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-c34472859da14a81bfe0f74e60f15c43 | ord-3ba57ccfe5a34447a527ebdf41b92a16 | CCC(CCCl)O[Si](C)(C)C(C)(C)C.ClC1C=CCC1>>CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C | ClCCC(O[Si](C)(C)C(C)(C)C)CC.ClCCC(CC)O[Si](C)(C)CC(C)C.[Mg].ClC1C=CCC1>>CC(C)(C)[Si](OC(CCC1C=CCC1)CC)(C)C | Cl[CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18].Cl[CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1)[O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18] | CCC(CCCl)O[Si](C)(C)C(C)(C)C.ClC1C=CCC1 | CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C | null | null | O1CCCC1 | C-C Coupling | Negishi | 9a6bf7e2b45e73e51c658250a4e70cb08f6a32ab7a16b4f9f48c368b31fb4ddc | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | C1=CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].Cl-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1 | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 8 substituting (5-chloro-3-pentyloxy)(2,2-dimethylethyl)dimethylsilane {3-chloro-1-ethylpropoxy)(1,1-dimethylethyl)dimethylsilane} (78 g, 0.33 moles) diluted in tetrahydrofuran (100 ml), granular magnesium (24 g, 1.00 moles), tetrahydrofuran (100 ml), 0.1M... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Other | O1CCCC1 | null | null | CCC(CCCl)O[Si](C)(C)C(C)(C)C.ClC1C=CCC1>O1CCCC1>CCC(CCC1C=CCC1)O[Si](C)(C)C(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-543ea79e85d34e10aec88caf76c63806 | CCC(CCC1CCC2C1C(=O)C2(Cl)Cl)O[Si](C)(C)C(C)(C)C>>CCC(O)CCC1CCC2CC(=O)CC12 | ClC1(C2CCC(C2C1=O)CCC(CC)O[Si](C)(C)C(C)(C)C)Cl.C(C)(=O)O>>OC(CCC1C2CC(CC2CC1)=O)CC | CC(C)(C)[Si](C)(C)[O:4][CH:3]([CH2:2][CH3:1])[CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]2[C:11](Cl)(Cl)[C:14](=[O:13])[CH:15]12>>[CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]2[CH2:11][C:12](=[O:13])[CH2:14][CH:15]12 | CCC(CCC1CCC2C1C(=O)C2(Cl)Cl)O[Si](C)(C)C(C)(C)C | CCC(O)CCC1CCC2CC(=O)CC12 | null | [Zn] | null | Miscellaneous | OtherReaction | 9effe9ff7c6443669142a1c7a078b54734f4d2831d56d45f96978b7def37a05d | 560a6c3db720aae4822f753684f064d3c8e0f78a775f2c005666bddb9f2d9f3f | O=C1CC2CCCC2C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4].Cl-[C;H0;D4;+0:5]1(-Cl)-[C:6](-[C:7])-[C:8](-[C:9])-[C;H0;D3;+0:10]-1=[O;H0;D1;+0:11]>>[C:3]-[C:2](-[C:4])-[OH;D1;+0:1].[C:9]-[C:8]1-[CH2;D2;+0:10]-[C:12](=[O;H0;D1;+0:11])-[CH2;D2;+0:5]-[C:6]-1-[C:7] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 11 substituting the starting material prepared in Example 28, 6,6-dichloro-2-(3-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)bicyclo[3.2.0]heptan-7-one {7,7-dichloro-4-[3,[[(1,1-dimethylethyl)dimethylsilyl]oxy]pentyl]bicyclo[3.2.0]heptan-6-one} and isomers... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ketone.TMS ether protective group | Ketone.Secondary alcohol | C1CC2CCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | HCl | [Zn] | null | null | CCC(CCC1CCC2C1C(=O)C2(Cl)Cl)O[Si](C)(C)C(C)(C)C>[Zn]>CCC(O)CCC1CCC2CC(=O)CC12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-63b7993915c24de48ec7a1100da8140b | CCCCCCCBr.ClC1C=CCC1>>CCCCCCCC1C=CCC1 | [Mg].ClC1C=CCC1.BrCCCCCCC>>C(CCCCCC)C1C=CCC1 | Br[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].Cl[CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH:9]=[CH:10][CH2:11][CH2:12]1 | CCCCCCCBr.ClC1C=CCC1 | CCCCCCCC1C=CCC1 | null | null | O1CCCC1 | C-C Coupling | Negishi | 9a6bf7e2b45e73e51c658250a4e70cb08f6a32ab7a16b4f9f48c368b31fb4ddc | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | C1=CCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].Cl-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[C:5]-[C:6]-[C:7]=[C:8]-1 | 51.8 | [{"value": 51.8, "product": "C(CCCCCC)C1C=CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure followed is the same as that described in Example 8 substituting the starting material, 1-bromoheptane (100 g, 0.56 moles) dissolved in tetrahydrofuran (100 ml), granular magnesium (25 g) in tetrahydrofuran (100 ml), 0.1M solution of Li2CuCl4 (1.7 mmoles), and 3-chlorocyclopentene (57 g, 0.56 moles) disso... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Br- | O1CCCC1 | null | null | CCCCCCCBr.ClC1C=CCC1>O1CCCC1>CCCCCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c403607f8ccd43679d3b8e809a75d37e | CCCCCCCC1CCC2C1C(=O)C2(Cl)Cl>>CCCCCCCC1CCC2CC(=O)CC12 | [N+](=[N-])=C.CO.CCOCC.ClC1(C2CCC(C2C1=O)CCCCCCC)Cl>>C(CCCCCC)C1C2CC(CC2CC1)=O | Cl[C:12]1(Cl)[CH:11]2[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH:16]2[C:13]1=[O:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:14])[CH2:15][CH:16]12 | CCCCCCCC1CCC2C1C(=O)C2(Cl)Cl | CCCCCCCC1CCC2CC(=O)CC12 | null | [Zn] | C(C)(=O)O | Miscellaneous | OtherReaction | 6050860f35ae5af9e58730800299ac063699469fe49874c3285b01ddb51fa9b3 | 510f73c0542a4709f5dbd47f0097dd621dcba00c89e507092b234119b8c2f41f | O=C1CC2CCCC2C1 | Cl-[C;H0;D4;+0:1]1(-Cl)-[C:2]2-[C:3]-[C:4]-[C:5](-[C:6])-[CH;D3;+0:7]-2-[C;H0;D3;+0:8]-1=[O;D1;H0:9]>>[C:6]-[C:5]1-[C:4]-[C:3]-[C:2]2-[CH2;D2;+0:1]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[C:10]-[CH;D3;+0:7]-2-1 | null | [] | 70 | CELSIUS | null | null | The procedure followed is the same as that described in Example 29 substituting the starting material from Example 34, 6,6-dichloro-2-(hept-1-yl)bicyclo[3.2.0]heptan-7-one {7,7-dichloro-4-heptylbicyclo[3.2.0]heptan-6-one} and isomers (14.2 g, 0.051 moles), an etheral diazomethane solution (175 ml), methanol (5 ml), and... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ketone | Ketone | C1CC2CCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | [Zn].C(C)(=O)O | 70 | null | CCCCCCCC1CCC2C1C(=O)C2(Cl)Cl>[Zn].C(C)(=O)O>CCCCCCCC1CCC2CC(=O)CC12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9304ce1b45c546198b92a8d99296d05b | CCOC(=O)CCCC(CC)OCC>>CCOC(CC)CCCCO | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)OC(CCCC(=O)OCC)CC.C(C)OC(CCCC(=O)OCC)CC>>C(C)OC(CCCCO)CC | CCO[C:10]([CH2:9][CH2:8][CH2:7][CH:4]([O:3][CH2:2][CH3:1])[CH2:5][CH3:6])=[O:11]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11] | CCOC(=O)CCCC(CC)OCC | CCOC(CC)CCCCO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | null | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | A solution of tetrahydrofuran (2000 ml) and lithium aluminum hydride (46 g, 1.21 moles) is cooled in a -60° C. dry ice/ethanol bath. The starting material prepared in Example 36, ethyl 5-ethoxyheptanoate (302 g ,1.49 moles) is diluted in tetrahydrofuran (300 ml) and added dropwise to the stirring reaction. After the ad... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | null | HO- | O1CCCC1 | null | null | CCOC(=O)CCCC(CC)OCC>O1CCCC1>CCOC(CC)CCCCO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ef755968333d418193b548fbcc4d892b | CCOC(CC)CCCCO.O=S(Cl)Cl>>CCOC(CC)CCCCCl | S(=O)(Cl)Cl.C(C)OC(CCCCO)CC.C(C)OC(CCCCO)CC.N1=CC=CC=C1>>ClCCCCC(CC)OCC | O[CH2:10][CH2:9][CH2:8][CH2:7][CH:4]([O:3][CH2:2][CH3:1])[CH2:5][CH3:6].O=S(Cl)[Cl:11]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][Cl:11] | CCOC(CC)CCCCO.O=S(Cl)Cl | CCOC(CC)CCCCCl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | null | [] | null | null | null | null | The starting material prepared in Example 37, 5-ethoxyheptanol (238 g, 1.49 moles) is diluted in pyridine (128 g, 1.62 moles). The solution is stirred at room temperature and thionyl chloride (388 g, 3.22 moles) is added dropwise over 2 hours, after which time the reaction is heated in a 70° C. water bath for 2 additio... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | null | HCl | O | null | null | CCOC(CC)CCCCO.O=S(Cl)Cl>O>CCOC(CC)CCCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a625257d3ef147089e923ee98322cb61 | CCOC(CC)CCCCCl.ClC1C=CCC1>>CCOC(CC)CCCCC1C=CCC1 | ClCCCCC(CC)OCC.ClCCCCC(CC)OCC.[Mg].ClC1C=CCC1>>C(C)OC(CCCCC1C=CCC1)CC | Cl[CH2:10][CH2:9][CH2:8][CH2:7][CH:4]([O:3][CH2:2][CH3:1])[CH2:5][CH3:6].Cl[CH:11]1[CH:12]=[CH:13][CH2:14][CH2:15]1>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH3:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH:12]=[CH:13][CH2:14][CH2:15]1 | CCOC(CC)CCCCCl.ClC1C=CCC1 | CCOC(CC)CCCCC1C=CCC1 | null | null | O1CCCC1 | C-C Coupling | Negishi | 9a6bf7e2b45e73e51c658250a4e70cb08f6a32ab7a16b4f9f48c368b31fb4ddc | d4cf29bb0f2586f258c9eb5d3edb710b86094a4be60be4638a5468606055dcb5 | C1=CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].Cl-[CH;D3;+0:4]1-[C:5]=[C:6]-[C:7]-[C:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[C:5]=[C:6]-[C:7]-[C:8]-1 | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 8 with the following substitutions made: the starting material prepared in Example 38, 1-chloro-5-ethoxyheptane (162 g, 1.13 moles) dissolved in tetrahydrofuran (162 ml), granular magnesium (50 g, 2.1 moles) in tetrahydrofuran (500 ml), Li2CuCl4 (29.1 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary halide | null | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | Other | O1CCCC1 | null | null | CCOC(CC)CCCCCl.ClC1C=CCC1>O1CCCC1>CCOC(CC)CCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-bd94112c7a234fb8bd6af3e52a8d474a | CCC(O)CCC1CCC2CC(=O)CC12>>CCC(=O)CCC1CCC2CC(=O)CC12 | [Cr](=O)(=O)([O-])O[Cr](=O)(=O)[O-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.OC(CCC1C2CC(CC2CC1)=O)CC.OC(CCC1C2CCCC2CC1=O)CC.OC(CCC1C2CC(CC2CC1)=O)CC>>O=C(CCC1C2CC(CC2CC1)=O)CC | [CH3:1][CH2:2][CH:3]([OH:4])[CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]2[CH2:11][C:12](=[O:13])[CH2:14][CH:15]12>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]2[CH2:11][C:12](=[O:13])[CH2:14][CH:15]12 | CCC(O)CCC1CCC2CC(=O)CC12 | CCC(=O)CCC1CCC2CC(=O)CC12 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CC2CCCC2C1 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C;D1;H3:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C;D1;H3:6] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 13, making the following substitutions made: the starting material prepared in Example 31, 2-(3-hydroxypent-1-yl)bicyclo[3.3.0]octan-3-one {hexahydro-4-(3-hydroxypentyl)-2(1H)-pentalenone} (0.8 g, 3.8 mmoles), and pyridinium dichromate (0.82 g, 2.1 mmoles)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | C1CC2CCCC2C1 | null | C(Cl)Cl | null | null | CCC(O)CCC1CCC2CC(=O)CC12>C(Cl)Cl>CCC(=O)CCC1CCC2CC(=O)CC12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4bfd13e2c66f4c80905465f8201f5229 | O=C1CC2CCC(CCCCCO)C2C1>>O=CCCCCC1CCC2CC(=O)CC12 | [Cr](=O)(=O)([O-])O[Cr](=O)(=O)[O-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.OCCCCCC1C2CC(CC2CC1)=O.OCCCCCC1C2CC(CC2CC1)=O.OCCCCCC1C2CC(CC2CC1)=O>>C(=O)CCCCC1C2CC(CC2CC1)=O | [OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]2[CH2:11][C:12](=[O:13])[CH2:14][CH:15]12>>[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]2[CH2:11][C:12](=[O:13])[CH2:14][CH:15]12 | O=C1CC2CCC(CCCCCO)C2C1 | O=CCCCCC1CCC2CC(=O)CC12 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C1CC2CCCC2C1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 13 substituting the starting material prepared in Example 11, 2-(5-hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxypentyl)-2(1H)-pentalenone} (0.3 g, 1.4 mmoles), and pyridinium dichromate (0.80 g, 2.1 mmoles) dissolved in methylene chlor... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CC2CCCC2C1 | null | C(Cl)Cl | null | null | O=C1CC2CCC(CCCCCO)C2C1>C(Cl)Cl>O=CCCCCC1CCC2CC(=O)CC12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8925cec102084632920e4fddf72535c1 | CC(=O)O.CCC(CCCCC1CCC2CC(O)CC12)OC>>CCC(CCCCC1CCC2CC(OC(C)=O)CC12)OC | COC(CCCCC1C2CC(CC2CC1)O)CC.C(C)(=O)O>>C(C)(=O)OC1CC2CCC(C2C1)CCCCC(CC)OC | O[C:15]([CH3:16])=[O:17].[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][CH:13]([OH:14])[CH2:18][CH:19]12)[O:20][CH3:21]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][CH:13]([O:14][C:15]([CH3:16])=[O:17])[CH2:18][CH:19]12)[O:20][CH3:21] | CC(=O)O.CCC(CCCCC1CCC2CC(O)CC12)OC | CCC(CCCCC1CCC2CC(OC(C)=O)CC12)OC | null | null | null | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | C1CC2CCCC2C1 | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 24 substituting 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]-7octanol {octahydro-4-(5-methoxyheptyl)-2-pentalenol} (1.0 g, 4.0 mmoles), and glacial acetic acid (7 ml). The product is kugelrohred under reduced pressure leaving a clear, colorless oil (0.7 g, 2.5 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | C1CC2CCCC2C1 | HO- | null | null | null | CC(=O)O.CCC(CCCCC1CCC2CC(O)CC12)OC>>CCC(CCCCC1CCC2CC(OC(C)=O)CC12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-84333a5b19d34faba23cff08212dd607 | CCC(CCCCC1CCC2CC(O)CC12)OC.CI>>CCC(CCCCC1CCC2CC(OC)CC12)OC | CI.[I-].[Na+].COC(CCCCC1C2CC(CC2CC1)O)CC>>COC1CC2CCC(C2C1)CCCCC(CC)OC | [CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][CH:13]([OH:14])[CH2:16][CH:17]12)[O:18][CH3:19].I[CH3:15]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][CH:13]([O:14][CH3:15])[CH2:16][CH:17]12)[O:18][CH3:19] | CCC(CCCCC1CCC2CC(O)CC12)OC.CI | CCC(CCCCC1CCC2CC(OC)CC12)OC | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | C1CC2CCCC2C1 | I-[CH3;D1;+0:1].[C:2]-[C:3](-[OH;D1;+0:4])-[C:5]>>[C:2]-[C:3](-[O;H0;D2;+0:4]-[CH3;D1;+0:1])-[C:5] | null | [] | 50 | CELSIUS | null | null | The starting material, 2-(5-methoxyhept-1-yl)bicyclo[3.3.0]7 octanol {octahydro-4-(5-methoxyheptyl)-2-pentalenol} (1.0 g, 3.9 mmoles) is added to a reaction vessel containing sodium iodide (0.12 g, 4.9 mmoles) and tetrahydrofuran (12 ml). The solution is stirred while methyl iodide (0.84 g, 5.9 mmoles) is rapidly added... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | C1CC2CCCC2C1 | HI | O1CCCC1 | 50 | null | CCC(CCCCC1CCC2CC(O)CC12)OC.CI>O1CCCC1>CCC(CCCCC1CCC2CC(OC)CC12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-aaa9d570889e44ab9e15ae39b0318a51 | O=C1CC2CCC(CCCCCO)C2C1>>O=C(O)CCCC=C1CCC2CC(=O)CC12 | [Mn](=O)(=O)(=O)[O-].[K+].OCCCCCC1C2CC(CC2CC1)=O.C([O-])([O-])=O.[Na+].[Na+]>>C(=O)(O)CCCC=C1C2CC(CC2CC1)=O | [CH2:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:14])[CH2:15][CH:16]12>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][C:13](=[O:14])[CH2:15][CH:16]12 | O=C1CC2CCC(CCCCCO)C2C1 | O=C(O)CCCC=C1CCC2CC(=O)CC12 | null | null | null | Oxidation | OtherReaction | 0a1f1fd3a0ed8fad42c785435557b7f0d81f3db664befdeda6bc9aab3f28f157 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | [CH]=C1CCC2CC(=O)CC12 | [O;D1;H0:1]=[C:2]-[C:3]-[C:4]1-[C:5]-[C:6]-[C:7]-[CH;D3;+0:8]-1-[CH2;D2;+0:9]-[C:10]-[C:11]-[C:12]-[CH2;D2;+0:13]-[O;D1;H1:14]>>[O;D1;H0:1]=[C:2]-[C:3]-[C:4]1-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:8]-1=[CH;D2;+0:9]-[C:10]-[C:11]-[C:12]-[C;H0;D3;+0:13](=[O;D1;H0:15])-[O;D1;H1:14] | null | [] | null | null | 12 | HOUR | 2-(5-Hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone} (0.5 g, 2.4 mmoles) is mixed with a 10% solution of sodium carbonate (0.51 ml). The reaction is cooled in an ice bath and solution of potassium permanganate (0.48 g dissolved in 12 ml water) is slowly added over 10 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | C1CC2CCCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | null | null | 12 | O=C1CC2CCC(CCCCCO)C2C1>>O=C(O)CCCC=C1CCC2CC(=O)CC12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d95ff23f497e4e0b8acb3c3cb9cb64fc | CCC(CCCCC1CCC2CC(=O)CC12)OC>>CCC(CCCCC1CCC2CCCC12)OC | Cl.COC(CCCCC1C2CC(CC2CC1)=O)CC.[OH-].[K+].O.NN>>COC(CCCCC1C2CCCC2CC1)CC | O=[C:13]1[CH2:12][CH:11]2[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:2][CH3:1])[O:16][CH3:17])[CH:15]2[CH2:14]1>>[CH3:1][CH2:2][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH:15]12)[O:16][CH3:17] | CCC(CCCCC1CCC2CC(=O)CC12)OC | CCC(CCCCC1CCC2CCCC12)OC | null | null | C(COCCO)O | Reduction | OtherReaction | 3540313b77edc713ba6ab7d3be08a141d46ad0c8919a2a40493918efc5f6633d | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | C1CC2CCCC2C1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1>>[C:3]1-[C:2]-[CH2;D2;+0:1]-[C:5]-[C:4]-1 | null | [] | 95 | CELSIUS | null | null | 2-(5-Methoxyhept-1-y)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} (5 g, 19.8 mmoles) is mixed with diethylene glycol (27 ml) and potassium hydroxide (3.8 g, 6.7 mmoles). The reaction is stirred and mixed with 80% hydrazine hydrate (2.8 ml, 7.0 mmoles). The reaction is heated to 95° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CC2CCCC2C1 | C1CC2CCCC2C1 | C1CC2CCCC2C1 | Other | C(COCCO)O | 95 | null | CCC(CCCCC1CCC2CC(=O)CC12)OC>C(COCCO)O>CCC(CCCCC1CCC2CCCC12)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5212f1ae92a448f185b8372f231a0c2d | CC(C)(C)[Si](C)(C)Cl.OCCCCCl>>CC(C)C[Si](C)(C)OCCCCCl | CN(C=O)C.ClCCCCO.[Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1>>ClCCCCO[Si](C)(C)CC(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13]>>[CH3:1][CH:2]([CH3:3])[CH2:4][Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13] | CC(C)(C)[Si](C)(C)Cl.OCCCCCl | CC(C)C[Si](C)(C)OCCCCCl | null | null | null | Protection | OtherReaction | 16b089e75ae0faeb6299d6901714a961ddf80ba40eb5191df04d4efe8b4a1af5 | a12fb6ee4294c877f426f603ce64d893e39b302f1553f4ca246c599e7a8e7068 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[CH3;D1;+0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[CH2;D2;+0:7]-[CH;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 7 substituting 4-chlorobutanol (326 g, 3.00 moles), tert-butyldimethylsilyl chloride (500 g, 3.31 moles), imidazole (225 g, 3.30 moles), and dimethylformamide (1600 ml). The crude product is fractionally distilled under reduced vacuum leaving a clear, colo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | Silyl protective group | null | null | null | HCl | null | null | null | CC(C)(C)[Si](C)(C)Cl.OCCCCCl>>CC(C)C[Si](C)(C)OCCCCCl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d698bcc6c8a84c5db225fe974c31b177 | CC(C)(C)[Si](C)(C)OCCCCC1C=CCC1>>OCCCCC1C=CCC1 | C1(C=CCC1)CCCCO[Si](C)(C)C(C)(C)C.F>>OCCCCC1C=CCC1 | CC(C)(C)[Si](C)(C)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1 | CC(C)(C)[Si](C)(C)OCCCCC1C=CCC1 | OCCCCC1C=CCC1 | null | null | C(C)#N | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | C1=CCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | The procedure followed is the same as that described in Example 12 substituting 3-(5-[(1,1-dimethylethyl)dimethylsiloxy]but-1-yl)cyclopentene {[4-(2-cyclopenten-1-yl)butoxy](1,1dimethylethyl)dimethylsilane} (100 g, 0.407 moles), 5% hydrofluoric acid (78 ml), acetonitrile (1500 ml). The crude product is kugelrohred unde... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | C1=CCCC1 | Other | C(C)#N | null | null | CC(C)(C)[Si](C)(C)OCCCCC1C=CCC1>C(C)#N>OCCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0471832c8b414493b0ecb67e377b1ac4 | CS(=O)(=O)Cl.OCCCCC1C=CCC1>>ClCCCCC1C=CCC1 | O.N1=CC=CC=C1.OCCCCC1C=CCC1.CS(=O)(=O)Cl>>ClCCCCC1C=CCC1 | CS(=O)(=O)[Cl:1].O[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1>>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH:7]=[CH:8][CH2:9][CH2:10]1 | CS(=O)(=O)Cl.OCCCCC1C=CCC1 | ClCCCCC1C=CCC1 | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | 58d25ddf86b8daa38762ecb08ed922faa2d01716f69924f9b8413703fe1b3fc7 | d5d71bad4297b1f4f93dd1d1d9cddf0bb6fadb3f4dca1f84369c4074a39097d6 | C1=CCCC1 | C-S(=O)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | null | [] | 70 | CELSIUS | null | null | 3-(4-Hydroxybut-1-yl)cyclopentene {2-cyclopentene-1-butanol}(51 g, 0.37 moles) is diluted in dimethylformamide (100 ml) and added to pyridine (38 g, 0.40 moles). The solution is stirred and methane sulfonyl chloride (46 g, 0.40 moles) is added dropwise in the course of 10 minutes. The reaction is then heated in a 70° C... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Primary halide | null | null | C1=CCCC1 | HO- | CN(C=O)C | 70 | null | CS(=O)(=O)Cl.OCCCCC1C=CCC1>CN(C=O)C>ClCCCCC1C=CCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f299fc50d6c74d1d92fec367d9ed7c37 | Cc1ccccc1.c1ccc(OCC2CO2)cc1>>Oc1ccccc1Cc1ccccc1O | C(C1CO1)OC1=CC=CC=C1.C1(=CC=CC=C1)C.CCN(CC)CCCN.CC(C)O>>C1=CC=C(C(=C1)CC2=CC=CC=C2O)O | [CH3:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.C(C1C[O:15]1)[O:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15] | Cc1ccccc1.c1ccc(OCC2CO2)cc1 | Oc1ccccc1Cc1ccccc1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bb6c1871491a83bd83810eb7781ecfb2a06e2253712c12c98bd77417b9f2ec80 | dba1d8ee27fd5f8263a0d509262d6485399952dd96c7ed49cbf1cbbdd570ee62 | c1ccc(Cc2ccccc2)cc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].[c:7]:[c:8](-[O;H0;D2;+0:9]-C-C1-C-[O;H0;D2;+0:10]-1):[cH;D2;+0:11]:[c:12]:[c:13]>>[OH;D1;+0:10]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:2](-[CH2;D2;+0:1]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:8](-[OH;D1;+0:9]):[c:7]):[c:3] | null | [] | null | null | 4 | HOUR | 252 g of Adeka Resin EP-4100, 16 g of PGE (phenyl glycidyl ether), 70 g of toluene and 70 g of IPA were added to 132 g of DEAPA and the addition reaction was carried out at 80° to 90° C. for 4 h while the solvent was refluxed. Then, toluene and IPA were distilled out. After thorough distillation of the solvent, a react... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | c1ccccc1.C1CO1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | 4 | Cc1ccccc1.c1ccc(OCC2CO2)cc1>>Oc1ccccc1Cc1ccccc1O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-92170fa1fd29492488edc107994fd7e3 | C1=CCC=C1.C=CC(=O)OC>>COC(=O)C1CC2C=CC1C2 | C1=CC=CC1.C(C=C)(=O)OC.CCOCC>>C12C(CC(C=C1)C2)C(=O)OC | [CH:7]1=[CH:8][CH:9]=[CH:10][CH2:11]1.[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]2[CH:8]=[CH:9][CH:10]1[CH2:11]2 | C1=CCC=C1.C=CC(=O)OC | COC(=O)C1CC2C=CC1C2 | null | null | null | C-C Coupling | Diels-Alder | e8180ec57d3d3ece629b666ef11ae88fefddc90074994afd75932f54941fac1c | 27001f1ecd9f36db81c888e1f64ec4ae5c90a52e134591258b49e526ba92011c | C1=CC2CCC1C2 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[C:7]1-[CH;D2;+0:8]=[CH;D2;+0:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-1>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[CH;D3;+0:11]2-[C:7]-[CH;D3;+0:8]-1-[CH;D2;+0:9]=[CH;D2;+0:10]-2 | null | [] | null | null | 8 | HOUR | In 100 ml of anhydrous ether at 0° C. is mixed 30 ml of cyclopentadiene and 32 ml of methyl acrylate. The ice bath is removed and the mixture allowed to stir overnight. The solvent, unreacted methyl acrylate, and cyclopentadiene are removed at ambient temperature at reduced pressure; as less material distilled out of t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl.Conjugated diene | Ester | C1=CCC=C1 | C1=CC2CCC1C2 | C1=CC2CCC1C2 | null | null | null | 8 | C1=CCC=C1.C=CC(=O)OC>>COC(=O)C1CC2C=CC1C2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1b99a694266642dc96a7c7a18f34cd87 | Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O.NC(CO)(CO)CO>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.NC(CO)(CO)CO | [Na+].[Cl-].[Na+].[Cl-].C(C(CO)(CO)N)O.Cl.SC[C@@H](O)[C@H](O)CS.C(C(CO)(CO)N)O.Cl.OP(OP(O)(OP(O)(O)=O)=O)(OC[C@@H]1[C@@H](O)C[C@H](N2C(NC(C(C)=C2)=O)=O)O1)=O.[Mg+2].[Cl-].[Cl-].[Mg+2].[Cl-].[Cl-].[As]([O-])(=O)(C)C.[Na+].C(C(CO)(CO)N)O.Cl>>C(C(CO)(CO)N)O.Cl.CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=O)(O)O)O | O=P(O)(O)OP(=O)(O)[O:15][P:12]([O:11][CH2:10][C@@H:9]1[C@@H:7]([OH:8])[CH2:6][C@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:20](=[O:21])[nH:19][c:17]2=[O:18])[O:16]1)(=[O:13])[OH:14].[NH2:23][C:24]([CH2:25][OH:26])([CH2:27][OH:28])[CH2:29][OH:30]>>[CH3:1][c:2]1[cH:3][n:4]([C@H:5]2[CH2:6][C@H:7]([OH:8])[C@@H:9]([CH2:10][O:11][P:1... | Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O.NC(CO)(CO)CO | Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.NC(CO)(CO)CO | null | null | null | Miscellaneous | OtherReaction | 6f4f8b0b326673b26c45b4eeed943ea8b2ea17f2ada5014b8af7ee19f1be2e27 | 9ee257419a2fba07634ccfcd6de7423150d51d4df7dcb11ed7a3a3e91405197a | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | O-P(-O)(=O)-O-P(-O)(=O)-[O;H0;D2;+0:1]-[#15:2](-[#8:3])(=[O;D1;H0:4])-[O;D1;H1:5]>>[#8:3]-[#15:2](=[O;D1;H0:4])(-[O;D1;H1:5])-[OH;D1;+0:1] | null | [] | null | null | null | null | First, a vector primer is synthesized. A vector, e.g. pCDVl, is treated with KpnI in an adequate solution such as a solution consisting of Tris-HCl buffer (e.g. pH 7.5, 10 mM), MgCl2 (e.g. 6 mM) and NaCl (e.g. 10 mM) to cut pCDVl at KpnI site. The DNA is incubated with terminal deoxynucleotidyltransferase at an appropr... | 10.6084/m9.figshare.5104873.v1 | null | Phosphate ester | Phosphate ester | null | null | c1cncnc1.C1CCOC1 | HO- | null | null | null | Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O2)c(=O)[nH]c1=O.NC(CO)(CO)CO>>Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)[nH]c1=O.NC(CO)(CO)CO |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-008175b035a744b9b2cb027beecf641d | CCCCCCCCC(O)CC>>CCCCCCCCC(=O)CC | CCCCCCCCC(CC)O.C([O-])(O)=O.[Na+].Cl[O-].[Ca+2].Cl[O-]>>CCCCCCCCC(CC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([OH:10])[CH2:11][CH3:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[CH2:11][CH3:12] | CCCCCCCCC(O)CC | CCCCCCCCC(=O)CC | null | null | C(C)#N | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | null | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C;D1;H3:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C;D1;H3:6] | null | [] | 28.5 | CELSIUS | 60 | HOUR | Forty grams (0.2 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol were dissolved in 400 ml of acetonitrile, and 23.5 g of sodium bicarbonate was added thereto with stirring. Next, 40.0 g of silica gel (MCB Grade 62 60-200 mesh) was added to the mixture, which was followed by the addition of 40.0 g (0.28 mol) of cal... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | null | null | C(C)#N | 28.5 | 60 | CCCCCCCCC(O)CC>C(C)#N>CCCCCCCCC(=O)CC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8693a1c2b895400fbdf2e6cab0d8b68e | CCCCCCCCC(O)CC>>CCCCCCCCC(=O)CC | C([O-])(O)=O.[Na+].CCCCCCCCC(CC)O.Cl[O-].[Ca+2].Cl[O-]>>CCCCCCCCC(CC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([OH:10])[CH2:11][CH3:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[CH2:11][CH3:12] | CCCCCCCCC(O)CC | CCCCCCCCC(=O)CC | null | null | C(C)#N | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | null | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C;D1;H3:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C;D1;H3:6] | null | [] | null | null | 18 | HOUR | Sodium bicarbonate (8.81 g, 0.105 mol) was added to a solution of 15.0 g (0.075 mol) of 3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol in 150 ml of acetonitrile. The reaction mixture was charged with 15.0 g of silica gel (MCB 60-200 mesh) and 15.0 g of calcium hypochlorite in sequence. The reaction mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | null | null | C(C)#N | null | 18 | CCCCCCCCC(O)CC>C(C)#N>CCCCCCCCC(=O)CC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4430b500143d425d90267f2830922157 | CC1(C)COC2(CCC(=O)CC2)OC1.CCCN.Cc1ccc(S(=O)(=O)O)cc1>>CCCN1CCC[C@@H]2CC(=O)CC[C@H]21 | CC1(COC2(OC1)CCC(CC2)=O)C.C(CC)N.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.O>>C(CC)N1CCC[C@@H]2CC(CC[C@@H]12)=O | CC1(C)[CH2:5]O[C:8]2(O[CH2:9]1)[CH2:7][CH2:6][C:10](=[O:11])[CH2:12][CH2:13]2.[CH3:1][CH2:2][CH2:3][NH2:4].O=S(=O)(O)c1ccc([CH3:14])cc1>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]2[CH2:9][C:10](=[O:11])[CH2:12][CH2:13][C@@H:14]12 | CC1(C)COC2(CCC(=O)CC2)OC1.CCCN.Cc1ccc(S(=O)(=O)O)cc1 | CCCN1CCC[C@@H]2CC(=O)CC[C@H]21 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | ba8b13bed13b494249e3480b40199b8313e5972d2da46d87ada1612e6394fa39 | dff5fd47dcf518bd115baae6b061bcffdb563e625502753211ff9446522da19b | O=C1CC[C@H]2NCCC[C@@H]2C1 | C-C1(-C)-[CH2;D2;+0:1]-O-[C;H0;D4;+0:2]2(-O-[CH2;D2;+0:3]-1)-[C:4]-[CH2;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8]-[CH2;D2;+0:9]-2.O-S(=O)(=O)-c1:c:c:c(-[CH3;D1;+0:10]):c:c:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[N;H0;D3;+0:13]1-[CH2;D2;+0:1]-[CH2;D2;+0:5]-[C:4]-[C@@H;D3;+0:2]2-[CH2;D2;+0:3]-[C;H0;D3;+0:6](=[O;... | null | [] | null | null | null | null | A 250 ml single neck round bottom flask fitted with a water separator containing 20 g of 3A sieves (Linde) was charged with 100 ml of toluene, 10.25 g (0.052 mol) of 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-one (Aldrich Chemical Company), 17.97 g (3.04 mmol) of n-propylamine (Baker) and 18 mg (0.09 mmol) of p-toluenes... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Ether.Ether.Primary amine | Ketone.Tertiary amine | C1CCC2(CC1)OCCCO2.c1ccccc1 | C1CC[C@H]2[NH]CCC[C@@H]2C1 | C1CC[C@H]2[NH]CCC[C@@H]2C1 | TsOH.HO- | C1(=CC=CC=C1)C | null | null | CC1(C)COC2(CCC(=O)CC2)OC1.CCCN.Cc1ccc(S(=O)(=O)O)cc1>C1(=CC=CC=C1)C>CCCN1CCC[C@@H]2CC(=O)CC[C@H]21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e765de5f47654addb30791e3c03fffd2 | CCOC(=O)c1cn(C)nc1Cl.O=S=O>>CCOC(=O)c1c(Cl)nn(C)c1S(=O)[O-] | ClC1=NN(C=C1C(=O)OCC)C.C(C)(C)[N-]C(C)C.[Li+].S(=O)=O>>ClC1=NN(C(=C1C(=O)OCC)S(=O)[O-])C.[Li+] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([Cl:8])[n:9][n:10]([CH3:11])[cH:12]1.[S:13](=[O:14])=[O:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([Cl:8])[n:9][n:10]([CH3:11])[c:12]1[S:13](=[O:14])[O-:15] | CCOC(=O)c1cn(C)nc1Cl.O=S=O | CCOC(=O)c1c(Cl)nn(C)c1S(=O)[O-] | null | null | C(C)OCC | Functional Group Addition | OtherReaction | b8e4f9f06d415b710b70b7cbcbda78aa093bb2aaa4894895da4fdf767c585916 | 69ece274e0104838fc859dee2bcf07ab566679ccfd515c3388e20b73f1d85347 | c1cn[nH]c1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[cH;D2;+0:6]:[#7;a:7](-[C;D1;H3:8]):[#7;a:9]:[c:10]:1-[Cl;D1;H0:11].[O;D1;H0:12]=[S;H0;D2;+0:13]=[O;H0;D1;+0:14]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:10](-[Cl;D1;H0:11]):[#7;a:9]:[#7;a:7](-[C;D1;H3:8]):[c;H0;D3;+0:6]:1-[S;H0;D3;+0:13](-[O-;H0;D1:14])=[O;D1;H0:12] | null | [] | -60 | CELSIUS | 30 | MINUTE | 5.0 g of ethyl 3-chloro-1-methylpyrazole-4-carboxylate was dispersed in dry diethyl ether under cooling at -60° C. or lower. Into this solution there was added lithium diisopropylamide (1.2 molar equivalent) and after stirring for an hour sulfur dioxide gas was passed into this solution for 30 minutes. After stirring a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1c[nH]nc1 | c1cn[nH]c1 | c1cn[nH]c1 | null | C(C)OCC | -60 | 0.5 | CCOC(=O)c1cn(C)nc1Cl.O=S=O>C(C)OCC>CCOC(=O)c1c(Cl)nn(C)c1S(=O)[O-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4bea319f54e043c18ca1eacb7f516b8c | CCOC(=O)Cl.CCOC(=O)c1c(Cl)nn(C)c1S(N)(=O)=O>>CCOC(=O)NS(=O)(=O)c1c(C(=O)OCC)c(Cl)nn1C | ClC1=NN(C(=C1C(=O)OCC)S(=O)(=O)N)C.ClC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(=O)NS(=O)(=O)C1=C(C(=NN1C)Cl)C(=O)OCC | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][S:7](=[O:8])(=[O:9])[c:10]1[c:11]([C:12](=[O:13])[O:14][CH2:15][CH3:16])[c:17]([Cl:18])[n:19][n:20]1[CH3:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][S:7](=[O:8])(=[O:9])[c:10]1[c:11]([C:12](=[O:13])[O:14][CH2:15][CH3:16])[c:17]([Cl:18])[n:19][n:20]1[CH3:21] | CCOC(=O)Cl.CCOC(=O)c1c(Cl)nn(C)c1S(N)(=O)=O | CCOC(=O)NS(=O)(=O)c1c(C(=O)OCC)c(Cl)nn1C | null | null | CC(=O)C | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 2f2696288009d2012d9ec2995f8be43c58fdee99389b7d218ed77c4bafda7b17 | 60493cac785f670383c62b059214a5eb4def232e11814f271849329f2f6b7966 | c1cn[nH]c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#7;a:5]:[#7;a:6]:[c:7]-[#16:8](-[NH2;D1;+0:9])(=[O;D1;H0:10])=[O;D1;H0:11]>>[#7;a:5]:[#7;a:6]:[c:7]-[#16:8](=[O;D1;H0:10])(=[O;D1;H0:11])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 88.4 | [{"value": 88.4, "product": "C(C)OC(=O)NS(=O)(=O)C1=C(C(=NN1C)Cl)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into 30 ml of dry acetone, there were added 5.35 g of 3-chloro-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide, 2.5 g of ethyl chloroformate and 4.14 g of anhydrous potassium carbonate and the mixture was refluxed for three hours. After cooling, acetone was evaporated and the residue was added into ice-water. After sep... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide | Sulfonamide.Carbamic ester | null | null | c1cn[nH]c1 | HCl | CC(=O)C | null | null | CCOC(=O)Cl.CCOC(=O)c1c(Cl)nn(C)c1S(N)(=O)=O>CC(=O)C>CCOC(=O)NS(=O)(=O)c1c(C(=O)OCC)c(Cl)nn1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-77f9d01c15454a0998d8a1279a36088d | CCOC(=O)Cl.COC(=O)C1=C(C)NC(=NC#N)NC1c1cccc(Cl)c1Cl>>CCOC(=O)N1C(=NC#N)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl | ClC(=O)OCC.C(#N)N=C1NC(C(=C(N1)C)C(=O)OC)C1=C(C(=CC=C1)Cl)Cl.C(C)N(CC)CC.ClC(=O)OCC>>C(#N)N=C1N(C(C(=C(N1)C)C(=O)OC)C1=C(C(=CC=C1)Cl)Cl)C(=O)OCC | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:6]1[C:7](=[N:8][C:9]#[N:10])[NH:11][C:12]([CH3:13])=[C:14]([C:15](=[O:16])[O:17][CH3:18])[CH:19]1[c:20]1[cH:21][cH:22][cH:23][c:24]([Cl:25])[c:26]1[Cl:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[C:7](=[N:8][C:9]#[N:10])[NH:11][C:12]([CH3:13])=[C:14]([C:15](=[O:16])[O:17][CH3:18])[... | CCOC(=O)Cl.COC(=O)C1=C(C)NC(=NC#N)NC1c1cccc(Cl)c1Cl | CCOC(=O)N1C(=NC#N)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl | null | null | O1CCCC1.CN(C=O)C | Protection | N-alkylation of secondary amines with alkyl halides | dc1019f9265d58175a7c68cb940ffcfeed4b405383f12dfe6c28bb9fad9427b6 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | N=C1NC=CC(c2ccccc2)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[#7:11]-[C:12](=[#7:13]-[C:14]#[N;D1;H0:15])-[NH;D2;+0:16]-[C:17]-1-[c:18]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[#7:11]-[C:12](=[#7:13]-[C:14]#[N;D1;H0:15])-[N;H0;D3;+0:16](-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 58.8 | [{"value": 58.8, "product": "C(#N)N=C1N(C(C(=C(N1)C)C(=O)OC)C1=C(C(=CC=C1)Cl)Cl)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | A suspension of 2-(cyanoimino)-6-(2,3-dichlorophenyl)-3,6-dihydro-4-methyl-5-pyrimidinecarboxylic acid, methyl ester (444 mg, 1.31 mmoles) in dry dimethylformamide (2 ml) and tetrahydrofuran (2 ml) was cooled to 0° C. and was treated with triethylamine (0.5 ml) followed by ethyl chloroformate (284 mg, 2.62 mmoles). Aft... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1=CNCNC1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1 | HCl | O1CCCC1.CN(C=O)C | 0 | 3 | CCOC(=O)Cl.COC(=O)C1=C(C)NC(=NC#N)NC1c1cccc(Cl)c1Cl>O1CCCC1.CN(C=O)C>CCOC(=O)N1C(=NC#N)NC(C)=C(C(=O)OC)C1c1cccc(Cl)c1Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0a3b14c7b922485e955378c7884aefb2 | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.COC(=N)N>>CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC1)C=C(C(=O)OCC)C(C)=O.S(=O)(=O)(O)O.COC(N)=N.C([O-])(O)=O.[Na+]>>COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C | O=[C:7]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:14][c:15]1[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23]1)[CH3:8].[NH2:9][C:10]([O:11][CH3:12])=[NH:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([O:11][CH3:12])=[N:13][CH:14]1[c:15]1[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-... | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.COC(=N)N | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1 | null | null | CN(C=O)C.C(C)(=O)OCC | Functional Group Addition | OtherReaction | 9f1202e283c567a005eda2f78f5cf6b8d5499a0601d061bbaa323632a00c4e55 | 236d42d1ec02a2fdb840ece71bec33a67ca67694e779d168e2cc0b28eec2fb71 | C1=CC(c2ccccc2)N=CN1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[#8:12]-[C:13](-[NH2;D1;+0:14])=[NH;D1;+0:15]>>[#8:12]-[C:13]1=[N;H0;D2;+0:15]-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[C;H0;D3;+0:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0... | 75.5 | [{"value": 75.5, "product": "COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A reaction mixture containing 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, ethyl ester (2.62 g, 10.0 mmole), 2-methylpseudourea sulfate (1.72 g, 10.0 mmole), and sodium bicarbonate (2.52 g, 30.0 mmole) in dimethylformamide (10 ml) was heated at 65°-70° C. for 16 hours. The reaction mixture was allowed to cool to ro... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Enamine.Ester | null | C1=CNC=NC1 | C1=CNC=NC1.c1ccccc1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | null | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.COC(=N)N>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-13857672a37f4505a6ebafc5780a12ef | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl>>CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C.ClC(=O)OCC>>COC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([O:11][CH3:12])=[N:13][CH:19]1[c:20]1[cH:21][cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28]1.Cl[C:14](=[O:15])[O:16][CH2:17][CH3:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[N:9]=[C:10]([O:11][CH3:12])[N:13]([C:14](=[O:15])[O:16][CH2:1... | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl | CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl.N1=CC=CC=C1 | Protection | OtherReaction | eca316a70362fa7398b5afea09b6374bfc5070d35ce91114a4cf2b60376bdbe3 | 87478e8ab5dbe98bc06cb0eaa27512eb3bf2920842993998b097867aeccd5207 | C1=CC(c2ccccc2)NC=N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](-[#8:13]-[C;D1;H3:14])=[N;H0;D2;+0:15]-[C:16]-1-[c:17]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D3;+0:12](-[#8:13]-[C;D1;H3:14])-[N;H0;D3;+0:15](-[C;H0;D... | null | [] | null | null | 1 | HOUR | A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (3.19 g, 10.0 mmoles) in dry dichloromethane (15 ml) and pyridine (4 ml) was cooled to 0° C. and treated dropwise with ethyl chloroformate (1.2 ml, 12.0 mmoles) under argon. After the addition was completed, the cool... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide.Ether.Ether | Carbamic ester.Ether.Ether | C1=CNC=NC1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1 | HCl | ClCCl.N1=CC=CC=C1 | null | 1 | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl>ClCCl.N1=CC=CC=C1>CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-438383d6124c46cb8272961628ebcff2 | CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.[NH4+]>>CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | COC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC.C(C)(=O)[O-].[NH4+]>>NC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC | CO[C:10]1=[N:9][C:7]([CH3:8])=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:18]([c:19]2[cH:20][cH:21][cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27]2)[N:12]1[C:13](=[O:14])[O:15][CH2:16][CH3:17].[NH4+:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[N:9]=[C:10]([NH2:11])[N:12]([C:13](=[O:14])[O:15][CH2:16][CH3:17]... | CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.[NH4+] | CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | O1CCCC1 | Functional Group Addition | OtherReaction | b1c2ed50ebe57a56905e819ac12c3597db2a91a9db9dc0798c49f64a98c4f816 | 3bcf8db5195703f7c25974e70dbd7a2dabdb5ba6f5d5ea664dce3ef0fbff8562 | C1=CC(c2ccccc2)NC=N1 | C-O-[C;H0;D3;+0:1]1=[#7:2]-[C:3](-[C;D1;H3:4])=[C:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9]-[#7:10]-1-[C:11](-[#8:12])=[O;D1;H0:13].[NH4+;D0:14]>>[#8:12]-[C:11](=[O;D1;H0:13])-[#7:10]1-[C:9]-[C:5](-[C:6](-[#8:7])=[O;D1;H0:8])=[C:3](-[C;D1;H3:4])-[#7:2]=[C;H0;D3;+0:1]-1-[NH2;D1;+0:14] | 107.9 | [{"value": 107.9, "product": "NC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | A solution of 2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (3.78 g, 9.66 mmoles of crude from previous reaction) in anhydrous tetrahydrofuran (20 ml) was cooled to 0° C. (ice bath) and a slow stream of ammonia gas was bubbled through it for approximately 5 minutes. Solid ammon... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary amine | C1=CN=C[NH]C1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1 | HO- | O1CCCC1 | null | 72 | CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.