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-0387783899c642a8b7eb4ba379bcdf5d | ord-c1e4715ed61c463392456f127089a013 | CCCCC12CCC(=O)C(Br)=C1c1ccc(O)cc1C2.CCCCCC>>C=C1CCC2(CCCC)Cc3cc(O)ccc3C2=C1Br | BrC=1C(CCC2(CC3=CC(=CC=C3C12)O)CCCC)=O.[Li]CCCC.CCCCCC>>BrC=1C(CCC2(CC3=CC(=CC=C3C12)O)CCCC)=C | O=[C:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][c:11]3[cH:12][c:13]([OH:14])[cH:15][cH:16][c:17]3[C:18]2=[C:19]1[Br:20].CCCCC[CH3:1]>>[CH2:1]=[C:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][c:11]3[cH:12][c:13]([OH:14])[cH:15][cH:16][c:17]3[C:18]2=[C:19]1[Br:20] | CCCCC12CCC(=O)C(Br)=C1c1ccc(O)cc1C2.CCCCCC | C=C1CCC2(CCCC)Cc3cc(O)ccc3C2=C1Br | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | O1CCCC1 | C-C Coupling | OtherReaction | 73dd4b4de03e44885902962d344ae12b8d61100cb66e2d30aaa505f073a7553b | 93d1d0c14c74e7b67ee3b36f962bbc71783135eee73a676c6ddf9dcb58a45254 | C=C1C=C2c3ccccc3CC2CC1 | C-C-C-C-C-[CH3;D1;+0:1].O=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6](=[C:7]-1-[Br;D1;H0:8])-[c:9]>>[Br;D1;H0:8]-[C:7]1=[C:6](-[c:9])-[C:5]-[C:4]-[C:3]-[C;H0;D3;+0:2]-1=[CH2;D1;+0:1] | null | [] | 0 | CELSIUS | 10 | MINUTE | A suspension of methyltriphenylphosphonium bromide (373 mg, 1.04 mmol) in anhydrous tetrahydrofuran (2 mL) was cooled in an ice bath and stirred under a nitrogen atmosphere while 2.5 N nBuLi in hexane (0.36 mL, 0.90 mmol) was added by syringe. The mixture was stirred at 0° C. for 10 minutes to complete formation of the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Vinyl | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1 | 0 | 0.166667 | CCCCC12CCC(=O)C(Br)=C1c1ccc(O)cc1C2.CCCCCC>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1>C=C1CCC2(CCCC)Cc3cc(O)ccc3C2=C1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e977cc0a97344407890f175b08eabeec | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)cc1C2 | BrC=1C(CCC2(CC3=CC(=CC=C3C12)OC)CCCC)=O.[Cu]C#N>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C#N)OC | Br[C:10]1=[C:13]2[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8]1=[O:9])[CH2:22][c:21]1[c:14]2[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]#[N:12])=[C:13]1[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]1[CH2:22]2 | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2 | CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)cc1C2 | null | null | CN1C(CCC1)=O | Miscellaneous | OtherReaction | 9adadf535edd63596f40811ded4b5d76fe0b83c469549ed7abf606d845021290 | 8953536f7fe46a44d657de6166386d42d9afab94586603b5dca76fc653fbf47b | O=C1C=C2c3ccccc3CC2CC1 | Br-[C;H0;D3;+0:1](=[C:2](-[C:3])-[c:4])-[C:5](=[O;D1;H0:6])-[C:7]>>[C:3]-[C:2](=[C;H0;D3;+0:1](-[C:8]#[N;D1;H0:9])-[C:5](=[O;D1;H0:6])-[C:7])-[c:4] | 81 | [{"value": 81.0, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C#N)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | A solution of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg, 0.138 mmol) in anhydrous 1-methyl-2-pyrrolidinone (0.276 mL) was treated with copper(I) cyanide (25 mg, 0.275 mmol). The resulting mixture was stirred under a nitrogen atmosphere and heated in an oil bath at 160° C. for 40 minutes. Th... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide | Ketone.Nitrile | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | Br- | CN1C(CCC1)=O | 160 | null | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2>CN1C(CCC1)=O>CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29b5c03d6765413ea7a1f79ffdd37133 | CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(C#N)=C1c1ccc(O)cc1C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C#N)OC.Cl.N1=CC=CC=C1>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C#N)O | C[O:18][c:17]1[cH:16][cH:15][c:14]2[c:20]([cH:19]1)[CH2:21][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]#[N:12])=[C:13]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]#[N:12])=[C:13]1[c:14]1[cH:15][cH:16][c:17]([OH:18])[cH:19][c:20]1[CH2:21]2 | CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)cc1C2 | CCCCC12CCC(=O)C(C#N)=C1c1ccc(O)cc1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 192.5 | CELSIUS | null | null | A mixture of 9a-butyl-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (17 mg) and pyridine hydrochloride (2 g) was placed under a nitrogen atmosphere and heated in an oil bath at 190-195° C. for 1 hour. After cooling to room temperature, the mixture was partitioned between EtOAc (20 ml) and water (30 mL). The or... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | null | 192.5 | null | CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(C#N)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38f635a0ee364faa8595c22f5d4de8f8 | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2.c1ccc([CH2][Sn]23[CH2]CCN(CC[CH2]2)CC[CH2]3)cc1>>CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(OC)cc1C2 | BrC=1C(CCC2(CC3=CC(=CC=C3C12)OC)CCCC)=O.C(C1=CC=CC=C1)[Sn]12CCCN(CCC1)CCC2>>C(C1=CC=CC=C1)C=1C(CCC2(CC3=CC(=CC=C3C12)OC)CCCC)=O | Br[C:10]1=[C:18]2[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8]1=[O:9])[CH2:27][c:26]1[c:19]2[cH:20][cH:21][c:22]([O:23][CH3:24])[cH:25]1.C1CN2CC[CH2][Sn]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)([CH2]1)[CH2]CC2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH2:11][c:12]3[c... | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2.c1ccc([CH2][Sn]23[CH2]CCN(CC[CH2]2)CC[CH2]3)cc1 | CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(OC)cc1C2 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_benzyl | 3021b6ee7125eedf347f194421a4ef6415260c3f4a43f20fe0cf50f76c5c60f3 | 9ee104fc2d9c1fefe82f5ea62791da6f9a31f1bd9f50dea4348bdecc37d4a644 | O=C1CCC2Cc3ccccc3C2=C1Cc1ccccc1 | Br-[C;H0;D3;+0:1](=[C:2](-[C:3])-[c:4])-[C:5](=[O;D1;H0:6])-[C:7].[c:8]:[c:9](-[CH2;D2;+0:10]-[Sn]12-[CH2]-C-C-N(-C-C-[CH2]-1)-C-C-[CH2]-2):[c:11]>>[C:3]-[C:2](=[C;H0;D3;+0:1](-[CH2;D2;+0:10]-[c:9](:[c:8]):[c:11])-[C:5](=[O;D1;H0:6])-[C:7])-[c:4] | 95 | [{"value": 95.0, "product": "C(C1=CC=CC=C1)C=1C(CCC2(CC3=CC(=CC=C3C12)OC)CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29.6 mg, 0.0847 mmol), 5-benzyl-1-aza-5-stanna-bicyclo[3.3.3]undecane (38.5 mg, 85% weight pure, 0.0935 mmol), and Pd(PPh3)4 (9.8 mg, 0.00848 mmol) in anhydrous toluene (1.3 mL) was degassed, placed under a nitrogen atmosphere, stirred, and h... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ketone.Tertiary amine.Tin | Ketone | C1=C2c3ccccc3CC2CCC1.C1CN2CC[CH2][Sn]([CH2]1)[CH2]CC2 | C1=C2c3ccccc3CC2CCC1 | c1ccccc1.C1=C2c3ccccc3CC2CCC1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | 100 | null | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2.c1ccc([CH2][Sn]23[CH2]CCN(CC[CH2]2)CC[CH2]3)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(OC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-704e1bcd500a470491743a4b68c37bf0 | CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(O)cc1C2 | C(C1=CC=CC=C1)C=1C(CCC2(CC3=CC(=CC=C3C12)OC)CCCC)=O.B(Br)(Br)Br>>C(C1=CC=CC=C1)C=1C(CCC2(CC3=CC(=CC=C3C12)O)CCCC)=O | C[O:23][c:22]1[cH:21][cH:20][c:19]2[c:25]([cH:24]1)[CH2:26][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)=[C:18]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)=[C:18]... | CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(OC)cc1C2 | CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(O)cc1C2 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1CCC2Cc3ccccc3C2=C1Cc1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3.5 | HOUR | A solution of 4-benzyl-9a-butyl-7-methoxy-1,2,9,9a-tetrahydrofluoren-3-one (25.9 mg, 0.718 mmol) in anhydrous CH2Cl2 (1.2 mL) was cooled in a dry ice-acetone bath and stirred under a nitrogen atmosphere while 1M BBr3 in CH2Cl2 (0.215 mL, 0.215 mmol) was added dropwise by syringe. The cooling bath was removed and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1=C2c3ccccc3CC2CCC1 | Other | C(Cl)Cl | null | 3.5 | CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(OC)cc1C2>C(Cl)Cl>CCCCC12CCC(=O)C(Cc3ccccc3)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3dd93824a4984141a072324890d98328 | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(OCOC)cc1>>CCCCC12CCC(=O)C(c3ccc(OCOC)cc3)=C1c1ccc(OC)cc1C2 | BrC=1C(CCC2(CC3=CC(=CC=C3C12)OC)CCCC)=O.C(CCC)[Sn](C1=CC=C(C=C1)OCOC)(CCCC)CCCC>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OCOC)OC | Br[C:10]1=[C:21]2[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8]1=[O:9])[CH2:30][c:29]1[c:22]2[cH:23][cH:24][c:25]([O:26][CH3:27])[cH:28]1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][O:17][CH3:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10... | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(OCOC)cc1 | CCCCC12CCC(=O)C(c3ccc(OCOC)cc3)=C1c1ccc(OC)cc1C2 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | 034107d4fe65a24d8b46c36ee84093572edbd96657c78798636ee8f3eb50d7b1 | 0538de7208f7c4515088af2db60bef2f5ed1a90c393cce7cf4a07985b831073d | O=C1CCC2Cc3ccccc3C2=C1c1ccccc1 | Br-[C;H0;D3;+0:1](=[C:2](-[C:3])-[c:4])-[C:5](=[O;D1;H0:6])-[C:7].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[C:3]-[C:2](=[C;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[C:5](=[O;D1;H0:6])-[C:7])-[c:4] | 84.5 | [{"value": 84.5, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OCOC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 22 | HOUR | A mixture of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (800 mg, 2.29 mmol), Pd(PPh3)4 (132 mg, 0.114 mmol), and tributyl-(4-methoxymethoxy-phenyl)-stannane (1.174 g, 2.75 mmol) in anhydrous toluene (11.5 mL) was placed under a nitrogen atmosphere and heated with stirring in an oil bath at 100° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ketone.Tin | Ketone | C1=C2c3ccccc3CC2CCC1.c1ccccc1 | c1ccccc1.C1=C2c3ccccc3CC2CCC1 | c1ccccc1.C1=C2c3ccccc3CC2CCC1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | 100 | 22 | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)cc1C2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(OCOC)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>CCCCC12CCC(=O)C(c3ccc(OCOC)cc3)=C1c1ccc(OC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e877446746d40fd8d3411e8cf355c24 | CCCCC12CCC(=O)C(c3ccc(OCOC)cc3)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OCOC)OC.Cl>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)O)OC | COC[O:15][c:14]1[cH:13][cH:12][c:11]([C:10]2=[C:18]3[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8]2=[O:9])[CH2:27][c:26]2[c:19]3[cH:20][cH:21][c:22]([O:23][CH3:24])[cH:25]2)[cH:17][cH:16]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]3)... | CCCCC12CCC(=O)C(c3ccc(OCOC)cc3)=C1c1ccc(OC)cc1C2 | CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2 | null | null | CO.CCOC(=O)C | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | O=C1CCC2Cc3ccccc3C2=C1c1ccccc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 108.6 | [{"value": 92.0, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 108.6, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A suspension of 9a-butyl-7-methoxy-4-(4-methoxymethoxy-phenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (813 mg, 2 mmol) in methanol (12 mL) was warmed in an oil bath at 60° C. and treated with aqueous 2N HCl (4 mL). The resulting mixture was stirred and heated at 60° C. for two hours, then cooled to room temperature and e... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | c1ccccc1.C1=C2c3ccccc3CC2CCC1 | HO- | CO.CCOC(=O)C | 60 | null | CCCCC12CCC(=O)C(c3ccc(OCOC)cc3)=C1c1ccc(OC)cc1C2>CO.CCOC(=O)C>CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a4333548b494637b07c329108b8dcf4 | CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2.ClCCN1CCCCC1>>CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(OC)cc1C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)O)OC.C([O-])([O-])=O.[Cs+].[Cs+].Cl.ClCCN1CCCCC1>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OCCN1CCCCC1)OC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:24][cH:25]3)=[C:26]1[c:27]1[cH:28][cH:29][c:30]([O:31][CH3:32])[cH:33][c:34]1[CH2:35]2.Cl[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=... | CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2.ClCCN1CCCCC1 | CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(OC)cc1C2 | null | null | CCOC(=O)C.CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1CCC2Cc3ccccc3C2=C1c1ccc(OCCN2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 96.3 | [{"value": 96.0, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OCCN1CCCCC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OCCN1CCCCC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of crude 9a-butyl-4-(4-hydroxyphenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (787 mg, approx. 2 mmol), cesium carbonate (1.564 g, 4.8 mmol), and 1-(2-chloroethyl)-piperidine monohydrochloride (442 mg, 2.4 mmol) in acetone (5 mL) was stirred and heated in an oil bath at 60° C. for 4 hours. After coolin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]CC1.C1=C2c3ccccc3CC2CCC1 | HCl | CCOC(=O)C.CC(=O)C | 60 | null | CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2.ClCCN1CCCCC1>CCOC(=O)C.CC(=O)C>CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(OC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c98b40057f6544e1a3bf91358949001b | CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(O)cc1C2 | CCS.[Al+3].[Cl-].[Cl-].[Cl-].Cl.C(=O)(O)[O-].[Na+].C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OCCN1CCCCC1)OC>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OCCN1CCCCC1)O | C[O:31][c:30]1[cH:29][cH:28][c:27]2[c:33]([cH:32]1)[CH2:34][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][N:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)[cH:24][cH:25]3)=[C:26]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:... | CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(OC)cc1C2 | CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(O)cc1C2 | null | null | CCOC(=O)C.O.O1CCCC1.C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1CCC2Cc3ccccc3C2=C1c1ccc(OCCN2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | 3 | MINUTE | An ice-cold solution of 9a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)-ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one (85 mg, 96% weight pure, 0.172 mmol) in anhydrous CH2Cl2 (1.2 mL) was placed under a nitrogen atmosphere and treated with EtSH (0.055 mL, 0.743 mmol). The resulting solution was added by syringe to AlC... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.C1=C2c3ccccc3CC2CCC1 | Other | CCOC(=O)C.O.O1CCCC1.C(Cl)Cl | 0 | 0.05 | CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(OC)cc1C2>CCOC(=O)C.O.O1CCCC1.C(Cl)Cl>CCCCC12CCC(=O)C(c3ccc(OCCN4CCCCC4)cc3)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97264f6f2909414bad48b9659123da7c | CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(O)cc1C2 | CC(C)S.C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)O)OC.[Al+3].[Cl-].[Cl-].[Cl-].Cl>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)O)O | C[O:23][c:22]1[cH:21][cH:20][c:19]2[c:25]([cH:24]1)[CH2:26][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]3)=[C:18]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]3)=[C:18]... | CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2 | CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(O)cc1C2 | null | null | CCOC(=O)C.C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1CCC2Cc3ccccc3C2=C1c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | null | null | An ice-cold solution of 9a-butyl-4-(4-hydroxy-phenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29 mg, 0.08 mmol) in anhydrous CH2Cl2 (1 mL) was added to AlCl3 (96 mg, 0.72 mmol) contained in an ice cooled flask. The mixture was stirred at 0° C. under a nitrogen atmosphere and treated with 2-propanethiol (0.056 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1=C2c3ccccc3CC2CCC1 | Other | CCOC(=O)C.C(Cl)Cl | 0 | null | CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(OC)cc1C2>CCOC(=O)C.C(Cl)Cl>CCCCC12CCC(=O)C(c3ccc(O)cc3)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-adef68c798704d7e9c50dde96c01cffe | CCCCC12CCC(=O)C(c3ccc(OS(=O)(=O)C(F)(F)F)cc3)=C1c1ccc(OC)cc1C2.CCC[CH2][Sn](/[CH]=C/C(=O)OC)([CH2]CCC)[CH2]CCC>>CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)OC)cc3)=C1c1ccc(OC)cc1C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)OC.C(CCC)[Sn](/C=C/C(=O)OC)(CCCC)CCCC.[Cl-].[Li+]>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)/C=C/C(=O)OC)OC | O=S(=O)(O[c:14]1[cH:13][cH:12][c:11]([C:10]2=[C:23]3[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8]2=[O:9])[CH2:32][c:31]2[c:24]3[cH:25][cH:26][c:27]([O:28][CH3:29])[cH:30]2)[cH:22][cH:21]1)C(F)(F)F.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)/[CH:15]=[CH:16]/[C:17](=[O:18])[O:19][CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]... | CCCCC12CCC(=O)C(c3ccc(OS(=O)(=O)C(F)(F)F)cc3)=C1c1ccc(OC)cc1C2.CCC[CH2][Sn](/[CH]=C/C(=O)OC)([CH2]CCC)[CH2]CCC | CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)OC)cc3)=C1c1ccc(OC)cc1C2 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C=O)C | C-C Coupling | Stille reaction_other OTf | b776466232e20bae8fda61cba5b8d23b6dd6bb33b4d0cbf8dc63285327f4decc | 46de4d1253710b3a7d4f46887df51b2ccba46e0a9427959558bd6f96ec8696eb | O=C1CCC2Cc3ccccc3C2=C1c1ccccc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)/[CH;D2;+0:1]=[C:2]/[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])/[C:2]=[CH;D2;+0:1]/[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | 96.4 | [{"value": 96.4, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)/C=C/C(=O)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 9a-butyl-7-methoxy-4-[4-(trifluoromethane-sulfonyloxy)-phenyl]-1,2,9,9a-tetrahydro-3H-fluoren-3-one (98.9 mg, 0.2 mmol), methyl (E)-3-tributylstannyl-acrylate (112.5 mg, 0.3 mmol) and lithium chloride (25.4 mg, 0.6 mmol) in anhydrous dimethylformamide (1.0 mL) was purged with nitrogen and treated with bis(... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Tin | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1=C2c3ccccc3CC2CCC1 | TfOH.HO-.