COc2ccc3c(c2)CCCC3)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A suspension of 3 g (9.4 mmol) of 4-cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether in 60 ml of ether was added dropwise under nitrogen to a suspension of 1 g (26 mmol) of lithium aluminum hydride in 50 ml of dry ether at 25° C. The mixture was then stirred under reflux for 3 h, cooled and hydrolyze... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | null | CCOCC | null | null | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C#N)cc3)ccc21>CCOCC>CC1(C)CCC(C)(C)c2cc(OCc3ccc(CN)cc3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-55e65ba344a54615b9308935a326faf5 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21>>CC1(C)CCC(C)(C)c2cc(OCc3ccc(CO)cc3)ccc21 | ClC(=O)OCC.CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C(=O)O)C.C(C)N(CC)CC.[BH4-].[Na+].Cl>>CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)CO)C | O=[C:18]([c:17]1[cH:16][cH:15][c:14]([CH2:13][O:12][c:11]2[cH:10][c:9]3[c:24]([cH:23][cH:22]2)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]3([CH3:7])[CH3:8])[cH:21][cH:20]1)[OH:19]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:... | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(CO)cc3)ccc21 | null | null | O.O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(COc2ccc3c(c2)CCCC3)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 37.7 | [{"value": 37.7, "product": "CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)CO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A solution of 0.97 g (9 mmol) of ethyl chloroformate in 5 ml of tetrahydrofuran was added dropwise to a solution of 3 g (9 mmol) of 4-carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether and 0.9 g (9 mmol) of triethylamine in 20 ml of dry tetrahydrofuran at 0° C. The mixture was stirred at 0° C for 30 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | Other | O.O1CCCC1 | 0 | 0.5 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21>O.O1CCCC1>CC1(C)CCC(C)(C)c2cc(OCc3ccc(CO)cc3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-508e4f8861e640268b8364640bb5ce17 | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21.CCI>>CCOC(=O)c1ccc(COc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 | O.CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C(=O)O)C.C([O-])([O-])=O.[K+].[K+].ICC>>CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C(=O)OCC)C | [OH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][C:23]3([CH3:24])[CH3:25])[cH:26][cH:27]1.I[CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH2:10][O:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:1... | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21.CCI | CCOC(=O)c1ccc(COc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccc(COc2ccc3c(c2)CCCC3)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:3])-[c:6] | 40.9 | [{"value": 40.9, "product": "CC1(C=2C=CC(=CC2C(CC1)(C)C)OCC1=CC=C(C=C1)C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2 g (6 mmol) of 4-carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether, 2.7 g (19.6 mmol) of anhydrous potassium carbonate and 19 g (12.4 