dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-316b06eac33b42fcb58fcb13962200ca | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)s1>>CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)s2)=CCC3(C)C)CC(OC)OC)cc1 | CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C.CC1=CC=C(S1)C1=CCC(C2=CC=C(C=C12)C=O)(C)C.C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.[Li]CCCC>>COC(C/C(=C\C1=CC=C2C(CC=C(C2=C1)C=1SC(=CC1)C)(C)C)/C1=CC=C(C(=O)OCC)C=C1)OC | CCOP(=O)(OCC)[C:31]([CH2:30][CH2:10][c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:37][cH:36]1)([O:32][CH3:33])[O:34][CH3:35].O=[CH:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([c:19]1[cH:20][cH:21][c:22]([CH3:23])[s:24]1)=[CH:25][CH2:26][C:27]2([CH3:28])[CH3:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])... | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)s1 | CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)s2)=CCC3(C)C)CC(OC)OC)cc1 | null | null | CCOCC.C1CCOC1 | C-C Coupling | OtherReaction | 2b2f01a2a3c2f6ea43954e1fcfb38220499a98de93d92d3a033fa1127e06f89d | 3598948eace7341b2f4800001ea9b7b5ac95eb54b4840cc8e83ad3a3413fcab8 | C1=C(c2cccs2)c2cc(/C=C/c3ccccc3)ccc2CC1 | C-C-O-P(=O)(-O-C-C)-[C;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10].O=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:3]-[#8:2]-[CH;D3;+0:1](-[#8:4]-[C;D1;H3:5])-[C:6]/[C;H0;D3;+0:7](=[CH;D2;+0:11]\[c:12](:[c:13]):[c:14])-[c:8](:[c:9]):[c:10] | null | [] | -10 | CELSIUS | 10 | MINUTE | To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 1.4 g, 3.6 mmol), in THF (20 mL) was added n-BuLi (1.6M solution in hexane, 2.5 mL, 4 mmol). The mixture was stirred for 20 minutes at -78° C. and 10 min. at -10° C. The reaction mixture was recooled to -78° C. and 1(5... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Ether | Ether.Ether | null | null | c1ccccc1.c1ccsc1.C1=Cc2ccccc2CC1 | HO- | CCOCC.C1CCOC1 | -10 | 0.166667 | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CCC(C)(C)c3ccc(C=O)cc32)s1>CCOCC.C1CCOC1>CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)s2)=CCC3(C)C)CC(OC)OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84ef26d1ad4b4ac3984632c87edd127d | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)s2)=CCC4(C)C)cc1>>Cc1ccc(C2=CCC(C)(C)c3cc4cccc(-c5ccc(C(=O)O)cc5)c4cc32)s1 | CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)OCC)C=C1)(C)C.CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)OCC)C=C1)(C)C.CO.[Li+].[OH-].O>>CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)O)C=C1)(C)C | CC[O:25][C:23]([c:22]1[cH:21][cH:20][c:19](-[c:18]2[cH:17][cH:16][cH:15][c:14]3[cH:13][c:12]4[c:30]([cH:29][c:28]32)[C:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[s:31]2)=[CH:7][CH2:8][C:9]4([CH3:10])[CH3:11])[cH:27][cH:26]1)=[O:24]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]3[cH:13][c:1... | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)s2)=CCC4(C)C)cc1 | Cc1ccc(C2=CCC(C)(C)c3cc4cccc(-c5ccc(C(=O)O)cc5)c4cc32)s1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1=C(c2cccs2)c2cc3c(-c4ccccc4)cccc3cc2CC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 16 | HOUR | To a stirred solution of ethyl 4-[1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate (Compound 3, 33 mg, 0.07 mmol), in THF (2 mL), MeOH (2 mL), was added aqueous LiOH (1M solution, 0.2 mL, 0.2 mmol). After 16 hours, water (2 mL) was added to the reaction mixture, about 50% of the organic solvent... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccsc1.C1=Cc2cc3ccccc3cc2CC1.c1ccccc1 | Other | C1CCOC1 | null | 16 | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)s2)=CCC4(C)C)cc1>C1CCOC1>Cc1ccc(C2=CCC(C)(C)c3cc4cccc(-c5ccc(C(=O)O)cc5)c4cc32)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9920e201f1844369a4f53eaad2b0509b | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1ccc(Br)cn1>>Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cn1 | CC=1C=CC(=CC1)S(=O)(=O)O.CC1(CCC(C2=CC(=CC=C12)Br)=O)C.CC1(CCC(C2=CC(=CC=C12)Br)=O)C.CC1=CC=C(C=N1)Br.[Li]CCCC.CCCCCC>>CC1=CC=C(C=N1)C1=CCC(C2=CC=C(C=C12)Br)(C)C | O=[C:6]1[CH2:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]21.Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:20][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]([CH3:10])([CH3:11])[c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]32)[cH:19][n:20]1 | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1ccc(Br)cn1 | Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cn1 | null | null | C1CCOC1.C(C)(=O)OCC | C-C Coupling | OtherReaction | a47af8a9ef2eff45998f816bbe9e56e7f4c32bc98200a98e04246e747fdb9d02 | 554b1bee1ccf92984990164979ec7aaf354dc2a70796dc88c3036796633e99e1 | C1=C(c2cccnc2)c2ccccc2CC1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O=[C;H0;D3;+0:7]1-[CH2;D2;+0:8]-[C:9]-[C:10]-[c:11]:[c:12]-1:[c:13]>>[c:13]:[c:12]1:[c:11]-[C:10]-[C:9]-[CH;D2;+0:8]=[C;H0;D3;+0:7]-1-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | null | [] | null | null | 1 | HOUR | To a cold (-78° C.) solution of 6-methyl-3-bromopyridine (890 mg, 5.2 mmol) in THF (15 mL) was added n-BuLi in hexane (1.6M solution, 3.5 mL, 5.6 mmol) and stirred for 1 hour. This mixture was added to a flask containing 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A, 1.35 g, 5.4 mmol), in THF (5 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | null | c1ccc2c(c1)CCCC2.c1ccncc1 | c1ccncc1.C1=Cc2ccccc2CC1 | c1ccncc1.C1=Cc2ccccc2CC1 | HBr | C1CCOC1.C(C)(=O)OCC | null | 1 | CC1(C)CCC(=O)c2cc(Br)ccc21.Cc1ccc(Br)cn1>C1CCOC1.C(C)(=O)OCC>Cc1ccc(C2=CCC(C)(C)c3ccc(Br)cc32)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-de21c57f77f8433f83a69b0d8925f4c7 | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)s2)=CCC4(C)C)cc1.Cc1ccc(C2(C=O)CCC(C)(C)c3ccccc32)cn1>>CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)nc2)=CCC4(C)C)cc1 | COC(C/C(=C\C1=CC=C2C(CC=C(C2=C1)C1=CC=C(C=C1)C)(C)C)/C1=CC=C(C(=O)OCC)C=C1)OC.Cl[Sn](Cl)(Cl)Cl.CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)OCC)C=C1)(C)C.CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)OCC)C=C1)(C)C.CC1=NC=C(C=C1)C1(CCC(C2=CC=CC=C12)(C)C)C=O.CC1=NC=C(C=C1)C1(CCC(C2=CC=CC=C12)(C)C)C=O.C(C... | Cc1ccc(C2=CCC(C)(C)c3c[c:14]4[cH:13][cH:12][cH:11][c:10](-[c:9]5[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:34][cH:33]5)[c:19]4cc32)s1.O=C[C:20]1([c:21]2[cH:22][cH:23][c:24]([CH3:25])[n:26][cH:27]2)[c:17]2[c:16]([cH:15]cc[cH:18]2)[C:30]([CH3:31])([CH3:32])[CH2:29][CH2:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c... | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)s2)=CCC4(C)C)cc1.Cc1ccc(C2(C=O)CCC(C)(C)c3ccccc32)cn1 | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)nc2)=CCC4(C)C)cc1 | null | null | ClCCl | Miscellaneous | OtherReaction | 39996f7512a61ca955b90712db036596da602ca6741bfbdae4a62ddb64b5e62c | 236fb416ed9d7dc0a069e43e118ef194ae8f5bcc33c36e67bb2c8f8e39c21895 | C1=C(c2cccnc2)c2cc3c(-c4ccccc4)cccc3cc2CC1 | C-c1:c:c:c(-C2=C-C-C(-C)(-C)-c3:c:[c;H0;D3;+0:1]4:[c:2]:[c:3]:[c:4]:[c:5](-[c:6]):[c;H0;D3;+0:7]:4:c:c:3-2):s:1.O=C-[C;H0;D4;+0:8]1(-[c:9](:[c:10]):[c:11]:[#7;a:12]:[c:13])-[CH2;D2;+0:14]-[C:15]-[C:16]-[c:17]2:[cH;D2;+0:18]:c:c:[cH;D2;+0:19]:[c:20]:2-1>>[c:10]:[c:9](-[C;H0;D3;+0:8]1=[CH;D2;+0:14]-[C:15]-[C:16]-[c:17]2:... | null | [] | null | null | null | null | This compound is prepared in accordance with the procedure described for the preparation of ethyl 4-[1(5-methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate (Compound 3), from 1(2-methyl-pyrid-5-yl)3,4-dihydro-4,4-dimethyl-naphthaldehyde (Compound K) by reaction with ethyl 4-(diethoxyphosphoryl-3,3-dime... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccsc1.C1=Cc2cc3ccccc3cc2CC1.c1ccc2c(c1)CCCC2 | C1=Cc2cc3ccccc3cc2CC1 | c1ccccc1.c1ccncc1.C1=Cc2cc3ccccc3cc2CC1 | Other | ClCCl | null | null | CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)s2)=CCC4(C)C)cc1.Cc1ccc(C2(C=O)CCC(C)(C)c3ccccc32)cn1>ClCCl>CCOC(=O)c1ccc(-c2cccc3cc4c(cc23)C(c2ccc(C)nc2)=CCC4(C)C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1e1b81ee8df24843ab572b0af6fcff4f | CC1(C)CC(=O)c2cc(Br)ccc2S1.Cc1ccc(Br)cc1>>Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)cc1 | CC1(SC2=CC=C(C=C2C(C1)=O)Br)C.CC1(SC2=CC=C(C=C2C(C1)=O)Br)C.CC=1C=CC(=CC1)S(=O)(=O)O.BrC1=CC=C(C=C1)C.[Li]C(C)(C)C.CCCCC>>CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)Br)C | O=[C:6]1[CH2:7][C:8]([CH3:9])([CH3:10])[S:11][c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]21.Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[S:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]32)[cH:19][cH:20]1 | CC1(C)CC(=O)c2cc(Br)ccc2S1.Cc1ccc(Br)cc1 | Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)cc1 | null | null | ClCCl.C1CCOC1.C(C)OC(C)=O | C-C Coupling | OtherReaction | c3c8416337de9ee92dd67caeb2ca5c400887ed22f56bb904dc609881ad625180 | 554b1bee1ccf92984990164979ec7aaf354dc2a70796dc88c3036796633e99e1 | C1=C(c2ccccc2)c2ccccc2SC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=[C;H0;D3;+0:6]1-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#16:11]-[c:12]:[c:13]-1:[c:14]>>[C;D1;H3:9]-[C:8]1(-[C;D1;H3:10])-[#16:11]-[c:12]:[c:13](:[c:14])-[C;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])=[CH;D2;+0:7]-1 | null | [] | null | null | null | null | To a cold (-78° C.) solution of 4-bromotoluene (720 mg, 4.2 mmol) in THF (8 mL) was added t-BuLi in pentane (1.7M, 0.5 mL, 0.85 mmol). The mixture was warmed to ambient temperature over 30 minutes with stirring. This mixture was added to a flask containing 2,2-dimethyl-6-bromo-thiochroman-4-one (Compound M, 140 mg, 0.4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | null | c1ccc2c(c1)CCCS2.c1ccccc1 | c1ccccc1.C1=Cc2ccccc2SC1 | c1ccccc1.C1=Cc2ccccc2SC1 | HBr | ClCCl.C1CCOC1.C(C)OC(C)=O | null | null | CC1(C)CC(=O)c2cc(Br)ccc2S1.Cc1ccc(Br)cc1>ClCCl.C1CCOC1.C(C)OC(C)=O>Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f87472e8ca554a2c98f783fae6d659cb | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)cc1>>Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)cc1 | CN(C)C=O.CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)Br)C.CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)Br)C.