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C | 90 | null | CCCCC12CCC(=O)C(c3ccc(OS(=O)(=O)C(F)(F)F)cc3)=C1c1ccc(OC)cc1C2.CCC[CH2][Sn](/[CH]=C/C(=O)OC)([CH2]CCC)[CH2]CCC>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C>CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)OC)cc3)=C1c1ccc(OC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80bc9e40f544428a8eacc0993ff83f3d | CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)OC)cc3)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)O)cc3)=C1c1ccc(O)cc1C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)/C=C/C(=O)OC)OC.Cl.N1=CC=CC=C1.Cl.N1=CC=CC=C1>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C1=CC=C(C=C1)/C=C/C(=O)O)O | C[O:19][C:17](/[CH:16]=[CH:15]/[c:14]1[cH:13][cH:12][c:11]([C:10]2=[C:22]3[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8]2=[O:9])[CH2:30][c:29]2[c:23]3[cH:24][cH:25][c:26]([O:27]C)[cH:28]2)[cH:21][cH:20]1)=[O:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([c:11]3[cH:12][cH:13][c:14](/... | CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)OC)cc3)=C1c1ccc(OC)cc1C2 | CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)O)cc3)=C1c1ccc(O)cc1C2 | null | null | null | Deprotection | OtherReaction | 4cea9c1cf4071f9c3a5e0d042ee7e87c9888ee05636b0c5b9dfd162b490d7fb6 | 707aece9d1d6de1fa508344f68d9f46b61d18785c603f5e19232e661c94aa284 | O=C1CCC2Cc3ccccc3C2=C1c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4]=[C:5]/[c:6].C-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])/[C:4]=[C:5]/[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | 190 | CELSIUS | 2 | HOUR | A mixture of methyl (2E)-3-[4-(9a-butyl-7-methoxy-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-4-yl)phenyl]-2-propenoate (60 mg, 92% weight pure, 0.128 mmol) and pyridine hydrochloride (741 mg, 6.41 mmol) was placed under a nitrogen atmosphere, heated in an oil bath at 190° C., and stirred. The reaction flask was periodically ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid.Aromatic alcohol | null | null | c1ccccc1.C1=C2c3ccccc3CC2CCC1 | Other | null | 190 | 2 | CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)OC)cc3)=C1c1ccc(OC)cc1C2>>CCCCC12CCC(=O)C(c3ccc(/C=C/C(=O)O)cc3)=C1c1ccc(O)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea29327def8e4fbe9589fa709757dc0d | CCCCC1Cc2cc(OC)ccc2C1=O.NC(=O)CCC(=O)NBr>>CCCCC1Cc2c(ccc(OC)c2Br)C1=O | C(CCC)C1C(C2=CC=C(C=C2C1)OC)=O.BrNC(CCC(=O)N)=O>>BrC1=C2CC(C(C2=CC=C1OC)=O)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]2)[C:16]1=[O:17].NC(=O)CCC(=O)N[Br:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]2[Br:15])[C:16]1=[O:17] | CCCCC1Cc2cc(OC)ccc2C1=O.NC(=O)CCC(=O)NBr | CCCCC1Cc2c(ccc(OC)c2Br)C1=O | null | null | CCOC(=O)C.CN(C=O)C | Functional Group Interconversion | Bromination | 7edae5a3fcd7108ed4ae8780d7a956cfe7b0b617ac7185cf26b15e1960b63e69 | f0c47cfd4d5d7957b01579ba4ffee0b3c64b05d7411e52b95a7ea89b926af55c | O=C1CCc2ccccc21 | N-C(=O)-C-C-C(=O)-N-[Br;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](:[c:7]-[C:8]=[O;D1;H0:9])-[C:10]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](:[c:7]-[C:8]=[O;D1;H0:9])-[C:10] | 3 | [{"value": 3.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | A solution of 2-butyl-5-methoxy-1-indanone (1.869 g, 8.56 mmol) in anhydrous dimethylformamide (8.6 mL) was treated with N-bromosuccinamide (1.676 g, 9.42 mmol). The resulting mixture was stirred under a nitrogen atmosphere and at room temperature for 14 hours, and then heated in an oil bath at 50° C. for 4 hours. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide | Aromatic halide | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | CCOC(=O)C.CN(C=O)C | null | 14 | CCCCC1Cc2cc(OC)ccc2C1=O.NC(=O)CCC(=O)NBr>CCOC(=O)C.CN(C=O)C>CCCCC1Cc2c(ccc(OC)c2Br)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16948c22a2304cf0b6f9a96bed7293bb | CCCCC1Cc2c(ccc(OC)c2Br)C1=O.[CH3][Sn]([CH3])([CH3])[CH3]>>CCCCC1Cc2c(ccc(OC)c2C)C1=O | BrC1=C2CC(C(C2=CC=C1OC)=O)CCCC.[Li+].[Cl-].C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Sn](C)(C)(C)C>>C(CCC)C1C(C2=CC=C(C(=C2C1)C)OC)=O | Br[c:14]1[c:7]2[c:8]([cH:9][cH:10][c:11]1[O:12][CH3:13])[C:16](=[O:17])[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2.[CH3][Sn]([CH3])([CH3])[CH3:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]2[CH3:15])[C:16]1=[O:17] | CCCCC1Cc2c(ccc(OC)c2Br)C1=O.[CH3][Sn]([CH3])([CH3])[CH3] | CCCCC1Cc2c(ccc(OC)c2C)C1=O | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | O.CN(C=O)C | C-C Coupling | Stille reaction_other | 5f823a1f140c9788378795502c3f73833375dcf595f9e9d5f6b25610b5e941bf | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=C1CCc2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2](-[#8:3]):[c:4]):[c:5](:[c:6]-[C:7]=[O;D1;H0:8])-[C:9].[CH3;D1;+0:10]-[Sn](-[CH3])(-[CH3])-[CH3]>>[#8:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[CH3;D1;+0:10]):[c:5](:[c:6]-[C:7]=[O;D1;H0:8])-[C:9] | 496.7 | [{"value": 496.7, "product": "C(CCC)C1C(C2=CC=C(C(=C2C1)C)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 4-bromo-2-butyl-5-methoxy-1-indanone (1.159 g, 3.90 mmol) in anhydrous dimethylformamide (39 mL) was treated with LiCl (455 mg, 10.73 mmol), PPh3 (205 mg, 0.78 mmol), PdCl2(PPh3)2 (205 mg, 0.292 mmol) and Me4Sn (1.08 mL, 7.80 mmol). The mixture was placed under a nitrogen atmosphere, then stirred and heat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O.CN(C=O)C | 100 | null | CCCCC1Cc2c(ccc(OC)c2Br)C1=O.[CH3][Sn]([CH3])([CH3])[CH3]>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O.CN(C=O)C>CCCCC1Cc2c(ccc(OC)c2C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a4993889ca6480cb0bfdfaca22cc970 | C=CC(C)=O.CCCCC1Cc2c(ccc(OC)c2C)C1=O>>CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2C)C1=O | C(=C)C(=O)C.N12CCCCCC2=NCCC1.C(CCC)C1C(C2=CC=C(C(=C2C1)C)OC)=O>>C(CCC)C1(C(C2=CC=C(C(=C2C1)C)OC)=O)CCC(C)=O | [CH2:6]=[CH:7][C:8]([CH3:9])=[O:10].[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:11][c:12]2[c:13]([cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]2[CH3:20])[C:21]1=[O:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([CH2:6][CH2:7][C:8]([CH3:9])=[O:10])[CH2:11][c:12]2[c:13]([cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]2[CH3:20])[C:21]1=[O:22] | C=CC(C)=O.CCCCC1Cc2c(ccc(OC)c2C)C1=O | CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2C)C1=O | null | null | O1CCCC1.CCOCC | C-C Coupling | OtherReaction | c504c0d32586144b6874498db3cc99d4d5bb675e1b2e725385a0386d3f14ac05 | 68a0b2d4768a64505cf15a6dd6bbd75216aef3c50fb86aff9b39341b3e49f06d | O=C1CCc2ccccc21 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH2;D1;+0:5].[C:6]-[C:7]-[CH;D3;+0:8]1-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13]>>[C:6]-[C:7]-[C;H0;D4;+0:8]1(-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[C:2](-[C;D1;H3:1])=[O;D1;H0:3])-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13] | 81.4 | [{"value": 81.4, "product": "C(CCC)C1(C(C2=CC=C(C(=C2C1)C)OC)=O)CCC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | HOUR | Methyl vinyl ketone (MVK, 0.49 mL, 5.9 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.12 mL, 0.8 mmol) were added to a solution of impure 2-butyl-5-methoxy-4-methyl-1-indanone (0.90 g, 3.9 mmol) in anhydrous tetrahydrofuran (THF, 3.9 mL). The resulting solution was stirred at room temperature for 30 hours, then d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Vinyl | Ketone.Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | O1CCCC1.CCOCC | null | 30 | C=CC(C)=O.CCCCC1Cc2c(ccc(OC)c2C)C1=O>O1CCCC1.CCOCC>CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4d098d6e0c64655809c3a2af90167be | CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2C)C1=O>>CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2 | C(CCC)C1(C(C2=CC=C(C(=C2C1)C)OC)=O)CCC(C)=O.C(C)(=O)O.N1CCCC1>>C(CCC)C12CC3=C(C(=CC=C3C2=CC(CC1)=O)OC)C | O=[C:11]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH3:10])[CH2:21][c:20]2[c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]2[CH3:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[CH:10]=[C:11]1[c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]([CH3:19])[c:20]1[CH2:21]2 | CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2C)C1=O | CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2 | null | null | CCOCC.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:7]-[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[CH;D2;+0:11]-[C:10](=[O;D1;H0:12])-[C:9]-[C:8]-2 | 55.5 | [{"value": 55.5, "product": "C(CCC)C12CC3=C(C(=CC=C3C2=CC(CC1)=O)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of impure 2-butyl-5-methoxy-4-methyl-2-(3-oxo-butyl)-1-indanone (0.96 g, 3.17 mmol), acetic acid (0.182 mL, 3.18 mmol) and pyrrolidine (0.265 mL, 3.18 mmol) in anhydrous toluene (15.9 mL) was stirred and heated in an oil bath at 80° C. for 16 hours. After cooling, the reaction mixture was diluted with Et2O (... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | CCOCC.C1(=CC=CC=C1)C | 80 | null | CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2C)C1=O>CCOCC.C1(=CC=CC=C1)C>CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3003665ff944b9aba117505583cfbac | CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2>>CCCCC12CCC(=O)C=C1c1ccc(O)c(C)c1C2 | C(CCC)C12CC3=C(C(=CC=C3C2=CC(CC1)=O)OC)C.B(Br)(Br)Br>>C(CCC)C12CC3=C(C(=CC=C3C2=CC(CC1)=O)O)C | C[O:16][c:15]1[cH:14][cH:13][c:12]2[c:19]([c:17]1[CH3:18])[CH2:20][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[CH:10]=[C:11]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[CH:10]=[C:11]1[c:12]1[cH:13][cH:14][c:15]([OH:16])[c:17]([CH3:18])[c:19]1[CH2:20]2 | CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2 | CCCCC12CCC(=O)C=C1c1ccc(O)c(C)c1C2 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.1 | [{"value": 99.1, "product": "C(CCC)C12CC3=C(C(=CC=C3C2=CC(CC1)=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (28.4 mg, 0.1 mmol) in anhydrous CH2Cl2 (1.7 mL) was stirred under a nitrogen atmosphere and cooled in a dry ice-acetone bath while 1M BBr3 in CH2Cl2 (0.30 mL, 0.3 mmol) was added dropwise by syringe. The cooling bath was removed and the rea... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | C(Cl)Cl | null | 4 | CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2>C(Cl)Cl>CCCCC12CCC(=O)C=C1c1ccc(O)c(C)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f46b74a624d44e92b683ec8f7cb4db6a | BrBr.CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2>>CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(C)c1C2 | BrBr.C(CCC)C12CC3=C(C(=CC=C3C2=CC(CC1)=O)OC)C.C(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>>BrC=1C(CCC2(CC3=C(C(=CC=C3C12)OC)C)CCCC)=O | Br[Br:11].[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[CH:10]=[C:12]1[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([CH3:20])[c:21]1[CH2:22]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([Br:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([CH3:20])[c:21]1[CH2:... | BrBr.CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2 | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(C)c1C2 | null | null | O.C(Cl)Cl | Functional Group Interconversion | Bromination | 73ca391a48874f0a81f3694c6623ffb0a512c874931d8f551485082fa4a0d563 | c7222534d68e666d405fc6d911092ac63e3791780d01400eb414eff6e46c2a54 | O=C1C=C2c3ccccc3CC2CC1 | Br-[Br;H0;D1;+0:1].[C:2]-[C:3](=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[C:7])-[c:8]>>[Br;H0;D1;+0:1]-[C;H0;D3;+0:4](=[C:3](-[C:2])-[c:8])-[C:5](=[O;D1;H0:6])-[C:7] | 89 | [{"value": 89.0, "product": "BrC=1C(CCC2(CC3=C(C(=CC=C3C12)OC)C)CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A mixture of 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (133 mg, 0.468 mmol), CCl4 (0.94 mL), and NaHCO3 (196 mg, 2.333 mmol) was cooled in an ice bath and stirred. Bromine (0.024 mL, 0.467 mmol) was added while stirring and swirling the reaction mixture by hand. A gummy, red precipitate formed du... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HBr | O.C(Cl)Cl | null | 0.083333 | BrBr.CCCCC12CCC(=O)C=C1c1ccc(OC)c(C)c1C2>O.C(Cl)Cl>CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(C)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab9cbb76965644d483935f81bfcf3531 | C=CC(=O)CC.CCCCC1Cc2c(ccc(OC)c2C)C1=O>>CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2C)C1=O | C(CCC)C1C(C2=CC=C(C(=C2C1)C)OC)=O.C(=C)C(=O)CC.N12CCCCCC2=NCCC1.C(=C)C(=O)CC.N12CCCCCC2=NCCC1>>C(CCC)C1(C(C2=CC=C(C(=C2C1)C)OC)=O)CCC(CC)=O | [CH2:6]=[CH:7][C:8](=[O:9])[CH2:10][CH3:11].[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:12][c:13]2[c:14]([cH:15][cH:16][c:17]([O:18][CH3:19])[c:20]2[CH3:21])[C:22]1=[O:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][CH3:11])[CH2:12][c:13]2[c:14]([cH:15][cH:16][c:17]([O:18][CH3:19])[c:20]2[CH3:21... | C=CC(=O)CC.CCCCC1Cc2c(ccc(OC)c2C)C1=O | CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2C)C1=O | null | null | CCOC(=O)C.O1CCCC1 | C-C Coupling | OtherReaction | c504c0d32586144b6874498db3cc99d4d5bb675e1b2e725385a0386d3f14ac05 | 68a0b2d4768a64505cf15a6dd6bbd75216aef3c50fb86aff9b39341b3e49f06d | O=C1CCc2ccccc21 | [C:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH2;D1;+0:5].[C:6]-[C:7]-[CH;D3;+0:8]1-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D4;+0:8]1(-[C:7]-[C:6])-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13] | null | [] | 60 | CELSIUS | 24 | HOUR | A solution of 2-butyl-5-methoxy-4-methyl-1-indanone (100 mg, 0.43 mmol) in tetrahydrofuran (0.43 mL) was treated with ethyl vinyl ketone (EVK, 0.064 mL, 0.646 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.013 mL, 0.086 mmol). The resulting solution was stirred under a nitrogen atmosphere and heated in an oil bat... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Vinyl | Ketone.Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | CCOC(=O)C.O1CCCC1 | 60 | 24 | C=CC(=O)CC.CCCCC1Cc2c(ccc(OC)c2C)C1=O>CCOC(=O)C.O1CCCC1>CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-619e723c7b9e4e91bac3e3dc222ad9ee | CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2C)C1=O>>CCCCC1CC(=O)C(C)=C2c3ccc(OC)c(C)c3CC21 | C(CCC)C1(C(C2=CC=C(C(=C2C1)C)OC)=O)CCC(CC)=O>>C(CCC)C1CC(C(=C2C3=CC=C(C(=C3CC12)C)OC)C)=O | O=[C:11]1[c:12]2[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]([CH3:19])[c:20]2[CH2:21][C:22]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][C:7](=[O:8])[CH2:9][CH3:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][C:7](=[O:8])[C:9]([CH3:10])=[C:11]2[c:12]3[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]([CH3:19])[c:20]3[CH2:21][CH:... | CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2C)C1=O | CCCCC1CC(=O)C(C)=C2c3ccc(OC)c(C)c3CC21 | null | null | CCOC(=O)C.C(C)(=O)O.Cl | C-C Coupling | OtherReaction | c888d527cd34f70db2bbf846edb013cbea97961406b00a885b9ff6fb89e2805c | 6724ccabc3992a670343bf52a7363504b61386c3d76e13c5adf76934d5aec2b7 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C;H0;D4;+0:6]-1(-[CH2;D2;+0:7]-[C:8]-[C:9])-[CH2;D2;+0:10]-[C:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-[C;D1;H3:15]>>[C:9]-[C:8]-[CH2;D2;+0:7]-[CH;D3;+0:10]1-[C:11]-[C:12](=[O;D1;H0:13])-[C;H0;D3;+0:14](-[C;D1;H3:15])=[C;H0;D3;+0:1]2-[CH;D3;+0:6]-1-[C:5]-[c:4]:[c:2]-2:[c:3] | null | [] | 100 | CELSIUS | null | null | A solution of the crude diketone from step 1 in acetic acid (1 mL) and 6N HCl (1 mL) was stirred and heated in an oil bath at 100° C. for 5 hours. After cooling, the reaction mixture was diluted with EtOAc (20 mL), washed with water (10 mL) and brine (10 mL), dried over MgSO4, filtered, and the solvent evaporated under... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | CCOC(=O)C.C(C)(=O)O.Cl | 100 | null | CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2C)C1=O>CCOC(=O)C.C(C)(=O)O.Cl>CCCCC1CC(=O)C(C)=C2c3ccc(OC)c(C)c3CC21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5cbf2f7b75774d3da256736ac277ee13 | CCCCC1CC(=O)C(C)=C2c3ccc(OC)c(C)c3CC21>>CCCCC1CC(=O)C(C)=C2c3ccc(O)c(C)c3CC21 | B(Br)(Br)Br.C(CCC)C1CC(C(=C2C3=CC=C(C(=C3CC12)C)OC)C)=O>>C(CCC)C1CC(C(=C2C3=CC=C(C(=C3CC12)C)O)C)=O | C[O:16][c:15]1[cH:14][cH:13][c:12]2[c:19]([c:17]1[CH3:18])[CH2:20][CH:21]1[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][C:7](=[O:8])[C:9]([CH3:10])=[C:11]21>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][C:7](=[O:8])[C:9]([CH3:10])=[C:11]2[c:12]3[cH:13][cH:14][c:15]([OH:16])[c:17]([CH3:18])[c:19]3[CH2:20][CH:21]12 | CCCCC1CC(=O)C(C)=C2c3ccc(OC)c(C)c3CC21 | CCCCC1CC(=O)C(C)=C2c3ccc(O)c(C)c3CC21 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 4 | HOUR | A solution of 9a butyl-4,8-dimethyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (84 mg, 0.28 mmol) in anhydrous CH2Cl2 (3 mL) was placed under a nitrogen atmosphere, cooled in an acetone-dry ice bath, and treated with 1M BBr3 in CH2Cl2 (1.11 mL, 1.11 mmol). The cooling bath was removed and the reaction mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | C(Cl)Cl | null | 4 | CCCCC1CC(=O)C(C)=C2c3ccc(OC)c(C)c3CC21>C(Cl)Cl>CCCCC1CC(=O)C(C)=C2c3ccc(O)c(C)c3CC21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ea1ea522fe849c09b6b48ecf0c1b923 | CCCCC1Cc2cc(OC)ccc2C1=O.O=C1CCC(=O)N1Cl>>CCCCC1Cc2c(ccc(OC)c2Cl)C1=O | ClN1C(CCC1=O)=O.C(CCC)C1C(C2=CC=C(C=C2C1)OC)=O>>C(CCC)C1C(C2=CC=C(C(=C2C1)Cl)OC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14]2)[C:16]1=[O:17].O=C1CCC(=O)N1[Cl:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]2[Cl:15])[C:16]1=[O:17] | CCCCC1Cc2cc(OC)ccc2C1=O.O=C1CCC(=O)N1Cl | CCCCC1Cc2c(ccc(OC)c2Cl)C1=O | null | null | CCOC(=O)C.CN(C=O)C | Functional Group Interconversion | Chlorination | 810b77391b192e36eecbf89fbd0937a488e789bac7683cb9fabaa7cbc9c32e40 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C1CCc2ccccc21 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](:[c:7]-[C:8]=[O;D1;H0:9])-[C:10]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Cl;H0;D1;+0:1]):[c:6](:[c:7]-[C:8]=[O;D1;H0:9])-[C:10] | 15.4 | [{"value": 15.4, "product": "C(CCC)C1C(C2=CC=C(C(=C2C1)Cl)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | N-Chlorosuccinimide (505 mg, 3.8 mmol) was added to a solution of 2-butyl-5-methoxy-1-indanone (825 mg, 3.8 mmol) in anhydrous dimethylformamide (3.8 mL) and the resulting solution was stirred under nitrogen and at room temperature overnight. The reaction mixture was diluted with EtOAc (50 mL), washed with 5% aqueous N... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CCC2.C1CCNC1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | CCOC(=O)C.CN(C=O)C | null | 8 | CCCCC1Cc2cc(OC)ccc2C1=O.O=C1CCC(=O)N1Cl>CCOC(=O)C.CN(C=O)C>CCCCC1Cc2c(ccc(OC)c2Cl)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d1cb4b3435da4997860140228da64a57 | C=CC(=O)CC.CCCCC1Cc2c(ccc(OC)c2Cl)C1=O>>CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2Cl)C1=O | C(CCC)C1C(C2=CC=C(C(=C2C1)Cl)OC)=O.C(=C)C(=O)CC.N12CCCCCC2=NCCC1>>C(CCC)C1(C(C2=CC=C(C(=C2C1)Cl)OC)=O)CCC(CC)=O | [CH2:6]=[CH:7][C:8](=[O:9])[CH2:10][CH3:11].[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:12][c:13]2[c:14]([cH:15][cH:16][c:17]([O:18][CH3:19])[c:20]2[Cl:21])[C:22]1=[O:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][CH3:11])[CH2:12][c:13]2[c:14]([cH:15][cH:16][c:17]([O:18][CH3:19])[c:20]2[Cl:21])... | C=CC(=O)CC.CCCCC1Cc2c(ccc(OC)c2Cl)C1=O | CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2Cl)C1=O | null | null | CCOC(=O)C.O1CCCC1 | C-C Coupling | OtherReaction | c504c0d32586144b6874498db3cc99d4d5bb675e1b2e725385a0386d3f14ac05 | 68a0b2d4768a64505cf15a6dd6bbd75216aef3c50fb86aff9b39341b3e49f06d | O=C1CCc2ccccc21 | [C:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH2;D1;+0:5].