[NH4+]>O1CCCC1>CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-99317e12e9e34e248ca2fd650b9d5d3c | CC(=O)OC(C)=O.CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>>CCOC(=O)C1=C(C)NC(NC(C)=O)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | NC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC.C(C)(=O)OC(C)=O>>C(C)(=O)NC1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC | CC(=O)O[C:12]([CH3:13])=[O:14].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[N:9]=[C:10]([NH2:11])[N:15]([C:16](=[O:17])[O:18][CH2:19][CH3:20])[CH:21]1[c:22]1[cH:23][cH:24][cH:25][c:26]([N+:27](=[O:28])[O-:29])[cH:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][CH:10]([NH:11][C:12]([CH3:13])=[... | CC(=O)OC(C)=O.CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | CCOC(=O)C1=C(C)NC(NC(C)=O)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl.N1=CC=CC=C1.C(C)(=O)OCC | Acylation | OtherReaction | 5ec87a3b1bf24791a4c8488ee8bef0535555a9b55b669672dfa6916fc1582fb8 | 6fe27bbbed85c76011b0ecf3b870a2f04f68a63927d3ca59ff5dee3074c97427 | C1=CC(c2ccccc2)NCN1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[C:5](=[O;D1;H0:6])-[#7:7]1-[C:8]-[C:9](-[C:10](-[#8:11])=[O;D1;H0:12])=[C:13](-[C;D1;H3:14])-[N;H0;D2;+0:15]=[C;H0;D3;+0:16]-1-[NH2;D1;+0:17]>>[#8:4]-[C:5](=[O;D1;H0:6])-[#7:7]1-[C:8]-[C:9](-[C:10](-[#8:11])=[O;D1;H0:12])=[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[CH... | null | [] | null | null | 1 | HOUR | A suspension of 2-amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (550 mg, 1.46 mmoles, see Example 2) in dichloromethane (5.0 ml) and pyridine (0.5 ml) was treated with acetic anhydride (0.3 ml) and the reaction was allowed to stir at room temperature for 1 hour. The colorless react... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Enamine.Secondary amide | C1=CN=C[NH]C1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1 | HO- | ClCCl.N1=CC=CC=C1.C(C)(=O)OCC | null | 1 | CC(=O)OC(C)=O.CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1>ClCCl.N1=CC=CC=C1.C(C)(=O)OCC>CCOC(=O)C1=C(C)NC(NC(C)=O)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4d6ffa2e165a44e7922bf837ea8c5c06 | CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl>>CCOC(=O)C1=C(C)NC(=NS(C)(=O)=O)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | NC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC.CS(=O)(=O)Cl>>CC=1NC(N(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)=NS(=O)(=O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[N:9]=[C:10]([NH2:11])[N:16]([C:17](=[O:18])[O:19][CH2:20][CH3:21])[CH:22]1[c:23]1[cH:24][cH:25][cH:26][c:27]([N+:28](=[O:29])[O-:30])[cH:31]1.Cl[S:12]([CH3:13])(=[O:14])=[O:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10](=[N:11][S:12]([CH3:13]... | CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl | CCOC(=O)C1=C(C)NC(=NS(C)(=O)=O)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl.N1=CC=CC=C1.C(C)(=O)OCC | Acylation | OtherReaction | c2a1ef5705883bd6e87d317f790eb22f65135092696fa208be48c6a7b1a6eb13 | 78ebda42e45f87bf935b1a596d7daab94f4b43a8ff96463718a5a26dbb6697b9 | N=C1NC=CC(c2ccccc2)N1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10](-[C:11](-[#8:12])=[O;D1;H0:13])=[C:14](-[C;D1;H3:15])-[N;H0;D2;+0:16]=[C;H0;D3;+0:17]-1-[NH2;D1;+0:18]>>[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]1-[C:9]-[C:10](-[C:11](-[#8:12])=[O;D1;H0:13])=[C:14](-[C;D1;H3:15])-[NH;D2;+... | null | [] | 0 | CELSIUS | 8 | HOUR | A suspension of 2-amino-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (600 mg, 1.59 mmoles, see Example 2) in dichloromethane (5 ml) and pyridine (1.0 ml) was cooled to 0° C. under argon and was treated dropwise with methanesulfonyl chloride (0.42 ml, 5.26 mmoles). A catalytic amount of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Enamine | C1=CN=C[NH]C1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1 | HCl | ClCCl.N1=CC=CC=C1.C(C)(=O)OCC | 0 | 8 | CCOC(=O)C1=C(C)N=C(N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl>ClCCl.N1=CC=CC=C1.C(C)(=O)OCC>CCOC(=O)C1=C(C)NC(=NS(C)(=O)=O)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8e9a015962e348fea4c386a2ccfd19ac | CCOC(=O)C1=C(C)NC(=NC#N)NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl>>CCOC(=O)C1=C(C)NC(=NC#N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | C(#N)N=C1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C.ClC(=O)OCC>>C(#N)N=C1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10](=[N:11][C:12]#[N:13])[NH:14][CH:20]1[c:21]1[cH:22][cH:23][cH:24][c:25]([N+:26](=[O:27])[O-:28])[cH:29]1.Cl[C:15](=[O:16])[O:17][CH2:18][CH3:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10](=[N:11][C:12]#[N:13])[N:14]([C:15](=[O:16])... | CCOC(=O)C1=C(C)NC(=NC#N)NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl | CCOC(=O)C1=C(C)NC(=NC#N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | O1CCCC1.N1=CC=CC=C1 | Protection | N-alkylation of secondary amines with alkyl halides | dc1019f9265d58175a7c68cb940ffcfeed4b405383f12dfe6c28bb9fad9427b6 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | N=C1NC=CC(c2ccccc2)N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[#7:11]-[C:12](=[#7:13]-[C:14]#[N;D1;H0:15])-[NH;D2;+0:16]-[C:17]-1-[c:18]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[#7:11]-[C:12](=[#7:13]-[C:14]#[N;D1;H0:15])-[N;H0;D3;+0:16](-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 84.7 | [{"value": 84.7, "product": "C(#N)N=C1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 13 | HOUR | A suspension of 1,2,3,4-tetrahydro-2-cyanoimino-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (565 mg, 1.72 mmoles) in dry tetrahydrofuran (70 ml) and pyridine (2.0 ml) was cooled to 0° C. and treated with ethyl chloroformate (0.17 ml, 2.24 mmoles) dropwise under argon. After the addition was comp... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1=CNCNC1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1 | HCl | O1CCCC1.N1=CC=CC=C1 | 0 | 13 | CCOC(=O)C1=C(C)NC(=NC#N)NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl>O1CCCC1.N1=CC=CC=C1>CCOC(=O)C1=C(C)NC(=NC#N)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3b192540cb8b46fb9f0d012c1cb0ad9c | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl>>CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C.ClC(=O)OCC>>COC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([O:11][CH3:12])=[N:13][CH:19]1[c:20]1[cH:21][cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28]1.Cl[C:14](=[O:15])[O:16][CH2:17][CH3:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[N:9]=[C:10]([O:11][CH3:12])[N:13]([C:14](=[O:15])[O:16][CH2:1... | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl | CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl.N1=CC=CC=C1.C(C)(=O)OCC | Protection | OtherReaction | eca316a70362fa7398b5afea09b6374bfc5070d35ce91114a4cf2b60376bdbe3 | 87478e8ab5dbe98bc06cb0eaa27512eb3bf2920842993998b097867aeccd5207 | C1=CC(c2ccccc2)NC=N1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](-[#8:13]-[C;D1;H3:14])=[N;H0;D2;+0:15]-[C:16]-1-[c:17]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D3;+0:12](-[#8:13]-[C;D1;H3:14])-[N;H0;D3;+0:15](-[C;H0;D... | 94.8 | [{"value": 94.8, "product": "COC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (3.19 g, 10.0 mmoles) in dichloromethane (25 ml) and pyridine (5.0 ml) under argon was cooled to 0° C. and was treated dropwise with ethyl chloroformate (1.2 ml of 0.7%, 12.0 mmoles). After the addition was completed... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Acyl halide.Ether.Ether | Carbamic ester.Ether.Ether | C1=CNC=NC1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1 | HCl | ClCCl.N1=CC=CC=C1.C(C)(=O)OCC | null | 1 | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.CCOC(=O)Cl>ClCCl.N1=CC=CC=C1.C(C)(=O)OCC>CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-16733fb8f88e40cebbb31f02556d9601 | CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CN>>CCOC(=O)C1=C(C)N=C(NC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | COC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC.Cl.CN.C(C)(=O)[O-].[Na+]>>CC=1N=C(N(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)NC | CO[C:10]1=[N:9][C:7]([CH3:8])=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:19]([c:20]2[cH:21][cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28]2)[N:13]1[C:14](=[O:15])[O:16][CH2:17][CH3:18].[NH2:11][CH3:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[N:9]=[C:10]([NH:11][CH3:12])[N:13]([C:14](=[O:15])[O:16][C... | CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CN | CCOC(=O)C1=C(C)N=C(NC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | CN(C=O)C.C(C)(=O)OCC | Functional Group Addition | Displacement of ethoxy group by primary amine | 131eb1902bac976e49c8600384cf0ae2a963a7a5111a9f4c24f46aced88df93e | 0c0f392163842ed15dcbc1e41d4bd6239c42af0df98101681b3613b490f6c196 | C1=CC(c2ccccc2)NC=N1 | C-O-[C;H0;D3;+0:1]1=[#7:2]-[C:3](-[C;D1;H3:4])=[C:5](-[C:6](-[#8:7])=[O;D1;H0:8])-[C:9]-[#7:10]-1-[C:11](-[#8:12])=[O;D1;H0:13].[C;D1;H3:14]-[NH2;D1;+0:15]>>[#8:12]-[C:11](=[O;D1;H0:13])-[#7:10]1-[C:9]-[C:5](-[C:6](-[#8:7])=[O;D1;H0:8])=[C:3](-[C;D1;H3:4])-[#7:2]=[C;H0;D3;+0:1]-1-[NH;D2;+0:15]-[C;D1;H3:14] | 51.6 | [{"value": 51.6, "product": "CC=1N=C(N(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | A solution of 2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (3.71 g crude) in dimethylformamide (15 ml) was treated with methylamine hydrochloride (1.01 g, 15.0 mmoles) and sodium acetate (1.49 g, 17.0 mmoles). The reaction was allowed to stir at room temperature for 48 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary amine | C1=CN=C[NH]C1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 48 | CCOC(=O)C1=C(C)N=C(OC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CN>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)C1=C(C)N=C(NC)N(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-636e1c91627a464b867b72a4ae3c9a2a | CC(C)(C(=O)[O-])C(=O)[O-].C[O-].O=C(Cl)c1cc(F)c(F)c(F)c1F>>COC(=O)CC(=O)c1cc(F)c(F)c(F)c1F | FC1=C(C(=O)Cl)C=C(C(=C1F)F)F.C1(=CC=CC=C1)C.C[O-].[Na+].CC(C(=O)[O-])(C(=O)[O-])C>>FC1=C(C(=O)CC(=O)OC)C=C(C(=C1F)F)F | C[C:5](C)(C(=O)[O-])[C:3]([O-])=[O:4].[CH3:1][O-:2].Cl[C:6](=[O:7])[c:8]1[cH:9][c:10]([F:11])[c:12]([F:13])[c:14]([F:15])[c:16]1[F:17]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[c:8]1[cH:9][c:10]([F:11])[c:12]([F:13])[c:14]([F:15])[c:16]1[F:17] | CC(C)(C(=O)[O-])C(=O)[O-].C[O-].O=C(Cl)c1cc(F)c(F)c(F)c1F | COC(=O)CC(=O)c1cc(F)c(F)c(F)c1F | null | null | O.CN(C=O)C | C-C Coupling | OtherReaction | 9c255438d8e6adeba9ee52582b8e97af5f85bef382cd416953270ac55bd10486 | 4c7bc8856483317e0c04a17d8cd6aba13cdf5ed9f64b61fe01f230a819039f82 | c1ccccc1 | C-[C;H0;D4;+0:1](-C)(-C(=O)-[O-])-[C;H0;D3;+0:2](-[O-])=[O;D1;H0:3].Cl-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[O-;H0;D1:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8] | 45 | [{"value": 45.0, "product": "FC1=C(C(=O)CC(=O)OC)C=C(C(=C1F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 5 | MINUTE | A 500 ml, three-necked flask was set up in a heating mantle and equipped with a mechanical stirrer, an equilibrating type addition funnel, a thermometer, an inert gas (argon or nitrogen) inlet, and a distillation head set for downward distillation. The flask was charged with 100 ml of toluene, 2 ml of dimethylformamide... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone.Ester | null | null | c1ccccc1 | HCl | O.CN(C=O)C | 110 | 0.083333 | CC(C)(C(=O)[O-])C(=O)[O-].C[O-].O=C(Cl)c1cc(F)c(F)c(F)c1F>O.CN(C=O)C>COC(=O)CC(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2131771375784b5dbff2e1c2b9f89ab5 | CC(=O)OC[C@H]1O[C@@H](n2ccc(NC(=O)c3ccccc3)nc2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O>>Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1 | [NH4+].[OH-].C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1C(=O)N=C(NC(C2=CC=CC=C2)=O)C=C1.C(C)O>>[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)N=C(N)C=C1 | CC(=O)[O:10][CH2:9][C@H:8]1[O:7][C@@H:6]([n:5]2[cH:4][cH:3][c:2]([NH:1]C(=O)c3ccccc3)[n:17][c:15]2=[O:16])[C@H:13]([O:14]C(C)=O)[C@@H:11]1[O:12]C(C)=O>>[NH2:1][c:2]1[cH:3][cH:4][n:5]([C@@H:6]2[O:7][C@H:8]([CH2:9][OH:10])[C@@H:11]([OH:12])[C@H:13]2[OH:14])[c:15](=[O:16])[n:17]1 | CC(=O)OC[C@H]1O[C@@H](n2ccc(NC(=O)c3ccccc3)nc2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O | Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1 | null | null | CO | Reduction | OtherReaction | 54425038016c3633d27ea1b0eb33ebef03941a12d909f4146f948a8363c11160 | 4edb6540559eaf58184071417c79ce5154d44a88dbcb41dbd59a97d91c3666c8 | O=c1ncccn1[C@H]1CCCO1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5](-[#7;a:6]2:[c:7]:[#7;a:8]:[c:9](-[NH;D2;+0:10]-C(=O)-c3:c:c:c:c:c:3):[c:11]:[c:12]:2)-[C:13](-[O;H0;D2;+0:14]-C(-C)=O)-[C:15]-1-[O;H0;D2;+0:16]-C(-C)=O>>[NH2;D1;+0:10]-[c:9]1:[#7;a:8]:[c:7]:[#7;a:6](-[C:5]2-[#8:4]-[C:3](-[C:2]-[OH;D1;+0:1])-[C:15](-[OH;D1;+0:16])-[C:13]-... | null | [] | 70 | CELSIUS | 8 | HOUR | In methanol (50 ml) is dissolved 2',3',5'-tri-O-acetyl-N4 -benzoylcytidine (0.53 g) followed by addition of concentrated NH4OH (5 ml) with stirring at 70° C. The mixture is stirred at 70° C. for 2.5 hours, at the end of which time ethanol is added. The mixture is allowed to stand at room temperature overnight to give c... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Secondary amide | Primary alcohol.Secondary alcohol.Secondary alcohol.Primary amine | c1ccccc1 | null | c1cncnc1.C1CCOC1 | HO- | CO | 70 | 8 | CC(=O)OC[C@H]1O[C@@H](n2ccc(NC(=O)c3ccccc3)nc2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O>CO>Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4a7555b3ee7d41e19e75897c9406272c | CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=S | ClC=1C=CC2=C(C(=NC(C(N2)=O)C)C2=CC=CC=C2)C1.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>ClC=1C=CC2=C(C(=NC(C(N2)=S)C)C2=CC=CC=C2)C1 | O=[C:19]1[CH:2]([CH3:1])[N:3]=[C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH:18]1.S=P12SP3(=S)SP(=S)(S1)SP(=[S:20])(S2)S3>>[CH3:1][CH:2]1[N:3]=[C:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][c:17]2[NH:18][C:19]1=[S:20] | CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=S | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 06c6558ddc5f930e7336709ccbb961421cbf550e7ce970cceb112d907e5ce2fc | d2920cd05bf4135748938e381b9b1f7839b4c239209f6e5ccf529257462c8544 | S=C1CN=C(c2ccccc2)c2ccccc2N1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4](-[C;D1;H3:5])-[#7:6]=[C:7].S=P12-S-P3(=S)-S-P(=S)(-S-1)-S-P(=[S;H0;D1;+0:8])(-S-2)-S-3>>[C:7]=[#7:6]-[C:4](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[S;H0;D1;+0:8])-[#7:2]-[c:3] | 28.5 | [{"value": 28.5, "product": "ClC=1C=CC2=C(C(=NC(C(N2)=S)C)C2=CC=CC=C2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 7-chloro-1,3-dihydro-3-methyl-5-phenyl-2H-1,4 -benzodiazepin-2-one (10 g, 0.035 mol) in pyridine (300 ml), treated with P2S5 (8.0 g, 0.036 mol) was refluxed, under N2, for 2 hours then concentrated in vacuo. To remove the remaining pyridine the residue was combined with toluene twice with concentra... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | Thioamide | C1=NCCNc2ccccc21.S1P2SP3SP1SP(S2)S3 | C1=NCCNc2ccccc21 | c1ccccc1.C1=NCCNc2ccccc21 | Other | N1=CC=CC=C1 | null | null | CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=O.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>N1=CC=CC=C1>CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=S |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b4428ac60e6c496ca0f1e60747a77b73 | CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=S.NNC(=O)Cc1ccccc1>>CC1N=Cc2cc(Cl)ccc2-n2c(Cc3ccccc3)nnc21 | ClC=1C=CC2=C(C(=NC(C(N2)=S)C)C2=CC=CC=C2)C1.C1(=CC=CC=C1)CC(=O)NN.N#N>>ClC=1C=CC2=C(C=NC(C=3N2C(=NN3)CC3=CC=CC=C3)C)C1 | S=[C:23]1[CH:2]([CH3:1])[N:3]=[C:4](c2ccccc2)[c:5]2[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]2[NH:12]1.O=[C:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[NH:21][NH2:22]>>[CH3:1][CH:2]1[N:3]=[CH:4][c:5]2[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]2-[n:12]2[c:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21... | CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=S.NNC(=O)Cc1ccccc1 | CC1N=Cc2cc(Cl)ccc2-n2c(Cc3ccccc3)nnc21 | null | null | C(CCC)O | Miscellaneous | OtherReaction | 07a88595f792bc6322af4519f75698e485c7f9f24dbf3eb200352505e57aa5a2 | 3b2d4c81718445f7dd56a0e1b4f702aed2f01eaed1ebfa8f51314f13099ab430 | C1=NCc2nnc(Cc3ccccc3)n2-c2ccccc21 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[NH;D2;+0:4]-[NH2;D1;+0:5].S=[C;H0;D3;+0:6]1-[NH;D2;+0:7]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](:[c:12])-[C;H0;D3;+0:13](-c2:c:c:c:c:c:2)=[#7:14]-[C:15]-1-[C;D1;H3:16]>>[C;D1;H3:16]-[C:15]1-[#7:14]=[CH;D2;+0:13]-[c:11](:[c:12]):[c;H0;D3;+0:8](:[c:9]:[c:10])-[n;H0;D3;+0:7]2:[c;H0;D3;+0:1](-... | 48 | [{"value": 48.0, "product": "ClC=1C=CC2=C(C=NC(C=3N2C(=NN3)CC3=CC=CC=C3)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 7-chloro-1,3-dihydro-3-methyl-5-phenyl-2H-1,4 -benzodiazepine-2-thione (3.0 g, 0.01 mol), phenyl acetic acid hydrazide (4.95 g, 0.033 mol) and butanol (150 ml) was refluxed for 16 hours while N2 was being bubbled through the mixture. The reaction mixture was concentrated under high vacuum, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Thioamide.Substituted imine | Substituted imine | c1ccccc1.C1=NCCNc2ccccc21 | C1=NCc2nncn2c2ccccc21 | c1ccccc1.C1=NCc2nncn2c2ccccc21 | Other | C(CCC)O | null | null | CC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=S.NNC(=O)Cc1ccccc1>C(CCC)O>CC1N=Cc2cc(Cl)ccc2-n2c(Cc3ccccc3)nnc21 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-86a8574d1bbd4dc79c000e9ef7eb8599 | NNC(=O)Cc1ccccc1.S=C1CN=C(c2ccccc2)c2cc(I)ccc2N1>>Ic1ccc2c(c1)C(c1ccccc1)=NCc1nnc(Cc3ccccc3)n1-2 | IC=1C=CC2=C(C(=NCC(N2)=S)C2=CC=CC=C2)C1.C1(=CC=CC=C1)CC(=O)NN.N#N>>IC=1C=CC2=C(C(=NCC=3N2C(=NN3)CC3=CC=CC=C3)C3=CC=CC=C3)C1 | O=[C:20]([NH:19][NH2:18])[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.S=[C:17]1[CH2:16][N:15]=[C:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:6]2[c:5]([cH:4][cH:3][c:2]([I:1])[cH:7]2)[NH:28]1>>[I:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)=[N:15][CH2:16][c:17]1[n... | NNC(=O)Cc1ccccc1.S=C1CN=C(c2ccccc2)c2cc(I)ccc2N1 | Ic1ccc2c(c1)C(c1ccccc1)=NCc1nnc(Cc3ccccc3)n1-2 | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | 206cb76d75c0643ef89b881ae4cd8de0184640a06855af0c388333ee36485055 | 1e7b5d45c28f5d1767d2abb0c78792aee2714d99002ea329b67f9a89a7e53301 | c1ccc(Cc2nnc3n2-c2ccccc2C(c2ccccc2)=NC3)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[NH;D2;+0:4]-[NH2;D1;+0:5].S=[C;H0;D3;+0:6]1-[C:7]-[#7:8]=[C:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](:[c:13]:[c:14])-[NH;D2;+0:15]-1>>[c:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6]2:[n;H0;D3;+0:15]:1-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](:[c:11])-[C:9]=[#7:8]-[C:7]-2 | null | [] | null | null | null | null | A stirred mixture of 7-iodo-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione (3.78 g, 0.01 mol), phenylacetic acid hydrazide (4.5 g, 0.03 mol) and butanol (150 ml) was heated to reflux while N2 was bubbled through the mixture. After refluxing 17 hours the reaction mixture was concentrated under vacuum. The residue w... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Thioamide | null | C1=NCCNc2ccccc21 | C1=NCc2nncn2c2ccccc21 | c1ccccc1.C1=NCc2nncn2c2ccccc21.c1ccccc1 | Other | C(CCC)O | null | null | NNC(=O)Cc1ccccc1.S=C1CN=C(c2ccccc2)c2cc(I)ccc2N1>C(CCC)O>Ic1ccc2c(c1)C(c1ccccc1)=NCc1nnc(Cc3ccccc3)n1-2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e995768ce4124d389fe6c566008ff0b3 | CC(C)(C)OO>>CC(C)(C)OOC(C)(C)C | C(C)(C)(C)OO>>C(C)(C)(C)OOC(C)(C)C | [CH3:1][C:2]([O:5][OH:6])([CH3:7])[CH3:10]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][O:6][C:7]([CH3:8])([CH3:9])[CH3:10] | CC(C)(C)OO | CC(C)(C)OOC(C)(C)C | null | null | C(C)(C)(C)O | Miscellaneous | OtherReaction | 02ccdc1552f0d25981159566e4cf32844c9468fbdec510acb124fde41678a4d5 | 2ec0818fbc96fe73f8dba4ed1355f0cf8afdd08cba2c38ef397720fe84b408bd | null | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[#8:5]-[OH;D1;+0:6]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:5]-[O;H0;D2;+0:6]-[C;H0;D4;+0:4](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH3;D1;+0:3] | null | [] | null | null | null | null | in a dehydration step, dehydrating the mixture of tertiary butanol and tertiary butyl hydroperoxide to produce di-tertiary butyl peroxide,