[Li]CCCC>>CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=O)C | CN(C)[CH:16]=[O:17].Br[c:15]1[cH:14][cH:13][c:12]2[c:19]([cH:18]1)[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]1)=[CH:7][C:8]([CH3:9])([CH3:10])[S:11]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[S:11][c:12]3[cH:13][cH:14][c:15]([CH:16]=[O:17])[cH:18][c:19]32)[cH:20][cH:21]1 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)cc1 | Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)cc1 | null | null | C1CCOC1.CCCCCC | C-C Coupling | Bouveault aldehyde synthesis | 5e24dadaa092a277f2c69c11b9ad7aeee19678eeda8b9c0dcc303ef56c6ededb | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | C1=C(c2ccccc2)c2ccccc2SC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[C:7].C-N(-C)-[CH;D2;+0:8]=[O;D1;H0:9]>>[C:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH;D2;+0:8]=[O;D1;H0:9]):[c:2]:[c:3] | null | [] | -10 | CELSIUS | 5 | HOUR | To a cold (-78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-thiochrom-3-ene (Compound N, 280 mg, 0.81 mmol) in THF (5 mL) was added n-BuLi in hexane (1.6M solution, 0.66 mL). The mixture was gradually warmed to -10° C. over 25 min. and recooled to -78° C. To this solution was added DMF (80 mg, 1.1 mmol) and stirre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | C1=Cc2ccccc2SC1 | C1=Cc2ccccc2SC1 | c1ccccc1.C1=Cc2ccccc2SC1 | HBr | C1CCOC1.CCCCCC | -10 | 5 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)cc1>C1CCOC1.CCCCCC>Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6d1ee6ee5f4248aba938c037e104dcfb | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)cc1>>Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1 | CN(C)C=O.CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)Br)C.CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)Br)C.[Li]C(C)(C)C>>CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=O)C | CN(C)[CH:16]=[O:17].Br[c:15]1[cH:14][cH:13][c:12]2[c:19]([cH:18]1)[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:21][cH:20]1)=[CH:7][C:8]([CH3:9])([CH3:10])[O:11]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[O:11][c:12]3[cH:13][cH:14][c:15]([CH:16]=[O:17])[cH:18][c:19]32)[cH:20][cH:21]1 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)cc1 | Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1 | null | null | CCCCC.C1CCOC1.C(C)(=O)OCC | C-C Coupling | Bouveault aldehyde synthesis | a7d1f34b951069cb40e0531dd37007dbdcff477853b015ef8910246b0318b434 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | C1=C(c2ccccc2)c2ccccc2OC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[C:7].C-N(-C)-[CH;D2;+0:8]=[O;D1;H0:9]>>[C:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH;D2;+0:8]=[O;D1;H0:9]):[c:2]:[c:3] | null | [] | null | null | 30 | MINUTE | To a cold (-78° C.) solution of 2,2-dimethyl-4(tol-4-yl)-6-bromo-chrom-3-ene (Compound P, 480 mg, 1.45 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 1.1 mL) and the mixture was stirred for 30 minutes. DMF (200 mg, 2.9 mmol) was