[C:6]-[C:7]-[CH;D3;+0:8]1-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D4;+0:8]1(-[C:7]-[C:6])-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13] | 93.9 | [{"value": 93.9, "product": "C(CCC)C1(C(C2=CC=C(C(=C2C1)Cl)OC)=O)CCC(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of 2-butyl-4-chloro-5-methoxy-1-indanone (200 mg, 0.79 mmol) in anhydrous tetrahydrofuran (0.8 mL) was placed under a nitrogen atmosphere and treated with ethyl vinyl ketone (0.118 mL, 1.19 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (0.024 mL, 0.158 mmol). The resulting solution was stirred and hea... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Vinyl | Ketone.Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | CCOC(=O)C.O1CCCC1 | 60 | null | C=CC(=O)CC.CCCCC1Cc2c(ccc(OC)c2Cl)C1=O>CCOC(=O)C.O1CCCC1>CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2Cl)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6121252028114c99b582eb81c90945f8 | CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2Cl)C1=O>>CCCCC12CCC(=O)C(C)=C1c1ccc(OC)c(Cl)c1C2 | C(CCC)C1(C(C2=CC=C(C(=C2C1)Cl)OC)=O)CCC(CC)=O>>C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C)OC)Cl | O=[C:12]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][CH3:11])[CH2:22][c:21]2[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]2[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([Cl:20])[c:21]1[CH2:2... | CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2Cl)C1=O | CCCCC12CCC(=O)C(C)=C1c1ccc(OC)c(Cl)c1C2 | null | null | CCOC(=O)C.C(C)(=O)O.Cl | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[C;D1;H3:13]>>[C:7]-[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[C;H0;D3;+0:12](-[C;D1;H3:13])-[C:10](=[O;D1;H0:11])-[C:9]-[C:8]-2 | 60.6 | [{"value": 60.6, "product": "C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 2 | DAY | A solution of 2-butyl-4-chloro-5-methoxy-2-(3-oxo-pentyl)-1-indanone (250 mg, 0.74 mmol) in acetic acid (2 mL) was diluted with 6N aqueous HCl (2 mL). The resulting mixture was stirred and heated in an oil bath at 90° C. for 18 hours, then kept at room temperature for 2 days. The mixture was diluted with EtOAc (20 mL),... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | CCOC(=O)C.C(C)(=O)O.Cl | 90 | 48 | CCCCC1(CCC(=O)CC)Cc2c(ccc(OC)c2Cl)C1=O>CCOC(=O)C.C(C)(=O)O.Cl>CCCCC12CCC(=O)C(C)=C1c1ccc(OC)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e71cb2ebf2654d4ba5d844ad5a953bf8 | CCCCC12CCC(=O)C(C)=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C)=C1c1ccc(O)c(Cl)c1C2 | C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C)OC)Cl.Cl.N1=CC=CC=C1>>C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C)O)Cl | C[O:17][c:16]1[cH:15][cH:14][c:13]2[c:20]([c:18]1[Cl:19])[CH2:21][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([OH:17])[c:18]([Cl:19])[c:20]1[CH2:21]2 | CCCCC12CCC(=O)C(C)=C1c1ccc(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(C)=C1c1ccc(O)c(Cl)c1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 195 | CELSIUS | null | null | A mixture of 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (36.6 mg) and pyridine hydrochloride (2.66) was stirred and heated in an oil bath at 190-200° C. for 80 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (20 mL) and water (30 mL). The organic phas... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | null | 195 | null | CCCCC12CCC(=O)C(C)=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C)=C1c1ccc(O)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3748d7f80bee42f6a817e582c782f3ac | CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2.COCCl>>CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2 | C(C)(C)N(C(C)C)CC.COCCl.C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)O.C(C)(C)N(C(C)C)CC.COCCl>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OCOC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:21][c:22]1[CH2:23]2.Cl[CH2:18][O:19][CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][O:19][CH3:20])[cH:2... | CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2.COCCl | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2 | null | null | CCOC(=O)C.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | O=C1C=C2c3ccccc3CC2CC1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 75.4 | [{"value": 75.4, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5.5 | HOUR | A solution of 9a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (5.30 g, 21 mmol) in anhydrous dimethylformamide (50 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated successively with N,N-diisopropyl-ethylamine (10.5 mL, 60 mmol) and chloromethyl methyl ether (3.45 mL, 41 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | C1=C2c3ccccc3CC2CCC1 | HCl | CCOC(=O)C.CN(C=O)C | null | 5.5 | CCCCC12CCC(=O)C(C)=C1c1ccc(O)cc1C2.COCCl>CCOC(=O)C.CN(C=O)C>CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95e98eaea1a94f0591c92261b6aa3074 | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.CI>>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2 | IC.C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OCOC.[Li+].CC(C)[N-]C(C)C.[NH4+].[Cl-].C(=O)=O.CC(=O)C>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)C)=O)C)OCOC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1=[C:18]([CH3:19])[C:20](=[O:21])[CH2:22][CH2:24]2.I[CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1=[C:18]([CH3:19])[C:20](=... | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.CI | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2 | null | null | C1CCOC1.CCOC(=O)C | C-C Coupling | Methylation with MeI_secondary | 5ad82e3a335a3b61932305272f1c5165265cfa3d334bee0a6b6bb8d630fc2131 | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C1C=C2c3ccccc3CC2CC1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3]1=[C:4](-[c:5])-[C:6]-[C:7]-[CH2;D2;+0:8]-[C:9]-1=[O;D1;H0:10]>>[C;D1;H3:2]-[C:3]1=[C:4](-[c:5])-[C:6]-[C:7]-[CH;D3;+0:8](-[CH3;D1;+0:1])-[C:9]-1=[O;D1;H0:10] | null | [] | 0 | CELSIUS | 30 | MINUTE | A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (162 mg, 0.52 mmol) in anhydrous THF (2.5 mL) was cooled in an ice bath and stirred under a nitrogen atmosphere while 0.4M LDA in THF (1.55 mL, 0.62 mmol) was added by syringe. After stirring at 0° C. for 30 minutes, the solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HI | C1CCOC1.CCOC(=O)C | 0 | 0.5 | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.CI>C1CCOC1.CCOC(=O)C>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62b89ac0566e47018eebadecdf9ff60c | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2.CCCI>>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(CCC)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)C)=O)C)OCOC.[Li+].CC(C)[N-]C(C)C.ICCC>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)(CCC)C)=O)C)OCOC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1=[C:18]([CH3:19])[C:20](=[O:21])[CH:22]([CH3:23])[CH2:27]2.I[CH2:24][CH2:25][CH3:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1... | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2.CCCI | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(CCC)C2 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 2d1eeb1a4c757ce03bc2ed50cc7f2b79e982da0747960d20374c2a44a78b6ea2 | 836e0f77354d9f44b98dde88e343d5cebbf81f14d452aa51d1e50ec699999492 | O=C1C=C2c3ccccc3CC2CC1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C;D1;H3:4]-[C:5]1=[C:6](-[c:7])-[C:8]-[C:9]-[CH;D3;+0:10](-[C;D1;H3:11])-[C:12]-1=[O;D1;H0:13]>>[C;D1;H3:4]-[C:5]1=[C:6](-[c:7])-[C:8]-[C:9]-[C;H0;D4;+0:10](-[C;D1;H3:11])(-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3])-[C:12]-1=[O;D1;H0:13] | null | [] | -78 | CELSIUS | null | null | A solution of (2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (110 mg, 0.34 mmol) in anhydrous THF (1.5 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated with 0.4M LDA in THF (1 mL, 0.4 mmol). After stirring at 0° C. for 30 minutes, the solution was c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HI | C1CCOC1 | -78 | null | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2.CCCI>C1CCOC1>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(CCC)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58e5100c1cca454d952bc1df3a46b49a | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(CCC)C2>>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(C)(CCC)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)(CCC)C)=O)C)OCOC.Cl>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)(CCC)C)=O)C)O | COC[O:10][c:9]1[cH:8][c:7]2[c:13]([cH:12][cH:11]1)[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[C:19]([CH3:20])([CH2:21][CH2:22][CH3:23])[CH2:24][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]3[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[C:19](... | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(CCC)C2 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(C)(CCC)C2 | null | null | CO | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | O=C1C=C2c3ccccc3CC2CC1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 85 | CELSIUS | null | null | A solution of (2SR,9aRS)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-2-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (40 mg, 0.11 mmol) in methanol (approx. 0.5-1 mL) was placed under a nitrogen atmosphere and treated with 2N aqueous HCl (0.165 mL, 0.37 mmol). The resulting yellow solution was stirred and heated in an oil bat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | HO- | CO | 85 | null | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(CCC)C2>CO>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(C)(CCC)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1cea5b97e21b47708df149edb4f91295 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2.CI>>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(C)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)C)=O)C)OCOC.[Li+].CC(C)[N-]C(C)C.IC>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)(C)C)=O)C)OCOC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1=[C:18]([CH3:19])[C:20](=[O:21])[CH:22]([CH3:23])[CH2:25]2.I[CH3:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1=[C:18]([CH3:19]... | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2.CI | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(C)C2 | null | null | C1CCOC1 | C-C Coupling | Methylation with MeI_tertiary | 5ad82e3a335a3b61932305272f1c5165265cfa3d334bee0a6b6bb8d630fc2131 | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C1C=C2c3ccccc3CC2CC1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3]1=[C:4](-[c:5])-[C:6]-[C:7]-[CH;D3;+0:8](-[C;D1;H3:9])-[C:10]-1=[O;D1;H0:11]>>[C;D1;H3:2]-[C:3]1=[C:4](-[c:5])-[C:6]-[C:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[CH3;D1;+0:1])-[C:10]-1=[O;D1;H0:11] | null | [] | -78 | CELSIUS | null | null | A solution of (2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (39 mg, 0.12 mmol) in anhydrous THF (1.0 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated with 0.4M LDA in THF (0.39 mL, 0.16 mmol). After stirring at 0° C. for 30 minutes, the yellow solu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HI | C1CCOC1 | -78 | null | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)C2.CI>C1CCOC1>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(C)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b696197867354374bb82affcc3d1f4f4 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(C)C2>>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(C)(C)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)(C)C)=O)C)OCOC.Cl.C(=O)(O)[O-].[Na+]>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)(C)C)=O)C)O | COC[O:10][c:9]1[cH:8][c:7]2[c:13]([cH:12][cH:11]1)[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[C:19]([CH3:20])([CH3:21])[CH2:22][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]3[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[C:19]([CH3:20])([CH3:2... | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(C)C2 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(C)(C)C2 | null | null | CO.CCOC(=O)C | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | O=C1C=C2c3ccccc3CC2CC1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 67.5 | CELSIUS | null | null | A solution of 9a-butyl-7-methoxymethoxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (28 mg, 0.08 mmol) in methanol (2 mL) was placed under a nitrogen atmosphere and treated with 2N aqueous HCl (0.12 mL, 0.24 mmol). The resulting yellow solution was stirred and heated in an oil bath at 55-80° C. for 45 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | HO- | CO.CCOC(=O)C | 67.5 | null | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(C)(C)C2>CO.CCOC(=O)C>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(C)(C)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-823a4e2ec3744ad0aa61ce7065b5483c | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.II>>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(I)C2 | [Li+].CC(C)[N-]C(C)C.C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OCOC.II>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)I)=O)C)OCOC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1=[C:18]([CH3:19])[C:20](=[O:21])[CH2:22][CH2:24]2.I[I:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1=[C:18]([CH3:19])[C:20](=[O... | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.II | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(I)C2 | null | null | C1CCOC1.CCOC(=O)C | Functional Group Interconversion | OtherReaction | 73ce905e1642fa0e07c12cc5678c93e00cb126654e05346b16307491c72f308f | fe149a07f370bdd2ea40b2dff4f3462711fb34a60b8733c443efdeb5ab4d5c53 | O=C1C=C2c3ccccc3CC2CC1 | I-[I;H0;D1;+0:1].[C;D1;H3:2]-[C:3]1=[C:4](-[c:5])-[C:6]-[C:7]-[CH2;D2;+0:8]-[C:9]-1=[O;D1;H0:10]>>[C;D1;H3:2]-[C:3]1=[C:4](-[c:5])-[C:6]-[C:7]-[CH;D3;+0:8](-[I;H0;D1;+0:1])-[C:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (134 mg, 0.43 mmol) in anhydrous THF (2.5 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated with 0.4M LDA in THF (1.2 mL, 0.48 mmol). After stirring at 0° C. for 30 minutes, the enolate solution was coole... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary halide | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HI | C1CCOC1.CCOC(=O)C | null | null | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.II>C1CCOC1.CCOC(=O)C>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(I)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4279359932d424a94d83bc5d764d5a1 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(I)C2>>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(I)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)I)=O)C)OCOC.Cl.C(=O)(O)[O-].[Na+]>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)I)=O)C)O | COC[O:10][c:9]1[cH:8][c:7]2[c:13]([cH:12][cH:11]1)[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([I:20])[CH2:21][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]3[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([I:20])[CH2:21]2 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(I)C2 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(I)C2 | null | null | CO.CCOC(=O)C | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | O=C1C=C2c3ccccc3CC2CC1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 70 | CELSIUS | null | null | A suspension of (2SR,9aRS)-9a-butyl-2-iodo-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg, 0.11 mmol) in methanol (3.5 mL) was placed under a nitrogen atmosphere, heated in an oil bath at 70° C. to affect solution, then treated with 2N aqueous HCl (0.195 mL, 0.39 mmol). The resulting solution was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | HO- | CO.CCOC(=O)C | 70 | null | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(I)C2>CO.CCOC(=O)C>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(I)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1359d29ce9324090968a6c78e5d5d25d | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.C[Si](C)(C)Cl>>CCCCC12CC=C(O[Si](C)(C)C)C(C)=C1c1ccc(OCOC)cc1C2 | Cl[Si](C)(C)C.C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OCOC.[Li+].CC(C)[N-]C(C)C.C(=O)(O)[O-].[Na+].C(=O)=O.CC(=O)C>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(=CC1)O[Si](C)(C)C)C)OCOC | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:14]([CH3:15])=[C:16]1[c:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][O:23][CH3:24])[cH:25][c:26]1[CH2:27]2.Cl[Si:10]([CH3:11])([CH3:12])[CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH:7]=[C:8]([O:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[C:14]([CH3:15])=[... | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.C[Si](C)(C)Cl | CCCCC12CC=C(O[Si](C)(C)C)C(C)=C1c1ccc(OCOC)cc1C2 | null | null | C1CCOC1.CCOC(=O)C | Acylation | OtherReaction | 588731292d95bafa6ace96d9ff24559ce1957afa3790246098cafd64029214d6 | c13dd54c2034fa9746e04e6d624199b4092538f90a428225c0e821f09d4466f2 | C1=CCC2Cc3ccccc3C2=C1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[C;D1;H3:5]-[C:6]1=[C:7](-[c:8])-[C:9]-[C:10]-[CH2;D2;+0:11]-[C;H0;D3;+0:12]-1=[O;H0;D1;+0:13]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[O;H0;D2;+0:13]-[C;H0;D3;+0:12]1=[CH;D2;+0:11]-[C:10]-[C:9]-[C:7](=[C:6]-1-[C;D1;H3:5])-[c:8] | null | [] | 0 | CELSIUS | 30 | MINUTE | A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (163 mg, 0.52 mmol) in anhydrous THF (2.5 mL) was cooled in an ice bath and stirred under a nitrogen atmosphere while 0.4M LDA in THF (1.9 mL, 0.78 mmol) was added by syringe. After stirring at 0° C. for 30 minutes, the solution was c... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Silyl protective group | Silyl protective group | C1=C2c3ccccc3CC2CCC1 | C1=CCC2Cc3ccccc3C2=C1 | C1=CCC2Cc3ccccc3C2=C1 | HCl | C1CCOC1.CCOC(=O)C | 0 | 0.5 | CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2.C[Si](C)(C)Cl>C1CCOC1.CCOC(=O)C>CCCCC12CC=C(O[Si](C)(C)C)C(C)=C1c1ccc(OCOC)cc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72dc067bf29f4615811dcb079c390574 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(O)C2>>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(O)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)O)=O)C)OCOC.Cl>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)O)=O)C)O | COC[O:10][c:9]1[cH:8][c:7]2[c:13]([cH:12][cH:11]1)[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([OH:20])[CH2:21][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]3[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([OH:20])[CH2:21]2 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(O)C2 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(O)C2 | null | null | CO.CCOC(=O)C | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | O=C1C=C2c3ccccc3CC2CC1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | null | null | A solution of (2SR,9aRS)-9a-butyl-2-hydroxy-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (73 mg, 0.22 mmol) in methanol (5 mL) was placed under a nitrogen atmosphere, treated with 2N aqueous HCl (0.33 mL, 0.66 mmol), and stirred with heating in an oil bath at 80° C. for 30 minutes. After cooling to ro... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | HO- | CO.CCOC(=O)C | 80 | null | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(O)C2>CO.CCOC(=O)C>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(O)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6135e02ccc8a47dd9175ba392412cef1 | C=CCBr.CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2>>C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O | C(C=C)Br.C(CCC)C12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OCOC.[Li+].CC(C)[N-]C(C)C.Cl.C(=O)=O.CC(=O)C>>C(C=C)C1CC2(CC3=CC(=CC=C3C2=C(C1=O)C)OCOC)CCCC | Br[CH2:3][CH:2]=[CH2:1].[CH2:4]1[CH2:5][C:6]2([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][c:12]3[cH:13][c:14]([O:15][CH2:16][O:17][CH3:18])[cH:19][cH:20][c:21]3[C:22]2=[C:23]([CH3:24])[C:25]1=[O:26]>>[CH2:1]=[CH:2][CH2:3][CH:4]1[CH2:5][C:6]2([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][c:12]3[cH:13][c:14]([O:15][CH2:16][O:17][CH3... | C=CCBr.CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2 | C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O | null | null | C1CCOC1.CCOC(=O)C | C-C Coupling | OtherReaction | e2c7d74e8f73814e3527352c2cc5c462d7ae54bf350f989a871b42e01d15041a | f5ccd90096c3201115eb6510107831f398bf8f80381c3ea6084a10b0ebb25a81 | O=C1C=C2c3ccccc3CC2CC1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C;D1;H3:4]-[C:5]1=[C:6](-[c:7])-[C:8]-[C:9]-[CH2;D2;+0:10]-[C:11]-1=[O;D1;H0:12]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:10]1-[C:9]-[C:8]-[C:6](=[C:5](-[C;D1;H3:4])-[C:11]-1=[O;D1;H0:12])-[c:7] | null | [] | null | null | null | null | A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (230 mg, 0.73 mmol) in anhydrous THF (3.8 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated with freshly prepared 0.4M LDA in THF (2.2 mL, 0.88 mmol). The resulting solution was stirred at 0° C. for 30 mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Allyl | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HBr | C1CCOC1.CCOC(=O)C | null | null | C=CCBr.CCCCC12CCC(=O)C(C)=C1c1ccc(OCOC)cc1C2>C1CCOC1.CCOC(=O)C>C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30c070b61f1b4129a0cb3214237639c6 | C1COCCO1.C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O>>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2 | C(C=C)C1CC2(CC3=CC(=CC=C3C2=C(C1=O)C)OCOC)CCCC.O1CCOCC1>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)CC(CO)=O)=O)C)OCOC | C1C[O:27]CC[O:25]1.[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16]3[C:17]1=[C:18]([CH3:19])[C:20](=[O:21])[CH:22]([CH2:23][CH:24]=[CH2:26])[CH2:28]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][c:16... | C1COCCO1.C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2 | null | null | O | Functional Group Interconversion | OtherReaction | 667ca994095416535757cb9f161b113c486928eb5d344a0fe640637a77786136 | b5efe610ee05d133e43d6cd5169de83ef9e451cf7c4171956516c2320bb703ea | O=C1C=C2c3ccccc3CC2CC1 | C1-C-[O;H0;D2;+0:1]-C-C-[O;H0;D2;+0:2]-1.[CH2;D1;+0:3]=[CH;D2;+0:4]-[C:5]-[C:6]-[C:7]=[O;D1;H0:8]>>[O;D1;H0:8]=[C:7]-[C:6]-[C:5]-[C;H0;D3;+0:4](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[OH;D1;+0:1] | null | [] | null | null | 15 | MINUTE | A solution of (2SR,9aSR)-2-allyl-9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (170 mg, 0.48 mmol) in dioxane (9 mL) was diluted with water (3 mL) and treated with a single crystal of OSO4 followed by NaIO4 (125 mg, 0.58 mmol). The mixture was stirred at room temperature for 15 minutes, treate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Allyl | Ketone.Primary alcohol | C1COCCO1 | null | C1=C2c3ccccc3CC2CCC1 | Other | O | null | 0.25 | C1COCCO1.C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O>O>CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91f58590443c4623a63d18722cfb6815 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC=O)C2>>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC=O)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)CC=O)=O)C)OCOC.Cl>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)CC=O)=O)C)O | COC[O:10][c:9]1[cH:8][c:7]2[c:13]([cH:12][cH:11]1)[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([CH2:20][CH:21]=[O:22])[CH2:23][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]3[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([CH2:20][C... | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC=O)C2 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC=O)C2 | null | null | CO.CCOC(=O)C | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | O=C1C=C2c3ccccc3CC2CC1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 67.1 | [{"value": 67.1, "product": "C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)CC=O)=O)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of (2RS,9aSR)-9a-butyl-7-methoxymethoxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (85 mg) in methanol (1 mL) was diluted with 2N HCl (0.36 mL, 0.72 mmol). The resulting mixture was stirred at room temperature for 30 minutes followed by heating in an oil bath at 80° C. for 40 minutes. On co... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | HO- | CO.CCOC(=O)C | null | 0.5 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC=O)C2>CO.CCOC(=O)C>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC=O)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d0e5e3c98d34755babed58fc6c14987 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC=O)C2>>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CCO)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)CC=O)=O)C)O.[BH4-].[Na+]>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)CCO)=O)C)O | [CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]3[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([CH2:20][CH:21]=[O:22])[CH2:23]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]3[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([CH2:20][CH2:2... | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC=O)C2 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CCO)C2 | null | null | CC(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=C1C=C2c3ccccc3CC2CC1 | [O;D1;H0:1]=[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[O;H0;D1;+0:6]>>[O;D1;H0:1]=[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-[OH;D1;+0:6] | null | [] | null | null | 40 | MINUTE | A solution of (2RS,9aSR)-9a-butyl-7-hydroxy-4-methyl-2-(2-oxo-ethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (17 mg, 0.05 mmol) in 2-propanol (2 mL) was treated with NaBH4 (1.9 mg, 0.05 mmol) and the mixture was stirred at room temperature for 40 minutes. The solvent was evaporated under vacuum. The residue was taken up i... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | null | CC(C)O | null | 0.666667 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC=O)C2>CC(C)O>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CCO)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf2f58d1d9b2468d8835b967eb71e56a | C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O>>C=CCC1CC2(CCCC)Cc3cc(O)ccc3C2=C(C)C1=O | C(C=C)C1CC2(CC3=CC(=CC=C3C2=C(C1=O)C)OCOC)CCCC.Cl>>C(C=C)C1CC2(CC3=CC(=CC=C3C2=C(C1=O)C)O)CCCC | COC[O:15][c:14]1[cH:13][c:12]2[c:18]([cH:17][cH:16]1)[C:19]1=[C:20]([CH3:21])[C:22](=[O:23])[CH:4]([CH2:3][CH:2]=[CH2:1])[CH2:5][C:6]1([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11]2>>[CH2:1]=[CH:2][CH2:3][CH:4]1[CH2:5][C:6]2([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][c:12]3[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]3[C:19]2=[C:20]... | C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O | C=CCC1CC2(CCCC)Cc3cc(O)ccc3C2=C(C)C1=O | null | null | C1CCOC1.CCOC(=O)C | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | O=C1C=C2c3ccccc3CC2CC1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 50 | CELSIUS | null | null | A solution of (2SR,9aSR)-2-allyl-9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (5 mg, 0.015 mmol) in THF (0.5 mL) was treated with 6N HCl (0.5 mL) and the resulting solution was heated at 50° C. overnight. The mixture was diluted with EtOAc (30 mL), washed with 5% NaHCO3 and brine, dried over ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | HO- | C1CCOC1.CCOC(=O)C | 50 | null | C=CCC1CC2(CCCC)Cc3cc(OCOC)ccc3C2=C(C)C1=O>C1CCOC1.CCOC(=O)C>C=CCC1CC2(CCCC)Cc3cc(O)ccc3C2=C(C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b15b3e94ee9748ad969eea6cc232a478 | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2>>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2 | C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)CC(CO)=O)=O)C)OCOC.Cl>>C(CCC)C12CC3=CC(=CC=C3C2=C(C(C(C1)CC(CO)=O)=O)C)O | COC[O:10][c:9]1[cH:8][c:7]2[c:13]([cH:12][cH:11]1)[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[CH:19]([CH2:20][C:21](=[O:22])[CH2:23][OH:24])[CH2:25][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]3[C:14]1=[C:15]([CH3:16])[C:17](=[O:18])[C... | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2 | CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2 | null | null | CO | Reduction | OtherReaction | 92f30feec6876d2f8c7439342f0f488fd5811a8fdb3b3cb63d7289bd57242715 | 3165f563067f8d27bb50b0da034e3e854d1ead7f745de7cf575f7ca4cf677789 | O=C1C=C2c3ccccc3CC2CC1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of (2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (24 mg, 0.06 mmol) in methanol (1 mL) was treated with 2N HCl (0.36 mL, 0.18 mmol) and the resulting solution was heated at reflux for 20 minutes. After cooling, the mixture was concentrated under ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | HO- | CO | null | null | CCCCC12Cc3cc(OCOC)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2>CO>CCCCC12Cc3cc(O)ccc3C1=C(C)C(=O)C(CC(=O)CO)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0bd1b0c03f844d7a23d87971c34bc62 | CCCI.COc1ccc2c(c1)C=CC2>>CCCC1C=Cc2cc(OC)ccc21 | [NH4+].[Cl-].COC=1C=C2C=CCC2=CC1.[Li]C.ICCC>>COC=1C=C2C=CC(C2=CC1)CCC | I[CH2:3][CH2:2][CH3:1].[CH2:4]1[CH:5]=[CH:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]21>>[CH3:1][CH2:2][CH2:3][CH:4]1[CH:5]=[CH:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]21 | CCCI.COc1ccc2c(c1)C=CC2 | CCCC1C=Cc2cc(OC)ccc21 | null | null | CCOCC | C-C Coupling | OtherReaction | ee93cac7990a00c1dd3a845ddbd566fe7d8a8ffc7df7c031c0125f10973487d9 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | C1=Cc2ccccc2C1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[c:4]:[c:5]1:[c:6]-[C:7]=[C:8]-[CH2;D2;+0:9]-1>>[C;D1;H3:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:9]1-[C:8]=[C:7]-[c:6]:[c:5]-1:[c:4] | 108.3 | [{"value": 108.3, "product": "COC=1C=C2C=CC(C2=CC1)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 5-methoxy-1H-indene (0.895 g, 6.12 mmol) in anhydrous Et2O (7.5 mL) was treated with 1.4M MeLi in Et2O (4.7 mL, 6.58 mmol) added dropwise over 10 minutes. The resulting hazy solution was stirred at room temperature an additional 15 minutes, then cooled in an ice bath and treated with iodopropane (1.00 mL,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | C1=Cc2ccccc2C1 | HI | CCOCC | null | 0.25 | CCCI.COc1ccc2c(c1)C=CC2>CCOCC>CCCC1C=Cc2cc(OC)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7b0953821a446b293b603d05a892eeb | CCCC1C=Cc2cc(OC)ccc21>>CCCC1CCc2ccc(OC)cc21 | COC=1C=C2C=CC(C2=CC1)CCC.C(C)O>>COC1=CC=C2CCC(C2=C1)CCC | [CH3:1][CH2:2][CH2:3][CH:4]1[CH:5]=[CH:6][c:14]2[c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13]2>>[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]21 | CCCC1C=Cc2cc(OC)ccc21 | CCCC1CCc2ccc(OC)cc21 | null | [Pd] | null | Miscellaneous | OtherReaction | 01ad2b60de955da99a059ed8e67687c8e839e9c53d04e18169490b4081371a85 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2c(c1)CCC2 | [C:1]-[C:2]-[CH;D3;+0:3]1-[CH;D2;+0:4]=[CH;D2;+0:5]-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[c:9]:[c:10]:[c;H0;D3;+0:11]:2-1>>[C:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c;H0;D3;+0:11]2:[c:10]:[c:9]:[c:8]:[c:7]:[c;H0;D3;+0:6]:2-1 | null | [] | null | null | 60 | MINUTE | The mixture of indenes from step 1 (1.24 g, approx. 6.1 mmol) was dissolved in ethanol (40 mL), treated with 10% Pd on carbon (58 mg), and hydrogenated at 40 psi and room temperature for 60 minutes. The catalyst was removed by filtration and the filtrate was evaporated under vacuum to provide a mixture (1.287 g) of 6-m... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ccccc2C1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | [Pd] | null | 1 | CCCC1C=Cc2cc(OC)ccc21>[Pd]>CCCC1CCc2ccc(OC)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f65a22cc30c4c71b7a3d15e3263d86d | CCCC1CCc2ccc(OC)cc21.[O]=[Mn](=[O])(=[O])[O-]>>CCCC1CC(=O)c2ccc(OC)cc21 | COC1=CC=C2CCC(C2=C1)CCC.[O-][Mn](=O)(=O)=O.[K+]>>COC=1C=C2C(CC(C2=CC1)=O)CCC | [CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][c:15]21.[O]=[Mn](=[O])([O-])=[O:7]>>[CH3:1][CH2:2][CH2:3][CH:4]1[CH2:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[cH:14][c:15]21 | CCCC1CCc2ccc(OC)cc21.[O]=[Mn](=[O])(=[O])[O-] | CCCC1CC(=O)c2ccc(OC)cc21 | null | [O-]S(=O)(=O)[O-].[Cu+2] | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 32ab24ed955b97edb4307c2f3e4046b88d7a3304f9d6f8e3f49a6ef57e022b90 | a196f7191876ee39420290ab9d6c2b9eeb3251b37ae345fc435efba1949a85d9 | O=C1CCc2ccccc21 | [O-]-[Mn](=[O;H0;D1;+0:1])(=[O])=[O].[c:2]:[c:3]1:[c:4]-[C:5]-[C:6]-[CH2;D2;+0:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:7]1-[C:6]-[C:5]-[c:4]:[c:3]-1:[c:2] | 15.1 | [{"value": 15.1, "product": "COC=1C=C2C(CC(C2=CC1)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of indans from step 2 (1.287 g, approx. 6.1 mmol) in CH2Cl2 (50 mL) was treated with a finely ground mixture of KMnO4 (7.00 g) and CuSO4.xH2O. The resulting mixture was heated at reflux for 89 hours, then cooled to room temperature and filtered through a celite pad. The filtrate was dried over MgSO4, filter... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | [O-]S(=O)(=O)[O-].[Cu+2].C(Cl)Cl | null | null | CCCC1CCc2ccc(OC)cc21.[O]=[Mn](=[O])(=[O])[O-]>[O-]S(=O)(=O)[O-].[Cu+2].C(Cl)Cl>CCCC1CC(=O)c2ccc(OC)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61d811177b4e4cd88b1e29266c8ae876 | CCC1(CC=O)OCCO1.CCCC1CC(=O)c2ccc(OC)cc21>>CCCC1c2cc(OC)ccc2C(=O)C1CCC1(CC)OCCO1 | Cl.[OH-].[K+].COC=1C=C2C(CC(C2=CC1)=O)CCC.C(C)C1(OCCO1)CC=O>>C(C)C1(OCCO1)CCC1C(C2=CC=C(C=C2C1CCC)OC)=O | O=[CH:16][CH2:17][C:18]1([CH2:19][CH3:20])[O:21][CH2:22][CH2:23][O:24]1.[CH3:1][CH2:2][CH2:3][CH:4]1[c:5]2[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11][c:12]2[C:13](=[O:14])[CH2:15]1>>[CH3:1][CH2:2][CH2:3][CH:4]1[c:5]2[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11][c:12]2[C:13](=[O:14])[CH:15]1[CH2:16][CH2:17][C:18]1([CH2:19][CH3:20... | CCC1(CC=O)OCCO1.CCCC1CC(=O)c2ccc(OC)cc21 | CCCC1c2cc(OC)ccc2C(=O)C1CCC1(CC)OCCO1 | null | [Pd] | C(C)O | C-C Coupling | OtherReaction | 68e28f9095e1f150f32da6921211b9a27c818a0dd75d077bb5baa7c9b256c798 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C1c2ccccc2CC1CCC1OCCO1 | O=[CH;D2;+0:1]-[C:2]-[C:3](-[#8:4])-[#8:5].[C:6]-[C:7]1-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]-1>>[#8:4]-[C:3](-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:8]1-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]-[C:7]-1-[C:6])-[#8:5] | 29.1 | [{"value": 29.1, "product": "C(C)C1(OCCO1)CCC1C(C2=CC=C(C=C2C1CCC)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 5-methoxy-3-propyl-1-indanone (184 mg, 0.90 mmol) and (2-ethyl-[1,3]dioxolan-2-yl)acetaldehyde (173 mg, 1.20 mmol) was treated with a solution of KOH (85% wt. pure, 20 mg, 0.30 mmol) in ethanol (1.0 mL). The resulting mixture was stirred at room temperature for 30 minutes, then treated with 10% Pd on carbo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2.C1COCO1 | Other | [Pd].C(C)O | null | 0.5 | CCC1(CC=O)OCCO1.CCCC1CC(=O)c2ccc(OC)cc21>[Pd].C(C)O>CCCC1c2cc(OC)ccc2C(=O)C1CCC1(CC)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7dd6343aeafb46f08ecf5adfe3390eb6 | CCCC1c2cc(OC)ccc2C2=C(C)C(=O)CCC21>>CCCC1c2cc(O)ccc2C2=C(C)C(=O)CCC21 | COC1=CC=C2C3=C(C(CCC3C(C2=C1)CCC)=O)C.B(Br)(Br)Br>>OC1=CC=C2C3=C(C(CCC3C(C2=C1)CCC)=O)C | C[O:8][c:7]1[cH:6][c:5]2[c:11]([cH:10][cH:9]1)[C:12]1=[C:13]([CH3:14])[C:15](=[O:16])[CH2:17][CH2:18][CH:19]1[CH:4]2[CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH:4]1[c:5]2[cH:6][c:7]([OH:8])[cH:9][cH:10][c:11]2[C:12]2=[C:13]([CH3:14])[C:15](=[O:16])[CH2:17][CH2:18][CH:19]12 | CCCC1c2cc(OC)ccc2C2=C(C)C(=O)CCC21 | CCCC1c2cc(O)ccc2C2=C(C)C(=O)CCC21 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2.6 | HOUR | A solution of (9SR,9aSR)-7-methoxy-4-methyl-9-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (38.3 mg, 0.142 mmol) in anhydrous CH2Cl2 (1.1 mL) was placed under a nitrogen atmosphere, cooled in a dry ice-acetone bath, and stirred while 1M BBr3 in CH2Cl2 (0.354 mL, 0.345 mmol) was added by syringe. The cooling bath was rem... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | C(Cl)Cl | null | 2.6 | CCCC1c2cc(OC)ccc2C2=C(C)C(=O)CCC21>C(Cl)Cl>CCCC1c2cc(O)ccc2C2=C(C)C(=O)CCC21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5089406476cf406e8260118814d5a2c0 | CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2Cl)C1=O>>CCCCC12CCC(=O)C=C1c1ccc(OC)c(Cl)c1C2 | C(CCC)C1C(C2=CC=C(C(=C2C1)Cl)OC)=O.C(=C)C(=O)C.C[O-].[Na+].CO.C(CCC)C1(C(C2=CC=C(C(=C2C1)Cl)OC)=O)CCC(C)=O.N1CCCC1.C(C)(=O)O>>C(CCC)C12CC3=C(C(=CC=C3C2=CC(CC1)=O)OC)Cl | O=[C:11]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH3:10])[CH2:21][c:20]2[c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]2[Cl:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[CH:10]=[C:11]1[c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[c:18]([Cl:19])[c:20]1[CH2:21]2 | CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2Cl)C1=O | CCCCC12CCC(=O)C=C1c1ccc(OC)c(Cl)c1C2 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:7]-[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[CH;D2;+0:11]-[C:10](=[O;D1;H0:12])-[C:9]-[C:8]-2 | null | [] | null | null | 90 | MINUTE | A solution 2-butyl-4-chloro-5-methoxy-1-indanone (550 mg, 2.03 mmol) in tetrahydrofuran (4.06 mL) was treated with methyl vinyl ketone (0.203 mL, 2.44 mmol) and 0.5N sodium methoxide in methanol (0.812 mL, 0.406 mmol). The mixture was stirred at room temperature for 90 minutes to effect conversion to 2-butyl-4-chloro-5... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | O1CCCC1.C1(=CC=CC=C1)C | null | 1.5 | CCCCC1(CCC(C)=O)Cc2c(ccc(OC)c2Cl)C1=O>O1CCCC1.C1(=CC=CC=C1)C>CCCCC12CCC(=O)C=C1c1ccc(OC)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9cf6287b0a4c41f28bee99b9776571b1 | BrBr.CCCCC12CCC(=O)C=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2 | C(CCC)C12CC3=C(C(=CC=C3C2=CC(CC1)=O)OC)Cl.C([O-])(O)=O.[Na+].BrBr>>BrC=1C(CCC2(CC3=C(C(=CC=C3C12)OC)Cl)CCCC)=O | Br[Br:11].