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Peroxide | null | null | null | Other | C(C)(C)(C)O | null | null | CC(C)(C)OO>C(C)(C)(C)O>CC(C)(C)OOC(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c10dcc8b316f45a3af934c62a87ba264 | CC(C)(C)OO>>CC(C)(C)OOC(C)(C)C | C(C)(C)(C)OO>>C(C)(C)(C)OOC(C)(C)C | [CH3:1][C:2]([O:5][OH:6])([CH3:7])[CH3:10]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][O:6][C:7]([CH3:8])([CH3:9])[CH3:10] | CC(C)(C)OO | CC(C)(C)OOC(C)(C)C | null | null | C(C)(C)(C)O | Miscellaneous | OtherReaction | 02ccdc1552f0d25981159566e4cf32844c9468fbdec510acb124fde41678a4d5 | 2ec0818fbc96fe73f8dba4ed1355f0cf8afdd08cba2c38ef397720fe84b408bd | null | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[#8:5]-[OH;D1;+0:6]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:5]-[O;H0;D2;+0:6]-[C;H0;D4;+0:4](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH3;D1;+0:3] | null | [] | null | null | null | null | in a dehydration step, dehydrating the mixture of tertiary butanol and tertiary butyl hydroperoxide to produce di-tertiary butyl peroxide.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Peroxide | null | null | null | Other | C(C)(C)(C)O | null | null | CC(C)(C)OO>C(C)(C)(C)O>CC(C)(C)OOC(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-20376965539d4e4198a7ac8265bea5a2 | CC(C)(C)OO>>CC(C)(C)OOC(C)(C)C | C(C)(C)(C)OO>>C(C)(C)(C)OOC(C)(C)C | [CH3:1][C:2]([O:5][OH:6])([CH3:7])[CH3:10]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][O:6][C:7]([CH3:8])([CH3:9])[CH3:10] | CC(C)(C)OO | CC(C)(C)OOC(C)(C)C | null | null | C(C)(C)(C)O | Miscellaneous | OtherReaction | 02ccdc1552f0d25981159566e4cf32844c9468fbdec510acb124fde41678a4d5 | 2ec0818fbc96fe73f8dba4ed1355f0cf8afdd08cba2c38ef397720fe84b408bd | null | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[#8:5]-[OH;D1;+0:6]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:5]-[O;H0;D2;+0:6]-[C;H0;D4;+0:4](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH3;D1;+0:3] | null | [] | null | null | null | null | in a dehydration step, dehydrating the mixture of tertiary butanol and tertiary butyl hydroperoxide to produce di-tertiary butyl peroxide,
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Peroxide | null | null | null | Other | C(C)(C)(C)O | null | null | CC(C)(C)OO>C(C)(C)(C)O>CC(C)(C)OOC(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-85b0f79cfcc6468cb16a2ae9eb3cebf4 | CC(=O)CC(C)C.ClCc1ccccc1.O.[OH-].[OH-]>>O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 | O.[OH-].[Ca+2].[OH-].C(C1=CC=CC=C1)Cl.C(C(C)C)C(=O)C>>C1(=CC=CC=C1)CC(C(=O)O)=O.C1(=CC=CC=C1)CC(=O)O | [CH3:2][CH:7]([CH2:6][C:12]([CH3:4])=[O:13])[CH3:14].Cl[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[OH2:15].[OH-:1].[OH-:3]>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[O:13]=[C:14]([OH:15])[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(=O)CC(C)C.ClCc1ccccc1.O.[OH-].[OH-] | O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 | null | [CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2] | null | Aromatic Heterocycle Formation | OtherReaction | 4b643df42ad19cc1b37e527e993e8dcf1fd3b99323657c449455d166f3b36a4b | eeef4573bc5b5be296e3cc6c38276fbee56a0adf2640694babded885d25c242c | c1ccccc1.c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[CH;D3;+0:6](-[CH3;D1;+0:7])-[CH2;D2;+0:8]-[C;H0;D3;+0:9](-[CH3;D1;+0:10])=[O;H0;D1;+0:11].[OH-;D0:12].[OH-;D0:13].[OH2;D0;+0:14]>>[O;D1;H0:15]=[C;H0;D3;+0:10](-[CH2;D2;+0:8]-[c;H0;D3;+0:6]1:[c:16]:[c:17]:[c:18]:[c:19]:[cH;D2;+0:9]:1)-[C;H0;D3;+0:7](=[O;H0;D1;+0:12])-[... | null | [] | null | null | null | null | Into a stainless steel-made autoclave of 135 ml capacity were introduced 25 ml of water, 6.2 g of calcium hydroxide, 5.1 g of benzyl chloride and 25 ml of the organic solution of methyl isobutyl ketone containing the cobalt carbonyl catalyst and recovered in Example 3 to form a reaction mixture. The reaction and subseq... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Carboxylic acid.Carboxylic acid.Ketone | null | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | [CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2] | null | null | CC(=O)CC(C)C.ClCc1ccccc1.O.[OH-].[OH-]>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a8275080990447e0b936e5a0779a1f12 | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-]>>O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 | [OH-].[Ca+2].[OH-].C(C1=CC=CC=C1)Cl.C(C)(=O)C1=CC=CC=C1>>C1(=CC=CC=C1)CC(C(=O)O)=O.C1(=CC=CC=C1)CC(=O)O | [O:1]=[C:2]([CH3:4])[c:17]1[cH:16][cH:14][cH:20][cH:19][cH:18]1.Cl[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[OH-:3].[OH-:15]>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[O:13]=[C:14]([OH:15])[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-] | O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 | null | [CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2] | O | Acylation | OtherReaction | b25df58b87bd4ccffdf753564f1b87928374b13d5245f5195360559dc95cd1ae | 6317597a979cad5aa4420b90631b68f3f78d8239e7c7a313e9c1d9f7cb6f4662 | c1ccccc1.c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1.[OH-;D0:14].[OH-;D0:15]>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[OH;D1;+0:14])-[C;H0;D3;+0:5](=[O;D1;H0:16])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:17]=[C;H0;D3;+0:12](-[OH;D... | null | [] | null | null | null | null | Into a stainless steel-made autoclave of 135 ml capacity were introduced 25 ml of water, 6.2 g of calcium hydroxide, 5.1 g of benzyl chloride and 25 ml of the organic solution of acetophenone containing the cobalt carbonyl catalyst and recovered in Example 2 to form a reaction mixture. The reaction and subsequent proce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Carboxylic acid.Carboxylic acid.Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | [CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2].O | null | null | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-]>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2].O>O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-153ada47a0d1474199f382bca6a97f00 | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-]>>O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 | [OH-].[Ca+2].[OH-].C(C1=CC=CC=C1)Cl.C(C)(=O)C1=CC=CC=C1>>C1(=CC=CC=C1)CC(C(=O)O)=O.C1(=CC=CC=C1)CC(=O)O | [O:1]=[C:2]([CH3:4])[c:17]1[cH:16][cH:14][cH:20][cH:19][cH:18]1.Cl[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[OH-:3].[OH-:15]>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[O:13]=[C:14]([OH:15])[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-] | O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 | null | [CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2] | O | Acylation | OtherReaction | b25df58b87bd4ccffdf753564f1b87928374b13d5245f5195360559dc95cd1ae | 6317597a979cad5aa4420b90631b68f3f78d8239e7c7a313e9c1d9f7cb6f4662 | c1ccccc1.c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1.[OH-;D0:14].[OH-;D0:15]>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[OH;D1;+0:14])-[C;H0;D3;+0:5](=[O;D1;H0:16])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:17]=[C;H0;D3;+0:12](-[OH;D... | null | [] | null | null | null | null | Into a stainless steel-made autoclave of 135 ml capacity were introduced 25 ml of water, 4.7 g of calcium hydroxide, 3.8 g of benzyl chloride and 50 ml of the organic solution of acetophenone containing the cobalt carbonyl catalyst and recovered in Example 6 to form a reaction mixture. The reaction and subsequent proce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Carboxylic acid.Carboxylic acid.Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | [CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2].O | null | null | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-]>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2].O>O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-10e8d4b87b4942fabeaab416fd0cc188 | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-]>>O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 | [OH-].[Ca+2].[OH-].C(C1=CC=CC=C1)Cl.C(C)(=O)C1=CC=CC=C1>>C1(=CC=CC=C1)CC(C(=O)O)=O.C1(=CC=CC=C1)CC(=O)O | [O:1]=[C:2]([CH3:4])[c:17]1[cH:16][cH:14][cH:20][cH:19][cH:18]1.Cl[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[OH-:3].[OH-:15]>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[O:13]=[C:14]([OH:15])[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-] | O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 | null | [CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2] | O | Acylation | OtherReaction | b25df58b87bd4ccffdf753564f1b87928374b13d5245f5195360559dc95cd1ae | 6317597a979cad5aa4420b90631b68f3f78d8239e7c7a313e9c1d9f7cb6f4662 | c1ccccc1.c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1.[OH-;D0:14].[OH-;D0:15]>>[O;D1;H0:7]=[C;H0;D3;+0:6](-[OH;D1;+0:14])-[C;H0;D3;+0:5](=[O;D1;H0:16])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:17]=[C;H0;D3;+0:12](-[OH;D... | null | [] | null | null | null | null | Into a stainless steel-made autoclave of 135 ml capacity were introduced 25 ml of water, 4.7 g of calcium hydroxide, 3.8 g of benzyl chloride and 50 ml of the organic solution of acetophenone containing the cobalt carbonyl catalyst and recovered in Example 7 to form a reaction mixture. The reaction and subsequent proce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Carboxylic acid.Carboxylic acid.Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | [CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2].O | null | null | CC(=O)c1ccccc1.ClCc1ccccc1.[OH-].[OH-]>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2].O>O=C(O)C(=O)Cc1ccccc1.O=C(O)Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ba6a97fb487747b8b1d5268be92029b9 | CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.Oc1ccccc1>>C=C(C)c1ccccc1O | C1(=CC=CC=C1)O.OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)O.[OH-].[Na+].OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)O>>C(=C)(C)C1=C(C=CC=C1)O | Oc1ccc([C:2](c2ccc(O)cc2)([CH3:1])[CH3:3])cc1.[c:4]1([OH:10])[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[OH:10] | CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.Oc1ccccc1 | C=C(C)c1ccccc1O | null | [Hg] | null | Heteroatom Alkylation and Arylation | OtherReaction | d3ed0a44d3de393ca95faa4bf02e316e0098c7a77ee09d116f9f77a337230a70 | 3bb2a0693ea5057cd042cea0aec64aa5c8da8b8c11ea14dad84b40ea5b83337b | c1ccccc1 | O-c1:c:c:c(-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[CH3;D1;+0:3])-c2:c:c:c(-O):c:c:2):c:c:1.[OH;D1;+0:4]-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[CH2;D1;+0:3])-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c;H0;D3;+0:10]:1-[OH;D1;+0:4] | null | [] | null | null | 50 | MINUTE | A distillation flask equipped with a Vigreux column was charged with 70.0 g. (0.31 mole) of bisphenol A [2,2-bis(p-hydroxyphenyl)propane] and 0.2 g. of sodium hydroxide. The bisphenol A was pyrolyzed under reduced pressure at a bath temperature of 200° to 270° C. Over a period of about 50 minutes and under 10 mm. of pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | Aromatic alcohol.Vinyl | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | [Hg] | null | 0.833333 | CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.Oc1ccccc1>[Hg]>C=C(C)c1ccccc1O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-6ee95f6e6ecf4cd4a00b3665941096fd | CC(=CCc1c(C)c(O)c(C)c(C)c1O)CO.COS(=O)(=O)OC>>COc1c(C)c(C)c(OC)c(CC=C(C)CO)c1C | OC1=C(C(=C(C(=C1C)C)O)C)CC=C(CO)C.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+].S(=O)(=O)(OC)OC.[Br-].C(C)(C)(C)[NH3+]>>COC1=C(C(=C(C(=C1C)C)OC)C)CC=C(CO)C | [OH:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([OH:9])[c:11]([CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][OH:17])[c:18]1[CH3:19].O=S(=O)(O[CH3:1])O[CH3:10]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][CH:13]=[C:14]([CH3:15])[CH2:16][OH:17])[c:18]1[CH3:19] | CC(=CCc1c(C)c(O)c(C)c(C)c1O)CO.COS(=O)(=O)OC | COc1c(C)c(C)c(OC)c(CC=C(C)CO)c1C | null | null | O.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | fb1095592b840fd614706aea5353046ecf68855980b5ab9c0a4590b6d3f34f57 | b56a881cca53d645d3ea21c88aa2f444e6fbc0455e71d7569115c4e79d3bc912 | c1ccccc1 | O=S(=O)(-O-[CH3;D1;+0:1])-O-[CH3;D1;+0:2].[OH;D1;+0:3]-[c:4]1:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:8]-[c:7]1:[c:6]:[c:5]:[c:4](-[O;H0;D2;+0:3]-[CH3;D1;+0:2]):[c:10]:[c:9]:1 | 372.9 | [{"value": 372.9, "product": "COC1=C(C(=C(C(=C1C)C)OC)C)CC=C(CO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 3 | HOUR | A mixture of 3.0 g of 4-(2',5'-dihydroxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol, 40 ml of methylene chloride, 6 ml of water, 5.6 g of sodium hydroxide, 0.6 g of potassium carbonate, 1.6 g of dimethyl sulphate and 0.25 g of tert.butylammonium bromide is stirred well at 30° C. under argon for 3 hours and thereafter... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HO- | O.C(Cl)Cl | 30 | 3 | CC(=CCc1c(C)c(O)c(C)c(C)c1O)CO.COS(=O)(=O)OC>O.C(Cl)Cl>COc1c(C)c(C)c(OC)c(CC=C(C)CO)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fd24838512664f5e9442ce1f96d1f3cb | CC(C)(C)OO.COc1c(C)c(C)c(OC)c(CC=C(C)CO)c1C>>COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C | [OH-].[Na+].C(=O)(OCCCC)[C@@H](O)[C@H](O)C(=O)OCCCC.COC1=C(C(=C(C(=C1C)C)OC)C)CC=C(CO)C.C(C)(C)(C)OO>>COC1=C(C(=C(C(=C1C)C)OC)C)C[C@@H]1[C@](CO)(C)O1 | CC(C)(C)O[OH:14].[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][CH:13]=[C:15]([CH3:16])[CH2:17][OH:18])[c:19]1[CH3:20]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][C@H:13]2[O:14][C@:15]2([CH3:16])[CH2:17][OH:18])[c:19]1[CH3:20] | CC(C)(C)OO.COc1c(C)c(C)c(OC)c(CC=C(C)CO)c1C | COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 98841c7908d6944738a6b55a503cceb5c5be782664839c4601a36c4146b0a273 | 42a03c3e3056d859131de561fc8292c06b2910df7e46ddbdd3187d6cec35220b | c1ccc(C[C@@H]2CO2)cc1 | C-C(-C)(-C)-O-[OH;D1;+0:1].[C;D1;H3:2]-[C;H0;D3;+0:3](-[C:4]-[O;D1;H1:5])=[CH;D2;+0:6]-[C:7]-[c:8]>>[C;D1;H3:2]-[C@;H0;D4;+0:3]1(-[C:4]-[O;D1;H1:5])-[O;H0;D2;+0:1]-[C@@H;D3;+0:6]-1-[C:7]-[c:8] | 98 | [{"value": 98.0, "product": "COC1=C(C(=C(C(=C1C)C)OC)C)C[C@@H]1[C@](CO)(C)O1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 0.594 ml of titanium tetraisopropoxide is dissolved in 10 ml of dry methylene chloride. Thereupon, 524 ml of dibutyl D-tartrate are added dropwise at -20° C. and the mixture is left to stand at -20° C. for 10 minutes. 197 mg of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol are then added and subsequen... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Ether | null | C1CO1 | c1ccccc1.C1CO1 | HO- | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].C(Cl)Cl | null | 0.166667 | CC(C)(C)OO.COc1c(C)c(C)c(OC)c(CC=C(C)CO)c1C>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].C(Cl)Cl>COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a0d5e8a417344026b54840fa34c293db | COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C>>COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C | COC1=C(C(=C(C(=C1C)C)OC)C)C[C@@H]1[C@](CO)(C)O1.[H][H]>>COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](CO)(O)C | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][C@@H:13]2[C@@:14]([CH3:15])([CH2:17][OH:18])[O:16]2)[c:19]1[CH3:20]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][CH2:13][C@:14]([CH3:15])([OH:16])[CH2:17][OH:18])[c:19]1[CH3:20] | COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C | null | [Ni] | O.CO | Reduction | OtherReaction | fb68e1f7e7aa0012b71755c2e659c5ca3af240790d29315ee068c102a1263dc2 | ac77f1c31bbb4f9df2f7d9b876f6243f6ca37479f36d1e779ab0e1e90922def4 | c1ccccc1 | [C;D1;H3:1]-[C@;H0;D4;+0:2]1(-[C:3]-[O;D1;H1:4])-[O;H0;D2;+0:5]-[C@@H;D3;+0:6]-1-[C:7]-[c:8]>>[C;D1;H3:1]-[C@@;H0;D4;+0:2](-[OH;D1;+0:5])(-[C:3]-[O;D1;H1:4])-[CH2;D2;+0:6]-[C:7]-[c:8] | 86.4 | [{"value": 55.0, "product": "COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](CO)(O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](CO)(O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 185 mg of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol are dissolved in 5 ml of methanol and the solution is subsequently diluted with 5 ml of water. Thereupon, Raney-nickel is added and the mixture is heated at reflux under hydrogen for 2 hours. After the hydrogen uptake has finished ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary alcohol | C1CO1 | null | c1ccccc1 | null | [Ni].O.CO | null | null | COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C>[Ni].O.CO>COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f8f528d14d0e4430996d206144ceb5bb | COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C>>COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C | COC1=C(C(=C(C(=C1C)C)OC)C)C[C@@H]1[C@](CO)(C)O1.C[Si](Cl)(C)C.C([O-])(O)=O.[Na+]>>COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](CO)(O)C | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][C@@H:13]2[C@@:14]([CH3:15])([CH2:17][OH:18])[O:16]2)[c:19]1[CH3:20]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][CH2:13][C@:14]([CH3:15])([OH:16])[CH2:17][OH:18])[c:19]1[CH3:20] | COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C | null | null | N1=CC=CC=C1 | Reduction | OtherReaction | fb68e1f7e7aa0012b71755c2e659c5ca3af240790d29315ee068c102a1263dc2 | ac77f1c31bbb4f9df2f7d9b876f6243f6ca37479f36d1e779ab0e1e90922def4 | c1ccccc1 | [C;D1;H3:1]-[C@;H0;D4;+0:2]1(-[C:3]-[O;D1;H1:4])-[O;H0;D2;+0:5]-[C@@H;D3;+0:6]-1-[C:7]-[c:8]>>[C;D1;H3:1]-[C@@;H0;D4;+0:2](-[OH;D1;+0:5])(-[C:3]-[O;D1;H1:4])-[CH2;D2;+0:6]-[C:7]-[c:8] | null | [] | null | null | 1 | HOUR | 1.10 g of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol are dissolved in 2 ml of pyridine. 0.5 ml of trimethylchlorosilane is then added and the mixture is left to stand at room temperature for 1 hour. Thereupon, sodium bicarbonate solution is added and the mixture is extracted with tol... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Tertiary alcohol | C1CO1 | null | c1ccccc1 | null | N1=CC=CC=C1 | null | 1 | COc1c(C)c(C)c(OC)c(C[C@H]2O[C@]2(C)CO)c1C>N1=CC=CC=C1>COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-533e35f56f7b4649b1ef091a7ffdfaa5 | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C.Cc1ccc(S(=O)(=O)Cl)cc1>>COc1c(C)c(C)c(OC)c(CC[C@](C)(O)COS(=O)(=O)c2ccccc2C)c1C | S(=O)(=O)(C1=CC=C(C)C=C1)Cl.COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](CO)(O)C.Cl.N1=CC=CC=C1>>COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](COS(=O)(=O)C1=C(C=CC=C1)C)(O)C | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][CH2:13][C@:14]([CH3:15])([OH:16])[CH2:17][OH:18])[c:29]1[CH3:30].Cl[S:19](=[O:20])(=[O:21])[c:22]1[cH:23][cH:24][c:27]([CH3:28])[cH:26][cH:25]1>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][CH2:13][C@:... | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C.Cc1ccc(S(=O)(=O)Cl)cc1 | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)COS(=O)(=O)c2ccccc2C)c1C | null | null | C(Cl)Cl | Acylation | OtherReaction | 05fa5c39bec607db4d2ecbdc0d03c290b9a310bbf0fb1c4f6cab56ff403f2979 | cac1a51abad701d3f26583520679a70ff72a7c9f3ad49ba72aafddf242cb8589 | O=S(=O)(OCCCCc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[C;D1;H3:8]):[c:9]:[cH;D2;+0:10]:1.