added, the mixture was warmed to ambient temperature and stirred for 3 h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | C1=Cc2ccccc2OC1 | C1=Cc2ccccc2OC1 | c1ccccc1.C1=Cc2ccccc2OC1 | HBr | CCCCC.C1CCOC1.C(C)(=O)OCC | null | 0.5 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)cc1>CCCCC.C1CCOC1.C(C)(=O)OCC>Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b76082d12d914f36b18aec03d29abfbc | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1>>CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)cc2)=CC(C)(C)O4)cc1 | CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=O)C.CC1(OC2=CC=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=O)C.C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.[Li]CCCC.Cl[Sn](Cl)(Cl)Cl>>C(C)OC(C1=CC=C(C=C1)C=1C=CC2=C(C=C3C(=CC(OC3=C2)(C)C)C2=CC=C(C=C2)C)C1)=O | CCOP(=O)(OCC)C(CC[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:34][cH:33]1)(OC)OC.Cc1ccc(C2=CC(C)(C)O[c:13]3[cH:12][cH:11][c:10](C=O)[cH:19][c:18]32)cc1.O=Cc1c[cH:14][c:15]2[c:16]([cH:17]1)[C:20]([c:21]1[cH:22][cH:23][c:24]([CH3:25])[cH:26][cH:27]1)=[CH:28][C:29]([CH3:30])([CH3:31])[O:32]2>>[CH3:1][CH2:2... | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1 | CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)cc2)=CC(C)(C)O4)cc1 | null | null | ClCCl.C(C)(=O)OCC.C1CCOC1.CCCCCC | C-C Coupling | OtherReaction | 6e6362a8ad89a209dd7889b3c4332e01c06fd5caa1d0b96d0a95b914d25571b4 | 29e075ac73e82e24bd34799d4232e189cb74ca7871e12b92450dd8aec52bf0f5 | C1=C(c2ccccc2)c2cc3cc(-c4ccccc4)ccc3cc2OC1 | C-C-O-P(=O)(-O-C-C)-C(-C-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])(-O-C)-O-C.C-c1:c:c:c(-C2=C-C(-C)(-C)-O-[c;H0;D3;+0:6]3:[c:7]:[c:8]:[c;H0;D3;+0:9](-C=O):[c:10]:[c;H0;D3;+0:11]:3-2):c:c:1.O=C-c1:[cH;D2;+0:12]:[c:13]2:[c:14](:[cH;D2;+0:15]:c:1)-[#8:16]-[C:17]-[C:18]=[C:19]-2-[c:20]>>[c:20]-[C:19]1=[C:18]-[C:17]-[#8:1... | null | [] | null | null | 5 | MINUTE | To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 1.4 g, 3.6 mmol) in THF (9 mL) was added n-BuLi in hexane (1.6M solution, 2.8 mL). The mixture was gradually warmed to ambient temperature over 30 minutes and stirred for 5 minutes. To this mixture was added 2,2-dimeth... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Ether.Ether.Ether | null | c1ccccc1.c1ccccc1.C1=Cc2ccccc2OC1.C1=Cc2ccccc2OC1 | c1ccccc1.C1=Cc2cc3ccccc3cc2OC1 | c1ccccc1.c1ccccc1.C1=Cc2cc3ccccc3cc2OC1 | HO- | ClCCl.C(C)(=O)OCC.C1CCOC1.CCCCCC | null | 0.083333 | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)cc1>ClCCl.C(C)(=O)OCC.C1CCOC1.CCCCCC>CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)cc2)=CC(C)(C)O4)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ce9ba6d29abf487e99efa02a019289b9 | CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)cc2)=CC(C)(C)O4)cc1>>Cc1ccc(C2=CC(C)(C)Oc3cc4ccc(-c5ccc(C(=O)O)cc5)cc4cc32)cc1 | CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)O)C=C1)(C)C.CC1=CC=C(S1)C1=CCC(C2=CC3=CC=CC(=C3C=C12)C1=CC=C(C(=O)O)C=C1)(C)C.CC1(OC2=CC3=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=C(C=C3)C3=CC=C(C(=O)OCC)C=C3)C.CC1(OC2=CC3=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=C(C=C3)C3=CC=C(C(=O)OCC)C=C3)C>>CC1(OC2=CC3=C(C=C2C(=C1)C1=CC=C(C=C1)C)C=C(... | CC[O:24][C:22]([c:21]1[cH:20][cH:19][c:18](-[c:17]2[cH:16][cH:15][c:14]3[cH:13][c:12]4[c:30]([cH:29][c:28]3[cH:27]2)[C:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][cH:31]2)=[CH:7][C:8]([CH3:9])([CH3:10])[O:11]4)[cH:26][cH:25]1)=[O:23]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[O:11][c:12]3[cH:1... | CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)cc2)=CC(C)(C)O4)cc1 | Cc1ccc(C2=CC(C)(C)Oc3cc4ccc(-c5ccc(C(=O)O)cc5)cc4cc32)cc1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1=C(c2ccccc2)c2cc3cc(-c4ccccc4)ccc3cc2OC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | By following the procedure employed for the preparation of 4-[1(5-methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoic acid (Compound 4), ethyl 4-[2,2-dimethyl-4-(tol-4-yl)-benzo(1,2-g)-chrom-3-en-7-yl]benzoate (Compound 9, 10 mg, 0.02 mmol), was converted into the title compound using LiOH in water (0.2 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1=Cc2cc3ccccc3cc2OC1.c1ccccc1 | Other | null | null | null | CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)cc2)=CC(C)(C)O4)cc1>>Cc1ccc(C2=CC(C)(C)Oc3cc4ccc(-c5ccc(C(=O)O)cc5)cc4cc32)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-83e15b83e75e4245842999ea5170336e | CC1(C)CC(=O)c2cc(Br)ccc2O1.Cc1cccs1>>Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)s1 | CC1(OC2=CC=C(C=C2C(C1)=O)Br)C.CC=1SC=CC1.[Li]CCCC.CCCCCC>>CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)Br)C | O=[C:6]1[CH2:7][C:8]([CH3:9])([CH3:10])[O:11][c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]21.[CH3:1][c:2]1[cH:3][cH:4][cH:5][s:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[O:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]32)[s:19]1 | CC1(C)CC(=O)c2cc(Br)ccc2O1.Cc1cccs1 | Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)s1 | null | null | C1CCOC1.C(C)(=O)OCC | C-C Coupling | OtherReaction | a318d7e44b957e47c5df4c5948f3011bf3c3df3a0d7d04396e05bd72aeae0dab | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | C1=C(c2cccs2)c2ccccc2OC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[c:7]:[c:8]-1:[c:9].[#16;a:10]1:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1>>[C;D1;H3:4]-[C:3]1(-[C;D1;H3:5])-[#8:6]-[c:7]:[c:8](:[c:9])-[C;H0;D3;+0:1](-[c;H0;D3;+0:14]2:[#16;a:10]:[c:11]:[c:12]:[c:13]:2)=[CH;D2;+0:2]-1 | null | [] | null | null | 15 | MINUTE | To a cold (-78° C.) solution of 2-methylthiophene (820 mg, 8.3 mmol) in THF (16 mL) was added n-BuLi in hexane (1.6M, 4.4 mL, 8.5 mmol). The mixture was warmed to ambient temperature and stirred for 15 minutes. This solution was added to a flask containing cold (-78° C.) solution of 2,2-dimethyl-6-bromo-chroman-4-one (... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCCO2.c1ccsc1 | c1ccsc1.C1=Cc2ccccc2OC1 | c1ccsc1.C1=Cc2ccccc2OC1 | HO- | C1CCOC1.C(C)(=O)OCC | null | 0.25 | CC1(C)CC(=O)c2cc(Br)ccc2O1.Cc1cccs1>C1CCOC1.C(C)(=O)OCC>Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9f2a11bfe87a4bf99972d2587a25f59f | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)s1>>Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1 | CN(C)C=O.CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)Br)C.CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)Br)C.