[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[CH:10]=[C:12]1[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([Cl:20])[c:21]1[CH2:22]2>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([Br:11])=[C:12]1[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]([Cl:20])[c:21]1[CH2:22... | BrBr.CCCCC12CCC(=O)C=C1c1ccc(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2 | null | null | ClCCl.C(Cl)Cl | Functional Group Interconversion | Bromination | 73ca391a48874f0a81f3694c6623ffb0a512c874931d8f551485082fa4a0d563 | c7222534d68e666d405fc6d911092ac63e3791780d01400eb414eff6e46c2a54 | O=C1C=C2c3ccccc3CC2CC1 | Br-[Br;H0;D1;+0:1].[C:2]-[C:3](=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[C:7])-[c:8]>>[Br;H0;D1;+0:1]-[C;H0;D3;+0:4](=[C:3](-[C:2])-[c:8])-[C:5](=[O;D1;H0:6])-[C:7] | null | [] | null | null | 30 | MINUTE | A solution of 9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (555 mg, 1.82 mmol) in anhydrous dichloromethane (18.2 mL) was treated with sodium bicarbonate (765 mg, 9.1 mmol) and bromine (0.093 mL, 1.82 mmol). The mixture was stirred at room temperature for 30 minutes and then diluted with CH2Cl2 (50 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkenyl halide | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HBr | ClCCl.C(Cl)Cl | null | 0.5 | BrBr.CCCCC12CCC(=O)C=C1c1ccc(OC)c(Cl)c1C2>ClCCl.C(Cl)Cl>CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2585e949972544e68ec775b4010b196e | CCCCC12CCC(=O)C(C(F)(F)F)=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C(F)(F)F)=C1c1ccc(O)c(Cl)c1C2 | B(Br)(Br)Br.C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C(F)(F)F)OC)Cl.B(Br)(Br)Br>>C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C(F)(F)F)O)Cl | C[O:20][c:19]1[cH:18][cH:17][c:16]2[c:23]([c:21]1[Cl:22])[CH2:24][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]([F:12])([F:13])[F:14])=[C:15]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]([F:12])([F:13])[F:14])=[C:15]1[c:16]1[cH:17][cH:18][c:19]([OH:20])[c:... | CCCCC12CCC(=O)C(C(F)(F)F)=C1c1ccc(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(C(F)(F)F)=C1c1ccc(O)c(Cl)c1C2 | null | null | ClCCl.C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 95 | MINUTE | A solution of 9a-butyl-8-chloro-7-methoxy-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (32 mg, 0.086 mmol) in anhydrous dichloromethane (0.86 mL) was cooled in a dry ice-acetone bath (−78° C.) and the solution was treated with 1M boron tribromide in dichloromethane (0.258 mL, 0.258 mmol). The cooling bath w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | ClCCl.C(Cl)Cl | null | 1.583333 | CCCCC12CCC(=O)C(C(F)(F)F)=C1c1ccc(OC)c(Cl)c1C2>ClCCl.C(Cl)Cl>CCCCC12CCC(=O)C(C(F)(F)F)=C1c1ccc(O)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e31e21fba51466aaf8cfe2488e576b3 | C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2>>C=C(OCC)C1=C2c3ccc(OC)c(Cl)c3CC2(CCCC)CCC1=O | BrC=1C(CCC2(CC3=C(C(=CC=C3C12)OC)Cl)CCCC)=O.C(CCC)[Sn](C(=C)OCC)(CCCC)CCCC>>C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C(=C)OCC)OC)Cl | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[C:2](=[CH2:1])[O:3][CH2:4][CH3:5].Br[C:6]1=[C:7]2[c:8]3[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([Cl:15])[c:16]3[CH2:17][C:18]2([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][C:25]1=[O:26]>>[CH2:1]=[C:2]([O:3][CH2:4][CH3:5])[C:6]1=[C:7]2[c:8]3[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]... | C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2 | C=C(OCC)C1=C2c3ccc(OC)c(Cl)c3CC2(CCCC)CCC1=O | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_other | 9c48440b626589bda452d19ba29733afd2b18391c3ba2e9aaffdf5d6a1aee497 | d1092acfedce3fd35bb9bbd3772a9f24078f9c16eee7ceb70d0a0949d0e81c99 | O=C1C=C2c3ccccc3CC2CC1 | Br-[C;H0;D3;+0:1](=[C:2](-[C:3])-[c:4])-[C:5](=[O;D1;H0:6])-[C:7].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[C;H0;D3;+0:8](=[C;D1;H2:9])-[#8:10]-[C:11]>>[C:3]-[C:2](=[C;H0;D3;+0:1](-[C;H0;D3;+0:8](=[C;D1;H2:9])-[#8:10]-[C:11])-[C:5](=[O;D1;H0:6])-[C:7])-[c:4] | 76 | [{"value": 76.0, "product": "C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C(=C)OCC)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 4-bromo-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (90 mg, 0.235 mmol) in anhydrous toluene (1.2 mL) was treated with tributyl(1-ethoxyvinyl)stannane (0.111 mL, 0.352 mmol) and bis(triphenylphosphine)palladium(II) chloride (33 mg, 0.047 mmol). The mixture was placed under a nitrogen ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ketone.Ether.Vinyl.Tin | Ketone.Ether | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1(=CC=CC=C1)C | 100 | null | C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1(=CC=CC=C1)C>C=C(OCC)C1=C2c3ccc(OC)c(Cl)c3CC2(CCCC)CCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-194006f950674b50a93e6edc19549752 | C=C(OCC)C1=C2c3ccc(OC)c(Cl)c3CC2(CCCC)CCC1=O>>CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(OC)c(Cl)c1C2 | C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C(=C)OCC)OC)Cl.Cl>>C(C)(=O)C=1C(CCC2(CC3=C(C(=CC=C3C12)OC)Cl)CCCC)=O | CC[O:13][C:11]([C:10]1=[C:14]2[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8]1=[O:9])[CH2:24][c:23]1[c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[c:21]1[Cl:22])=[CH2:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]([CH3:12])=[O:13])=[C:14]1[c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20]... | C=C(OCC)C1=C2c3ccc(OC)c(Cl)c3CC2(CCCC)CCC1=O | CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(OC)c(Cl)c1C2 | null | null | O.C(C)O | Miscellaneous | OtherReaction | 3e02cda7ca3208f28d8355e2c059d63c9e4eb2c7eba0cae088d693f3c74db23e | 215582e9637166736070a53bb588f4e45b0dfc6c974d1df4c97ac5a98451627c | O=C1C=C2c3ccccc3CC2CC1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[CH2;D1;+0:3])-[C:4](=[C:5](-[C:6])-[c:7])-[C:8](=[O;D1;H0:9])-[C:10]>>[C:6]-[C:5](=[C:4](-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;H0;D1;+0:1])-[C:8](=[O;D1;H0:9])-[C:10])-[c:7] | null | [] | 80 | CELSIUS | null | null | The product from step 1 in ethanol (1.0 mL), water (0.2 mL) and aqueous 2N HCl (0.2 mL) was stirred and heated in an oil bath at 80° C. for 40 minutes. After cooling, the mixture was partitioned between EtOAc (20 mL) and water (20 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and eva... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Vinyl | Ketone | null | null | C1=C2c3ccccc3CC2CCC1 | Other | O.C(C)O | 80 | null | C=C(OCC)C1=C2c3ccc(OC)c(Cl)c3CC2(CCCC)CCC1=O>O.C(C)O>CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(OC)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49e41638e01341c08bfbc41dd6e4affb | CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(O)c(Cl)c1C2 | C(C)(=O)C=1C(CCC2(CC3=C(C(=CC=C3C12)OC)Cl)CCCC)=O.Cl.N1=CC=CC=C1>>C(C)(=O)C=1C(CCC2(CC3=C(C(=CC=C3C12)O)Cl)CCCC)=O | C[O:19][c:18]1[cH:17][cH:16][c:15]2[c:22]([c:20]1[Cl:21])[CH2:23][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]([CH3:12])=[O:13])=[C:14]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]([CH3:12])=[O:13])=[C:14]1[c:15]1[cH:16][cH:17][c:18]([OH:19])[c:20]([Cl:21... | CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(O)c(Cl)c1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 200 | CELSIUS | null | null | A mixture of 4-acetyl-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (54 mg) and pyridine hydrochloride (3.5 g) was heated in an oil bath at 200° C. for one hour. After cooling to room temperature, the mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with b... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | null | 200 | null | CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C(C)=O)=C1c1ccc(O)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e993677936f64b12a731aaf297bed3e9 | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)c(Cl)c1C2 | BrC=1C(CCC2(CC3=C(C(=CC=C3C12)OC)Cl)CCCC)=O.[Cu]C#N>>C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C#N)OC)Cl | Br[C:10]1=[C:13]2[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8]1=[O:9])[CH2:23][c:22]1[c:14]2[cH:15][cH:16][c:17]([O:18][CH3:19])[c:20]1[Cl:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]#[N:12])=[C:13]1[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[c:20]([Cl:21])[c:22]1[CH2:23]2 | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)c(Cl)c1C2 | null | null | CN1C(CCC1)=O | Miscellaneous | OtherReaction | 9adadf535edd63596f40811ded4b5d76fe0b83c469549ed7abf606d845021290 | 8953536f7fe46a44d657de6166386d42d9afab94586603b5dca76fc653fbf47b | O=C1C=C2c3ccccc3CC2CC1 | Br-[C;H0;D3;+0:1](=[C:2](-[C:3])-[c:4])-[C:5](=[O;D1;H0:6])-[C:7]>>[C:3]-[C:2](=[C;H0;D3;+0:1](-[C:8]#[N;D1;H0:9])-[C:5](=[O;D1;H0:6])-[C:7])-[c:4] | 73.5 | [{"value": 73.5, "product": "C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C#N)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A solution of 4-bromo-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (103 mg, 0.268 mmol) in anhydrous 1-methyl-2-pyrrolidinone (0.54 mL) was treated with copper(I) cyanide (24 mg, 0.268 mmol). The mixture was placed under a nitrogen atmosphere, stirred, and heated in an oil bath at 150° C. for 1.5 ho... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide | Ketone.Nitrile | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | Br- | CN1C(CCC1)=O | 150 | null | CCCCC12CCC(=O)C(Br)=C1c1ccc(OC)c(Cl)c1C2>CN1C(CCC1)=O>CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4492a1316c2143eaaae289f2e539a4d5 | CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C#N)=C1c1ccc(O)c(Cl)c1C2 | C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C#N)OC)Cl.Cl.N1=CC=CC=C1>>C(CCC)C12CC3=C(C(=CC=C3C2=C(C(CC1)=O)C#N)O)Cl | C[O:18][c:17]1[cH:16][cH:15][c:14]2[c:21]([c:19]1[Cl:20])[CH2:22][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]#[N:12])=[C:13]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]#[N:12])=[C:13]1[c:14]1[cH:15][cH:16][c:17]([OH:18])[c:19]([Cl:20])[c:21]1[CH2:22]2 | CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(C#N)=C1c1ccc(O)c(Cl)c1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 200 | CELSIUS | null | null | A mixture of 9a-butyl-8-chloro-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (65 mg) and pyridine hydrochloride (4.2 g) was heated in an oil bath at 200° C. for 85 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | null | 200 | null | CCCCC12CCC(=O)C(C#N)=C1c1ccc(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C#N)=C1c1ccc(O)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-964e1b3c9e4a4ee4925791c3c6f268ce | CCCCCC(=O)Cl.COc1ccccc1F>>CCCCCC(=O)c1ccc(OC)c(F)c1 | Cl.[Cl-].[Al+3].[Cl-].[Cl-].FC1=C(C=CC=C1)OC.C(CCCCC)(=O)Cl>>FC=1C=C(C=CC1OC)C(CCCCC)=O | Cl[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7].[cH:8]1[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]1 | CCCCCC(=O)Cl.COc1ccccc1F | CCCCCC(=O)c1ccc(OC)c(F)c1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:6]:[c:5] | 90.4 | [{"value": 90.4, "product": "FC=1C=C(C=CC1OC)C(CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | Aluminum chloride (6.5 g, 48.8 mmol) was added to a stirred mixture of 1-fluoro-2-methoxybenzene (5.0 mL, 44.4 mmol) and hexanoyl chloride (7.5 mL, 53.3 mmol) at room temperature. The mixture warmed and HCl evolution occurred. The resulting mixture was stirred at room temperature for 45 minutes and then partitioned bet... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | 0.75 | CCCCCC(=O)Cl.COc1ccccc1F>>CCCCCC(=O)c1ccc(OC)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a97121dbeb748ada83910f7c64b7fb6 | CCCCC1Cc2cc(OC)c(F)cc2C1=O>>CCCCC1Cc2cc(O)c(F)cc2C1=O | C(CCC)C1C(C2=CC(=C(C=C2C1)OC)F)=O.Cl.N1=CC=CC=C1>>C(CCC)C1C(C2=CC(=C(C=C2C1)O)F)=O | C[O:10][c:9]1[cH:8][c:7]2[c:14]([cH:13][c:11]1[F:12])[C:15](=[O:16])[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[cH:8][c:9]([OH:10])[c:11]([F:12])[cH:13][c:14]2[C:15]1=[O:16] | CCCCC1Cc2cc(OC)c(F)cc2C1=O | CCCCC1Cc2cc(O)c(F)cc2C1=O | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1CCc2ccccc21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 95.1 | [{"value": 95.1, "product": "C(CCC)C1C(C2=CC(=C(C=C2C1)O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | null | null | A mixture of 2-butyl-6-fluoro-5-methoxy-1-indanone (2.0 g) and pyridine hydrochloride (15.0 g) was heated in an oil bath at 200° C. for 75 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (100 mL) and water (75 mL) containing brine (25 mL). The organic phase was washed with brine (5... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCC2 | Other | null | 200 | null | CCCCC1Cc2cc(OC)c(F)cc2C1=O>>CCCCC1Cc2cc(O)c(F)cc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-003b390b794440cdb243ce9841e7b453 | CCCCC1Cc2cc(O)c(F)cc2C1=O.O=C1CCC(=O)N1Br>>CCCCC1Cc2c(cc(F)c(O)c2Br)C1=O | BrN1C(CCC1=O)=O.C(CCC)C1C(C2=CC(=C(C=C2C1)O)F)=O>>BrC1=C2CC(C(C2=CC(=C1O)F)=O)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][c:10]([F:11])[c:12]([OH:13])[cH:14]2)[C:16]1=[O:17].O=C1CCC(=O)N1[Br:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][c:10]([F:11])[c:12]([OH:13])[c:14]2[Br:15])[C:16]1=[O:17] | CCCCC1Cc2cc(O)c(F)cc2C1=O.O=C1CCC(=O)N1Br | CCCCC1Cc2c(cc(F)c(O)c2Br)C1=O | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | 810b77391b192e36eecbf89fbd0937a488e789bac7683cb9fabaa7cbc9c32e40 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C1CCc2ccccc21 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[c:3](:[c:4]-[C:5]=[O;D1;H0:6]):[cH;D2;+0:7]:[c:8](-[O;D1;H1:9]):[c:10]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7](:[c:8](-[O;D1;H1:9]):[c:10]):[c:3](:[c:4]-[C:5]=[O;D1;H0:6])-[C:2] | 90.9 | [{"value": 90.9, "product": "BrC1=C2CC(C(C2=CC(=C1O)F)=O)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | N-Bromosuccinimide (1.41 g, 7.93 mmol) was added to a solution of 2-butyl-6-fluoro-5-hydroxy-1-indanone (1.76 g, 7.93 mmol) in anhydrous N,N-dimethylformamide (15 mL). The resulting solution was stirred at room temperature for two hours. The solvent was evaporated under vacuum and the residue was partitioned between Et... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CCC2.C1CCNC1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | CN(C=O)C | null | 2 | CCCCC1Cc2cc(O)c(F)cc2C1=O.O=C1CCC(=O)N1Br>CN(C=O)C>CCCCC1Cc2c(cc(F)c(O)c2Br)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-835f01ea929a484fbdde0611e5ce74b3 | CCCCC1Cc2c(cc(F)c(O)c2Br)C1=O.CI>>CCCCC1Cc2c(cc(F)c(OC)c2Br)C1=O | BrC1=C2CC(C(C2=CC(=C1O)F)=O)CCCC.CI.C([O-])(O)=O.[Na+]>>BrC1=C2CC(C(C2=CC(=C1OC)F)=O)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][c:10]([F:11])[c:12]([OH:13])[c:15]2[Br:16])[C:17]1=[O:18].I[CH3:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]2[Br:16])[C:17]1=[O:18] | CCCCC1Cc2c(cc(F)c(O)c2Br)C1=O.CI | CCCCC1Cc2c(cc(F)c(OC)c2Br)C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | O=C1CCc2ccccc21 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 81.6 | [{"value": 81.6, "product": "BrC1=C2CC(C(C2=CC(=C1OC)F)=O)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | A mixture of 4-bromo-2-butyl-6-fluoro-5-hydroxy-1-indanone (2.17 g, 7.23 mmol), N,N-dimethylformamide (14.5 mL), methyl iodide (0.675 mL, 10.84 mmol), and sodium bicarbonate (1.50 g, 18.1 mmol) was stirred at room temperature for 17 hours. The solvent was evaporated under vacuum. The residue in EtOAc (150 mL) was washe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CCC2 | HI | CN(C=O)C | null | 17 | CCCCC1Cc2c(cc(F)c(O)c2Br)C1=O.CI>CN(C=O)C>CCCCC1Cc2c(cc(F)c(OC)c2Br)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-270913168eb241f99a23be25455ccdcc | CCCCC1Cc2c(cc(F)c(OC)c2Br)C1=O.[CH3][Sn]([CH3])([CH3])[CH3]>>CCCCC1Cc2c(cc(F)c(OC)c2C)C1=O | BrC1=C2CC(C(C2=CC(=C1OC)F)=O)CCCC.C[Sn](C)(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cl-].[Li+]>>C(CCC)C1C(C2=CC(=C(C(=C2C1)C)OC)F)=O | Br[c:15]1[c:7]2[c:8]([cH:9][c:10]([F:11])[c:12]1[O:13][CH3:14])[C:17](=[O:18])[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6]2.[CH3][Sn]([CH3])([CH3])[CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]2[CH3:16])[C:17]1=[O:18] | CCCCC1Cc2c(cc(F)c(OC)c2Br)C1=O.[CH3][Sn]([CH3])([CH3])[CH3] | CCCCC1Cc2c(cc(F)c(OC)c2C)C1=O | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C=O)C | C-C Coupling | Stille reaction_other | 5f823a1f140c9788378795502c3f73833375dcf595f9e9d5f6b25610b5e941bf | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=C1CCc2ccccc21 | Br-[c;H0;D3;+0:1](:[c:2](-[#8:3]):[c:4]):[c:5](:[c:6]-[C:7]=[O;D1;H0:8])-[C:9].[CH3;D1;+0:10]-[Sn](-[CH3])(-[CH3])-[CH3]>>[#8:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[CH3;D1;+0:10]):[c:5](:[c:6]-[C:7]=[O;D1;H0:8])-[C:9] | 24.5 | [{"value": 24.5, "product": "C(CCC)C1C(C2=CC(=C(C(=C2C1)C)OC)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 4-bromo-2-butyl-6-fluoro-5-methoxy-1-indanone (1.86 g, 5.94 mmol), bis(triphenylphosphine)palladium(II) chloride (208 mg, 0.297 mmol), tetramethyltin (0.989 mL, 7.128 mmol), triphenylphosphine (156 mg, 0.594 mmol), lithium chloride (504 mg, 11.88 mmol), and anhydrous N,N-dimethyl-formamide (11.9 mL) was pl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C | 100 | null | CCCCC1Cc2c(cc(F)c(OC)c2Br)C1=O.[CH3][Sn]([CH3])([CH3])[CH3]>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C=O)C>CCCCC1Cc2c(cc(F)c(OC)c2C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3bfd2b8db18a4c68b99e3c5c20362e76 | CCCCC1(CCC(=O)CCC)Cc2c(cc(F)c(OC)c2C)C1=O>>CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(C)c1C2 | C(CCC)C1(C(C2=CC(=C(C(=C2C1)C)OC)F)=O)CCC(CCC)=O.C(CCC)C1C(C2=CC(=C(C(=C2C1)C)OC)F)=O.C(=C)C(=O)CCC.N12CCCCCC2=NCCC1.Cl>>C(CCC)C12CC3=C(C(=C(C=C3C2=C(C(CC1)=O)CC)F)OC)C | O=[C:13]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][CH2:11][CH3:12])[CH2:24][c:23]2[c:14]1[cH:15][c:16]([F:17])[c:18]([O:19][CH3:20])[c:21]2[CH3:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH2:11][CH3:12])=[C:13]1[c:14]1[cH:15][c:16]([F:17])[c:18]([O:19][CH3:2... | CCCCC1(CCC(=O)CCC)Cc2c(cc(F)c(OC)c2C)C1=O | CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(C)c1C2 | null | null | C(C)(=O)O.O1CCCC1 | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[C:13]-[C;D1;H3:14]>>[C:7]-[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[C;H0;D3;+0:12](-[C:13]-[C;D1;H3:14])-[C:10](=[O;D1;H0:11])-[C:9]-[C:8]-2 | null | [] | 50 | CELSIUS | 64 | HOUR | A solution of 2-butyl-6-fluoro-5-methoxy-4-methyl-1-indanone (118 mg, 0.47 mmol) in anhydrous tetrahydrofuran (0.47 mL) was treated with propyl vinyl ketone (0.065 mL, 0.56 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.0143 mL, 0.094 mmol). The mixture was stirred and heated in an oil bath at 50° C. for 6 hours and t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | C(C)(=O)O.O1CCCC1 | 50 | 64 | CCCCC1(CCC(=O)CCC)Cc2c(cc(F)c(OC)c2C)C1=O>C(C)(=O)O.O1CCCC1>CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(C)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a350b29a8dfe43538f450062d73c643c | CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(C)c1C2>>CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(O)c(C)c1C2 | C(CCC)C12CC3=C(C(=C(C=C3C2=C(C(CC1)=O)CC)F)OC)C.B(Br)(Br)Br>>C(CCC)C12CC3=C(C(=C(C=C3C2=C(C(CC1)=O)CC)F)O)C | C[O:19][c:18]1[c:16]([F:17])[cH:15][c:14]2[c:22]([c:20]1[CH3:21])[CH2:23][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH2:11][CH3:12])=[C:13]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH2:11][CH3:12])=[C:13]1[c:14]1[cH:15][c:16]([F:17])[c:18]([OH:19])[c:20]([CH3:... | CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(C)c1C2 | CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(O)c(C)c1C2 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 90 | MINUTE | A solution of 9a-butyl-4-ethyl-6-fluoro-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (93 mg, 0.28 mmol) in anhydrous dichloromethane (1.4 mL) was cooled in a dry ice-acetone bath (−78° C.) and the solution treated with 1M boron tribromide in dichloromethane (1.4 mL, 1.4 mmol). The cooling bath was removed an... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | ClCCl | null | 1.5 | CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(C)c1C2>ClCCl>CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(O)c(C)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec39dbd4e6074985880755ae6356933c | CCCCCC(=O)Cl.COc1c(F)cccc1Cl>>CCCCCC(=O)c1cc(F)c(OC)c(Cl)c1 | Cl.[Cl-].[Al+3].[Cl-].[Cl-].ClC1=C(C(=CC=C1)F)OC.C(CCCCC)(=O)Cl>>ClC=1C=C(C=C(C1OC)F)C(CCCCC)=O | Cl[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7].[cH:8]1[cH:9][c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]([Cl:16])[cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]([Cl:16])[cH:17]1 | CCCCCC(=O)Cl.COc1c(F)cccc1Cl | CCCCCC(=O)c1cc(F)c(OC)c(Cl)c1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:6]:[c:5] | null | [] | null | null | 67 | HOUR | Aluminum chloride (1.16 g, 8.72 mmol) was added to a stirred mixture of 1-chloro-3-fluoro-2-methoxybenzene (1.00 mL, 8.72 mmol) and hexanoyl chloride (1.47 mL, 10.46 mmol) at room temperature. The mixture warmed and HCl evolution occurred. The resulting mixture was stirred at room temperature for 67 hours and then part... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | null | null | 67 | CCCCCC(=O)Cl.COc1c(F)cccc1Cl>>CCCCCC(=O)c1cc(F)c(OC)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-644c4332f59e457193dc2c4b5fdfdc26 | C=O.CCCCCC(=O)c1cc(F)c(OC)c(Cl)c1>>CCCCC1Cc2c(cc(F)c(OC)c2Cl)C1=O | ClC=1C=C(C=C(C1OC)F)C(CCCCC)=O.C=O.C([O-])([O-])=O.[K+].[K+]>>C(CCC)C1C(C2=CC(=C(C(=C2C1)Cl)OC)F)=O | O=[CH2:6].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:17]([c:8]1[cH:7][c:15]([Cl:16])[c:12]([O:13][CH3:14])[c:10]([F:11])[cH:9]1)=[O:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][c:7]2[c:8]([cH:9][c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]2[Cl:16])[C:17]1=[O:18] | C=O.CCCCCC(=O)c1cc(F)c(OC)c(Cl)c1 | CCCCC1Cc2c(cc(F)c(OC)c2Cl)C1=O | null | null | CO | C-C Coupling | OtherReaction | be5065257dca5929b2d78368822674c085beb35c1db50df521ad25c0f1e1d5d4 | 2250efeff48c31e3815cbf34eea492a4c680e679ee80813f830cfdaaf31b101f | O=C1CCc2ccccc21 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10](-[Cl;D1;H0:11]):[c:12]>>[C:2]-[C:3]-[CH;D3;+0:4]1-[CH2;D2;+0:1]-[c;H0;D3;+0:9](:[c:10](-[Cl;D1;H0:11]):[c:12]):[c:7](:[c:8])-[C:5]-1=[O;D1;H0:6] | null | [] | 50 | CELSIUS | null | null | A mixture of the crude 1-(3-chloro-5-fluoro-4-methoxyphenyl)-1-hexanone from step 1, methanol (8.7 mL), 37% aqueous formaldehyde (0.786 mL, 10.5 mmol), and potassium carbonate (1.2 g, 8.72 mmol) was stirred and heated in an oil bath at 50° C. for 7 hours. The mixture was evaporated under vacuum and the residue partitio... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ketone | Ketone | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HO- | CO | 50 | null | C=O.CCCCCC(=O)c1cc(F)c(OC)c(Cl)c1>CO>CCCCC1Cc2c(cc(F)c(OC)c2Cl)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ce351c7b8ea4f2facd72afa9105e46c | CCCCC12CCC(=O)C(C)=C1c1cc(F)c(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C)=C1c1cc(F)c(O)c(Cl)c1C2 | C(CCC)C12CC3=C(C(=C(C=C3C2=C(C(CC1)=O)C)F)OC)Cl.Cl.N1=CC=CC=C1>>C(CCC)C12CC3=C(C(=C(C=C3C2=C(C(CC1)=O)C)F)O)Cl | C[O:18][c:17]1[c:15]([F:16])[cH:14][c:13]2[c:21]([c:19]1[Cl:20])[CH2:22][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH3:11])=[C:12]1[c:13]1[cH:14][c:15]([F:16])[c:17]([OH:18])[c:19]([Cl:20])[c:21]1[CH2:22... | CCCCC12CCC(=O)C(C)=C1c1cc(F)c(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(C)=C1c1cc(F)c(O)c(Cl)c1C2 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 200 | CELSIUS | null | null | The product mixture from step 3 and pyridine hydrochloride (5.3 g) were combined and heated in an oil bath at 200° C. for 90 minutes. After cooling, the mixture was partitioned between EtOAc (50 mL) and water (50 ml). The organic phase was washed with brine (50 mL), dried over MgSO4, filtered, and evaporated under vacu... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | null | 200 | null | CCCCC12CCC(=O)C(C)=C1c1cc(F)c(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C)=C1c1cc(F)c(O)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-325295534468402fb193b69d30d93a94 | CCCCC1(CCC(=O)CCC)Cc2c(cc(F)c(OC)c2Cl)C1=O>>CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(Cl)c1C2 | C[O-].[Na+].CO.N12CCCCCC2=NCCC1.C(CCC)C1(C(C2=CC(=C(C(=C2C1)Cl)OC)F)=O)CCC(CCC)=O.Cl.C(=C)C(=O)CCC>>C(CCC)C12CC3=C(C(=C(C=C3C2=C(C(CC1)=O)CC)F)OC)Cl | O=[C:13]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH2:10][CH2:11][CH3:12])[CH2:24][c:23]2[c:14]1[cH:15][c:16]([F:17])[c:18]([O:19][CH3:20])[c:21]2[Cl:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([CH2:11][CH3:12])=[C:13]1[c:14]1[cH:15][c:16]([F:17])[c:18]([O:19][CH3:20... | CCCCC1(CCC(=O)CCC)Cc2c(cc(F)c(OC)c2Cl)C1=O | CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(Cl)c1C2 | null | null | C(C)(=O)O.O1CCCC1 | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[C:13]-[C;D1;H3:14]>>[C:7]-[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[C;H0;D3;+0:12](-[C:13]-[C;D1;H3:14])-[C:10](=[O;D1;H0:11])-[C:9]-[C:8]-2 | null | [] | 60 | CELSIUS | null | null | A sample of the crude product from step 2 in the preceding example (386 mg, 1.36 mmol) in anhydrous tetrahydrofuran (2.7 mL) was treated with propyl vinyl ketone (0.188 mL, 1.63 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.041 mL, 0.272 mmol). The mixture was stirred and heated in an oil bath at 60° C. for two hours... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | C(C)(=O)O.O1CCCC1 | 60 | null | CCCCC1(CCC(=O)CCC)Cc2c(cc(F)c(OC)c2Cl)C1=O>C(C)(=O)O.O1CCCC1>CCCCC12CCC(=O)C(CC)=C1c1cc(F)c(OC)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f4004a05731743db9d750d86b5473e91 | CCCCC1(CCC(C)=O)Cc2c(cc(F)c(OC)c2Cl)C1=O>>CCCCC12CCC(=O)C=C1c1cc(F)c(OC)c(Cl)c1C2 | N1CCCC1.C(C)(=O)O.C(CCC)C1C(C2=CC(=C(C(=C2C1)Cl)OC)F)=O.C(=C)C(=O)C.C[O-].[Na+].CO.C(CCC)C1(C(C2=CC(=C(C(=C2C1)Cl)OC)F)=O)CCC(C)=O>>C(CCC)C12CC3=C(C(=C(C=C3C2=CC(CC1)=O)F)OC)Cl | O=[C:11]1[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][C:8](=[O:9])[CH3:10])[CH2:22][c:21]2[c:12]1[cH:13][c:14]([F:15])[c:16]([O:17][CH3:18])[c:19]2[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[CH:10]=[C:11]1[c:12]1[cH:13][c:14]([F:15])[c:16]([O:17][CH3:18])[c:19]([Cl:20])[c:21]1[CH2:22]2 | CCCCC1(CCC(C)=O)Cc2c(cc(F)c(OC)c2Cl)C1=O | CCCCC12CCC(=O)C=C1c1cc(F)c(OC)c(Cl)c1C2 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:7]-[C:6]12-[C:5]-[c:4]:[c:2](:[c:3])-[C;H0;D3;+0:1]-1=[CH;D2;+0:11]-[C:10](=[O;D1;H0:12])-[C:9]-[C:8]-2 | null | [] | null | null | 5.5 | HOUR | A solution of crude 2-butyl-4-chloro-6-fluoro-5-methoxy-1-indanone (386 mg, 1.4 mmol) in tetrahydrofuran (2.8 mL) was treated with methyl vinyl ketone (0.150 mL, 1.78 mmol) and 0.5N sodium methoxide in methanol (1.1 mL, 0.56 mmol). The mixture was stirred at room temperature for 5.5 hours to effect conversion to 2-buty... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | O1CCCC1.C1(=CC=CC=C1)C | null | 5.5 | CCCCC1(CCC(C)=O)Cc2c(cc(F)c(OC)c2Cl)C1=O>O1CCCC1.C1(=CC=CC=C1)C>CCCCC12CCC(=O)C=C1c1cc(F)c(OC)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72b7c7dabe5b4cf6835bd1c3a2ab8214 | CCCCC12CCC(=O)C(Br)=C1c1cc(F)c(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(Br)=C1c1cc(F)c(O)c(Cl)c1C2 | BrC=1C(CCC2(CC3=C(C(=C(C=C3C12)F)OC)Cl)CCCC)=O.B(Br)(Br)Br>>BrC=1C(CCC2(CC3=C(C(=C(C=C3C12)F)O)Cl)CCCC)=O | C[O:18][c:17]1[c:15]([F:16])[cH:14][c:13]2[c:21]([c:19]1[Cl:20])[CH2:22][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([Br:11])=[C:12]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([Br:11])=[C:12]1[c:13]1[cH:14][c:15]([F:16])[c:17]([OH:18])[c:19]([Cl:20])[c:21]1[CH2:22]2 | CCCCC12CCC(=O)C(Br)=C1c1cc(F)c(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(Br)=C1c1cc(F)c(O)c(Cl)c1C2 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | A solution of 4-bromo-9a-butyl-8-chloro-6-fluoro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (31 mg, 0.077 mmol) in anhydrous dichloromethane (0.5 mL) was cooled in a dry ice-acetone bath (−78° C.) and the solution treated with 1M boron tribromide in dichloromethane (0.231 mL, 0.231 mmol). The cooling bath was remov... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | ClCCl | null | 1 | CCCCC12CCC(=O)C(Br)=C1c1cc(F)c(OC)c(Cl)c1C2>ClCCl>CCCCC12CCC(=O)C(Br)=C1c1cc(F)c(O)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2114ab91aa8947dd91beb80fa17fd697 | CCCCC12CCC(=O)C(C(F)(F)F)=C1c1cc(F)c(OC)c(Cl)c1C2>>CCCCC12CCC(=O)C(C(F)(F)F)=C1c1cc(F)c(O)c(Cl)c1C2 | C(CCC)C12CC3=C(C(=C(C=C3C2=C(C(CC1)=O)C(F)(F)F)F)OC)Cl.B(Br)(Br)Br>>C(CCC)C12CC3=C(C(=C(C=C3C2=C(C(CC1)=O)C(F)(F)F)F)O)Cl | C[O:21][c:20]1[c:18]([F:19])[cH:17][c:16]2[c:24]([c:22]1[Cl:23])[CH2:25][C:5]1([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]([F:12])([F:13])[F:14])=[C:15]12>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:6][CH2:7][C:8](=[O:9])[C:10]([C:11]([F:12])([F:13])[F:14])=[C:15]1[c:16]1[cH:17][c:18]([F:19])[c:2... | CCCCC12CCC(=O)C(C(F)(F)F)=C1c1cc(F)c(OC)c(Cl)c1C2 | CCCCC12CCC(=O)C(C(F)(F)F)=C1c1cc(F)c(O)c(Cl)c1C2 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1C=C2c3ccccc3CC2CC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | A solution of 9a-butyl-8-chloro-6-fluoro-7-methoxy-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (39 mg, 0.10 mmol) in anhydrous dichloromethane (1.0 mL) was cooled in a dry ice-acetone bath (−78° C.) and the solution was treated with 1M boron tribromide in dichloromethane (0.3 mL, 0.3 mmol). The cooling bat... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=C2c3ccccc3CC2CCC1 | Other | ClCCl | null | 1 | CCCCC12CCC(=O)C(C(F)(F)F)=C1c1cc(F)c(OC)c(Cl)c1C2>ClCCl>CCCCC12CCC(=O)C(C(F)(F)F)=C1c1cc(F)c(O)c(Cl)c1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-787cbd4a712c4b168df30fdb5fe09b66 | C=CC(=O)CC.COc1ccc2c(c1)CC(CCO)C2=O>>CCC(=O)CCC1(CCO)Cc2cc(OC)ccc2C1=O | OCCC1C(C2=CC=C(C=C2C1)OC)=O.C(=C)C(=O)CC.C[O-].[Na+]>>OCCC1(C(C2=CC=C(C=C2C1)OC)=O)CCC(CC)=O | [CH3:1][CH2:2][C:3](=[O:4])[CH:5]=[CH2:6].[CH:7]1([CH2:8][CH2:9][OH:10])[CH2:11][c:12]2[cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18][c:19]2[C:20]1=[O:21]>>[CH3:1][CH2:2][C:3](=[O:4])[CH2:5][CH2:6][C:7]1([CH2:8][CH2:9][OH:10])[CH2:11][c:12]2[cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18][c:19]2[C:20]1=[O:21] | C=CC(=O)CC.COc1ccc2c(c1)CC(CCO)C2=O | CCC(=O)CCC1(CCO)Cc2cc(OC)ccc2C1=O | null | null | CO.CCOC(=O)C | C-C Coupling | OtherReaction | c504c0d32586144b6874498db3cc99d4d5bb675e1b2e725385a0386d3f14ac05 | 68a0b2d4768a64505cf15a6dd6bbd75216aef3c50fb86aff9b39341b3e49f06d | O=C1CCc2ccccc21 | [C:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH2;D1;+0:5].[C:6]-[C:7]-[CH;D3;+0:8]1-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13]>>[C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C;H0;D4;+0:8]1(-[C:7]-[C:6])-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13] | 93 | [{"value": 93.0, "product": "OCCC1(C(C2=CC=C(C=C2C1)OC)=O)CCC(CC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of 2-(2-hydroxyethyl)-5-methoxy-1-indanone (105 mg, 0.51 mmol) in methanol (2.0 mL) at room temperature was treated with ethyl vinyl ketone (EVK, 0.102 mL) and 0.5M sodium methoxide in methanol (0.204 mL, 0.1 mmol). The mixture was stirred in a capped flask and heated in an oil bath at 60° C. for 8 hours. Af... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Vinyl | Ketone.Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | CO.CCOC(=O)C | 60 | null | C=CC(=O)CC.COc1ccc2c(c1)CC(CCO)C2=O>CO.CCOC(=O)C>CCC(=O)CCC1(CCO)Cc2cc(OC)ccc2C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ca20c97881a46a7b3a605c4a606073c | COc1ccc2c(c1)CC1(CCOS(C)(=O)=O)CCC(=O)C(C)=C21.[I-]>>COc1ccc2c(c1)CC1(CCI)CCC(=O)C(C)=C21 | CS(=O)(=O)OCCC12CCC(C(=C1C=1C=CC(=CC1C2)OC)C)=O.[I-].[Na+]>>ICCC12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC | CS(=O)(=O)O[CH2:12][CH2:11][C:10]12[CH2:9][c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[C:20]1=[C:18]([CH3:19])[C:16](=[O:17])[CH2:15][CH2:14]2.[I-:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][C:10]1([CH2:11][CH2:12][I:13])[CH2:14][CH2:15][C:16](=[O:17])[C:18]([CH3:19])=[C:20]21 | COc1ccc2c(c1)CC1(CCOS(C)(=O)=O)CCC(=O)C(C)=C21.[I-] | COc1ccc2c(c1)CC1(CCI)CCC(=O)C(C)=C21 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 119410ad0456baafba3b2935b12d3e44977c506a6dd8cacdd3e4fe37abe9db9f | ddf832dd4937bef392b42ed4281006ae20524cc7fc61b350edeb12d7b5bf783f | O=C1C=C2c3ccccc3CC2CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[C:5].[I-;H0;D0:6]>>[C:5]=[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 64 | [{"value": 64.0, "product": "ICCC12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.6, "product": "ICCC12CC3=CC(=CC=C3C2=C(C(CC1)=O)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of 2-(2-methoxy-5-methyl-6-oxo-6,7,8,9-tetrahydro-8aH-fluoren-8a-yl)ethyl methanesulfonate (49.7 mg, 0.142 mmol) in acetone (2.0 mL) was treated with sodium iodide (85 mg, 0.57 mmol) and the resulting mixture was stirred and heated in an oil bath at 60° C. for 16 hours. After cooling, the mixture was diluted... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Primary halide | null | null | C1=C2c3ccccc3CC2CCC1 | MsOH.HO- | CC(=O)C | 60 | null | COc1ccc2c(c1)CC1(CCOS(C)(=O)=O)CCC(=O)C(C)=C21.[I-]>CC(=O)C>COc1ccc2c(c1)CC1(CCI)CCC(=O)C(C)=C21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd4a17db7fd44b94ad9c395a089d4e4a | CCC(C)(C)C(=O)C(=O)N1CCC[C@H]1C(=O)O.NNc1ccccn1>>CCC(C)(C)C(=O)C(=O)N1CCCC1C(=O)NNc1ccccn1 | O=C(C(C(CC)(C)C)=O)N1[C@@H](CCC1)C(=O)O.CCN(C(C)C)C(C)C.N(N)C1=NC=CC=C1.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F.COC([C@H]1NCCC1)=O>>N1=C(C=CC=C1)NNC(=O)C1N(CCC1)C(C(C(CC)(C)C)=O)=O | O[C:15]([C@H:14]1[N:10]([C:8]([C:6]([C:3]([CH2:2][CH3:1])([CH3:4])[CH3:5])=[O:7])=[O:9])[CH2:11][CH2:12][CH2:13]1)=[O:16].[NH2:17][NH:18][c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1>>[CH3:1][CH2:2][C:3]([CH3:4])([CH3:5])[C:6](=[O:7])[C:8](=[O:9])[N:10]1[CH2:11][CH2:12][CH2:13][CH:14]1[C:15](=[O:16])[NH:17][NH:18][c:19]1[... | CCC(C)(C)C(=O)C(=O)N1CCC[C@H]1C(=O)O.NNc1ccccn1 | CCC(C)(C)C(=O)C(=O)N1CCCC1C(=O)NNc1ccccn1 | null | CN(C)C=1C=CN=CC1 | C1CCOC1.O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 87776deec7c8d787307af11af64c4c1226af5b5e46e4fe8124762f384e2eebf3 | 82203b4f77b2f7d17908f28dcc1ecc7f616d152f963b273ffea1254f61a0fe2d | O=C(NNc1ccccn1)C1CCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@@H;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[#7:7]-1-[C:8](=[O;D1;H0:9])-[C:10]=[O;D1;H0:11].[#7;a:12]:[c:13]-[#7:14]-[NH2;D1;+0:15]>>[#7;a:12]:[c:13]-[#7:14]-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[#7:7]-1-[C:8](=[O;D1;H0:9])-[C:10]=[O;D1;H0:11] | null | [] | null | null | 24 | HOUR | A mixture of (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidine-carboxylic acid (482 mg, 2 mmol), prepared from L-proline methyl ester according to the procedure described in WO 96/40633, 2-hydrazinopyridine (364 mg, 2 mmol), PyBrop (932 mg, 2 mmol), DMAP (4-dimethyaminopyridine, 122 mg) and DIEA (4 mL) in THF (dry, 5... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid | Acylhydrazine | null | null | C1CC[NH]C1.c1ccncc1 | HO- | CN(C)C=1C=CN=CC1.C1CCOC1.O.C(C)(=O)OCC | null | 24 | CCC(C)(C)C(=O)C(=O)N1CCC[C@H]1C(=O)O.NNc1ccccn1>CN(C)C=1C=CN=CC1.C1CCOC1.O.C(C)(=O)OCC>CCC(C)(C)C(=O)C(=O)N1CCCC1C(=O)NNc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46f3493837464fa1985f3dcce3aef5a5 | COC(=O)C1CCCCN1C(=O)C(=O)c1cccs1>>O=C(C(=O)N1CCCCC1C(=O)O)c1cccs1 | O=C(C(C=1SC=CC1)=O)N1C(CCCC1)C(=O)OC.[Li+].[OH-].Cl>>O=C(C(C=1SC=CC1)=O)N1C(CCCC1)C(=O)O | C[O:13][C:11]([CH:10]1[N:5]([C:3]([C:2](=[O:1])[c:14]2[cH:15][cH:16][cH:17][s:18]2)=[O:4])[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:12]>>[O:1]=[C:2]([C:3](=[O:4])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:11](=[O:12])[OH:13])[c:14]1[cH:15][cH:16][cH:17][s:18]1 | COC(=O)C1CCCCN1C(=O)C(=O)c1cccs1 | O=C(C(=O)N1CCCCC1C(=O)O)c1cccs1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(C(=O)N1CCCCC1)c1cccs1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 16 | HOUR | Intermediate 2 (2.45 g, 8.72 mmol) was dissolved in MeOH (50 mL). LiOH solution (1 N, 13 mL) was added at 0° C., and the mixture was stirred at the same temperature for 2 h and at room temperature for 16 h. The reaction mixture was acidified with 1 N HCl, and extracted with ethyl acetate. The organic phase was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccsc1 | Other | CO | null | 16 | COC(=O)C1CCCCN1C(=O)C(=O)c1cccs1>CO>O=C(C(=O)N1CCCCC1C(=O)O)c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-617a12e0035e4410b97f42be63d9aec7 | Cc1cc(C(F)(F)F)cc(NN)n1.O=C(C(=O)N1CCCCC1C(=O)O)c1cccs1>>Cc1cc(C(F)(F)F)cc(NNC(=O)C2CCCCN2C(=O)C(=O)c2cccs2)n1 | O=C(C(C=1SC=CC1)=O)N1C(CCCC1)C(=O)O.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.N(N)C1=NC(=CC(=C1)C(F)(F)F)C>>CC1=CC(=CC(=N1)NNC(=O)C1N(CCCC1)C(C(C=1SC=CC1)=O)=O)C(F)(F)F | [CH3:1][c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][c:10]([NH:11][NH2:12])[n:30]1.O[C:13](=[O:14])[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:21](=[O:22])[C:23](=[O:24])[c:25]1[cH:26][cH:27][cH:28][s:29]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[cH:9][c:10]([NH:11][NH:12][C:13](=[O:14])[CH:15]2[CH... | Cc1cc(C(F)(F)F)cc(NN)n1.O=C(C(=O)N1CCCCC1C(=O)O)c1cccs1 | Cc1cc(C(F)(F)F)cc(NNC(=O)C2CCCCN2C(=O)C(=O)c2cccs2)n1 | null | CN(C)C=1C=CN=CC1 | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 87776deec7c8d787307af11af64c4c1226af5b5e46e4fe8124762f384e2eebf3 | 82203b4f77b2f7d17908f28dcc1ecc7f616d152f963b273ffea1254f61a0fe2d | O=C(C(=O)N1CCCCC1C(=O)NNc1ccccn1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[C:8]=[O;D1;H0:9])-[C:10].[#7;a:11]:[c:12]-[#7:13]-[NH2;D1;+0:14]>>[#7;a:11]:[c:12]-[#7:13]-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[C:8]=[O;D1;H0:9])-[C:10] | null | [] | null | null | null | null | From Intermediate 3 (267 mg, 1 mmol), 2-hydrazino-6-methyl-4-trifluoromethylpyridine (191 mg, 1 mmol), PyBrop (466 mg, 1 mmol), DMAP (122 mg) and DIEA (2 mL) in THF (30 mL), using the same procedure for Compound 1, the title compound was obtained as a white solid; 110 mg (25%). MS (m/z) 441 (M+1).