mmol) of iodoethane in 18 ml of butanone were refluxed for 7 h. The mixture was then poured into water and extracted with ether, and the organic phase was washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1.c1ccc2c(c1)CCCC2 | HI | CC(CC)=O | null | null | CC1(C)CCC(C)(C)c2cc(OCc3ccc(C(=O)O)cc3)ccc21.CCI>CC(CC)=O>CCOC(=O)c1ccc(COc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-46be299854ee4a8dbe1a9893d4f4ca6f | CC1(C)CCC(C)(C)c2cc(CBr)ccc21.CCOC(=O)c1ccc(O)cc1>>CCOC(=O)c1ccc(OCc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 | O.BrCC1=CC=2C(CCC(C2C=C1)(C)C)(C)C.OC1=CC=C(C(=O)OCC)C=C1.C([O-])([O-])=O.[K+].[K+]>>CC1(C=2C=CC(=CC2C(CC1)(C)C)COC1=CC=C(C=C1)C(=O)OCC)C | Br[CH2:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][C:23]2([CH3:24])[CH3:25].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:26][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:... | CC1(C)CCC(C)(C)c2cc(CBr)ccc21.CCOC(=O)c1ccc(O)cc1 | CCOC(=O)c1ccc(OCc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2ccc3c(c2)CCCC3)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 50.8 | [{"value": 50.8, "product": "CC1(C=2C=CC(=CC2C(CC1)(C)C)COC1=CC=C(C=C1)C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10 g (36 mmol) of 2-bromomethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene, 6 g (36 mmol) of ethyl 4-hydroxybenzoate and 7.2 g (52 mmol) of anhydrous potassium carbonate in 60 ml of dimethylformamide were refluxed for 5.25 h. The mixture was then poured into water and extracted several times with ether, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2c(c1)CCCC2 | HBr | CN(C=O)C | null | null | CC1(C)CCC(C)(C)c2cc(CBr)ccc21.CCOC(=O)c1ccc(O)cc1>CN(C=O)C>CCOC(=O)c1ccc(OCc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0a7405fa2b2340d382586106ada0c630 | CC(=O)OC(C)=O.COC(=O)c1ccc(CNc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1>>COC(=O)c1ccc(CN(C(C)=O)c2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 | O.C(=O)(OC)C1=CC=C(CNC2=CC=3C(CCC(C3C=C2)(C)C)(C)C)C=C1.C(C)(=O)OC(C)=O.C(C)N(CC)CC>>C(C)(=O)N(CC1=CC=C(C=C1)C(=O)OC)C1=CC=2C(CCC(C2C=C1)(C)C)(C)C | CC(=O)O[C:11]([CH3:12])=[O:13].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][c:14]2[cH:15][cH:16][c:17]3[c:18]([cH:19]2)[C:20]([CH3:21])([CH3:22])[CH2:23][CH2:24][C:25]3([CH3:26])[CH3:27])[cH:28][cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]([C:11]([CH3:12])=[O:13])[c:14]2[cH... | CC(=O)OC(C)=O.COC(=O)c1ccc(CNc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 | COC(=O)c1ccc(CN(C(C)=O)c2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 | null | null | ClCCl | Acylation | Aminolysis of esters | 72a6d1966b6b15ac7195d4682af251dc9ffac857f784a4242970ab5c7a529369 | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | c1ccc(CNc2ccc3c(c2)CCCC3)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5](-[NH;D2;+0:6]-[C:7]-[c:8]):[c:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:6](-[C:7]-[c:8])-[c:5](:[c:4]):[c:9] | null | [] | null | null | null | null | 4.2 g (12 mmol) of N-(4-carbomethoxybenzyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine (from Example 11) and 1.6 ml (16 mmol) of acetic anhydride and 2.3 ml (17 mmol) of triethylamine in 100 ml of dichloromethane were stirred at room temperature. After the reaction was complete, the solution was poured into... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | ClCCl | null | null | CC(=O)OC(C)=O.COC(=O)c1ccc(CNc2ccc3c(c2)C(C)(C)CCC3(C)C)cc1>ClCCl>COC(=O)c1ccc(CN(C(C)=O)c2ccc3c(c2)C(C)(C)CCC3(C)C)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3975e3cba1d24b4fba5c7e42d9b53709 | CC1(C)CCC(C)(C)c2cc(SCc3ccc(C(=O)O)cc3)ccc21.[O-][I+3]([O-])([O-])[O-]>>CC1(C)CCC(C)(C)c2cc(S(=O)Cc3ccc(C(=O)O)cc3)ccc21 | I(=O)(=O)(=O)[O-].[Na+].CC1(C=2C=CC(=CC2C(CC1)(C)C)SCC1=CC=C(C=C1)C(=O)O)C.Cl>>CC1(C=2C=CC(=CC2C(CC1)(C)C)S(=O)CC1=CC=C(C=C1)C(=O)O)C | [CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([S:12][CH2:14][c:15]3[cH:16][cH:17][c:18]([C:19](=[O:20])[OH:21])[cH:22][cH:23]3)[cH:24][cH:25][c:26]21.[O-][I+3]([O-])([O-])[O-:13]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([S:12](=[O:13])[CH2:14][c:15... | CC1(C)CCC(C)(C)c2cc(SCc3ccc(C(=O)O)cc3)ccc21.[O-][I+3]([O-])([O-])[O-] | CC1(C)CCC(C)(C)c2cc(S(=O)Cc3ccc(C(=O)O)cc3)ccc21 | null | null | CN(C=O)C.C(C)O.O | Oxidation | OtherReaction | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=S(Cc1ccccc1)c1ccc2c(c1)CCCC2 | [O-;H0;D1:1]-[I+3](-[O-])(-[O-])-[O-].[c:2]:[c:3](-[S;H0;D2;+0:4]-[C:5]-[c:6]):[c:7]>>[O;H0;D1;+0:1]=[S;H0;D3;+0:4](-[C:5]-[c:6])-[c:3](:[c:2]):[c:7] | 39.6 | [{"value": 39.6, "product": "CC1(C=2C=CC(=CC2C(CC1)(C)C)S(=O)CC1=CC=C(C=C1)C(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 3.4 g (16 mmol) of sodium periodate in 30 ml of water was added dropwise to 5.3 g (15 mmol) of the thioether from Example 10 in a mixture of 150 ml of ethanol and 40 ml of dimethylformamide at 0° C., and the mixture was then stirred at the same temperature for 2 hours and at room temperature overnight. Th... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | I- | CN(C=O)C.C(C)O.O | null | 8 | CC1(C)CCC(C)(C)c2cc(SCc3ccc(C(=O)O)cc3)ccc21.[O-][I+3]([O-])([O-])[O-]>CN(C=O)C.C(C)O.O>CC1(C)CCC(C)(C)c2cc(S(=O)Cc3ccc(C(=O)O)cc3)ccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6f275656c8da41b3801c8b460fc918fa | Cc1cc(C2=CC(C)(C)CC(C)(C)C2)ccc1F.O=C(OO)c1cccc(Cl)c1>>Cc1cc(C23CC(C)(C)CC(C)(C)C2O3)ccc1F | FC1=C(C=C(C=C1)C1=CC(CC(C1)(C)C)(C)C)C.OP(=O)([O-])[O-].[K+].[K+].ClC1=CC(=CC=C1)C(=O)OO>>FC1=C(C=C(C=C1)C12C(C(CC(C1)(C)C)(C)C)O2)C | [CH3:1][c:2]1[cH:3][c:4]([C:5]2=[CH:14][C:11]([CH3:12])([CH3:13])[CH2:10][C:7]([CH3:8])([CH3:9])[CH2:6]2)[cH:16][cH:17][c:18]1[F:19].O=C(O[OH:15])c1cccc(Cl)c1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]23[CH2:6][C:7]([CH3:8])([CH3:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH:14]2[O:15]3)[cH:16][cH:17][c:18]1[F:19] | Cc1cc(C2=CC(C)(C)CC(C)(C)C2)ccc1F.O=C(OO)c1cccc(Cl)c1 | Cc1cc(C23CC(C)(C)CC(C)(C)C2O3)ccc1F | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 7cee396be0f6ae79b424df065d0e9e65c066fbe8972302e80868a1efcff9512b | c40ffbbc3249442e5ee39aaa69a55be7ac2fa45f48637395e415c565c1288454 | c1ccc(C23CCCCC2O3)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])=[CH;D2;+0:12]-1>>[C;D1;H3:2]-[C:3]1(-[C;D1;H3:4])-[C:5]-[C:6]-[C:7]-[C;H0;D4;+0:8]2(-[c:9](:[c:10]):[c:11])-[O;H0;D2;+0:1]-[CH;D3;+0:12]-1-2 | 88 | [{"value": 88.0, "product": "FC1=C(C=C(C=C1)C12C(C(CC(C1)(C)C)(C)C)O2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.5, "product": "FC1=C(C=C(C=C1)C12C(C(CC(C1)(C)C)(C)C)O2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | A solution of meta-chloroperbenzoic acid (20 g, 90 mmol) in 250 ml of CH2Cl2 is added dropwise to a cooled (0° C.) solution of 1-fluoro-2-methyl-4-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)benzene (15 g, 61 mmol) and K2HPO4 (21 g, 90 mmol) in dry CH2Cl2 (100 ml). The resulting milky solution is stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | Ether | C1=CCCCC1.c1ccccc1 | C1CCC2OC2C1 | c1ccccc1.C1CCC2OC2C1 | HCl | C(Cl)Cl | null | 14 | Cc1cc(C2=CC(C)(C)CC(C)(C)C2)ccc1F.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>Cc1cc(C23CC(C)(C)CC(C)(C)C2O3)ccc1F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4f4f202b0c7649758da42a8dec41db76 | Cc1cc(C23CC(C)(C)CC(C)(C)C2O3)ccc1F>>Cc1cc(C2CC(C)(C)CC(C)(C)C2=O)ccc1F | FC1=C(C=C(C=C1)C12C(C(CC(C1)(C)C)(C)C)O2)C>>FC1=C(C=C(C=C1)C1C(C(CC(C1)(C)C)(C)C)=O)C | [CH3:1][c:2]1[cH:3][c:4]([C:5]23[CH2:6][C:7]([CH3:8])([CH3:9])[CH2:10][C:11]([CH3:12])([CH3:13])[CH:14]2[O:15]3)[cH:16][cH:17][c:18]1[F:19]>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]2[CH2:6][C:7]([CH3:8])([CH3:9])[CH2:10][C:11]([CH3:12])([CH3:13])[C:14]2=[O:15])[cH:16][cH:17][c:18]1[F:19] | Cc1cc(C23CC(C)(C)CC(C)(C)C2O3)ccc1F | Cc1cc(C2CC(C)(C)CC(C)(C)C2=O)ccc1F | null | null | CCOCC.C1=CC=CC=C1 | Miscellaneous | OtherReaction | 8ec7f40fa31a913229f3be27a8e864c7048d16f232c5a7a46a87f0c28e7d1259 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCCCC1c1ccccc1 | [C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-[C;H0;D4;+0:7]2(-[c:8](:[c:9]):[c:10])-[O;H0;D2;+0:11]-[CH;D3;+0:12]-1-2>>[C;D1;H3:1]-[C:2]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[C;H0;D3;+0:12]-1=[O;H0;D1;+0:11] | 80 | [{"value": 80.0, "product": "FC1=C(C=C(C=C1)C1C(C(CC(C1)(C)C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a cooled solution (0° C.) of the epoxide from Example 1, Step A above (32.7 g, 125 mmol) in benzene (200 ml) is added dropwise 7.6 ml BF3 ·OEt2 (62 mmol). The cooling bath is removed and the reaction mixture warmed to room temperature and stirred for 2 hours. The benzene is removed under reduced pressure and provide... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1CCC2OC2C1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | null | CCOCC.C1=CC=CC=C1 | null | 2 | Cc1cc(C23CC(C)(C)CC(C)(C)C2O3)ccc1F>CCOCC.C1=CC=CC=C1>Cc1cc(C2CC(C)(C)CC(C)(C)C2=O)ccc1F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5ce452de6da847909012d9a70df1b395 | Cc1cc(C2CC(C)(C)CC(C)(C)C2(O)C#C[Si](C)(C)C)ccc1F>>Cc1cc(C2=C(C#C[Si](C)(C)C)C(C)(C)CC(C)(C)C2)ccc1F | C[Si](C)(C)C#CC1(C(CC(CC1(C)C)(C)C)C1=CC(=C(C=C1)F)C)O.CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC>>C[Si](C)(C)C#CC1=C(CC(CC1(C)C)(C)C)C1=CC(=C(C=C1)F)C | O[C:6]1([C:7]#[C:8][Si:9]([CH3:10])([CH3:11])[CH3:12])[CH:5]([c:4]2[cH:3][c:2]([CH3:1])[c:23]([F:24])[cH:22][cH:21]2)[CH2:20][C:17]([CH3:18])([CH3:19])[CH2:16][C:13]1([CH3:14])[CH3:15]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]2=[C:6]([C:7]#[C:8][Si:9]([CH3:10])([CH3:11])[CH3:12])[C:13]([CH3:14])([CH3:15])[CH2:16][C:17]([CH3:18])... | Cc1cc(C2CC(C)(C)CC(C)(C)C2(O)C#C[Si](C)(C)C)ccc1F | Cc1cc(C2=C(C#C[Si](C)(C)C)C(C)(C)CC(C)(C)C2)ccc1F | null | null | C(C)#N.O | Functional Group Interconversion | OtherReaction | bb751e8d8bac081516d1433e6fec088b316018c4b9e2465f1f9c878bad0b1e7c | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=C(c2ccccc2)CCCC1 | O-[C;H0;D4;+0:1]1(-[C:2]#[C:3]-[#14:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[C:12]-[C:13]-[C:14]-[C:15]-1(-[C;D1;H3:16])-[C;D1;H3:17]>>[C;D1;H3:5]-[#14:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[C:3]#[C:2]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[C:12]-[C:13]-[C:14]-[C:15]-1... | 67 | [{"value": 67.0, "product": "C[Si](C)(C)C#CC1=C(CC(CC1(C)C)(C)C)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the hydroxy acetylene from Example 1, Step C above (20 g, 55.5 mmol) in acetonitrile (250 ml) is added 20 g (83 mmol) of Burgess reagent. The reaction mixture is heated at reflux for 14 hours, cooled to room temperature and diluted with H2O (1 L). The aqueous solution is extracted with ether and the co... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | C1CCCCC1 | C1=CCCCC1 | c1ccccc1.C1=CCCCC1 | HO- | C(C)#N.O | null | null | Cc1cc(C2CC(C)(C)CC(C)(C)C2(O)C#C[Si](C)(C)C)ccc1F>C(C)#N.O>Cc1cc(C2=C(C#C[Si](C)(C)C)C(C)(C)CC(C)(C)C2)ccc1F |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-30b768947e544f58a83c823717346385 | Cc1cc(C2=C(C#C[Si](C)(C)C)C(C)(C)CC(C)(C)C2)ccc1F>>C#CC1=C(c2ccc(F)c(C)c2)CC(C)(C)CC1(C)C | C[Si](C)(C)C#CC1=C(CC(CC1(C)C)(C)C)C1=CC(=C(C=C1)F)C.C(C)(=O)O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(#C)C1=C(CC(CC1(C)C)(C)C)C1=CC(=C(C=C1)F)C | C[Si](C)(C)[C:1]#[C:2][C:3]1=[C:4]([c:5]2[cH:6][cH:7][c:8]([F:9])[c:10]([CH3:11])[cH:12]2)[CH2:13][C:14]([CH3:15])([CH3:16])[CH2:17][C:18]1([CH3:19])[CH3:20]>>[CH:1]#[C:2][C:3]1=[C:4]([c:5]2[cH:6][cH:7][c:8]([F:9])[c:10]([CH3:11])[cH:12]2)[CH2:13][C:14]([CH3:15])([CH3:16])[CH2:17][C:18]1([CH3:19])[CH3:20] | Cc1cc(C2=C(C#C[Si](C)(C)C)C(C)(C)CC(C)(C)C2)ccc1F | C#CC1=C(c2ccc(F)c(C)c2)CC(C)(C)CC1(C)C | null | null | C1CCOC1.CCOCC | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | C1=C(c2ccccc2)CCCC1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[C:3](=[C:4](-[c:5])-[C:6])-[C:7]>>[C:6]-[C:4](-[c:5])=[C:3](-[C:2]#[CH;D1;+0:1])-[C:7] | 98 | [{"value": 98.0, "product": "C(#C)C1=C(CC(CC1(C)C)(C)C)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of the product from Example 1, Step D above (5 g, 14.6 mmol), and acetic acid (1.3 ml, 21.9 mmol) in THF (15 ml) at 0° C. is added tetrabutylammonium fluoride in THF (1M, 21.9 ml, 21.9 mmol). The resulting solution is stirred for 12 hours at room temperature, diluted with ether and washed with saturated a... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | C1=CCCCC1.c1ccccc1 | Other | C1CCOC1.CCOCC | null | 12 | Cc1cc(C2=C(C#C[Si](C)(C)C)C(C)(C)CC(C)(C)C2)ccc1F>C1CCOC1.CCOCC>C#CC1=C(c2ccc(F)c(C)c2)CC(C)(C)CC1(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9544b342e8b6458bac2c64b1a2c39d77 | CC(C)Cc1ccccc1.COc1ccc2ccccc2c1.c1ccc2c(c1)CCCC2>>CC(C)Cc1ccc(C(C)C(=O)O)cc1 | C1=CC=CC2=CC=CC=C12.C1CCCC2=CC=CC=C12.C1(=CC=CC=C1)OC.COC1=CC2=CC=CC=C2C=C1.C(C(C)C)C1=CC=CC=C1>>OC(=O)C(C)C1=CC=C(CC(C)C)C=C1 | [CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:14][cH:15]1.c1ccc2c[c:11]([O:12][CH3:10])ccc2c1.c1ccc2c(c1)CCC[CH2:9]2>>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([CH:9]([CH3:10])[C:11](=[O:12])[OH:13])[cH:14][cH:15]1 | CC(C)Cc1ccccc1.COc1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | CC(C)Cc1ccc(C(C)C(=O)O)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 43854ac68e6b362cc70ec003ae9c53a0cd7ba5a9412787463058beb669774160 | 5e8ff715284d2753472609e3a99a03d1debb677f7d7e353b2a8ba368120e8e19 | c1ccccc1 | C1-C-[CH2;D2;+0:1]-c2:c:c:c:c:c:2-C-1.[CH3;D1;+0:2]-[O;H0;D2;+0:3]-[c;H0;D3;+0:4]1:c:c:c2:c:c:c:c:c:2:c:1.[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[CH3;D1;+0:2]-[CH;D3;+0:1](-[C;H0;D3;+0:4](-[O;D1;H1:10])=[O;H0;D1;+0:3])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | null | null | null | null | Surprisingly, only a few methods for a stereospecific chemical synthesis for 2-aryl-alkanoic acids, especially 2-aryl-propionic acids, are known. Piccolo et al. (J. Org. Chem. 50, 3945-3946, 1985) describe a stereospecific synthesis by the alkylation of benzene or isobutylbenzene with (S)-methyl-2-(chlorosulfonyl)-oxy ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Carboxylic acid | c1ccccc1.c1ccc2ccccc2c1.c1ccc2c(c1)CCCC2 | c1ccccc1 | c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | CC(C)Cc1ccccc1.COc1ccc2ccccc2c1.c1ccc2c(c1)CCCC2>C1(=CC=CC=C1)C>CC(C)Cc1ccc(C(C)C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d915f9e724c34bff918fbcf5d34e9611 | CC(C)NC(C)C.CCC1=N[C@@H](COC)[C@H](c2ccccc2)O1.CCC1=N[C@@H](COC)[C@H](c2ccccc2)O1>>COCC1N=C(C2(C)C=CC(CC(C)C)=CC2)OC1c1ccccc1 | C1CCOC1.C(C)(C)NC(C)C.C[Li].C(C)C=1O[C@H]([C@@H](N1)COC)C1=CC=CC=C1.C1CCOC1.C(C)(C)[N-]C(C)C.[Li+].[Br-].C1CCOC1.[Cl-].[Na+].C(C)C=1O[C@H]([C@@H](N1)COC)C1=CC=CC=C1.C1CCOC1>>CC1(CC=C(C=C1)CC(C)C)C=1OC(C(N1)COC)C1=CC=CC=C1 | CC(C)NC(C)[CH3:14].[CH3:1][O:2][CH2:3][C@@H:4]1[N:5]=[C:6]([CH2:7][CH3:8])[O:18][C@H:19]1[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.COC[C@@H]1N=[C:12]([CH2:13][CH3:15])O[C@H]1c1c[cH:10][cH:11][cH:16][cH:17]1>>[CH3:1][O:2][CH2:3][CH:4]1[N:5]=[C:6]([C:7]2([CH3:8])[CH:9]=[CH:10][C:11]([CH2:12][CH:13]([CH3:14])[CH3:15])=[... | CC(C)NC(C)C.CCC1=N[C@@H](COC)[C@H](c2ccccc2)O1.CCC1=N[C@@H](COC)[C@H](c2ccccc2)O1 | COCC1N=C(C2(C)C=CC(CC(C)C)=CC2)OC1c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | b93798b2a4617495f363980bc632712fc4a3efeb15812f14a660d79f68875cd2 | 65bdc187ccffb20164ee1a46c967e081a6b3e14c29368f87af76f0367fea6139 | C1=CCC(C2=NCC(c3ccccc3)O2)C=C1 | C-C(-C)-N-C(-C)-[CH3;D1;+0:1].C-O-C-[C@H]1-N=[C;H0;D3;+0:2](-[CH2;D2;+0:3]-[C;D1;H3:4])-O-[C@@H]-1-c1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:c:1.