[C:11]-[C:12]-[OH;D1;+0:13]>>[C:11]-[C:12]-[O;H0;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:10]:[c:9]:[c;H0;D3;+0:7]:1-[C;D1;H3:8] | 95 | [{"value": 95.0, "product": "COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](COS(=O)(=O)C1=C(C=CC=C1)C)(O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 237 mg of tosyl chloride and 350 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol are dissolved in 1 ml of methylene chloride. 0.180 ml of pyridine is then added dropwise at 0° C. and the mixture is left to stand at 0° C. for 1 hour and then at room temperature for 16 hours. Thereupon, 1 g... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Sulfonate | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 1 | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CO)c1C.Cc1ccc(S(=O)(=O)Cl)cc1>C(Cl)Cl>COc1c(C)c(C)c(OC)c(CC[C@](C)(O)COS(=O)(=O)c2ccccc2C)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c42ddd7a3bc84fa58a01dcb51e554183 | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)COS(=O)(=O)c2ccccc2C)c1C>>COc1c(C)c(C)c(OC)c(CC[C@@]2(C)CO2)c1C | COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](COS(=O)(=O)C1=C(C=CC=C1)C)(O)C.[OH-].[K+].C(Cl)Cl>>COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@]1(CO1)C | Cc1ccccc1S(=O)(=O)O[CH2:16][C@@:14]([CH2:13][CH2:12][c:11]1[c:8]([O:9][CH3:10])[c:6]([CH3:7])[c:4]([CH3:5])[c:3]([O:2][CH3:1])[c:18]1[CH3:19])([CH3:15])[OH:17]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][CH2:13][C@@:14]2([CH3:15])[CH2:16][O:17]2)[c:18]1[CH3:19] | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)COS(=O)(=O)c2ccccc2C)c1C | COc1c(C)c(C)c(OC)c(CC[C@@]2(C)CO2)c1C | null | null | C(C)O | Miscellaneous | OtherReaction | e132dc586e19dbc6cb4e504bb57e29e9052cbd84ad46c7e371d334ee582782b9 | c663fd873f494e81442ab4a5691529ab669d9af11fb41d588cbf59c17ec92125 | c1ccc(CCC2CO2)cc1 | C-c1:c:c:c:c:c:1-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[OH;D1;+0:5]>>[C:3]-[C:2]1(-[C;D1;H3:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-1 | 98 | [{"value": 98.0, "product": "COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@]1(CO1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 177 mg of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1-toluylsulphonyloxy-2-butanol are dissolved in 1 ml of ethanol and treated with 0.3 ml of alcoholic potassium hydroxide solution (1.5N). The mixture is left to stand at room temperature for 10 minutes, 30 ml of methylene chloride are then added and th... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Sulfonate | Ether | c1ccccc1 | C1CO1 | c1ccccc1.C1CO1 | HO- | C(C)O | null | 0.166667 | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)COS(=O)(=O)c2ccccc2C)c1C>C(C)O>COc1c(C)c(C)c(OC)c(CC[C@@]2(C)CO2)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5b0c068bddba4660a3c804cef037e9b1 | CC(C)CCC[C@@H](C)CCC[C@@H](C)CCBr.COc1c(C)c(C)c(OC)c(CC[C@@]2(C)CO2)c1C>>COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)c1C | [Cl-].[NH4+].[Mg].C[C@@H](CCBr)CCC[C@@H](CCCC(C)C)C.COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@]1(CO1)C>>COC1=C(C(=C(C(=C1C)C)OC)C)CC[C@@](CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)(O)C | Br[CH2:18][CH2:19][C@H:20]([CH3:21])[CH2:22][CH2:23][CH2:24][C@H:25]([CH3:26])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:31])[CH3:32].[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8]([O:9][CH3:10])[c:11]([CH2:12][CH2:13][C@:14]2([CH3:15])[O:16][CH2:17]2)[c:33]1[CH3:34]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[c:6]([CH3:7])[c:8](... | CC(C)CCC[C@@H](C)CCC[C@@H](C)CCBr.COc1c(C)c(C)c(OC)c(CC[C@@]2(C)CO2)c1C | COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)c1C | null | [Cu+] | C(C)OCC | C-C Coupling | OtherReaction | 5d7fd2213bdefc919c4a67aa9dd845496d7e65becaaf7289aa12a19777f29696 | b28ee6fc1bef2bb3abcf915f58c4c26d1378d5f3a5d3536b1fb1879f975bf701 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[C@@;H0;D4;+0:6]1(-[C;D1;H3:7])-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-1>>[C:4]-[C:5]-[C@;H0;D4;+0:6](-[C;D1;H3:7])(-[OH;D1;+0:9])-[CH2;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 16 | HOUR | 5.8 mmol of (3R,7R)-3,7,11-trimethyl-dodecyl bromide are heated at reflux for 1/4 hour in 20 ml of diethyl ether with etched magnesium. 1 g of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butane and 0.9 g of copper(I) 2-propylacetylide (or 1.2 g of copper(I) bromide-dimethyl sulphide complex) are... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Tertiary alcohol | C1CO1 | null | c1ccccc1 | Br- | [Cu+].C(C)OCC | null | 16 | CC(C)CCC[C@@H](C)CCC[C@@H](C)CCBr.COc1c(C)c(C)c(OC)c(CC[C@@]2(C)CO2)c1C>[Cu+].C(C)OCC>COc1c(C)c(C)c(OC)c(CC[C@](C)(O)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fd416b8ee8f64b7291e0922cc5033067 | CC(=O)OC/C(C)=C/Cc1c(C)c(OC(C)=O)c(C)c(C)c1OC(C)=O>>CC(=O)Oc1c(C)c(C)c(OC(C)=O)c(C/C=C(\C)CO)c1C | C([O-])(O)=O.[Na+].C(C)(=O)OC\C(=C\CC1=C(C(=C(C(=C1C)OC(C)=O)C)C)OC(C)=O)\C.B(F)(F)F.CCOCC>>C(C)(=O)OC1=C(C(=C(C(=C1C)C)OC(C)=O)C)C/C=C(/CO)\C | CC(=O)[O:21][CH2:20]/[C:18](=[CH:17]/[CH2:16][c:15]1[c:10]([O:11][C:12]([CH3:13])=[O:14])[c:8]([CH3:9])[c:6]([CH3:7])[c:5]([O:4][C:2]([CH3:1])=[O:3])[c:22]1[CH3:23])[CH3:19]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[c:6]([CH3:7])[c:8]([CH3:9])[c:10]([O:11][C:12]([CH3:13])=[O:14])[c:15]([CH2:16]/[CH:17]=[C:18](\[CH3:19])[CH2:20]... | CC(=O)OC/C(C)=C/Cc1c(C)c(OC(C)=O)c(C)c(C)c1OC(C)=O | CC(=O)Oc1c(C)c(C)c(OC(C)=O)c(C/C=C(\C)CO)c1C | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]/[C:3](-[C;D1;H3:4])=[C:5]/[C:6]>>[C:6]/[C:5]=[C:3](\[C;D1;H3:4])-[C:2]-[OH;D1;+0:1] | 90.5 | [{"value": 90.5, "product": "C(C)(=O)OC1=C(C(=C(C(=C1C)C)OC(C)=O)C)C/C=C(/CO)\\C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.0 g of (E)-4-(2',5'-diacetoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenyl acetate are dissolved in 50 ml of methanol and treated with 0.2 g of boron trifluoride etherate. The mixture is boiled at reflux for 4 hours, then cooled to room temperature and poured into aqueous sodium bicarbonate solution. The aqueous solu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | CO | null | null | CC(=O)OC/C(C)=C/Cc1c(C)c(OC(C)=O)c(C)c(C)c1OC(C)=O>CO>CC(=O)Oc1c(C)c(C)c(OC(C)=O)c(C/C=C(\C)CO)c1C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-db8c3bfdb4b147168d544c9a87d5e659 | COCOC.COc1cc([N+](=O)[O-])c2nc(C)ccc2c1>>COCOc1cc([N+](=O)[O-])c2nc(C)ccc2c1 | COCOC.CC1=NC2=C(C=C(C=C2C=C1)OC)[N+](=O)[O-].B(Br)(Br)Br.I>>CC1=NC2=C(C=C(C=C2C=C1)OCOC)[N+](=O)[O-] | COC[O:2][CH3:1].[CH3:3][O:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]2[n:12][c:13]([CH3:14])[cH:15][cH:16][c:17]2[cH:18]1>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]2[n:12][c:13]([CH3:14])[cH:15][cH:16][c:17]2[cH:18]1 | COCOC.COc1cc([N+](=O)[O-])c2nc(C)ccc2c1 | COCOc1cc([N+](=O)[O-])c2nc(C)ccc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 75bdd6ea063d3e23ab52d9bf5ff8b383cc0531b0d821f4e3a1b2a1a4a250160b | 1587615f2d92695e6dabc98b4de5974a954cefbc5b0227a691c7e479943202c8 | c1ccc2ncccc2c1 | C-O-C-[O;H0;D2;+0:1]-[C;D1;H3:2].[CH3;D1;+0:3]-[#8:4]-[c:5]>>[C;D1;H3:2]-[O;H0;D2;+0:1]-[CH2;D2;+0:3]-[#8:4]-[c:5] | null | [] | null | null | null | null | The preparation of chelators where R8 and R9 are part of a quinoline ring and W=OH begins, for example, with 2-methyl-6-methoxy-8-nitroquinoline. The methoxy group could be cleaved with BBr3 or hot HI to yield a 6-hydroxy group, which could then be protected by reaction with dimethoxymethane under acid catalysis to yie... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether | Ether.Ether | null | null | c1ccc2ncccc2c1 | HO- | null | null | null | COCOC.COc1cc([N+](=O)[O-])c2nc(C)ccc2c1>>COCOc1cc([N+](=O)[O-])c2nc(C)ccc2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7fe5eddca4bb4adf902f4296a00c90fb | C#C[Si](C)(C)C.O=CCOc1ccccc1>>C[Si](C)(C)C#CC(O)COc1ccccc1 | O(C1=CC=CC=C1)CC=O.C[Si](C)(C)C#C.C(CCC)[Li].Cl>>O(C1=CC=CC=C1)CC(C#C[Si](C)(C)C)O | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6].[CH:7](=[O:8])[CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][CH:7]([OH:8])[CH2:9][O:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | C#C[Si](C)(C)C.O=CCOc1ccccc1 | C[Si](C)(C)C#CC(O)COc1ccccc1 | null | null | CCCCCC.CCOCC.CCCCCC.C1CCOC1 | C-C Coupling | OtherReaction | 42afd678d98a8163623d8ebca1b8ff680f8c3731194582a1a473aa6e02e8609f | b29b57d2147a53ea7c817995e3c3ae1515f67e3a22cfb0f6c6d5362a4f9ae9ea | c1ccccc1 | [#8:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4].[C;D1;H3:5]-[#14:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C:9]#[CH;D1;+0:10]>>[#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C;H0;D2;+0:10]#[C:9]-[#14:6](-[C;D1;H3:5])(-[C;D1;H3:7])-[C;D1;H3:8] | 41.7 | [{"value": 41.7, "product": "O(C1=CC=CC=C1)CC(C#C[Si](C)(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 15 | MINUTE | To 7.2 g of trimethylsilylacetylene dissolved in 110 ml of THF and cooled to -20° C. was added 46.2 ml of 1.55M n-butyl lithium in hexane. The mixture was allowed to come to room temperature for 15 minutes, recooled to -20° C., and treated dropwise with 5.3 g of phenoxyacetaldehyde (II) in THF. After the addition was c... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Alkyne | Secondary alcohol.Alkyne | null | null | c1ccccc1 | null | CCCCCC.CCOCC.CCCCCC.C1CCOC1 | -20 | 0.25 | C#C[Si](C)(C)C.O=CCOc1ccccc1>CCCCCC.CCOCC.CCCCCC.C1CCOC1>C[Si](C)(C)C#CC(O)COc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9a0fa21a3b5245a2a7bee1f86b762e6c | CCCCC1C=CC(=O)C1=CCCCCCC(=O)OC.OO>>CCCCC1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2 | [Cl-].[NH4+].OO.[H-].[Na+].C(CCC)C1C=CC(C1=CCCCCCC(=O)OC)=O>>O1C=2C(C(C(C21)CCCC)=CCCCCCC(=O)OC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:6](=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:14])[O:15][CH3:16])[C:17](=[O:18])[CH:19]=[CH:20]1.O[OH:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[C:6](=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:14])[O:15][CH3:16])[C:17](=[O:18])[C:19]2=[C:20]1[O:21]2 | CCCCC1C=CC(=O)C1=CCCCCCC(=O)OC.OO | CCCCC1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2 | null | null | CO | Acylation | OtherReaction | 2396866f7f7583ded92016a7164e3f917e388b1bf81a8bfc435eb60bfaeefbfc | f43dcecaa39ffffd400b174dc6ece1f02280e4e66fdfb302bb02973c46ac9f91 | [CH]=C1CC2=C(O2)C1=O | O-[OH;D1;+0:1].[C:2]-[C:3]1-[CH;D2;+0:4]=[CH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8]-1=[C:9]-[C:10]>>[C:2]-[C:3]1-[C:8](=[C:9]-[C:10])-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:5]2=[C;H0;D3;+0:4]-1-[O;H0;D2;+0:1]-2 | 72 | [{"value": 72.0, "product": "O1C=2C(C(C(C21)CCCC)=CCCCCCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 660 mg (2.37 mmol) of 4-butyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone was dissolved in 10 ml of methanol. With ice cooling and stirring, 1.2 ml of 30% aqueous hydrogen peroxide and then 0.23 ml of 1N sodium hydride were added to the solution and the mixture was stirred at 0° C. for 20 minutes. Saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Peroxide | Ketone.Ether | C1=CCCC1 | C1CC2=C(C1)O2 | C1CC2=C(C1)O2 | HO- | CO | null | null | CCCCC1C=CC(=O)C1=CCCCCCC(=O)OC.OO>CO>CCCCC1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5a9561b519a84b979202aaeaf20d37af | CCCCC1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl>>CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | O1C=2C(C(C(C21)CCCC)=CCCCCCC(=O)OC)=O.Cl.C(O)([O-])=O.[Na+]>>ClC=1C(C(C(C1)CCCC)=CCCCCCC(=O)OC)=O | O1[C:6]2=[C:7]1[C:9](=[O:10])[C:11](=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH3:21])[CH:5]2[CH2:4][CH2:3][CH2:2][CH3:1].[ClH:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH:6]=[C:7]([Cl:8])[C:9](=[O:10])[C:11]1=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH3:21] | CCCCC1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl | CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | null | null | CC(=O)C | Miscellaneous | OtherReaction | ba845fc069021182670d7ec8a447d91b2aa970589b7cb337b5a12838787467a6 | 00af72396d1460b19559b8ee1f8c687771c8b48becb8b943784d96f70b48b223 | [CH]=C1CC=CC1=O | [C:1]-[C:2]=[C:3]1-[C:4](-[C:5])-[C;H0;D3;+0:6]2=[C;H0;D3;+0:7](-O-2)-[C:8]-1=[O;D1;H0:9].[ClH;D0;+0:10]>>[C:1]-[C:2]=[C:3]1-[C:4](-[C:5])-[CH;D2;+0:6]=[C;H0;D3;+0:7](-[Cl;H0;D1;+0:10])-[C:8]-1=[O;D1;H0:9] | 9 | [{"value": 9.0, "product": "ClC=1C(C(C(C1)CCCC)=CCCCCCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 50 | MINUTE | 300 mg (1.02 mmol) of 2,3-epoxy-4-butyl-5-(6-methoxycarbonylhexylidene)cyclopentenone was dissolved in 3 ml of acetone. 0.5 ml of concentrated hydrochloric acid was added to the solution and the mixture was stirred for 50 minutes. A saturated aqueous solution of sodium hydrogen carbonate was added thereto and was extra... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Alkenyl halide.Ketone | C1CC2=C(C1)O2 | C1=CCCC1 | C1=CCCC1 | Other | CC(=O)C | null | 0.833333 | CCCCC1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl>CC(=O)C>CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-66849e19f2dd45bda6a5b16a7d070d63 | CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC>>CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)O | Cl.P(=O)([O-])([O-])[O-].ClC=1C(C(C(C1)CCCC)=CCCCCCC(=O)OC)=O.S(=O)(=O)([O-])[O-].[NH4+].[NH4+]>>ClC=1C(C(C(C1)CCCC)=CCCCCCC(=O)O)=O | C[O:20][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[C:11]1[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH:6]=[C:7]([Cl:8])[C:9]1=[O:10])=[O:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH:6]=[C:7]([Cl:8])[C:9](=[O:10])[C:11]1=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[OH:20] | CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)O | null | null | CC(=O)C | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | [CH]=C1CC=CC1=O | 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] | 39.2 | [{"value": 39.0, "product": "ClC=1C(C(C(C1)CCCC)=CCCCCCC(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.2, "product": "ClC=1C(C(C(C1)CCCC)=CCCCCCC(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 60 | HOUR | 20 ml of phosphate buffer (pH8) was added to a solution of 200 mg (0.64 mmol) of 2-chloro-4-butyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone in 15 ml of acetone, and then 0.4 ml of an aqueous solution of pig liver esterase was added. The mixture was stirred at 30° C. for 60 hours. 1N hydrochloric acid was added t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1=CCCC1 | Other | CC(=O)C | 30 | 60 | CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC>CC(=O)C>CCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e533bfae54e94f988bfce1aa6ba01c96 | CCCCCCCCC1C=CC(=O)C1=CCCCCCC(=O)OC.Cl>>CCCCCCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | Cl.[H][H].C1(=CC=CC=C1)[Se]Cl.C1(=CC=CC=C1)[Se]Cl.C(CCCCCCC)C1C=CC(C1=CCCCCCC(=O)OC)=O>>ClC=1C(C(C(C1)CCCCCCCC)=CCCCCCC(=O)OC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:10]=[CH:11][C:13](=[O:14])[C:15]1=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:23])[O:24][CH3:25].[ClH:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:10]=[C:11]([Cl:12])[C:13](=[O:14])[C:15]1=[CH:16][CH2:17][CH2:18]... | CCCCCCCCC1C=CC(=O)C1=CCCCCCC(=O)OC.Cl | CCCCCCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | null | null | N1=CC=CC=C1.O.ClCCl | Functional Group Addition | Chlorination | 7266d5dce8871cef553f26177f6f3680968f8159cbb75208a70c3e6daade63e6 | d0508de3e3d7781004117c79f0f41db7f03b7838c48a40b94f26a583fbdc0c3f | [CH]=C1CC=CC1=O | [C:1]-[C:2]=[C:3]1-[C:4]-[C:5]=[CH;D2;+0:6]-[C:7]-1=[O;D1;H0:8].[ClH;D0;+0:9]>>[C:1]-[C:2]=[C:3]1-[C:4]-[C:5]=[C;H0;D3;+0:6](-[Cl;H0;D1;+0:9])-[C:7]-1=[O;D1;H0:8] | 53 | [{"value": 53.0, "product": "ClC=1C(C(C(C1)CCCCCCCC)=CCCCCCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.1, "product": "ClC=1C(C(C(C1)CCCCCCCC)=CCCCCCC(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 17 mg (51 mmol) of 4-octyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone was dissolved in 1 ml of dichloromethane and 23 μl (280 μmol) of pyridine was added thereto. With stirring, 49 mg (254 mmol) of phenyl selenium chloride was added to the mixture and the reaction mixture was refluxed. 10 hours later, 23 μl (280 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | N1=CC=CC=C1.O.ClCCl | null | null | CCCCCCCCC1C=CC(=O)C1=CCCCCCC(=O)OC.Cl>N1=CC=CC=C1.O.ClCCl>CCCCCCCCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-75cc88c9f3e8425b88b8b37838a6f11c | COC(=O)CCCCCC=C1C(=O)C=CC1CCC(C)CCC=C(C)C.OO.[Cl-].[OH-]>>CC(C)=CCCC(C)CCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)O.COC(=O)CCCCCC=C1C(=O)C(Cl)=CC1CCC(C)CCC=C(C)C.COC(=O)CCCCCC=C1CC=CC1=O | [Cl-].[NH4+].CC(CCC1C=CC(C1=CCCCCCC(=O)OC)=O)CCC=C(C)C.OO.[OH-].[Na+]>>ClC=1C(C(C(C1)CCC(CCC=C(C)C)C)=CCCCCCC(=O)OC)=O.COC(=O)CCCCCC=C1CC=CC1=O.ClC=1C(C(C(C1)CCC(CCC=C(C)C)C)=CCCCCCC(=O)O)=O | [CH3:1][C:51](=[CH:50][CH2:49][CH2:48][CH:46]([CH2:45][CH2:44][CH:43]1[C:37](=[CH:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:29]([O:28][CH3:27])=[O:30])[C:38](=[O:39])[CH:40]=[CH:42]1)[CH3:47])[CH3:53].[OH:16][OH:25].[Cl-:14].[OH-:26]>>[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][CH:11]1[... | COC(=O)CCCCCC=C1C(=O)C=CC1CCC(C)CCC=C(C)C.OO.[Cl-].[OH-] | CC(C)=CCCC(C)CCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)O.COC(=O)CCCCCC=C1C(=O)C(Cl)=CC1CCC(C)CCC=C(C)C.COC(=O)CCCCCC=C1CC=CC1=O | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 6eae51fe57134a8f21f185db1c6ea8c1c1a76ff9e1b4d7a17e90d366b6397660 | 79dc615d349763fd9069459aeada187ffaa44b10f2b782f6c963d211de2deec8 | [CH]=C1CC=CC1=O.[CH]=C1CC=CC1=O.[CH]=C1CC=CC1=O | [C:1]-[C:2]=[C;H0;D3;+0:3](-[C;D1;H3:4])-[CH3;D1;+0:5].[C:6]-[C:7]=[C:8]1-[C:9]-[C:10]=[CH;D2;+0:11]-[C:12]-1=[O;D1;H0:13].[Cl-;H0;D0:14].[OH-;D0:15].[OH;D1;+0:16]-[OH;D1;+0:17]>>[C:18]-[C:19](=[O;H0;D1;+0:17])-[OH;D1;+0:15].[C:20]=[C:21](-[C;D1;H3:22])-[CH3;D1;+0:5].[C:23]=[C:24](-[Cl;H0;D1;+0:14])-[C:25](=[O;H0;D1;+0... | 9 | [{"value": 8.0, "product": "ClC=1C(C(C(C1)CCC(CCC=C(C)C)C)=CCCCCCC(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 422 mg (1.17 mmol) of 4-(3,7-dimethyl-6-octen-1-yl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone was dissolved in 4 ml of methanol. With ice cooling and stirring, 600 μl (5.85 mmol) of 30% aqueous hydrogen peroxide and further 40 μl (40 mmol) of an aqueous solution of 1N sodium hydroxide were added thereto. After t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Peroxide | Alkenyl halide.Alkenyl halide.Carboxylic acid.Ketone.Ketone.Ketone.Ester | C1=CCCC1 | C1=CCCC1.C1=CCCC1.C1=CCCC1 | C1=CCCC1.C1=CCCC1.C1=CCCC1 | null | CO | null | 2 | COC(=O)CCCCCC=C1C(=O)C=CC1CCC(C)CCC=C(C)C.OO.[Cl-].[OH-]>CO>CC(C)=CCCC(C)CCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)O.COC(=O)CCCCCC=C1C(=O)C(Cl)=CC1CCC(C)CCC=C(C)C.COC(=O)CCCCCC=C1CC=CC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-253b657113ad46e7a6369acb204fc5d8 | CCCCCCC=C[C@@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl>>CCCCCCC=C[C@H]1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | O1C=2C(C([C@H](C21)C=CCCCCCC)=CCCCCCC(=O)OC)=O.Cl.C(O)([O-])=O.[Na+]>>ClC=1C(C([C@H](C1)C=CCCCCCC)=CCCCCCC(=O)OC)=O | O1[C:10]2=[C:11]1[C:13](=[O:14])[C:15](=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:23])[O:24][CH3:25])[C@H:9]2[CH:8]=[CH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[ClH:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][C@H:9]1[CH:10]=[C:11]([Cl:12])[C:13](=[O:14])[C:15]1=[CH:16][CH2:17][CH2:... | CCCCCCC=C[C@@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl | CCCCCCC=C[C@H]1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | null | null | CC(=O)C | Miscellaneous | OtherReaction | ba845fc069021182670d7ec8a447d91b2aa970589b7cb337b5a12838787467a6 | 00af72396d1460b19559b8ee1f8c687771c8b48becb8b943784d96f70b48b223 | [CH]=C1CC=CC1=O | [C:1]-[C:2]=[C:3]1-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6]2=[C;H0;D3;+0:7](-O-2)-[C:8]-1-[C:9]=[C:10]-[C:11].