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid | Acylhydrazine | null | null | c1ccncc1.C1CC[NH]CC1.c1ccsc1 | HO- | CN(C)C=1C=CN=CC1.C1CCOC1 | null | null | Cc1cc(C(F)(F)F)cc(NN)n1.O=C(C(=O)N1CCCCC1C(=O)O)c1cccs1>CN(C)C=1C=CN=CC1.C1CCOC1>Cc1cc(C(F)(F)F)cc(NNC(=O)C2CCCCN2C(=O)C(=O)c2cccs2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7d8656799d6241dcb7cc7ca2a9e1f1af | COC(=O)C1CCN1S(=O)(=O)Cc1ccccc1>>O=C(O)C1CCN1S(=O)(=O)Cc1ccccc1 | COC(=O)C1N(CC1)S(=O)(=O)CC1=CC=CC=C1.[OH-].[Li+]>>C1(=CC=CC=C1)CS(=O)(=O)N1C(CC1)C(=O)O | C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][N:7]1[S:8](=[O:9])(=[O:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][N:7]1[S:8](=[O:9])(=[O:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | COC(=O)C1CCN1S(=O)(=O)Cc1ccccc1 | O=C(O)C1CCN1S(=O)(=O)Cc1ccccc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=S(=O)(Cc1ccccc1)N1CCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 82,829.6 | [{"value": 83.0, "product": "C1(=CC=CC=C1)CS(=O)(=O)N1C(CC1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82829.6, "product": "C1(=CC=CC=C1)CS(=O)(=O)N1C(CC1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 1-Phenylmethanesulfonyl-azetidine-2-carboxylic acid methyl ester (1.13 g, 4.19 mmoles) was dissolved in methanol (20 mL) and cooled to 0° C. Treatment of this solution with aqueous lithium hydroxide (7.75 mL, 1 M) was followed by warming to ambient temperature over a 3 hour period. Most of the methanol was removed in v... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]C1.c1ccccc1 | Other | CO | 0 | null | COC(=O)C1CCN1S(=O)(=O)Cc1ccccc1>CO>O=C(O)C1CCN1S(=O)(=O)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67afd482a98941bbb70354163e05eb94 | Cc1ccc(C=O)cc1F>>Cc1ccc(C(C)O)cc1F | FC=1C=C(C=O)C=CC1C.C[Mg]Br.Cl>>OC(C)C1=CC(=C(C=C1)C)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:8])[cH:9][c:10]1[F:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([CH3:7])[OH:8])[cH:9][c:10]1[F:11] | Cc1ccc(C=O)cc1F | Cc1ccc(C(C)O)cc1F | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | 100.5 | [{"value": 100.5, "product": "OC(C)C1=CC(=C(C=C1)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To an ice-cold solution of 3-fluoro-4-methylbenzaldehyde (50 mg, 0.36 mmol) in THF (0.5 mL) was added dropwise a 0.93 M solution (0.47 mL) of methylmagnesium bromide (0.44 mmol) in THF. The temperature of the reaction mixture was allowed to rise back to room temperature, at which the reaction mixture was stirred for 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | null | 1 | Cc1ccc(C=O)cc1F>C1CCOC1>Cc1ccc(C(C)O)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0498ef0e78694a75a5377ea196575744 | Cc1ccc(C(C)O)cc1F>>CC(=O)c1ccc(C)c(F)c1 | OC(C)C1=CC(=C(C=C1)C)F.C=1C=C[NH+]=CC1.[O-][Cr](=O)(=O)Cl>>FC=1C=C(C=CC1C)C(C)=O | [CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[c:9]([F:10])[cH:11]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[c:9]([F:10])[cH:11]1 | Cc1ccc(C(C)O)cc1F | CC(=O)c1ccc(C)c(F)c1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccccc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6] | 86.7 | [{"value": 86.0, "product": "FC=1C=C(C=CC1C)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "FC=1C=C(C=CC1C)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-(1-hydroxyethyl)-2-fluorotoluene (55.8 mg, 0.36 mmol) in methylene chloride (1 mL) were added molecular sieve 4A (56.0 mg) and PCC 94.0 mg (0.43 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through Celite, and the filtrate was concentrated under... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1 | null | C(Cl)Cl | null | 1 | Cc1ccc(C(C)O)cc1F>C(Cl)Cl>CC(=O)c1ccc(C)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-592233984b9b4dd7b002c45f0958065b | CC(=O)c1ccc(C)c(F)c1.CCOC(=O)C(=O)C(=O)OCC>>CCOC(=O)C(O)(CC(=O)c1ccc(C)c(F)c1)C(=O)OCC | FC=1C=C(C=CC1C)C(C)=O.O=C(C(=O)OCC)C(=O)OCC>>C(C)OC(=O)C(C(=O)OCC)(CC(=O)C1=CC(=C(C=C1)C)F)O | [CH3:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([CH3:15])[c:16]([F:17])[cH:18]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[C:19](=[O:20])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([OH:7])([CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([CH3:15])[c:16]([F:17])[cH:18]1)[C:19](=[O:20])[O:21][CH2:22... | CC(=O)c1ccc(C)c(F)c1.CCOC(=O)C(=O)C(=O)OCC | CCOC(=O)C(O)(CC(=O)c1ccc(C)c(F)c1)C(=O)OCC | null | null | null | C-C Coupling | OtherReaction | e88a4a7d8d6b5dee5ec6739bba985b00a792654307585b505d721a6c4424a1e7 | 622d9e177646f51219fadf1ea3ee007cb7d9c42cff173da68f5fdf3c13916e74 | c1ccccc1 | [CH3;D1;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[OH;D1;+0:10])(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | 79.3 | [{"value": 79.3, "product": "C(C)OC(=O)C(C(=O)OCC)(CC(=O)C1=CC(=C(C=C1)C)F)O", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 48 | HOUR | A mixture of 3′-fluoro-4′-methylacetophenone (4.92 g, 32.3 mmol) and diethyl ketomalonate (6.19 g, 35.6 mmol) was stirred at 120° C. for 48 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and the mixture was purified by column chromatography on silica gel [silica gel 100 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone.Ester.Ester.Tertiary alcohol | null | null | c1ccccc1 | null | null | 120 | 48 | CC(=O)c1ccc(C)c(F)c1.CCOC(=O)C(=O)C(=O)OCC>>CCOC(=O)C(O)(CC(=O)c1ccc(C)c(F)c1)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9eae8e4020a414d90a4fd0e994de72c | CCOC(=O)C(O)(CC(=O)c1ccc(C)c(F)c1)C(=O)OCC.NN>>Cc1ccc(-c2cc(C(=O)O)c(=O)[nH]n2)cc1F | [OH-].[Na+].C(C)OC(=O)C(C(=O)OCC)(CC(=O)C1=CC(=C(C=C1)C)F)O.O.NN.Cl>>C(=O)(O)C=1C(NN=C(C1)C1=CC(=C(C=C1)C)F)=O | CCO[C:12]([C:8](O)([CH2:7][C:6](=O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:17]([F:18])[cH:16]1)[C:9](=[O:10])[O:11]CC)=[O:13].[NH2:14][NH2:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12](=[O:13])[nH:14][n:15]2)[cH:16][c:17]1[F:18] | CCOC(=O)C(O)(CC(=O)c1ccc(C)c(F)c1)C(=O)OCC.NN | Cc1ccc(-c2cc(C(=O)O)c(=O)[nH]n2)cc1F | null | null | C(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | ebc1b4166a3a2c5ebd997173df1a8f4786085ddbe534c5ee805b61ad55c292e1 | f0716b7f64b3a238ee9f3d2ce4fc900dee4f01e88461c96dbe61fcf07f5faeb5 | O=c1ccc(-c2ccccc2)n[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3](-O)(-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-[C:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-C-C.[NH2;D1;+0:14]-[NH2;D1;+0:15]>>[O;D1;H0:12]=[C:11](-[OH;D1;+0:13])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:... | 87.7 | [{"value": 87.7, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of ethyl 2-ethoxycarbonyl-4-(3-fluoro-4-methylphenyl)-2-hydroxy-4-oxobutanoate (8.41 9, 25.8 mmol) in isopropanol (100 mL) was added hydrazine monohydrate (2.84 g, 56.8 mmol), and the mixture was heated under stirring at 100 for 6 hours. Then, 2 mol/L sodium hydroxide was added, and the mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Ester.Tertiary alcohol | Carboxylic acid | null | c1cnncc1 | c1ccccc1.c1cnncc1 | HO- | C(C)(C)O | null | 6 | CCOC(=O)C(O)(CC(=O)c1ccc(C)c(F)c1)C(=O)OCC.NN>C(C)(C)O>Cc1ccc(-c2cc(C(=O)O)c(=O)[nH]n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-447057a76e4c472e8ee185e270a27f68 | CC(C)CBr.COC(=O)c1cc(-c2ccc(C)c(F)c2)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O | C(O)([O-])=O.[Na+].FC=1C=C(C=CC1C)C=1C=C(C(NN1)=O)C(=O)OC.C([O-])([O-])=O.[K+].[K+].C(C(C)C)Br>>FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC | Br[CH2:18][CH:19]([CH3:20])[CH3:21].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([CH3:12])[c:13]([F:14])[cH:15]2)[n:16][nH:17][c:22]1=[O:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([CH3:12])[c:13]([F:14])[cH:15]2)[n:16][n:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[c:2... | CC(C)CBr.COC(=O)c1cc(-c2ccc(C)c(F)c2)n[nH]c1=O | COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 456217c8bdd4490079dbc0339e1b1eedc560d0b24ec9d54c4ed1fbd8e71fb3dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1ccc(-c2ccccc2)n[nH]1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[#7;a:12]:[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4]):[#7;a:12]:[c:13] | 85 | [{"value": 84.9, "product": "FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | To a solution of 6-(3-fluoro-4-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one (5.28 g, 20.0 mmol) in N,N-dimethylformamide (40 mL) were added potassium carbonate (5.53 g, 40.0 mmol) and isobutyl bromide (3.29 g, 24.0 mmol), and the mixture was stirred at 80° C. for 1 hour. The temperature of the reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnncc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1 | HBr | CN(C=O)C | 80 | 1 | CC(C)CBr.COC(=O)c1cc(-c2ccc(C)c(F)c2)n[nH]c1=O>CN(C=O)C>COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab1294f86fcd4655a65edddcfbdbb4bc | COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O>>Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F | Cl.[OH-].[Na+].FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC.O>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O | C[O:11][C:9]([c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[c:21]([F:22])[cH:20]2)[n:19][n:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[c:12]1=[O:13])=[O:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[n:19]2)[cH:20][c:21]1[F:22] | COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)n[nH]1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 93.8 | [{"value": 93.8, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 15 | MINUTE | To a suspension of 6-(3-fluoro-4-methylphenyl)-2-isobutyl-4-methoxycarbonyl-2H-pyridazin-3-one (5.27 g, 16.6 mmol) in methanol (50 mL) was added a 2 mol/L aqueous sodium hydroxide (50 mL), and the mixture was stirred at 60° C. for 15 minutes. The temperature of the reaction mixture was allowed to drop back to room temp... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1 | Other | CO | 60 | 0.25 | COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O>CO>Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d75da831e89b460095cd01caa65390ca | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2nn(CC(C)C)c(=O)c(O)c2C)cc1F | C(OCC)(=O)Cl.C1CCOC1.Cl.[BH4-].[Na+].C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C)N(CC)CC.C1CCOC1>>FC=1C=C(C=CC1C)C=1C(=C(C(N(N1)CC(C)C)=O)O)C | O=[C:18]([c:15]1[c:13](=[O:14])[n:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[n:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[c:20]([F:21])[cH:19]2)[cH:17]1)[OH:16]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[c:13](=[O:14])[c:15]([OH:16])[c:17]2[CH3:18])[cH:19][c:20]1[F:21] | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F | Cc1ccc(-c2nn(CC(C)C)c(=O)c(O)c2C)cc1F | null | null | O | Miscellaneous | OtherReaction | 50b37df3879a3cb84a59a03d9c916437bc7d466fe1499b85b20332fbfc13cc6a | 9b981ffa1dc2208a196fed475e723ee668e37655a0b8fbe764684c618ae17839 | O=c1ccc(-c2ccccc2)n[nH]1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5](-[c:6]):[#7;a:7]:[#7;a:8](-[C:9]):[c:10]:1=[O;D1;H0:11]>>[C:9]-[#7;a:8]1:[#7;a:7]:[c:5](-[c:6]):[c;H0;D3;+0:4](-[CH3;D1;+0:1]):[c;H0;D3;+0:3](-[OH;D1;+0:2]):[c:10]:1=[O;D1;H0:11] | 25 | [{"value": 25.0, "product": "FC=1C=C(C=CC1C)C=1C(=C(C(N(N1)CC(C)C)=O)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 4-carboxy-6-(3-fluoro-4-methyl-phenyl)-2-isobutyl-2H-pyridazin-3-one (4.53 g, 14.9 mmol) in THF (40 mL) was added triethylamine (1.66 g, 16.4 mmol). To the ice-cooled mixture was added dropwise a solution of ethyl chlorocarbonate (1.78 g, 16.4 mmol) in THF (5 mL), and the mixture was stirred for 30 min... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aromatic alcohol | c1ccnnc1 | c1ccnnc1 | c1ccccc1.c1ccnnc1 | Other | O | null | 0.5 | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F>O>Cc1ccc(-c2nn(CC(C)C)c(=O)c(O)c2C)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-545ec692753a43dfb8f282d8b901e30d | CS(=O)(=O)Cl.Cc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)CO.C(C)N(CC)CC.CS(=O)(=O)Cl.C(O)([O-])=O.[Na+]>>FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C | Cl[S:11]([CH3:12])(=[O:13])=[O:14].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][OH:10])[c:15](=[O:16])[n:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[n:22]2)[cH:23][c:24]1[F:25]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][O:10][S:11]([CH3:12])(=[O:13])=[O:14])[c:15](=[O:16])[n:17]([CH2:18][CH:19](... | CS(=O)(=O)Cl.Cc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1F | Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | O=c1ccc(-c2ccccc2)n[nH]1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7;a:5]:[c:6]:[c:7]-[C:8]-[OH;D1;+0:9]>>[#7;a:5]:[c:6]:[c:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 70.4 | [{"value": 70.4, "product": "FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.1, "product": "FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To an ice-cold solution of 6-(3-fluoro-4-methyl-phenyl)-4-hydroxymethyl-2-isobutyl-2H-pyridazin-3-one (1.08 g, 3.73 mmol) in methylene chloride (20 mL) were added triethylamine (491 mg, 4.85 mmol) and methanesulfonyl chloride (513 mg, 4.48 mmol), and the mixture was stirred for 1 hour. A saturated aqueous solution of s... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccnnc1 | HCl | C(Cl)Cl | null | 1 | CS(=O)(=O)Cl.Cc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1F>C(Cl)Cl>Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe9e652ae9ab4faca893097b8edf8b1c | CC(C)(C)OC(=O)N1CCNCC1.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | O.FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.C([O-])([O-])=O.[K+].[K+].N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O | [NH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]1.CS(=O)(=O)O[CH2:30][c:15]1[c:13](=[O:14])[n:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[n:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[c:32]([F:33])[cH:31]2)[cH:29]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]([CH2:9][C... | CC(C)(C)OC(=O)N1CCNCC1.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 20463218c281e2c61bf0173d651b213ee8033fd2ccbdfc94848e31db5e0e51b8 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:4](-[c:5]):[c;H0;D3;+0:3](-[CH3;D1;+0:1]):[c;H0;D3;+0:2](-[N;H0;D3;+0:14]2-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-2):[c:9]:... | 92.9 | [{"value": 92.4, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | To a solution of 6-(3-fluoro-4-methylphenyl)-2-isobutyl-4-methanesulfonyloxy methyl-2H-pyridazin-3-one (100 mg, 0.27 mmol) in acetonitrile (1 mL) were added potassium carbonate (56.3 mg, 0.41 mmol) and tert-butyl 1-piperazine-carboxylate (60.7 mg, 0.33 mmol), and the mixture was stirred at 80° C. for 2 hours. The tempe... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccnnc1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1 | MsOH.HO- | C(C)#N | 80 | 2 | CC(C)(C)OC(=O)N1CCNCC1.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>C(C)#N>Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-255e4d7378f140328c7e6ec5faa61ba2 | Cc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2cc(CN3CCNCC3)c(=O)n(CC(C)C)n2)cc1F.Cl | C(C)OCC.C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O.Cl>>Cl.Cl.FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCNCC1 | CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][N:10]([CH2:9][c:8]2[cH:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[c:25]([F:26])[cH:24]3)[n:23][n:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[c:16]2=[O:17])[CH2:15][CH2:14]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][N:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[c:16](=[... | Cc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1F | Cc1ccc(-c2cc(CN3CCNCC3)c(=O)n(CC(C)C)n2)cc1F.Cl | null | null | C(C)(=O)OCC | Miscellaneous | Boc amine deprotection | ca9288c3be1743ea424604bf62770990eec893f8f7f07c612f680fef8b15531e | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | O=c1[nH]nc(-c2ccccc2)cc1CN1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 75 | [{"value": 75.0, "product": "Cl.Cl.FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-(4-tert-butoxycarbonyl-1-piperazinyl)methyl-6-(3-fluoro-4-methylphenyl)-2-isobutyl-2H-pyridazin-3-one (115 mg, 0.25 mmol) in ethyl acetate (2 mL) was added a 4 mol/L solution (2 mL) of hydrochloric acid in ethyl acetate, and the mixture was stirred at 50 for 1 hour. The temperature of the reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1ccnnc1.C1C[NH]CCN1 | HO- | C(C)(=O)OCC | null | 1 | Cc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1F>C(C)(=O)OCC>Cc1ccc(-c2cc(CN3CCNCC3)c(=O)n(CC(C)C)n2)cc1F.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-409e1ee3b5d24cd29adbd3d222778aab | Cl>>Cl.Cl | Cl.FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C>>Cl.Cl.FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C | [ClH:28]>>[ClH:28].[ClH:29] | Cl | Cl.Cl | null | null | CO.C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 63.7 | [{"value": 63.7, "product": "Cl.Cl.FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-(3-fluoro-4-methylphenyl)-2-isobutyl-4-(4-methyl-1-piperazinyl)methyl-2H-pyridazin-3-one (94.4 mg, 0.25 mmol) in methanol (1 mL) was added dropwise at room temperature under stirring a 4 mol/L solution (0.15 mL) of hydrochloric acid in ethyl acetate. The solvent was distilled off under reduced pressu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | CO.C(C)(=O)OCC | null | null | Cl>CO.C(C)(=O)OCC>Cl.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f4fc513dafa4ea6aad188ea8bbf6697 | CNC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2cc(CN(C)C)c(=O)n(CC(C)C)n2)cc1F | FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.CNC>>CN(C)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O | [NH:10]([CH3:11])[CH3:12].CS(=O)(=O)O[CH2:9][c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[c:22]([F:23])[cH:21]2)[n:20][n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[c:13]1=[O:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][N:10]([CH3:11])[CH3:12])[c:13](=[O:14])[n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[... | CNC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | Cc1ccc(-c2cc(CN(C)C)c(=O)n(CC(C)C)n2)cc1F | null | null | O | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)n[nH]1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 80.9 | [{"value": 80.9, "product": "CN(C)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | To 6-(3-fluoro-4-methylphenyl)-2-isobutyl-4-methane-sulfonyloxymethyl-2H-pyridazin-3-one (100 mg, 0.27 mmol) was added a 40% aqueous dimethylamine (1 mL), and the mixture was stirred at 80° C. for 2 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and then, water was added. T... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1 | MsOH.HO- | O | 80 | 2 | CNC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>O>Cc1ccc(-c2cc(CN(C)C)c(=O)n(CC(C)C)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c710a98177e24ecea9f95a6057b7ad14 | COc1ccc(C2=NN(CC3CC3)C(=O)C(OC)C2=C=O)cc1F.Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F>>COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1F | C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C(C(C1=O)OC)=C=O)C1=CC(=C(C=C1)OC)F>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O | COC1C(=O)N(C[CH:17]2[CH2:18][CH2:19]2)N=C([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:22]([F:23])[cH:21]2)C1=C=O.Cc1ccc(-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16]C(C)C)[n:20]2)cc1F>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][CH:... | COc1ccc(C2=NN(CC3CC3)C(=O)C(OC)C2=C=O)cc1F.Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1F | null | null | null | C-C Coupling | OtherReaction | 1baeab77a2d9456e7a32be1a7498dec1a8014ae556d713c79bcb77b4e4e75090 | 017f711087a5cfc6cbc30665004ce603e128db6c57513baa4a730b058257fb7c | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-C(-C)-[CH2;D2;+0:1]-[#7;a:2]1:[#7;a:3]:[c;H0;D3;+0:4](-c2:c:c:c(-C):c(-F):c:2):[c:5]:[c:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[c:10]:1.C-O-C1-C(=O)-N(-C-[CH;D3;+0:11]2-[C:12]-[C:13]-2)-N=C(-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18])-C-1=C=O>>[O;D1;H0:8]=[C:7](-[O;D1;H1:9])-[c:6]1:[c:10]:[#7;a:2](-[CH2;D2;+0:1]-[CH... | 98.9 | [{"value": 98.9, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-cyclo-propylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methoxy-carbonyl-2H-pyridazin-3-one was reacted to yield the title compound as yellow crystals (yield: 98.9%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide.Aromatic halide.Ether | null | C1=NNCCC1.C1CC1.c1ccccc1.c1ccccc1.c1ccnnc1 | c1ccccc1.c1ccnnc1.C1CC1 | c1ccccc1.c1ccnnc1.C1CC1 | HF | null | null | null | COc1ccc(C2=NN(CC3CC3)C(=O)C(OC)C2=C=O)cc1F.Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F>>COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29d215b07747424baa326c57ae8e04df | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1F | FC=1C=C(C=CC1C)C=1C(=C(C(N(N1)CC(C)C)=O)O)C.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O>>C1(CC1)CN1N=C(C=C(C1=O)CO)C1=CC(=C(C=C1)OC)F | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21]([F:22])[cH:20]2)[n:19][n:14]([CH2:15][CH:16]2[CH2:17][CH2:18]2)[c:12]1=[O:13])[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]3[CH2:17][CH2:18]3)[n:19]2)[cH:20][c:21]1[F:22] | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 21.3 | [{"value": 21.3, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow fine-needles (yield: 21.3%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.C1CC1 | Other | null | null | null | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24caefb412d641299dc0356bb3b2eb83 | COc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1F.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F | FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.C1(CC1)CN1N=C(C=C(C1=O)CO)C1=CC(=C(C=C1)OC)F>>C1(CC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:16](=[O:17])[n:18]([CH2:19][CH:20]3[CH2:21][CH2:22]3)[n:23]2)[cH:24][c:25]1[F:26].Cc1ccc(-c2cc(CO[S:12]([CH3:13])(=[O:14])=[O:15])c(=O)n(CC(C)C)n2)cc1F>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][O:11][S:12]([CH3:13])(=[O:14]... | COc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1F.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Functional Group Interconversion | OtherReaction | 8b0e3d7bee01c1cd08d5b9300989bcd9434e06e13b2628e4e267ebe847060d81 | 91ea60d6fa98857424dec1beabf111ed8901abdf48d6e9b2323a22e8ccca105d | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c:c(-C-O-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4]):c:1=O.[#7;a:5]:[c:6]:[c:7]-[C:8]-[OH;D1;+0:9]>>[#7;a:5]:[c:6]:[c:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 80.4 | [{"value": 80.4, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (9), 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl) -4-hydroxymethyl-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow needles (yield: 80.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Primary alcohol | Mesylate | c1ccccc1.c1ccnnc1 | null | c1ccccc1.c1ccnnc1.C1CC1 | HF | null | null | null | COc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1F.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6888d75665f483bbf89bb734af68f01 | CN.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>CNCc1cc(-c2ccc(OC)c(F)c2)nn(CC2CC2)c1=O | C1(CC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.CN.C(C)O>>C1(CC1)CN1N=C(C=C(C1=O)CNC)C1=CC(=C(C=C1)OC)F | [CH3:1][NH2:2].CS(=O)(=O)O[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]([F:14])[cH:15]2)[n:16][n:17]([CH2:18][CH:19]2[CH2:20][CH2:21]2)[c:22]1=[O:23]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]([F:14])[cH:15]2)[n:16][n:17]([CH2:18][CH:19]2[CH2:20][CH... | CN.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F | CNCc1cc(-c2ccc(OC)c(F)c2)nn(CC2CC2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:11]-[C;D1;H3:10]):[c:8]:1=[O;D1;H0:9] | 65.5 | [{"value": 65.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one (160 mg, 0.42 mmol) in 30% methylamine/ethanol (5 mL) was stirred at 80° C. for 4 hours in a sealed tube. The solvent was distilled off under reduced pressure, and the residue was purified by preparative thin-la... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1ccnnc1.c1ccccc1.C1CC1 | MsOH.HO- | null | null | null | CN.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>CNCc1cc(-c2ccc(OC)c(F)c2)nn(CC2CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af59a80c4f7f4dd69a14246df32e874b | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.CN1CCNCC1>>C1(CC1)CN1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC(=C(C=C1)OC)F | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([F:28])[cH:26]2)[n:25][n:20]([CH2:21][CH:22]2[CH2:23][CH2:24]2)[c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]3[CH2:12][CH2:13][N:14]([CH3:15]... | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 73.8 | [{"value": 73.8, "product": "C1(CC1)CN1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 73.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.C1CC1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfd306210c44435dac7c631e7d34723f | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.c1ccc(CN2CCNCC2)cc1>>COc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC3CC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.C(C1=CC=CC=C1)N1CCNCC1>>C(C1=CC=CC=C1)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O | CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([F:34])[cH:32]2)[n:31][n:26]([CH2:27][CH:28]2[CH2:29][CH2:30]2)[c:24]1=[O:25].[NH:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][CH2:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH... | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.c1ccc(CN2CCNCC2)cc1 | COc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCN(Cc3ccccc3)CC2)cc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 97.7 | [{"value": 97.7, "product": "C(C1=CC=CC=C1)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methane-sulfonyloxymethyl-2H-pyridazin-3-one and 1-benzylpiperazine were reacted to yield the title compound as a yellow oil (yield: 97.7%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1.C1CC1 | MsOH.HO- | null | null | null | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.c1ccc(CN2CCNCC2)cc1>>COc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b22b684fe264dafbcb44e4cb70461a5 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O | [NH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([F:34])[cH:32]2)[n:31][n:26]([CH2:27][CH:28]2[CH2:29][CH2:30]2)[c:24]1=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]... | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 98.9 | [{"value": 98.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methane-sulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a pale brown oil (yield: 98.9%).
Conditions: See reaction.notes.procedure_details.
Workup: were re... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.C1CC1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0cf4acc0e65e454d8e4597bc7e4fb977 | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCNCC3)c(=O)n(CC3CC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O.C([O-])([O-])=O.[K+].[K+]>>C1(CC1)CN1N=C(C=C(C1=O)CN1CCNCC1)C1=CC(=C(C=C1)OC)F | CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][N:11]([CH2:10][c:9]2[cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:26]([F:27])[cH:25]3)[n:24][n:19]([CH2:20][CH:21]3[CH2:22][CH2:23]3)[c:17]2=[O:18])[CH2:16][CH2:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16... | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CN3CCNCC3)c(=O)n(CC3CC3)n2)cc1F | null | null | O | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC1CC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 69.2 | [{"value": 69.2, "product": "C1(CC1)CN1N=C(C=C(C1=O)CN1CCNCC1)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "C1(CC1)CN1N=C(C=C(C1=O)CN1CCNCC1)C1=CC(=C(C=C1)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 4-(4-tert-Butoxycarbonyl-1-piperazinyl)methyl-2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazine-3-one (220 mg, 0.47 mmol) was dissolved in ice-cold trifluoroacetic acid (2 mL), and at the same temperature, the mixture was stirred for 15 minutes. Water (10 mL) was added to the reaction mixture. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1ccnnc1.C1C[NH]CCN1.C1CC1 | HO- | O | null | 0.25 | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CC3)n2)cc1F>O>COc1ccc(-c2cc(CN3CCNCC3)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-238e053add69416583ec29575c2096aa | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.O=C1NC(=O)c2ccccc21>>COc1ccc(-c2cc(CN3C(=O)c4ccccc4C3=O)c(=O)n(CC3CC3)n2)cc1F | O.C1(CC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K]>>C1(CC1)CN1N=C(C=C(C1=O)CN1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)F | CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]([F:32])[cH:30]2)[n:29][n:24]([CH2:25][CH:26]2[CH2:27][CH2:28]2)[c:22]1=[O:23].[NH:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]3[C:12](=[... | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.O=C1NC(=O)c2ccccc21 | COc1ccc(-c2cc(CN3C(=O)c4ccccc4C3=O)c(=O)n(CC3CC3)n2)cc1F | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Alkylation of amines | 8c55c1be63954a68557ba4cda7025bc5216a4a18e41dee3e27297e05487159d8 | 3761faea2e60c075e79428329c94e300333bad052ba97daeccc915afb3519a77 | O=C1c2ccccc2C(=O)N1Cc1cc(-c2ccccc2)nn(CC2CC2)c1=O | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[O;D1;H0:10]=[C:11]1-[NH;D2;+0:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:12]2-[C:11](=[O;D1;H0:10])-[c:16]:[c:15]-[C:13]-2=[O;D1;H0:14]):[c:8]:1=[O;D1;H0:9] | 81.8 | [{"value": 81.0, "product": "C1(CC1)CN1N=C(C=C(C1=O)CN1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "C1(CC1)CN1N=C(C=C(C1=O)CN1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | To a solution of 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one (220 mg, 0.57 mmol) in N,N-dimethylformamide (5 mL) was added potassium phthalimide (160 mg, 0.87 mmol), and the mixture was stirred at 80° C. for 2 hours. Water (30 mL) was added to the reaction mixture. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccnnc1.c1ccc2c(c1)C[NH]C2.C1CC1 | MsOH.HO- | CN(C=O)C | 80 | 2 | COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1F.O=C1NC(=O)c2ccccc21>CN(C=O)C>COc1ccc(-c2cc(CN3C(=O)c4ccccc4C3=O)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38d2c167043c4980b48ac9206ec0428a | COc1ccc(-c2cc(CN3C(=O)c4ccccc4C3=O)c(=O)n(CC3CC3)n2)cc1F>>COc1ccc(-c2cc(CN)c(=O)n(CC3CC3)n2)cc1F | C1(CC1)CN1N=C(C=C(C1=O)CN1C(C=2C(C1=O)=CC=CC2)=O)C2=CC(=C(C=C2)OC)F.O.NN>>NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O | O=C1c2ccccc2C(=O)[N:11]1[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21]([F:22])[cH:20]2)[n:19][n:14]([CH2:15][CH:16]2[CH2:17][CH2:18]2)[c:12]1=[O:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][NH2:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]3[CH2:17][CH2:18]3)[n:19]2)[cH:20][c:... | COc1ccc(-c2cc(CN3C(=O)c4ccccc4C3=O)c(=O)n(CC3CC3)n2)cc1F | COc1ccc(-c2cc(CN)c(=O)n(CC3CC3)n2)cc1F | null | null | CO | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[c:3]:[c:4]:[#7;a:5])-C(=O)-c2:c:c:c:c:c:2-1>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[NH2;D1;+0:1] | 99.7 | [{"value": 97.8, "product": "NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-cyclopropylmethyl-6-(3-fluoro-4-methoxypheyl)-4-phthalimidomethyl-2H-pyridazin-3-one (190 mg, 0.43 mmol) in methanol (5 mL) was added hydrazine monohydrate (110 mg, 2.20 mmol), and the mixture was heated under reflux for 2 hours. Methanol was distilled off, and chloroform (20 mL) was added to the res... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1ccnnc1.C1CC1 | HO- | CO | null | null | COc1ccc(-c2cc(CN3C(=O)c4ccccc4C3=O)c(=O)n(CC3CC3)n2)cc1F>CO>COc1ccc(-c2cc(CN)c(=O)n(CC3CC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d070f2e59f204245b53f8b942c85a307 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC=1C=C(C=CC1OC)C=1C(=C(C(N(N1)CC(C)C)=O)OS(=O)(=O)C)C.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC(C)C)=O | [NH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.CS(=O)(=O)O[c:9]1[c:8](C)[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([F:34])[cH:32]2)[n:31][n:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[c:24]1=[O:25].Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2[CH3:10... | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1CN1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-[c;H0;D3;+0:2]1:[c:3](-[c:4]):[#7;a:5]:[#7;a:6](-[C:7]):[c:8](=[O;D1;H0:9]):[c;H0;D3;+0:10]:1-O-S(-C)(=O)=O.[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:3](-[c:4]):[cH;D2;+0:... | 94.3 | [{"value": 94.3, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(3-fluoro-4-methoxyphenyl)-2-isobutyl-4-methane-sulfonyloxy-methyl-2H-pyridazin-3-one and tert-butyl 1-piperazine-carboxylate were reacted to yield the title compound as a yellow oil (yield: 94.3%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1CNCC[NH]1.c1ccnnc1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a890b21ea1b4a5fba0835c8a826d216 | CN1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC(C)C)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC=1C=C(C=CC1OC)C=1C(=C(C(N(N1)CC(C)C)=O)OS(=O)(=O)C)C.CN1CCNCC1>>FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[c:9]1[c:8](C)[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([F:28])[cH:26]2)[n:25][n:20]([CH2:21][CH:22]([CH3:23])[CH3:24])[c:18]1=[O:19].Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2[CH3:10])cc1F>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c... | CN1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC(C)C)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1CN1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-[c;H0;D3;+0:2]1:[c:3](-[c:4]):[#7;a:5]:[#7;a:6](-[C:7]):[c:8](=[O;D1;H0:9]):[c;H0;D3;+0:10]:1-O-S(-C)(=O)=O.[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:3](-[c:4]):[cH;D2;+0:... | 80.9 | [{"value": 80.9, "product": "FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(3-fluoro-4-methoxyphenyl)-2-isobutyl-4-methanesulfonyloxy-methyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 80.9%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1CNCC[NH]1.c1ccnnc1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CN1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC(C)C)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41ba53391d074cb3803addfbb5300834 | COC1C(=O)NN=C(c2ccc(C)c(F)c2)C1=C=O.O=C(O)c1cc(-c2ccccc2)n[nH]c1=O>>COC(=O)c1cc(-c2ccccc2)n[nH]c1=O | FC=1C=C(C=CC1C)C=1C(C(C(NN1)=O)OC)=C=O.C(=O)(O)C=1C(NN=C(C1)C1=CC=CC=C1)=O>>COC(=O)C=1C(NN=C(C1)C1=CC=CC=C1)=O | Cc1ccc(C2=NNC(=O)C(O[CH3:1])C2=C=O)cc1F.[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][nH:15][c:16]1=[O:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][nH:15][c:16]1=[O:17] | COC1C(=O)NN=C(c2ccc(C)c(F)c2)C1=C=O.O=C(O)c1cc(-c2ccccc2)n[nH]c1=O | COC(=O)c1cc(-c2ccccc2)n[nH]c1=O | null | null | null | Heteroatom Alkylation and Arylation | O-methylation | 271dcd3906504ae2d6e121d10bca7a3a0f064ba1774506d60dea989df3d3484a | 2f542dc6f0dfac8dbe5372e0f739640c8522541a995d8198c5c7f5141d6123a2 | O=c1ccc(-c2ccccc2)n[nH]1 | C-c1:c:c:c(-C2=N-N-C(=O)-C(-O-[CH3;D1;+0:1])-C-2=C=O):c:c:1-F.[#7;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[#7;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH3;D1;+0:1] | 98.9 | [{"value": 98.9, "product": "COC(=O)C=1C(NN=C(C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (5), 4-carboxy-6-phenyl-2H-pyridazin-3-one was reacted to yield the title compound as pale yellow crystals (yield: 98.9%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide.Aromatic halide.Carboxylic acid.Ether | Ester | c1ccccc1.C1=NNCCC1 | null | c1cnncc1.c1ccccc1 | HF | null | null | null | COC1C(=O)NN=C(c2ccc(C)c(F)c2)C1=C=O.O=C(O)c1cc(-c2ccccc2)n[nH]c1=O>>COC(=O)c1cc(-c2ccccc2)n[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0095c865a56e4289b73179372c43aea2 | COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O.COC(=O)c1cc(-c2ccccc2)n[nH]c1=O>>COC(=O)c1cc(-c2ccccc2)nn(CC(C)C)c1=O | FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC.COC(=O)C=1C(NN=C(C1)C1=CC=CC=C1)=O>>C(C(C)C)N1N=C(C=C(C1=O)C(=O)OC)C1=CC=CC=C1 | Cc1cc[c:8](-[c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:20](=[O:21])[n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[n:14]2)[cH:13]c1F.COC(=O)c1cc(-c2c[cH:12][cH:11][cH:10][cH:9]2)n[nH]c1=O>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])... | COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O.COC(=O)c1cc(-c2ccccc2)n[nH]c1=O | COC(=O)c1cc(-c2ccccc2)nn(CC(C)C)c1=O | null | null | null | Miscellaneous | OtherReaction | 7b30369b089395f834ea5a700f03ff7779f66f1cdc56a630ae059821527c476e | 7494cceafaa45c0a4e5f400921a6429ff2b5672c3e28c3ffe3859e2ee8af3168 | O=c1ccc(-c2ccccc2)n[nH]1 | C-O-C(=O)-c1:c:c(-c2:[cH;D2;+0:1]:[c:2]:[c:3]:[cH;D2;+0:4]:c:2):n:[nH]:c:1=O.C-c1:c:c:[c;H0;D3;+0:5](-[c:6](:[c:7]):[#7;a:8]:[#7;a:9](-[C:10]):[c:11]):[cH;D2;+0:12]:c:1-F>>[C:10]-[#7;a:9](:[c:11]):[#7;a:8]:[c:6](-[c;H0;D3;+0:5]1:[cH;D2;+0:12]:[cH;D2;+0:4]:[c:3]:[c:2]:[cH;D2;+0:1]:1):[c:7] | 94.1 | [{"value": 94.1, "product": "C(C(C)C)N1N=C(C=C(C1=O)C(=O)OC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 4-methoxycarbonyl-6-phenyl-2H-pyridazin-3-one was reacted to yield the title compound as a yellow oil (yield: 94.1%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | null | c1ccccc1.c1ccnnc1.c1ccccc1 | c1ccccc1 | c1ccnnc1.c1ccccc1 | HF | null | null | null | COC(=O)c1cc(-c2ccc(C)c(F)c2)nn(CC(C)C)c1=O.COC(=O)c1cc(-c2ccccc2)n[nH]c1=O>>COC(=O)c1cc(-c2ccccc2)nn(CC(C)C)c1=O |
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