[C;D1;H3:9]-[CH2;D2;+0:10]-[C:11]1=[#7:12]-[C:13]-[C:14]-[#8:15]-1>>[C;D1;H3:4]-[CH;D3;+0:3](-[CH3;D1;+0:1])-[CH2;D2;+0:2]-[C;H0;D3;+0:7]1=[CH;D2;+0:6]-[CH2;D2;+0... | 90 | [{"value": 90.0, "product": "CC1(CC=C(C=C1)CC(C)C)C=1OC(C(N1)COC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the compound II (155 g, 0.71 mol) in THF (1.6 L) under nitrogen is cooled to -75° C. in a dry-ice-acetone bath. A solution of 0.8 mol of lithium diisopropylamide, derived from 98 ml of diisopropylamine and 300 ml of 2,3M butylithium (methyllithium) in 750 ml of dry THF is prepared, and added under continu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amine | null | C1=NCCO1.c1ccccc1 | C1=CCCC=C1 | C1=NCCO1.C1=CCCC=C1.c1ccccc1 | HO- | null | null | null | CC(C)NC(C)C.CCC1=N[C@@H](COC)[C@H](c2ccccc2)O1.CCC1=N[C@@H](COC)[C@H](c2ccccc2)O1>>COCC1N=C(C2(C)C=CC(CC(C)C)=CC2)OC1c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-35982a95451c4e8385f818981ea12a16 | CC(C)(C)C(=O)Cl.Nc1cc2c(O)nc[nH]c-2n1>>CC(C)(C)C(=O)Nc1cc2c(O)nc[nH]c-2n1 | OC1=C2C(NC=N1)=NC(=C2)N.C(C(C)(C)C)(=O)Cl>>OC1=C2C(NC=N1)=NC(=C2)NC(C(C)(C)C)=O | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][c:8]1[cH:9][c:10]2[c:11]([OH:12])[n:13][cH:14][nH:15][c:16]-2[n:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]2[c:11]([OH:12])[n:13][cH:14][nH:15][c:16]-2[n:17]1 | CC(C)(C)C(=O)Cl.Nc1cc2c(O)nc[nH]c-2n1 | CC(C)(C)C(=O)Nc1cc2c(O)nc[nH]c-2n1 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cc2cnc[nH]c-2n1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[#7;a:7]:[c:8]:[#7;a:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[#7;a:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6]):[c:12] | 89.6 | [{"value": 89.0, "product": "OC1=C2C(NC=N1)=NC(=C2)NC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.6, "product": "OC1=C2C(NC=N1)=NC(=C2)NC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 3.0 g (0.02 mole) of 4-hydroxy-6-aminopyrrolo[2,3-d]pyrimidine and 8.4 g (0.07 mol) of pivaloyl chloride in 40 mL of pyridine is stirred for 30 minutes at from 80° to 90° C., the mixture then evaporated to dryness, and the residue dissolved in 30 mL of methanol. Addition of 10% aqueous ammonia yields 4.2 g... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ncc2cc[nH]c2n1 | HCl | N1=CC=CC=C1 | null | 0.5 | CC(C)(C)C(=O)Cl.Nc1cc2c(O)nc[nH]c-2n1>N1=CC=CC=C1>CC(C)(C)C(=O)Nc1cc2c(O)nc[nH]c-2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-099dba7b08f5439bb4cdf076de3f062d | CC(C)(C)C(=O)Nc1cc2c(O)n(I)c(I)nc-2n1>>CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1 | IC=1N(C(=C2C(N1)=NC(=C2)NC(C(C)(C)C)=O)O)I>>IN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O | I[c:15]1[n:13]([I:14])[c:11]([OH:12])[c:10]2[cH:9][c:8]([NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[n:18][c:17]-2[n:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]2[c:11]([OH:12])[n:13]([I:14])[cH:15][n:16][c:17]-2[n:18]1 | CC(C)(C)C(=O)Nc1cc2c(O)n(I)c(I)nc-2n1 | CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1 | null | [Zn] | C(C)(=O)O.O | Functional Group Interconversion | Aromatic dehalogenation | 26ad15a6cd6065fab54d262c57ea46217b9c0a5d9be9f2a942a86df9b473c507 