[ClH;D0;+0:12]>>[C:1]-[C:2]=[C:3]1-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[Cl;H0;D1;+0:12])=[CH;D2;+0:7]-[C:8]-1-[C:9]=[C:10]-[C:11] | 65 | [{"value": 65.0, "product": "ClC=1C(C([C@H](C1)C=CCCCCCC)=CCCCCCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 16 mg (46 microliters) of (4R)-2,3-epoxy-4-(1-octenyl)-5-(6-methoxylcarbonylhexylidene)cyclopentenone was dissolved in 1 ml of acetone. To the solution was added 0.1 ml of concentrated hydrochloric acid, and then the mixture was stirred for 30 minutes. A saturated aqueous solution of sodium hydrogencarbonate was added,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Alkenyl halide.Ketone | C1CC2=C(C1)O2 | C1=CCCC1 | C1=CCCC1 | Other | CC(=O)C | null | 0.5 | CCCCCCC=C[C@@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl>CC(=O)C>CCCCCCC=C[C@H]1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c2d48a2dec08485ab4d3d3bc6d7e1aee | CCCCCCC=C[C@@H]1C=CC(=O)C1=CCCCCCC(=O)OC.OO>>CCCCCCC=C[C@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2 | [Cl-].[NH4+].C(=CCCCCCC)[C@@H]1C=CC(C1=CCCCCCC(=O)OC)=O.OO>>O1C=2C(C([C@@H](C21)C=CCCCCCC)=CCCCCCC(=O)OC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][C@H:9]1[C:10](=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[O:19][CH3:20])[C:21](=[O:22])[CH:23]=[CH:24]1.O[OH:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][C@H:9]1[C:10](=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:1... | CCCCCCC=C[C@@H]1C=CC(=O)C1=CCCCCCC(=O)OC.OO | CCCCCCC=C[C@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2 | null | [OH-].[Na+] | CO | Acylation | OtherReaction | 2396866f7f7583ded92016a7164e3f917e388b1bf81a8bfc435eb60bfaeefbfc | f43dcecaa39ffffd400b174dc6ece1f02280e4e66fdfb302bb02973c46ac9f91 | [CH]=C1CC2=C(O2)C1=O | O-[OH;D1;+0:1].[C:2]-[C:3]=[C:4]1-[C:5](=[O;D1;H0:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[C:9]-1-[C:10]=[C:11]-[C:12]>>[C:2]-[C:3]=[C:4]1-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:7]2=[C;H0;D3;+0:8](-[O;H0;D2;+0:1]-2)-[C:9]-1-[C:10]=[C:11]-[C:12] | 78.7 | [{"value": 78.0, "product": "O1C=2C(C([C@@H](C21)C=CCCCCCC)=CCCCCCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "O1C=2C(C([C@@H](C21)C=CCCCCCC)=CCCCCCC(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a solution of 600 mg (1.8 mmol) of (4R)-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone in 6 ml of methanol was added 0.92 ml (9.0 mmol) of 30% aqueous hydrogen peroxide with ice cooling and stirring, and then 60 microliters (60 micromol) of 1N aqueous sodium hydroxide was added. The mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Peroxide | Ketone.Ether | C1=CCCC1 | C1CC2=C(C1)O2 | C1CC2=C(C1)O2 | HO- | [OH-].[Na+].CO | null | 0.75 | CCCCCCC=C[C@@H]1C=CC(=O)C1=CCCCCCC(=O)OC.OO>[OH-].[Na+].CO>CCCCCCC=C[C@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-81a9a4d8c7904d059454a7d52ad6da26 | CCCCCCC=C[C@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl>>CCCCCCC=C[C@H]1CC(Cl)C(=O)C1=CCCCCCC(=O)OC | C(O)([O-])=O.[Na+].O1C=2C(C([C@@H](C21)C=CCCCCCC)=CCCCCCC(=O)OC)=O.Cl>>ClC1C(C([C@H](C1)C=CCCCCCC)=CCCCCCC(=O)OC)=O | O1[C:10]2=[C:11]1[C:13](=[O:14])[C:15](=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:23])[O:24][CH3:25])[C@@H:9]2[CH:8]=[CH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[ClH:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][C@H:9]1[CH2:10][CH:11]([Cl:12])[C:13](=[O:14])[C:15]1=[CH:16][CH2:17][CH... | CCCCCCC=C[C@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl | CCCCCCC=C[C@H]1CC(Cl)C(=O)C1=CCCCCCC(=O)OC | null | null | CC(=O)C | Miscellaneous | OtherReaction | 293b5030895b139d178b47a359c8650184abde9083196ca4b483a65b177d202c | fb4630c416b88a48754b92561f3c6de7c245ce9f1bf38ec52fb646f938516079 | [CH]=C1CCCC1=O | [C:1]-[C:2]=[C:3]1-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6]2=[C;H0;D3;+0:7](-O-2)-[C:8]-1-[C:9]=[C:10]-[C:11].[ClH;D0;+0:12]>>[C:1]-[C:2]=[C:3]1-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6](-[Cl;H0;D1;+0:12])-[CH2;D2;+0:7]-[C:8]-1-[C:9]=[C:10]-[C:11] | 4 | [{"value": 4.0, "product": "ClC1C(C([C@H](C1)C=CCCCCCC)=CCCCCCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 450 mg (1.29 mmol) of (4S)-2,3-epoxy-4-(1-octenyl)-5-(6-methoxycarbonylhexylidene)cyclopentenone in 12 ml of acetone was added 2 ml of concentrated hydrochloric acid at room temperature under stirring. The mixture was stirred for 2 hours. A saturated aqueous solution of sodium hydrogencarbonate was add... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Secondary halide.Ketone | C1CC2=C(C1)O2 | C1CCCC1 | C1CCCC1 | Other | CC(=O)C | null | null | CCCCCCC=C[C@H]1C(=CCCCCCC(=O)OC)C(=O)C2=C1O2.Cl>CC(=O)C>CCCCCCC=C[C@H]1CC(Cl)C(=O)C1=CCCCCCC(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9b485789b41c43dd8117545ba68b1c3a | CCCCCCC=C[C@@H]1C=C(Cl)C(=O)C1=CCCCCC(=C=O)OC>>CCCCCCC=C[C@@H]1C=C(Cl)C(=O)C1=CCCCCCC(=O)O | Cl.P(=O)([O-])([O-])[O-].ClC=1C(C([C@@H](C1)C=CCCCCCC)=CCCCCC(OC)=C=O)=O.S(=O)(=O)([O-])[O-].[NH4+].[NH4+]>>ClC=1C(C([C@@H](C1)C=CCCCCCC)=CCCCCCC(=O)O)=O | C[O:24][C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[C:15]1[C@H:9]([CH:8]=[CH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH:10]=[C:11]([Cl:12])[C:13]1=[O:14])=[C:22]=[O:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][C@@H:9]1[CH:10]=[C:11]([Cl:12])[C:13](=[O:14])[C:15]1=[CH:16][CH2:17][CH2:18][CH2:19]... | CCCCCCC=C[C@@H]1C=C(Cl)C(=O)C1=CCCCCC(=C=O)OC | CCCCCCC=C[C@@H]1C=C(Cl)C(=O)C1=CCCCCCC(=O)O | null | null | CC(=O)C | Miscellaneous | OtherReaction | f5de369da24b333de819291bdaa47608f17ee67fd701a0566c82be684eeb5792 | ec9d1139a022c5ce99a2913da4a18fb1e432e39a424c83032aebd5532eca5773 | [CH]=C1CC=CC1=O | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](-[C:3]-[C:4])=[C;H0;D2;+0:5]=[O;D1;H0:6]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[OH;D1;+0:1] | 68 | [{"value": 68.0, "product": "ClC=1C(C([C@@H](C1)C=CCCCCCC)=CCCCCCC(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 100 | HOUR | 450 ml of 0.1M phosphate buffer (pH8) was added to a solution of 734 mg (2.0 mmol) of (4R)-2-chloro-4-(1-octenyl)-5-(6-methoxy-carbonylhexylidene)-2-cyclopentenone in 45 ml of acetone, and then 45 ml of an aqueous solution of pig liver esterase was added. The mixture was stirred at 30°-35° C. for 100 hours. 0.1N hydroc... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Carboxylic acid | null | null | C1=CCCC1 | Other | CC(=O)C | null | 100 | CCCCCCC=C[C@@H]1C=C(Cl)C(=O)C1=CCCCCC(=C=O)OC>CC(=O)C>CCCCCCC=C[C@@H]1C=C(Cl)C(=O)C1=CCCCCCC(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-57724bccc74849efa3b566690690b0cb | CCCCCC(O)C=CC1C=CC(=O)C1=Cc1cccc(OC(C)C(=O)OC)c1.Cl>>CCCCCC(O)C=CC1C=C(Cl)C(=O)C1=Cc1cccc(OC(C)C(=O)OC)c1 | [Cl-].[NH4+].C(O)([O-])=O.[Na+].OO.OC(C=CC1C=CC(C1=CC1=CC(=CC=C1)OC(C)C(=O)OC)=O)CCCCC.Cl.[OH-].[Na+]>>ClC=1C(C(C(C1)C=CC(CCCCC)O)=CC1=CC(=CC=C1)OC(C)C(=O)OC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([OH:7])[CH:8]=[CH:9][CH:10]1[CH:11]=[CH:12][C:14](=[O:15])[C:16]1=[CH:17][c:18]1[cH:19][cH:20][cH:21][c:22]([O:23][CH:24]([CH3:25])[C:26](=[O:27])[O:28][CH3:29])[cH:30]1.[ClH:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([OH:7])[CH:8]=[CH:9][CH:10]1[CH:11]=[C:12]([Cl:13])[C:14... | CCCCCC(O)C=CC1C=CC(=O)C1=Cc1cccc(OC(C)C(=O)OC)c1.Cl | CCCCCC(O)C=CC1C=C(Cl)C(=O)C1=Cc1cccc(OC(C)C(=O)OC)c1 | null | null | CC(=O)C.CO | Functional Group Addition | Chlorination | 7266d5dce8871cef553f26177f6f3680968f8159cbb75208a70c3e6daade63e6 | d0508de3e3d7781004117c79f0f41db7f03b7838c48a40b94f26a583fbdc0c3f | O=C1C=CCC1=Cc1ccccc1 | [C:1]=[C:2]-[C:3]1-[C:4]=[CH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8]-1=[C:9]-[c:10].[ClH;D0;+0:11]>>[C:1]=[C:2]-[C:3]1-[C:4]=[C;H0;D3;+0:5](-[Cl;H0;D1;+0:11])-[C:6](=[O;D1;H0:7])-[C:8]-1=[C:9]-[c:10] | 41 | [{"value": 41.0, "product": "ClC=1C(C(C(C1)C=CC(CCCCC)O)=CC1=CC(=CC=C1)OC(C)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.2 ml of 30% aqueous hydrogen peroxide was added to a solution of 100 mg (0.25 mmol) of 4-(3-hydroxy-1-octenyl)-5-[3-(1-methoxycarbonylethyloxy)-phenylmethylidene]-2-cyclopentenone in 2 ml of methanol under ice cooling and stirring, and then 50 microliters of 1N sodium hydroxide was added. The mixture was stirred at 0... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=CCCC1 | C1=CCCC1 | C1=CCCC1.c1ccccc1 | null | CC(=O)C.CO | null | null | CCCCCC(O)C=CC1C=CC(=O)C1=Cc1cccc(OC(C)C(=O)OC)c1.Cl>CC(=O)C.CO>CCCCCC(O)C=CC1C=C(Cl)C(=O)C1=Cc1cccc(OC(C)C(=O)OC)c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2371be08bb6a4081874bed775c17e646 | COC(=O)CCCC=CC=C1C(=O)C=CC1C=CC(O)C1CCCC1.Cl>>COC(=O)CCCC=CC=C1C(=O)C(Cl)=CC1C=CC(O)C1CCCC1 | [Cl-].[NH4+].C(O)([O-])=O.[Na+].OO.OC(C=CC1C=CC(C1=CC=CCCCC(=O)OC)=O)C1CCCC1.Cl.[OH-].[Na+]>>ClC=1C(C(C(C1)C=CC(C1CCCC1)O)=CC=CCCCC(=O)OC)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH:10]=[C:11]1[C:12](=[O:13])[CH:14]=[CH:16][CH:17]1[CH:18]=[CH:19][CH:20]([OH:21])[CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1.[ClH:15]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH:10]=[C:11]1[C:12](=[O:13])[C:14]([Cl:15])=[CH:16][CH:17]1[CH:1... | COC(=O)CCCC=CC=C1C(=O)C=CC1C=CC(O)C1CCCC1.Cl | COC(=O)CCCC=CC=C1C(=O)C(Cl)=CC1C=CC(O)C1CCCC1 | null | null | CC(=O)C.CO | Functional Group Addition | Chlorination | 7266d5dce8871cef553f26177f6f3680968f8159cbb75208a70c3e6daade63e6 | d0508de3e3d7781004117c79f0f41db7f03b7838c48a40b94f26a583fbdc0c3f | [CH]=C1C(=O)C=CC1C=CCC1CCCC1 | [C:1]=[C:2]-[C:3]1-[C:4]=[CH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8]-1=[C:9]-[C:10]=[C:11].[ClH;D0;+0:12]>>[C:1]=[C:2]-[C:3]1-[C:4]=[C;H0;D3;+0:5](-[Cl;H0;D1;+0:12])-[C:6](=[O;D1;H0:7])-[C:8]-1=[C:9]-[C:10]=[C:11] | 38 | [{"value": 38.0, "product": "ClC=1C(C(C(C1)C=CC(C1CCCC1)O)=CC=CCCCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.2 ml of 30% aqueous hydrogen peroxide was added to a solution of 65 mg (190 micromol) of 4-(3-hydroxy-3-cyclopentyl-1-propenyl)-5-(6-methoxycarbonyl-2-hexenylidene)-2-cyclopentenone in 2 ml of methanol under ice cooling and stirring, and then 50 microliters of 1N sodium hydroxide was added. The mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=CCCC1 | C1=CCCC1 | C1=CCCC1.C1CCCC1 | null | CC(=O)C.CO | null | null | COC(=O)CCCC=CC=C1C(=O)C=CC1C=CC(O)C1CCCC1.Cl>CC(=O)C.CO>COC(=O)CCCC=CC=C1C(=O)C(Cl)=CC1C=CC(O)C1CCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-47fd1f1e35484868b03f80f53d8b1bfc | CCCCC(C)CC(O)C=CC1C=CC(=O)C1=CCCCC=CC(=O)OC.Cl>>CCCCC(C)CC(O)C=CC1C=C(Cl)C(=O)C1=CCCCC=CC(=O)OC | [Cl-].[NH4+].C(O)([O-])=O.[Na+].OO.OC(C=CC1C=CC(C1=CCCCC=CC(=O)OC)=O)CC(CCCC)C.Cl.[OH-].[Na+]>>ClC=1C(C(C(C1)C=CC(CC(CCCC)C)O)=CCCCC=CC(=O)OC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH3:6])[CH2:7][CH:8]([OH:9])[CH:10]=[CH:11][CH:12]1[CH:13]=[CH:14][C:16](=[O:17])[C:18]1=[CH:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][C:25](=[O:26])[O:27][CH3:28].[ClH:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH3:6])[CH2:7][CH:8]([OH:9])[CH:10]=[CH:11][CH:12]1[CH:13]=[C:14]([Cl:15]... | CCCCC(C)CC(O)C=CC1C=CC(=O)C1=CCCCC=CC(=O)OC.Cl | CCCCC(C)CC(O)C=CC1C=C(Cl)C(=O)C1=CCCCC=CC(=O)OC | null | null | CC(=O)C.CO | Functional Group Addition | Chlorination | 7266d5dce8871cef553f26177f6f3680968f8159cbb75208a70c3e6daade63e6 | d0508de3e3d7781004117c79f0f41db7f03b7838c48a40b94f26a583fbdc0c3f | [CH]=C1CC=CC1=O | [C:1]=[C:2]-[C:3]1-[C:4]=[CH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[C:8]-1=[C:9]-[C:10].[ClH;D0;+0:11]>>[C:1]=[C:2]-[C:3]1-[C:4]=[C;H0;D3;+0:5](-[Cl;H0;D1;+0:11])-[C:6](=[O;D1;H0:7])-[C:8]-1=[C:9]-[C:10] | 47 | [{"value": 47.0, "product": "ClC=1C(C(C(C1)C=CC(CC(CCCC)C)O)=CCCCC=CC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.3 ml of 30% aqueous hydrogen peroxide was added to a solution of 160 mg (428 micromol) of 4-(3-hydroxy-5-methyl-1nonenyl)-5-(6-methoxycarbonyl-5-hexenylidene)-2-cyclopentenone in 5 ml of methanol under ice cooling and stirring, and then 60 microliters of 1N sodium hydroxide was added. The mixture was stirred at 0° C.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | CC(=O)C.CO | null | null | CCCCC(C)CC(O)C=CC1C=CC(=O)C1=CCCCC=CC(=O)OC.Cl>CC(=O)C.CO>CCCCC(C)CC(O)C=CC1C=C(Cl)C(=O)C1=CCCCC=CC(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-71e1a1b0be144d6eb80b570d1d6aa41b | CCCCCC=CC=C1C(=O)C=CC1CCCCCCC(=O)OC.Cl>>CCCCCC=CC=C1C(=O)C(Cl)=CC1CCCCCCC(=O)OC | [Cl-].[NH4+].OO.COC(=O)CCCCCCC1C=CC(C1=CC=CCCCCC)=O.Cl.[OH-].[Na+]>>ClC=1C(C(C(C1)CCCCCCC(=O)OC)=CC=CCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH:8]=[C:9]1[C:10](=[O:11])[CH:12]=[CH:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:23])[O:24][CH3:25].[ClH:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH:8]=[C:9]1[C:10](=[O:11])[C:12]([Cl:13])=[CH:14][CH:15]1[CH2:16][CH2:17][CH2:18][C... | CCCCCC=CC=C1C(=O)C=CC1CCCCCCC(=O)OC.Cl | CCCCCC=CC=C1C(=O)C(Cl)=CC1CCCCCCC(=O)OC | null | null | CC(=O)C.CO | Functional Group Addition | Chlorination | 7266d5dce8871cef553f26177f6f3680968f8159cbb75208a70c3e6daade63e6 | d0508de3e3d7781004117c79f0f41db7f03b7838c48a40b94f26a583fbdc0c3f | [CH]=C1CC=CC1=O | [C:1]=[C:2]-[C:3]=[C:4]1-[C:5]-[C:6]=[CH;D2;+0:7]-[C:8]-1=[O;D1;H0:9].[ClH;D0;+0:10]>>[C:1]=[C:2]-[C:3]=[C:4]1-[C:5]-[C:6]=[C;H0;D3;+0:7](-[Cl;H0;D1;+0:10])-[C:8]-1=[O;D1;H0:9] | 55 | [{"value": 55.0, "product": "ClC=1C(C(C(C1)CCCCCCC(=O)OC)=CC=CCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.5 ml of 30% aqueous hydrogen peroxide was added to a solution of 95 mg (286 mmol) of 4-(6-methoxycarbonylhexyl)-5-(2-octenylidene)-2-cyclopentenone in 4 ml of methanol under ice cooling and stirring, and then 0.1 ml of 1N sodium hydroxide was added. The mixture was stirred at 0° C. for 20 minutes. A saturated aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | CC(=O)C.CO | null | null | CCCCCC=CC=C1C(=O)C=CC1CCCCCCC(=O)OC.Cl>CC(=O)C.CO>CCCCCC=CC=C1C(=O)C(Cl)=CC1CCCCCCC(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ebf6fd0528a442078281daf54702e2bf | CCCCCC=CC=C1C(=O)C=CC1C/C=C\CCCC(=O)OC.Cl>>CCCCCC=CC=C1C(=O)C(Cl)=CC1C/C=C\CCCC(=O)OC | [Cl-].[NH4+].C(O)([O-])=O.[Na+].OO.COC(=O)CCC\C=C/CC1C=CC(C1=CC=CCCCCC)=O.Cl.[OH-].[Na+]>>ClC=1C(C(C(C1)C\C=C/CCCC(=O)OC)=CC=CCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH:8]=[C:9]1[C:10](=[O:11])[CH:12]=[CH:14][CH:15]1[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22](=[O:23])[O:24][CH3:25].[ClH:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH:8]=[C:9]1[C:10](=[O:11])[C:12]([Cl:13])=[CH:14][CH:15]1[CH2:16]/[CH:17]=[CH:18]\... | CCCCCC=CC=C1C(=O)C=CC1C/C=C\CCCC(=O)OC.Cl | CCCCCC=CC=C1C(=O)C(Cl)=CC1C/C=C\CCCC(=O)OC | null | null | CC(=O)C.CO | Functional Group Addition | Chlorination | 7266d5dce8871cef553f26177f6f3680968f8159cbb75208a70c3e6daade63e6 | d0508de3e3d7781004117c79f0f41db7f03b7838c48a40b94f26a583fbdc0c3f | [CH]=C1CC=CC1=O | [C:1]=[C:2]-[C:3]=[C:4]1-[C:5]-[C:6]=[CH;D2;+0:7]-[C:8]-1=[O;D1;H0:9].[ClH;D0;+0:10]>>[C:1]=[C:2]-[C:3]=[C:4]1-[C:5]-[C:6]=[C;H0;D3;+0:7](-[Cl;H0;D1;+0:10])-[C:8]-1=[O;D1;H0:9] | 49 | [{"value": 49.0, "product": "ClC=1C(C(C(C1)C\\C=C/CCCC(=O)OC)=CC=CCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.5 ml of 30% aqueous hydrogen peroxide was added to a solution of 68 mg (206 micromol) of 4-[(2Z)-6-methoxycarbonyl-2-hexenyl]-5-(2-octenylidene)-2-cyclopentenone in 5 ml of methanol under ice cooling and stirring, and then 50 microliters of 1N sodium hydroxide was added. The mixture was stirred at 0° C. for 20 minute... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | CC(=O)C.CO | null | null | CCCCCC=CC=C1C(=O)C=CC1C/C=C\CCCC(=O)OC.Cl>CC(=O)C.CO>CCCCCC=CC=C1C(=O)C(Cl)=CC1C/C=C\CCCC(=O)OC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-98581098cec54663807316b620000b2c | CCCCCC=CCC1C=CC(=O)C1=CCCCCCC(=O)OC.Cl>>CCCCCC=CCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | [Cl-].[NH4+].C(O)([O-])=O.[Na+].OO.C(C=CCCCCC)C1C=CC(C1=CCCCCCC(=O)OC)=O.Cl.[OH-].[Na+]>>ClC=1C(C(C(C1)CC=CCCCCC)=CCCCCCC(=O)OC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH:9]1[CH:10]=[CH:11][C:13](=[O:14])[C:15]1=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:23])[O:24][CH3:25].[ClH:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH:9]1[CH:10]=[C:11]([Cl:12])[C:13](=[O:14])[C:15]1=[CH:16][CH2:17][CH2:18][C... | CCCCCC=CCC1C=CC(=O)C1=CCCCCCC(=O)OC.Cl | CCCCCC=CCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC | null | null | CC(=O)C.CO | Functional Group Addition | Chlorination | 7266d5dce8871cef553f26177f6f3680968f8159cbb75208a70c3e6daade63e6 | d0508de3e3d7781004117c79f0f41db7f03b7838c48a40b94f26a583fbdc0c3f | [CH]=C1CC=CC1=O | [C:1]-[C:2]=[C:3]1-[C:4]-[C:5]=[CH;D2;+0:6]-[C:7]-1=[O;D1;H0:8].[ClH;D0;+0:9]>>[C:1]-[C:2]=[C:3]1-[C:4]-[C:5]=[C;H0;D3;+0:6](-[Cl;H0;D1;+0:9])-[C:7]-1=[O;D1;H0:8] | 54 | [{"value": 54.0, "product": "ClC=1C(C(C(C1)CC=CCCCCC)=CCCCCCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.3 ml of 30% aqueous hydrogen peroxide was added to a solution of 75 mg (226 micromol) of 4-(2-octenyl)-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone in 3 ml of methanol under ice cooling and stirring, and then 70 microliters of 1N sodium hydroxide was added. The mixture was stirred at 0° C. for 20 minutes. A satur... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | CC(=O)C.CO | null | null | CCCCCC=CCC1C=CC(=O)C1=CCCCCCC(=O)OC.Cl>CC(=O)C.CO>CCCCCC=CCC1C=C(Cl)C(=O)C1=CCCCCCC(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-44c50f781ba5490da11f8db6ee55c303 | COCCn1nc(Br)c([N+](=O)[O-])c1NCc1ccccc1>>COCCn1ncc(N)c1N.Cl | Cl.C(C1=CC=CC=C1)NC1=C(C(=NN1CCOC)Br)[N+](=O)[O-]>>Cl.Cl.NC=1C=NN(C1N)CCOC | O=[N+:9]([O-])[c:8]1[c:7](Br)[n:6][n:5]([CH2:4][CH2:3][O:2][CH3:1])[c:10]1[NH:11]Cc1ccccc1>>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[n:6][cH:7][c:8]([NH2:9])[c:10]1[NH2:11].[ClH:13] | COCCn1nc(Br)c([N+](=O)[O-])c1NCc1ccccc1 | COCCn1ncc(N)c1N.Cl | null | [Pd] | C(C)O | Functional Group Interconversion | OtherReaction | 1a1ea2d77aa1ba5d69a8f8fb1f23f83bda9d2cb9a369905216086ec607854ce1 | 6618bdd0b9d250673788de615aa5829ceae80c81ed829890857b83bf402e4cd0 | c1cn[nH]c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[C:4]):[c:5](-[NH;D2;+0:6]-C-c2:c:c:c:c:c:2):[c:7]:1-[N+;H0;D3:8](=O)-[O-]>>[C:4]-[#7;a:3]1:[#7;a:2]:[cH;D2;+0:1]:[c:7](-[NH2;D1;+0:8]):[c:5]:1-[NH2;D1;+0:6] | 27 | [{"value": 27.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 5-benzylamino-3-bromo-1-(2′-methoxyethyl)-4-nitropyrazole (4 g, 2.8 mmol) in ethanol (500 ml) containing a 10% Pd/C catalyst (Johnson-Mattey Type 487, dry weight 0.5 g) and 36% hydrochloric acid (0.57 g, 5.6 mmol) is hydrogenated in a Parr Autoclave (1 l) at 1 MPa for 1 hour. The catalyst is then removed b... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group.Secondary amine | Primary amine.Primary amine | c1cn[nH]c1.c1ccccc1 | c1c[nH]nc1 | c1c[nH]nc1 | HBr | [Pd].C(C)O | null | 1 | COCCn1nc(Br)c([N+](=O)[O-])c1NCc1ccccc1>[Pd].C(C)O>COCCn1ncc(N)c1N.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b8c3fe7d8c714fd3a9fe2ffe54494878 | CCOCOc1ccc(NC(=O)OC(C)(C)C)cc1C=CC(=O)OC>>CCOCOc1ccc(NC(=O)OC(C)(C)C)cc1C=CC(=O)O | O.[OH-].[Li+].C(C)(C)(C)OC(=O)NC=1C=CC(=C(C1)C=CC(=O)OC)OCOCC.P(=O)([O-])([O-])[O-]>>C(C)(C)(C)OC(=O)NC=1C=CC(=C(C1)C=CC(=O)O)OCOCC | C[O:24][C:22]([CH:21]=[CH:20][c:19]1[c:6]([O:5][CH2:4][O:3][CH2:2][CH3:1])[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18]1)=[O:23]>>[CH3:1][CH2:2][O:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][c:19]1[CH:20]=[CH:21]... | CCOCOc1ccc(NC(=O)OC(C)(C)C)cc1C=CC(=O)OC | CCOCOc1ccc(NC(=O)OC(C)(C)C)cc1C=CC(=O)O | null | null | O1CCCC1.O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[C:5]-[c:6]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]=[C:5]-[c:6] | null | [] | 60 | CELSIUS | 24 | HOUR | 2.53 g (0.06 mol) of lithium hydroxide monohydrate was added at 0° C. to a solution of 6.3 g (0.018 mol) of methyl 3-(5-tert.butoxycarbonylamino-2-ethoxymethoxyphenyl)acrylate from step D in 50 mL of tetrahydrofuran, 15 mL of methanol and 30 mL of water. The mixture was allowed to agitate 24 hours at 60° C. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | O1CCCC1.O.CO | 60 | 24 | CCOCOc1ccc(NC(=O)OC(C)(C)C)cc1C=CC(=O)OC>O1CCCC1.O.CO>CCOCOc1ccc(NC(=O)OC(C)(C)C)cc1C=CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a124ba7a30241d8aa00be3649b08b3c | COc1ccccc1C(=O)O>>O=C(O)c1ccccc1O | C(C=1C(=CC=CC1)OC)(=O)O>>C(C=1C(O)=CC=CC1)(=O)O | C[O:10][c:9]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[OH:10] | COc1ccccc1C(=O)O | O=C(O)c1ccccc1O | null | null | CO | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | -80 | CELSIUS | 20 | MINUTE | Salicylic acid was extracted and analyzed by HPLC using a modification of the methods described in Meuwly et al., 1993. For salicylic acid analysis, 0.3 to 0.5 gFW leaf tissue from E. orontii-infected leaves (7 dpi) was frozen in glass tubes with liquid nitrogen and either used directly or stored at −80° C. The frozen ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | CO | -80 | 0.333333 | COc1ccccc1C(=O)O>CO>O=C(O)c1ccccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e53b31a39b7e456887d2989addfbee81 | CCI.Oc1cccc(C(F)(F)F)c1>>CCOc1cccc(C(F)(F)F)c1 | C([O-])([O-])=O.[K+].[K+].C(C)C(=O)C.C(C)I.C(C)C(=O)C.FC(C=1C=C(C=CC1)O)(F)F>>C(C)OC=1C=C(C=CC1)C(F)(F)F | I[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1 | CCI.Oc1cccc(C(F)(F)F)c1 | CCOc1cccc(C(F)(F)F)c1 | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 2 | HOUR | Potassium carbonate (22.6 g) and then a mixture of methyl ethyl ketone (MEK) (150 mL) and ethyl iodide (47.8 g) were added to a mixture of MEK (310 mL) and 3-trifluoromethylphenol (a) (25.0 g) at room temperature, and the reaction mixture was heated and stirred for 2 hours. After returning the mixture to room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | O | null | 2 | CCI.Oc1cccc(C(F)(F)F)c1>O>CCOc1cccc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e2b1c3cd2a7f482abbd02b5942d73d0c | BrBr.CCOc1cccc(C(F)(F)F)c1>>CCOc1ccc(Br)c(C(F)(F)F)c1 | BrBr.C(C)OC=1C=C(C=CC1)C(F)(F)F.O>>BrC1=C(C=C(C=C1)OCC)C(F)(F)F | Br[Br:8].[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | BrBr.CCOc1cccc(C(F)(F)F)c1 | CCOc1ccc(Br)c(C(F)(F)F)c1 | null | null | CCOCC | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[F;D1;H0:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[C:3](-[F;D1;H0:2])(-[F;D1;H0:4])-[F;D1;H0:5]):[c:7] | 76.9 | [{"value": 76.9, "product": "BrC1=C(C=C(C=C1)OCC)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Bromine (18.2 g) was slowly added dropwise to Compound (b) (19.3 g) at room temperature, and then the mixture was stirred at room temperature for 1 hour. Water and ether were added for liquid separation, and the aqueous layer was extracted three times with ether. The organic layers were combined, washed with saturated ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CCOCC | null | 1 | BrBr.CCOc1cccc(C(F)(F)F)c1>CCOCC>CCOc1ccc(Br)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5820225fe8974a7692d95ff7a8e72a7a | CC(C)OB(OC(C)C)OC(C)C.CCOc1ccc(Br)c(C(F)(F)F)c1>>CCOc1ccc(OB(O)O)c(C(F)(F)F)c1 | BrC1=C(C=C(C=C1)OCC)C(F)(F)F.C(CCC)[Li].CCCCCC.Cl.B(OC(C)C)(OC(C)C)OC(C)C>>C(C)OC1=CC(=C(C=C1)OB(O)O)C(F)(F)F | CC(C)[O:8][B:9]([O:10]C(C)C)[O:11]C(C)C.Br[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:17][c:12]1[C:13]([F:14])([F:15])[F:16]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([O:8][B:9]([OH:10])[OH:11])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1 | CC(C)OB(OC(C)C)OC(C)C.CCOc1ccc(Br)c(C(F)(F)F)c1 | CCOc1ccc(OB(O)O)c(C(F)(F)F)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | e9dbfb9f314e618f498ba931f950b90cc87acea41f31fcecb8d08ba23aa7f8e1 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].C-C(-C)-[O;H0;D2;+0:10]-[#5:11](-[O;H0;D2;+0:12]-C(-C)-C)-[O;H0;D2;+0:13]-C(-C)-C>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[O;H0;D2;+0:13]-[#5:11](-[OH;D1;+0:10])-[OH;D1;+0:12]):[c:2]:[c:3] | 89.1 | [{"value": 89.1, "product": "C(C)OC1=CC(=C(C=C1)OB(O)O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | Compound (c) (10.0 g) dissolved in tetrahydrofuran (THF) (40 mL) was cooled to −78° C., a 1.6 M butyllithium/hexane solution (30 mL) was slowly added dropwise and the mixture was stirred at the same temperature for 2 hours. Triisopropyl borate (14.0 g) dissolved in THF (20 mL) was then slowly added dropwise at −78° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | O1CCCC1 | -78 | 2 | CC(C)OB(OC(C)C)OC(C)C.CCOc1ccc(Br)c(C(F)(F)F)c1>O1CCCC1>CCOc1ccc(OB(O)O)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f03a97a4a3344ae59edc0baf9053a4fa | CCOc1ccc(OB(O)O)c(C(F)(F)F)c1>>CCOc1ccc(O)c(C(F)(F)F)c1 | S(=O)(O)[O-].[Na+].O.OO.C(C)(=O)O.C(C)OC1=CC(=C(C=C1)OB(O)O)C(F)(F)F>>C(C)OC1=CC(=C(C=C1)O)C(F)(F)F | OB(O)[O:8][c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:14][c:9]1[C:10]([F:11])([F:12])[F:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | CCOc1ccc(OB(O)O)c(C(F)(F)F)c1 | CCOc1ccc(O)c(C(F)(F)F)c1 | null | null | C1CCOC1 | Reduction | OtherReaction | fe345bb6c7821a9564672f1988c64c3185a214564350fadef1076ff45aace7c9 | 7d1dae46abbe6fb3ac06fd763141303d5c3caa59881c040de4d3412b88a958a9 | c1ccccc1 | O-B(-O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97.7 | [{"value": 97.7, "product": "C(C)OC1=CC(=C(C=C1)O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Acetic acid (21.3 g) was added to a mixture of THF (200 mL) and Compound (d) (8.28 g) at room temperature, and the mixture was stirred at 0° C. under a nitrogen atmosphere. After adding 30% hydrogen peroxide water (40.1 g) dropwise, the resulting reaction mixture was carefully heated and stirred at 50° C. for 4 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic alcohol | null | null | c1ccccc1 | HO-.B | C1CCOC1 | 0 | null | CCOc1ccc(OB(O)O)c(C(F)(F)F)c1>C1CCOC1>CCOc1ccc(O)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3eaf5a5c4504444dad2bbf538ca8f3b7 | CCOc1ccc(O)c(C(F)(F)F)c1>>Oc1ccc(O)c(C(F)(F)F)c1 | B(Br)(Br)Br.C(C)OC1=CC(=C(C=C1)O)C(F)(F)F>>FC(C1=C(O)C=CC(=C1)O)(F)F | CC[O:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([C:8]([F:9])([F:10])[F:11])[cH:12]1 | CCOc1ccc(O)c(C(F)(F)F)c1 | Oc1ccc(O)c(C(F)(F)F)c1 | null | null | ClCCl | Deprotection | OtherReaction | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 63.2 | [{"value": 63.2, "product": "FC(C1=C(O)C=CC(=C1)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 2 | HOUR | Boron tribromide (11.8 g) was slowly added dropwise to dichloromethane (41 mL) cooled to −78° C., and then Compound (e) (6.47 g) dissolved in dichloromethane (60 mL) was slowly added dropwise at the same temperature and the mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into i... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | ClCCl | -78 | 2 | CCOc1ccc(O)c(C(F)(F)F)c1>ClCCl>Oc1ccc(O)c(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-587fa6dd1dba43fda10d118c83fddfdf | CC(=O)Cl.CCN(CC)CC.Nc1ccccc1C(=O)c1ccccc1>>CC(=O)Nc1ccccc1C(=O)c1ccccc1.Clc1cc(-c2ccccc2)c2ccccc2n1 | C(C)(=O)Cl.NC1=C(C(=O)C2=CC=CC=C2)C=CC=C1.C(C)N(CC)CC>>ClC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1.C(C)(=O)NC1=C(C(=O)C2=CC=CC=C2)C=CC=C1 | [CH3:1][C:2](=[O:3])[Cl:19].[CH2:20]([CH3:21])[N:35]([CH2:22][CH3:29])[CH2:31][CH3:32].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[Cl:19]... | CC(=O)Cl.CCN(CC)CC.Nc1ccccc1C(=O)c1ccccc1 | CC(=O)Nc1ccccc1C(=O)c1ccccc1.Clc1cc(-c2ccccc2)c2ccccc2n1 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 46d75ac072018cbbd3ecd461b14c4b1ba77c89ece17bc1203024fa5ac728c816 | 3f88f2fa590a6aeb915d21281f7e38e422e9d9748a42cdf602e60861bb0385b9 | O=C(c1ccccc1)c1ccccc1.c1ccc(-c2ccnc3ccccc23)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:3])=[O;D1;H0:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:8]-[CH3;D1;+0:9])-[CH2;D2;+0:10]-[CH3;D1;+0:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]-[C:16]=[O;D1;H0:17]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:4])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]-[C:16]=[O;D1;H0:17].[Cl... | null | [] | 0 | CELSIUS | 8 | HOUR | 2-Chloro-4-phenylquinoline was prepared by the following method (Rxn-1). 2-Aminobenzophenone (21 g, 106.5 mmol) was dissolved in methylene chloride (213 mL) and triethylamine (22.3 mL, 159.8 mmol) was added slowly. After cooling to 0° C., acetylchloride (8.3 mL, 117.2 mmol) was added to the reaction mixture dropwise. T... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Tertiary amine | Aromatic halide.Secondary amide | null | c1ccccc1.c1ccc2ncccc2c1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | Other | C(Cl)Cl | 0 | 8 | CC(=O)Cl.CCN(CC)CC.Nc1ccccc1C(=O)c1ccccc1>C(Cl)Cl>CC(=O)Nc1ccccc1C(=O)c1ccccc1.Clc1cc(-c2ccccc2)c2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c597b0d917254b1ebe98619b8d525b87 | CC(=O)Nc1ccccc1C(=O)c1ccccc1>>Oc1cc(-c2ccccc2)c2ccccc2n1 | [OH-].[Na+].C(C)(=O)NC1=C(C(=O)C2=CC=CC=C2)C=CC=C1>>OC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1 | O=[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][c:16]1[NH:17][C:2](=[O:1])[CH3:3]>>[OH:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1 | CC(=O)Nc1ccccc1C(=O)c1ccccc1 | Oc1cc(-c2ccccc2)c2ccccc2n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 00aaf5ce5dc9b7643b877d2850f4067e78d76ae658d32e537739978aba1c8e3f | 83a6df9894260a0b611d8c109c794c934b61476bc85b50e7010dd8ac5f7fddef | c1ccc(-c2ccnc3ccccc23)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:6](-[CH3;D1;+0:7])=[O;H0;D1;+0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[OH;D1;+0:8]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2](:[c:3]):[c:4](:[c:9]):[n;H0;D2;+0:5]:1 | null | [] | null | null | null | null | Sodium hydroxide (5 M, 1.8 g, 43.9 mmol) was added to a mixture of 2-acetamidobenzophenone (10.5 g, 43.9 mmol) in ethanol (439 mL). The mixture was heated to reflux for 3 hours, then cooled to room temperature and concentrated. Water and methylene chloride were added while stirring to form a white precipitate. The soli... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide | Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HO- | C(C)O | null | null | CC(=O)Nc1ccccc1C(=O)c1ccccc1>C(C)O>Oc1cc(-c2ccccc2)c2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-384b01392825410abd4d8cdf98b1c32b | O=P(Cl)(Cl)Cl.Oc1cc(-c2ccccc2)c2ccccc2n1>>Clc1cc(-c2ccccc2)c2ccccc2n1 | P(=O)(Cl)(Cl)Cl.OC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1>>ClC1=NC2=CC=CC=C2C(=C1)C1=CC=CC=C1 | O=P(Cl)(Cl)[Cl:1].O[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1>>[Cl:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1 | O=P(Cl)(Cl)Cl.Oc1cc(-c2ccccc2)c2ccccc2n1 | Clc1cc(-c2ccccc2)c2ccccc2n1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 27014e1419adc48e7dd5f2024d7f933bb85e42d4ec6c57e509da2884d477d689 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2ccnc3ccccc23)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6] | null | [] | null | null | null | null | Phosphorus oxychloride (37.4 mL, 402 mmol) was added to 2-hydroxy-4-phenylquinoline and the mixture was heated to reflux for 4 hours. Upon cooling to room temperature, the mixture was added slowly to stirring ice water yielding a white precipitate. The mixture was extracted with methylene chloride, and the organic phas... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.Oc1cc(-c2ccccc2)c2ccccc2n1>>Clc1cc(-c2ccccc2)c2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-deb84095cf784285b60ae40b3b6b63d9 | OC12CC3CC(C1)CC(O)(C3)C2.OC12CC3CC(CC(C3)C1)C2>>OC12CC3CC(O)(C1)CC(O)(C3)C2 | OC12CC3(CC(CC(C1)C3)C2)O.C(C)(=O)OC(C)=O.OC12CC3CC(CC(C1)C3)C2>>OC12CC3(CC(CC(C1)C3)(C2)O)O | [OH:1][C:2]12[CH2:3][CH:4]3[CH2:5][C:6]([OH:7])([CH2:8]1)[CH2:9][CH:10]([CH2:12]3)[CH2:13]2.C1C2CC3CC1CC([OH:11])(C2)C3>>[OH:1][C:2]12[CH2:3][CH:4]3[CH2:5][C:6]([OH:7])([CH2:8]1)[CH2:9][C:10]([OH:11])([CH2:12]3)[CH2:13]2 | OC12CC3CC(C1)CC(O)(C3)C2.OC12CC3CC(CC(C3)C1)C2 | OC12CC3CC(O)(C1)CC(O)(C3)C2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ddf536bd8f0671a0cd52b2a10083ba3c72af7efc652ab6f29311da6754480c5d | c0c64ba1d57edff273af7c37b63603ede4d82e581449029e0094db0e1c7e8e25 | C1C2CC3CC1CC(C2)C3 | [C:1]-[C:2]-[CH;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7].[OH;D1;+0:8]-C12-C-C3-C-C(-C-C(-C-3)-C-1)-C-2>>[C:1]-[C:2]-[C;H0;D4;+0:3](-[OH;D1;+0:8])(-[C:4]-[C:5])-[C:6]-[C:7] | null | [] | null | null | null | null | One mol of 1,3-dihydroxyadamantane was stirred in an acetic acid-acetic anhydride solution of CrO3, oxidizing agent, with heating. After carrying out the reaction for 8 hours, the reaction solution was neutralized to obtain a mixture of polyhydroxylated compounds of hydroxyadamantane. This mixture was partitioned by hi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Tertiary alcohol | C1C2CC3CC1CC(C2)C3.C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | C1C2CC3CC1CC(C2)C3 | Other | null | null | null | OC12CC3CC(C1)CC(O)(C3)C2.OC12CC3CC(CC(C3)C1)C2>>OC12CC3CC(O)(C1)CC(O)(C3)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-407416f81c6b4d9ebc2627a910470ccb | C[Si](C)(C)Cl.OC12CC3CC(O)(C1)CC(O)(C3)C2>>C[Si](C)(C)OC12CC3CC(O)(CC(O)(C3)C1)C2 | OC12CC3(CC(CC(C1)C3)(C2)O)O.CN(C)C.C[Si](C)(C)Cl>>OC12CC3(CC(CC(C1)C3)(C2)O[Si](C)(C)C)O | Cl[Si:2]([CH3:1])([CH3:3])[CH3:4].[OH:5][C:6]12[CH2:7][CH:8]3[CH2:9][C:10]([OH:11])([CH2:12][C:13]([OH:14])([CH2:15]3)[CH2:16]1)[CH2:17]2>>[CH3:1][Si:2]([CH3:3])([CH3:4])[O:5][C:6]12[CH2:7][CH:8]3[CH2:9][C:10]([OH:11])([CH2:12][C:13]([OH:14])([CH2:15]3)[CH2:16]1)[CH2:17]2 | C[Si](C)(C)Cl.OC12CC3CC(O)(C1)CC(O)(C3)C2 | C[Si](C)(C)OC12CC3CC(O)(CC(O)(C3)C1)C2 | null | null | C(Cl)Cl | Protection | Alcohol protection with silyl ethers | 9769bfd0e2301823e43c8e03cbd04c370095023efd8ba0f40deaf2a30665c67c | d4f7fc2e4845ce90b51777d3c64652d4a3aab88a89713e59aada938381b9c2e3 | C1C2CC3CC1CC(C2)C3 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](-[OH;D1;+0:7])(-[C:8])-[C:9]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4])(-[C:8])-[C:9] | null | [] | null | null | null | null | This 1,3,5-trihydroxyadamantane was dissolved in methylene chloride. To this solution were added a small amount of trimethylamine, and then an equimolar amount of trimethylsilyl chloride. Reaction was carried out at room temperature. The reaction product was partitioned by high performance liquid chromatography to obta... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Silyl protective group | Silyl protective group | null | null | C1C2CC3CC1CC(C2)C3 | HCl | C(Cl)Cl | null | null | C[Si](C)(C)Cl.OC12CC3CC(O)(C1)CC(O)(C3)C2>C(Cl)Cl>C[Si](C)(C)OC12CC3CC(O)(CC(O)(C3)C1)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9e2bc7ece64422aa680ac0d6978bd7c | C[Si](C)(C)Cl.O=C(Cl)C12CC3CC(O)(C1)CC(C(=O)Cl)(C3)C2>>C[Si](C)(C)OC12CC3CC(C(=O)Cl)(C1)CC(C(=O)Cl)(C3)C2 | ClC(=O)C12CC3(CC(CC(C1)C3)(C2)O)C(=O)Cl.CN(C)C.C[Si](C)(C)Cl>>ClC(=O)C12CC3(CC(CC(C1)C3)(C2)O[Si](C)(C)C)C(=O)Cl | Cl[Si:2]([CH3:1])([CH3:3])[CH3:4].[OH:5][C:6]12[CH2:7][CH:8]3[CH2:9][C:10]([C:11](=[O:12])[Cl:13])([CH2:14]1)[CH2:15][C:16]([C:17](=[O:18])[Cl:19])([CH2:20]3)[CH2:21]2>>[CH3:1][Si:2]([CH3:3])([CH3:4])[O:5][C:6]12[CH2:7][CH:8]3[CH2:9][C:10]([C:11](=[O:12])[Cl:13])([CH2:14]1)[CH2:15][C:16]([C:17](=[O:18])[Cl:19])([CH2:20... | C[Si](C)(C)Cl.O=C(Cl)C12CC3CC(O)(C1)CC(C(=O)Cl)(C3)C2 | C[Si](C)(C)OC12CC3CC(C(=O)Cl)(C1)CC(C(=O)Cl)(C3)C2 | null | null | C(Cl)Cl | Protection | Alcohol protection with silyl ethers | 9769bfd0e2301823e43c8e03cbd04c370095023efd8ba0f40deaf2a30665c67c | d4f7fc2e4845ce90b51777d3c64652d4a3aab88a89713e59aada938381b9c2e3 | C1C2CC3CC1CC(C2)C3 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[C:6](-[OH;D1;+0:7])(-[C:8])-[C:9]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4])(-[C:8])-[C:9] | null | [] | null | null | null | null | The 1,3-dichloroformyl-5-hydroxyadamantane was dissolved in methylene chloride. To this solution were added a small amount of trimethylamine, and then an eguimolar amount of trimethylsilyl chloride. Reaction was carried out at room temperature to obtain 1,3-dichloroformyl-5-trimethylsiloxyadamantane.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Silyl protective group | Silyl protective group | null | null | C1C2CC3CC1CC(C2)C3 | HCl | C(Cl)Cl | null | null | C[Si](C)(C)Cl.O=C(Cl)C12CC3CC(O)(C1)CC(C(=O)Cl)(C3)C2>C(Cl)Cl>C[Si](C)(C)OC12CC3CC(C(=O)Cl)(C1)CC(C(=O)Cl)(C3)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6aca018c334a4edeac4e4d277991a4b8 | C1=COCCC1.C=C(C)C(=O)O>>C=C(C)C(=O)OC1CCCCO1 | O1CCCC=C1.C(C(=C)C)(=O)O>>C(C(=C)C)(=O)OC1OCCCC1 | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[OH:6]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C1=COCCC1.C=C(C)C(=O)O | C=C(C)C(=O)OC1CCCCO1 | null | null | null | Heteroatom Alkylation and Arylation | oxa-Michael addition | be8f1700edf8e90b1fa14f5387071fe325a984e924174424b852a6e081d56dd5 | c1f1fae4448d1254e9587aa3614680eb16bfca39fe69f6c8606ef80f04deaebf | C1CCOCC1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C;D1;H2:7]=[C:8](-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12]>>[C;D1;H2:7]=[C:8](-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | null | [] | null | null | null | null | Dihydropyrane was added to methacrylic acid by the use of an acid catalyst to obtain tetrahydropyranyl methacrylate (Compound (III-G)).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Ester.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | null | null | null | C1=COCCC1.C=C(C)C(=O)O>>C=C(C)C(=O)OC1CCCCO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e336452b39fa4508bbc7dddb8f490850 | C1=COCCC1.C=C(C)C(=O)O>>C=C(C)C(=O)OC1CCCCO1 | O1CCCC=C1.C(C(=C)C)(=O)O>>C(C(=C)C)(=O)OC1OCCCC1 | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[OH:6]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:12]1 | C1=COCCC1.C=C(C)C(=O)O | C=C(C)C(=O)OC1CCCCO1 | null | null | null | Heteroatom Alkylation and Arylation | oxa-Michael addition | be8f1700edf8e90b1fa14f5387071fe325a984e924174424b852a6e081d56dd5 | c1f1fae4448d1254e9587aa3614680eb16bfca39fe69f6c8606ef80f04deaebf | C1CCOCC1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[C;D1;H2:7]=[C:8](-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12]>>[C;D1;H2:7]=[C:8](-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | null | [] | null | null | null | null | Dihydropyrane was added to methacrylic acid by the use of an acid catalyst to obtain tetrahydropyranyl methacrylate (Compound (III-g)).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Ester.Ether | C1=COCCC1 | C1CCOCC1 | C1CCOCC1 | null | null | null | null | C1=COCCC1.C=C(C)C(=O)O>>C=C(C)C(=O)OC1CCCCO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fd937ffa5add44f6acd39005f07019e9 | C=CC(=O)Cl.OC12CC3CC(CC(C3)C1)C2>>C=CC(=O)OC12CC3CC(CC(C3)C1)C2 | C12(CC3CC(CC(C1)C3)C2)O.C(C=C)(=O)Cl>>C(C=C)(=O)OC12CC3CC(CC(C1)C3)C2 | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[OH:5][C:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:14]1)[CH2:15]2>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][C:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:14]1)[CH2:15]2 | C=CC(=O)Cl.OC12CC3CC(CC(C3)C1)C2 | C=CC(=O)OC12CC3CC(CC(C3)C1)C2 | null | null | null | Acylation | Schotten-Baumann to ester | 98017bac06eb42265c00528a12d8ad0fd443a81d4f2c4b4bd7765730c559bb5b | cda6b3bfc0599ee5e7303a58cf8c674c7577cf9fbc7c186a45060ebd8ab26e4f | C1C2CC3CC1CC(C2)C3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[C:5]-[C:6](-[OH;D1;+0:7])(-[C:8])-[C:9]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4])(-[C:8])-[C:9] | null | [] | null | null | null | null | 1-Adamantanol and acrylic acid chloride were subjected to desalting reaction by using a basic catalyst to obtain adamantyl acrylate (Compound (III-h)).
Conditions: See reaction.notes.procedure_details.