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cc2c[nH]cnc-2n1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]:[c:5])-[c:6]:[c:7]:[#7;a:8]:1-[I;D1;H0:9]>>[I;D1;H0:9]-[#7;a:8]1:[c:7]:[c:6]-[c:3](:[#7;a:2]:[cH;D2;+0:1]:1):[#7;a:4]:[c:5] | null | [] | null | null | 18 | HOUR | To a mixture of 4.86 g of 2,3-diiodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine in 100 mL of glacial acetic acid and 25 mL of water are added 1.3 g (20 mmol) of zinc powder. The mixture is stirred at ambient temperature for 18 hours, diluted with 500 mL of water, and cooled. The solid is collected through filtra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncc2cc[nH]c2n1 | c1cc2cncnc2[nH]1 | c1cc2cncnc2[nH]1 | I- | [Zn].C(C)(=O)O.O | null | 18 | CC(C)(C)C(=O)Nc1cc2c(O)n(I)c(I)nc-2n1>[Zn].C(C)(=O)O.O>CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-08c77ae1ea2d4cbc9b60678aaa348fec | C#Cc1ccc(C(=O)N[C@@H](CCC(=O)OC)C(=O)OC)cc1.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1>>COC(=O)CC[C@H](NC(=O)c1ccc(C#Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)cc1)C(=O)OC | IN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O.C(#C)C1=CC=C(C(=O)N[C@@H](CCC(=O)OC)C(=O)OC)C=C1.C(C)N(CC)CC.O>>OC1=C2C(N=CN1C#CC1=CC=C(C(=O)N[C@@H](CCC(=O)OC)C(=O)OC)C=C1)=NC(=C2)NC(C(C)(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C@H:7]([NH:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([C:15]#[CH:16])[cH:34][cH:35]1)[C:36](=[O:37])[O:38][CH3:39].I[n:17]1[cH:18][n:19][c:20]2[n:21][c:22]([NH:23][C:24](=[O:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30][c:31]-2[c:32]1[OH:33]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH... | C#Cc1ccc(C(=O)N[C@@H](CCC(=O)OC)C(=O)OC)cc1.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1 | COC(=O)CC[C@H](NC(=O)c1ccc(C#Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)cc1)C(=O)OC | null | [Cu]I | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 2f759f114767b91e2231d010a7bf2c8670481fd3eb71a70def1ce9d9314ff239 | 0ff14f8ed0439469fe0912bb971ad27399d5e9d291750b4a0bb5781f426b3afa | C(#Cn1cnc2nccc-2c1)c1ccccc1 | I-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[#7;a:5])-[c:6]:[c:7]:1-[O;D1;H1:8].[CH;D1;+0:9]#[C:10]-[c:11]>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2]:[n;H0;D3;+0:1](-[C;H0;D2;+0:9]#[C:10]-[c:11]):[c:7](-[O;D1;H1:8]):[c:6]-1 | 65.4 | [{"value": 65.4, "product": "OC1=C2C(N=CN1C#CC1=CC=C(C(=O)N[C@@H](CCC(=O)OC)C(=O)OC)C=C1)=NC(=C2)NC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of 3.6 g (10 mmol) of well-dried 3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine in 40 mL of dimethylformamide are added 4.0 g (13.19 mmol) of dimethyl N-(4-ethynylbenzoyl)-L-glutamate, 0.38 g of copper (I) iodide, 3 mL of triethylamine, and 1.0 g of tetrakis-(triphenylphosphine)palladium. This mi... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | c1cc2cncnc2[nH]1 | c1cc2cncnc2[nH]1 | c1ccccc1.c1cc2cncnc2[nH]1 | HI | [Cu]I.CN(C=O)C | null | 2 | C#Cc1ccc(C(=O)N[C@@H](CCC(=O)OC)C(=O)OC)cc1.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1>[Cu]I.CN(C=O)C>COC(=O)CC[C@H](NC(=O)c1ccc(C#Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)cc1)C(=O)OC |
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