Workup: reaction | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary alcohol | Ester | null | null | C1C2CC3CC1CC(C2)C3 | HCl | null | null | null | C=CC(=O)Cl.OC12CC3CC(CC(C3)C1)C2>>C=CC(=O)OC12CC3CC(CC(C3)C1)C2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-321a0cd12c304585b11ba8073db5836a | CC(C)CC(=O)O.COC(=O)CCCCCCCCCCC(=O)O>>CC(C)CCCCCCCCCCCC(=O)O | C(CC(C)C)(=O)O.C(CCCCCCCCCCC(=O)O)(=O)OC>>CC(CCCCCCCCCCCC(=O)O)C | O=C(O)[CH2:4][CH:2]([CH3:1])[CH3:3].COC(=O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[OH:17]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[OH:17] | CC(C)CC(=O)O.COC(=O)CCCCCCCCCCC(=O)O | CC(C)CCCCCCCCCCCC(=O)O | null | null | null | C-C Coupling | OtherReaction | 670bffa6e4aee319afd78b1c2098c80d8119675719e75f068816d1d9c95d4c9c | 489f676fdaf25172f4744b8d899f2cf09f73606c36bced9ab9551a1f073033c0 | null | C-O-C(=O)-[CH2;D2;+0:1]-[C:2]-[C:3].O-C(=O)-[CH2;D2;+0:4]-[C:5](-[C;D1;H3:6])-[C;D1;H3:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH2;D2;+0:4]-[C:5](-[C;D1;H3:6])-[C;D1;H3:7] | null | [] | null | null | null | null | 13-methyltetradecanoic acid is synthesized electrolytically from isovaleric acid and methyl hydrogen dodecanedioate in methanolic solution, based on Kolbe electrolysis.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | null | null | null | null | HO- | null | null | null | CC(C)CC(=O)O.COC(=O)CCCCCCCCCCC(=O)O>>CC(C)CCCCCCCCCCCC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc60b71ab90445cab311ed1798fa62bf | C=CC(C)(O)CCC=C(C)C.O=C(O)C=Cc1ccc(O)cc1O>>C=CC(C)(CCC=C(C)C)OC(=O)C=Cc1ccc(O)cc1O | C=CC(O)(C)CCC=C(C)C.C(C)N(CC)CC.CN(C)[P+](N(C)C)(N(C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.OC1=C(C=CC(=C1)O)C=CC(=O)O>>CC(CCC=C(C)C)(C=C)OC(C=CC1=C(C=C(C=C1)O)O)=O | [CH2:1]=[CH:2][C:3]([CH3:4])([CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])[OH:11].O[C:12](=[O:13])[CH:14]=[CH:15][c:16]1[cH:17][cH:18][c:19]([OH:20])[cH:21][c:22]1[OH:23]>>[CH2:1]=[CH:2][C:3]([CH3:4])([CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])[O:11][C:12](=[O:13])[CH:14]=[CH:15][c:16]1[cH:17][cH:18][c:19]([OH:20])[cH:... | C=CC(C)(O)CCC=C(C)C.O=C(O)C=Cc1ccc(O)cc1O | C=CC(C)(CCC=C(C)C)OC(=O)C=Cc1ccc(O)cc1O | null | null | CN(C)C=O.C1CCOC1 | Protection | Esterification of Carboxylic Acids | 4fc51e99c8d41e062b04286df301b17a66d11ed324f4ef1ad52af450df5a149f | 851ee0305feb435b96f77460f854d4a90e8c7d0255370fbd7595161a6919e7ab | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[C:6]-[C:7](-[C;D1;H3:8])(-[OH;D1;+0:9])-[C:10]=[C;D1;H2:11]>>[C:6]-[C:7](-[C;D1;H3:8])(-[C:10]=[C;D1;H2:11])-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5] | null | [] | null | null | 1 | HOUR | To a solution of linalool (1.74 g, 11.3 mmol) and triethylamine (2.30 g, 22.6 mmol) in anhydrous THF (150 mL) stirred for 5 min at 22° C. is added 3-(2,4-dihydroxyphenyl)-acrylic acid (2.04 g, 11.3 mmol). To this heterogeneous solution is added BOP Reagent (5.00 g, 11.3 mmol; Aldrich #22,608-4) in DMF (10 mL), and the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C)C=O.C1CCOC1 | null | 1 | C=CC(C)(O)CCC=C(C)C.O=C(O)C=Cc1ccc(O)cc1O>CN(C)C=O.C1CCOC1>C=CC(C)(CCC=C(C)C)OC(=O)C=Cc1ccc(O)cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-29931067ae7f4dd5b8eb596caeb473e3 | CC(=CC(=O)O)c1ccc(O)cc1O.OCCc1ccccc1>>C/C(=C\C(=O)OCCc1ccccc1)c1ccc(O)cc1O | ON1N=NC2=C1C=CC=C2.C(CC1=CC=CC=C1)O.OC1=C(C=CC(=C1)O)C(=CC(=O)O)C.C1(CCCCC1)N=C=NC1CCCCC1>>C(CC1=CC=CC=C1)OC(\C=C(/C)\C1=C(C=C(C=C1)O)O)=O | O[C:4]([CH:3]=[C:2]([CH3:1])[c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][c:21]1[OH:22])=[O:5].[OH:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1]/[C:2](=[CH:3]\[C:4](=[O:5])[O:6][CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][c:21]1[OH:22] | CC(=CC(=O)O)c1ccc(O)cc1O.OCCc1ccccc1 | C/C(=C\C(=O)OCCc1ccccc1)c1ccc(O)cc1O | null | CN(C1=CC=NC=C1)C | O1CCCC1 | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | O=C(C=Cc1ccccc1)OCCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4](-[C;D1;H3:5])-[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4](\[C;D1;H3:5])-[c:6] | null | [] | 22 | CELSIUS | 10 | MINUTE | To a 0° C. solution of 9.7 g (0.050 mol) of 3-(2,4-dihydroxyphenyl)but-2-enoic acid in 500 mL of anhydrous tetrahydrofuran (THF) is added 10.3 g (0.050 mol) of 1,3-dicyclohexylcarbodiimide (DCC). After stirring for 10 min, 6.8 g (0.050 mol) of 1-hydroxybenzotriazole (HOBt), 5.5 g (0.045 mol) of phenethyl alcohol and 1.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.O1CCCC1 | 22 | 0.166667 | CC(=CC(=O)O)c1ccc(O)cc1O.OCCc1ccccc1>CN(C1=CC=NC=C1)C.O1CCCC1>C/C(=C\C(=O)OCCc1ccccc1)c1ccc(O)cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e27fdbc38b8b4db2b1d2d58530a7c696 | CC(=CC(=O)O)c1ccc(O)c(C(=O)c2ccccc2)c1O.CC(C)=CCCC(C)CCO>>C=C(C)CCCC(C)CCOC(=O)/C=C(\C)c1ccc(O)c(C(=O)c2ccccc2)c1O | C(C1=CC=CC=C1)(=O)C=1C(=C(C=CC1O)C(=CC(=O)O)C)O.CC(C)=CCCC(C)CCO.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC(CCOC(\C=C(/C)\C1=C(C(=C(C=C1)O)C(C1=CC=CC=C1)=O)O)=O)CCCC(=C)C | O[C:12](=[O:13])[CH:14]=[C:15]([CH3:16])[c:17]1[cH:18][cH:19][c:20]([OH:21])[c:22]([C:23](=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[c:31]1[OH:32].[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][OH:11]>>[CH2:1]=[C:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10][O:11][C:... | CC(=CC(=O)O)c1ccc(O)c(C(=O)c2ccccc2)c1O.CC(C)=CCCC(C)CCO | C=C(C)CCCC(C)CCOC(=O)/C=C(\C)c1ccc(O)c(C(=O)c2ccccc2)c1O | null | null | C1CCCCC1 | Acylation | OtherReaction | 72e65517cc7e8b00dfd6c407d3c73464bad2af3f8b5a137d2c010a1c3da6808b | 4e8068bfcdc17db5bff3352457032784c281792fd206d34ede620a25afe80b79 | O=C(c1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4](-[C;D1;H3:5])-[c:6].[C:7]-[C:8]-[CH;D2;+0:9]=[C;H0;D3;+0:10](-[C;D1;H3:11])-[CH3;D1;+0:12].[C:13]-[C:14]-[OH;D1;+0:15]>>[C:7]-[C:8]-[CH2;D2;+0:9]-[C;H0;D3;+0:10](-[C;D1;H3:11])=[CH2;D1;+0:12].[C:13]-[C:14]-[O;H0;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4](\[C;D1;H3:5])-... | null | [] | null | null | null | null | A solution of 3-(3-benzoyl-2,4-dihydroxyphenyl)-but-2-enoic acid (5.97 g, 20.0 mmol), citronellol (3.13 g, 20.0 mmol) and p-toluenesulfonic acid (1 g) in cyclohexane (150 mL) is refluxed for 6 h under vacuum using a Dean Stark separator. The reaction mixture is partitioned between methylene chloride (150 mL) and water ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester.Vinyl | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCCCC1 | null | null | CC(=CC(=O)O)c1ccc(O)c(C(=O)c2ccccc2)c1O.CC(C)=CCCC(C)CCO>C1CCCCC1>C=C(C)CCCC(C)CCOC(=O)/C=C(\C)c1ccc(O)c(C(=O)c2ccccc2)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e587ad890bb24abfac5365e413ada614 | CC1(C)O[C@H]2CO[C@@]3(COC(C)(C)O3)C(=O)[C@H]2O1.N[C@@H](CS)C(=O)O>>CC(=O)N[C@@H](CS)C(=O)O | CC1(OC[C@@]2(O1)C(=O)[C@@H]3[C@H](CO2)OC(O3)(C)C)C.N[C@@H](CS)C(=O)O.CC1(OC[C@@]2(O1)C(=O)[C@@H]3[C@H](CO2)OC(O3)(C)C)C>>C(C)(=O)N[C@@H](CS)C(=O)O | CC1(C)OC[C@@]2(OC[C@@H]3OC(C)([CH3:1])O[C@@H]3[C:2]2=[O:3])O1.[NH2:4][C@@H:5]([CH2:6][SH:7])[C:8](=[O:9])[OH:10]>>[CH3:1][C:2](=[O:3])[NH:4][C@@H:5]([CH2:6][SH:7])[C:8](=[O:9])[OH:10] | CC1(C)O[C@H]2CO[C@@]3(COC(C)(C)O3)C(=O)[C@H]2O1.N[C@@H](CS)C(=O)O | CC(=O)N[C@@H](CS)C(=O)O | null | null | null | Acylation | OtherReaction | fa2fbf4e751da494eb882dc217454a74afdbf31076f234821ecf16aea4cdd791 | c6edf3b000c300418d36194d4899b91a5cbe3b309a2cdb3ee1d06e0301344ab8 | null | C-C1(-C)-O-C-[C@@]2(-O-C-[C@H]3-O-C(-C)(-[CH3;D1;+0:1])-O-[C@H]-3-[C;H0;D3;+0:2]-2=[O;D1;H0:3])-O-1.[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[C:4]-[C:5](-[NH;D2;+0:6]-[C;H0;D3;+0:2](-[CH3;D1;+0:1])=[O;D1;H0:3])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | null | null | null | null | Cysteine is an amino acid with one chiral carbon atom. It exists as an L-enantiomer, a D-enantiomer or a racemic mixture of the L- and D-enantiomers. The L-enantiomer is the naturally occurring configuration.
Conditions: See reaction.notes.procedure_details.
Workup: a D-enantiomer or a racemic mixture of the L- and D-e... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Ether.Ether.Primary amine | Secondary amide | C1O[C@H]2CO[C@@]3(COCO3)C[C@H]2O1 | null | null | HO- | null | null | null | CC1(C)O[C@H]2CO[C@@]3(COC(C)(C)O3)C(=O)[C@H]2O1.N[C@@H](CS)C(=O)O>>CC(=O)N[C@@H](CS)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c7cdb97a3cc049f6887ac3a666b6ecef | BrCc1ccccc1.CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O>>Br.CC(C)(C)OC(=O)N[C@H](CC1=CN(Cc2ccccc2)CC=C1)C(=O)O | N([C@H](CC1=CC=CN=C1)C(=O)O)C(=O)OC(C)(C)C.C(C1=CC=CC=C1)Br>>N([C@H](CC=1C=CCN(C1)CC1=CC=CC=C1)C(=O)O)C(=O)OC(C)(C)C.Br | [Br:1][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH3:2][C:3]([CH3:4])([CH3:5])[O:6][C:7](=[O:8])[NH:9][C@H:10]([CH2:11][c:12]1[cH:13][n:14][cH:22][cH:23][cH:24]1)[C:25](=[O:26])[OH:27]>>[BrH:1].[CH3:2][C:3]([CH3:4])([CH3:5])[O:6][C:7](=[O:8])[NH:9][C@H:10]([CH2:11][C:12]1=[CH:13][N:14]([CH2:15][c:16]2[cH:17][... | BrCc1ccccc1.CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O | Br.CC(C)(C)OC(=O)N[C@H](CC1=CN(Cc2ccccc2)CC=C1)C(=O)O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 304518c2c55973f8aaef6fffbc07f0861e91de5aba1baf00fbc67fa251ca7ef5 | 1efd58b961fff8c3a4cbc238c6e7a94e191356761e928a3672e783aea247df4f | C1=CCN(Cc2ccccc2)C=C1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[C:7](-[O;D1;H1:8])-[C:9]-[C:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:1>>[BrH;D0;+0:1].[O;D1;H0:6]=[C:7](-[O;D1;H1:8])-[C:9]-[C:10]-[C;H0;D3;+0:11]1=[CH;D2;+0:12]-[N;H0;D3;+0:13](-[CH2;D2;+0:2]-[c:3](:[c:4]... | 85 | [{"value": 85.0, "product": "N([C@H](CC=1C=CCN(C1)CC1=CC=CC=C1)C(=O)O)C(=O)OC(C)(C)C.Br", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 16 | HOUR | Boc-D-Pal (1.36 g, 6.0 mmol) was suspended in 60 ml of acetonitrile. Benzyl bromide (about 50 mmol) was added and the mixture was warmed to 50° C. on a water bath. A cleasr solution resulted, and was stirred at room temperature for 16 hours. A white precipitate formed; TLC after 17 hours showed some starting remaining ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Enamine | c1ccncc1 | C1=CC[NH]C=C1 | C1=CC[NH]C=C1.c1ccccc1 | null | C(C)#N | 50 | 16 | BrCc1ccccc1.CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O>C(C)#N>Br.CC(C)(C)OC(=O)N[C@H](CC1=CN(Cc2ccccc2)CC=C1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ca85c2ed96042d393159cfb26c2e27e | CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O.CC(C)I>>CC(C)N1C=C(C[C@@H](NC(=O)OC(C)(C)C)C(=O)O)C=CC1 | N([C@H](CC1=CC=CN=C1)C(=O)O)C(=O)OC(C)(C)C.IC(C)C.IC(C)C>>N([C@H](CC=1C=CCN(C1)C(C)C)C(=O)O)C(=O)OC(C)(C)C | [n:4]1[cH:5][c:6]([CH2:7][C@@H:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C:17](=[O:18])[OH:19])[cH:20][cH:21][cH:22]1.I[CH:2]([CH3:1])[CH3:3]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH:5]=[C:6]([CH2:7][C@@H:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C:17](=[O:18])[OH:19])[CH:20]=[CH... | CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O.CC(C)I | CC(C)N1C=C(C[C@@H](NC(=O)OC(C)(C)C)C(=O)O)C=CC1 | null | null | O.CC(C)O | Heteroatom Alkylation and Arylation | OtherReaction | c29336215254ce4ae20ea83fd539521274ee89dfcecc5620650269efe535ff87 | 9358465a4cb0d45fe42e8b8024782b3cc211d7db401099f0d7b92b74de545434 | C1=CCNC=C1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[O;D1;H0:4]=[C:5](-[O;D1;H1:6])-[C:7]-[C:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[cH;D2;+0:14]:1>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[N;H0;D3;+0:13]1-[CH2;D2;+0:12]-[CH;D2;+0:11]=[CH;D2;+0:10]-[C;H0;D3;+0:9](-[C:8]-[C:7]-[C:5](=[O;D1;H0:4... | 78.3 | [{"value": 78.3, "product": "N([C@H](CC=1C=CCN(C1)C(C)C)C(=O)O)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 4 | DAY | Boc-D-Pal (4.0 g, 17.7 mmol) and Ag2O (8.0 g, 34.4 mmol) in 22 ml water was stirred at room temperature for 4 hours. The reaction vessel was cooled to 0° C., and 2-iodopropane (20.4 g, 120 mmol) in 40 ml 2-propanol was added. After addition was complete, the mixture was allowed to warm to room temperature and stirred f... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Enamine | c1ccncc1 | C1=CC[NH]C=C1 | C1=CC[NH]C=C1 | I- | O.CC(C)O | 0 | 96 | CC(C)(C)OC(=O)N[C@H](Cc1cccnc1)C(=O)O.CC(C)I>O.CC(C)O>CC(C)N1C=C(C[C@@H](NC(=O)OC(C)(C)C)C(=O)O)C=CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9e3068bffe940b1b43ce45b99d07218 | O=P(Cl)(Cl)Cl.Oc1ccc(Br)cc1>>O=P(Cl)(Cl)Oc1ccc(Br)cc1 | C1=CC(=CC=C1O)Br.C(C)N(CC)CC.P(=O)(Cl)(Cl)Cl>>P(OC1=CC=C(C=C1)Br)(=O)(Cl)Cl | Cl[P:2](=[O:1])([Cl:3])[Cl:4].[OH:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1>>[O:1]=[P:2]([Cl:3])([Cl:4])[O:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1 | O=P(Cl)(Cl)Cl.Oc1ccc(Br)cc1 | O=P(Cl)(Cl)Oc1ccc(Br)cc1 | null | null | CCOCC | Miscellaneous | OtherReaction | b17801427c07d2f25f6ec5c33ea9c05b448fd6f7825ed9766c7cea10bb44b337 | 3e7378b4ebca3e552a282152d42648e283315351a0f71a8f8097af160be93915 | c1ccccc1 | Cl-[P;H0;D4;+0:1](-[Cl;D1;H0:2])(-[Cl;D1;H0:3])=[O;D1;H0:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Cl;D1;H0:2]-[P;H0;D4;+0:1](-[Cl;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 8 | HOUR | Following the procedure described by McGuigan et al., 1993, Supra, a solution of p-bromophenol (13.20 g; 76.30 mmol) and distilled triethylamine (10.65 mL) in anhydrous Et2O (165 mL) was added dropwise into a vigorously stirred solution of phosphoryl chloride (8.5 mL; 91.2 mmol) in anhydrous Et2O (83 mL) at 0° C. over ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | null | null | c1ccccc1 | HCl | CCOCC | null | 8 | O=P(Cl)(Cl)Cl.Oc1ccc(Br)cc1>CCOCC>O=P(Cl)(Cl)Oc1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d744372890e4a39aa80023067573048 | CSc1ccc(N)cc1.Fc1ccc(CBr)cc1>>CSc1ccc(NCc2ccc(F)cc2)cc1 | CSC1=CC=C(N)C=C1.C(C)N(CC)CC.FC1=CC=C(CBr)C=C1>>FC1=CC=C(CNC2=CC=C(C=C2)SC)C=C1 | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:16][cH:17]1.Br[CH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[cH:16][cH:17]1 | CSc1ccc(N)cc1.Fc1ccc(CBr)cc1 | CSc1ccc(NCc2ccc(F)cc2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 31.2 | [{"value": 31.2, "product": "FC1=CC=C(CNC2=CC=C(C=C2)SC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To 5.0 mL (40.19 mmol) of 4-(methylthio)aniline and 8.4 mL (60.28 mmol) triethylamine dissloved in 30 mL dichloromethane was added 5.0 mL (40.19 mmol) 4-fluorobenzyl bromide. The mixture was stirred at room temperature for 12 h, partitioned between dichloromethane and sat. aqueous ammonium chloride, dried over MgSO4 an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | ClCCl | null | 12 | CSc1ccc(N)cc1.Fc1ccc(CBr)cc1>ClCCl>CSc1ccc(NCc2ccc(F)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-37bb686b853f49248cd3135d413cc407 | CS(=O)(=O)c1ccc(F)cc1.NC1CCNC1>>CS(=O)(=O)c1ccc(NC2CCNC2)cc1 | CS(=O)(=O)C1=CC=C(C=C1)F.NC1CNCC1.C([O-])([O-])=O.[K+].[K+]>>CS(=O)(=O)C1=CC=C(C=C1)NC1CNCC1 | F[c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:16][cH:15]1.[NH2:9][CH:10]1[CH2:11][CH2:12][NH:13][CH2:14]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][CH:10]2[CH2:11][CH2:12][NH:13][CH2:14]2)[cH:15][cH:16]1 | CS(=O)(=O)c1ccc(F)cc1.NC1CCNC1 | CS(=O)(=O)c1ccc(NC2CCNC2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CCNC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]-[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[#7:6]-[C:7]-[C:8](-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:10] | 102.6 | [{"value": 102.6, "product": "CS(=O)(=O)C1=CC=C(C=C1)NC1CNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 48 | HOUR | To 500 mg (2.87 mmol) 4-fluorophenyl methyl sulfone dissolved in 4 mL DMF was added 247 mg (2.87 mmol) 3-aminopyrrolidine followed by 793 mg (5.74 mmol) potassium carbonate. The mixture was heated to 70° C. and stirred for 48 h. Upon cooling to room temperature, the mixture was partitioned between EtOAc and water, drie... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCNC1 | HF | CN(C)C=O | 70 | 48 | CS(=O)(=O)c1ccc(F)cc1.NC1CCNC1>CN(C)C=O>CS(=O)(=O)c1ccc(NC2CCNC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e4fe89c52624b9c8f45d6c2f14b4bb6 | CS(=O)(=O)c1ccc(F)cc1.CSCCN>>CSCCNc1ccc(S(C)(=O)=O)cc1 | CS(=O)(=O)C1=CC=C(C=C1)F.CSCCN.C([O-])([O-])=O.[K+].[K+]>>CS(=O)(=O)C1=CC=C(C=C1)NCCSC | F[c:6]1[cH:7][cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15]1.[CH3:1][S:2][CH2:3][CH2:4][NH2:5]>>[CH3:1][S:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15]1 | CS(=O)(=O)c1ccc(F)cc1.CSCCN | CSCCNc1ccc(S(C)(=O)=O)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 47.4 | [{"value": 47.4, "product": "CS(=O)(=O)C1=CC=C(C=C1)NCCSC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 12 | HOUR | To 8.28 g (47.52 mmol) of 4-fluorophenyl methyl sulfone dissloved in 20 mL DMF was added 5.20 g (57.03 mmol) of 2-(methylthio)ethyl amine (1.2 eq.), followed by 13.13 g (95.04 mmol, 2 eq.) potassium carbonate. The mixture was heated to 65° C. and stirred for 12 h. Upon cooling to room temperature, the mixture was parti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CN(C)C=O | 65 | 12 | CS(=O)(=O)c1ccc(F)cc1.CSCCN>CN(C)C=O>CSCCNc1ccc(S(C)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9a4faf2fd423406690350473b80690da | CSc1ccc(N)cc1.O=Cc1cccnc1>>CSc1ccc(NCc2ccccn2)cc1 | CSC1=CC=C(N)C=C1.N1=CC(=CC=C1)C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>N1=C(C=CC=C1)CNC1=CC=C(C=C1)SC | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:15][cH:16]1.O=[CH:8][c:9]1[cH:10][cH:11][cH:12][n:14][cH:13]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[cH:15][cH:16]1 | CSc1ccc(N)cc1.O=Cc1cccnc1 | CSc1ccc(NCc2ccccn2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | fb13e17b0809d637ca013fb076793c3fb91597084725989cb0aac9b769474ee4 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(NCc2ccccn2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[cH;D2;+0:5]:[n;H0;D2;+0:6]:[cH;D2;+0:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[cH;D2;+0:5]:[cH;D2;+0:7]:[n;H0;D2;+0:6]:1):[c:11] | 100 | [{"value": 100.0, "product": "N1=C(C=CC=C1)CNC1=CC=C(C=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To 2.0 mL (16.07 mmol) of 4-(methylthio)aniline dissolved in 25 mL dichloromethane was added 1.52 mL (16.07 mmol) 3-pyridinecarboxaldehyde, followed by 5.11 g (24.11 mmol) sodium triacetoxyborohydride. The mixture was stirred at room temperature for 4 h, partitioned between EtOAc and brine, dried over MgSO4 and concent... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | Other | ClCCl | null | 4 | CSc1ccc(N)cc1.O=Cc1cccnc1>ClCCl>CSc1ccc(NCc2ccccn2)cc1 |
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