[Li]C(C)(C)C>>CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)C=O)C | CN(C)[CH:16]=[O:17].Br[c:15]1[cH:14][cH:13][c:12]2[c:19]([cH:18]1)[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[s:20]1)=[CH:7][C:8]([CH3:9])([CH3:10])[O:11]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[O:11][c:12]3[cH:13][cH:14][c:15]([CH:16]=[O:17])[cH:18][c:19]32)[s:20]1 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)s1 | Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1 | null | null | CCCCC.C1CCOC1.C(C)(=O)OCC | C-C Coupling | Bouveault aldehyde synthesis | a7d1f34b951069cb40e0531dd37007dbdcff477853b015ef8910246b0318b434 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | C1=C(c2cccs2)c2ccccc2OC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[C:7].C-N(-C)-[CH;D2;+0:8]=[O;D1;H0:9]>>[C:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH;D2;+0:8]=[O;D1;H0:9]):[c:2]:[c:3] | null | [] | null | null | 30 | MINUTE | To a cold (-78° C.) solution of 2,2-dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene (Compound R, 1.2 g, 3.6 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 2.3 mL). After 30 minutes, DMF (465 mg, 5 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 3 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | C1=Cc2ccccc2OC1 | C1=Cc2ccccc2OC1 | c1ccsc1.C1=Cc2ccccc2OC1 | HBr | CCCCC.C1CCOC1.C(C)(=O)OCC | null | 0.5 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Oc3ccc(Br)cc32)s1>CCCCC.C1CCOC1.C(C)(=O)OCC>Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4fc614d343484a3da54bc68b788f4a1f | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1>>CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)s2)=CC(C)(C)O4)cc1 | CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)C=O)C.CC1(OC2=CC=C(C=C2C(=C1)C=1SC(=CC1)C)C=O)C.C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.[Li]CCCC.Cl[Sn](Cl)(Cl)Cl>>C(C)OC(C1=CC=C(C=C1)C=1C=CC2=C(C=C3C(=CC(OC3=C2)(C)C)C=2SC(=CC2)C)C1)=O | CCOP(=O)(OCC)C(CC[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:33][cH:32]1)(OC)OC.Cc1ccc(C2=CC(C)(C)O[c:13]3[cH:12][cH:11][c:10](C=O)[cH:19][c:18]32)s1.O=Cc1c[cH:14][c:15]2[c:16]([cH:17]1)[C:20]([c:21]1[cH:22][cH:23][c:24]([CH3:25])[s:26]1)=[CH:27][C:28]([CH3:29])([CH3:30])[O:31]2>>[CH3:1][CH2:2][O:3][C:... | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1 | CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)s2)=CC(C)(C)O4)cc1 | null | null | ClCCl.C(C)(=O)OCC.C1CCOC1.CCCCCC | C-C Coupling | OtherReaction | 75fea9f9b6e94727dbe6d5fe3fe8b2db4ae63922d2a0c8099354d9953fbfe829 | 29e075ac73e82e24bd34799d4232e189cb74ca7871e12b92450dd8aec52bf0f5 | C1=C(c2cccs2)c2cc3cc(-c4ccccc4)ccc3cc2OC1 | C-C-O-P(=O)(-O-C-C)-C(-C-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])(-O-C)-O-C.C-c1:c:c:c(-C2=C-C(-C)(-C)-O-[c;H0;D3;+0:6]3:[c:7]:[c:8]:[c;H0;D3;+0:9](-C=O):[c:10]:[c;H0;D3;+0:11]:3-2):s:1.O=C-c1:[cH;D2;+0:12]:[c:13]2:[c:14](:[cH;D2;+0:15]:c:1)-[#8:16]-[C:17]-[C:18]=[C:19]-2-[c:20]:[#16;a:21]>>[#16;a:21]:[c:20]-[C:19]1... | null | [] | null | null | 5 | MINUTE | To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 690 mg, 1.75 mmol) in THF (8 mL) was added n-BuLi in hexane (1.6M solution, 1.1 mL). The mixture was gradually warmed to ambient temperature over 30 min and stirred for 5 minutes. The mixture was recooled to -78° C. an... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Ether.Ether.Ether | null | c1ccccc1.c1ccsc1.C1=Cc2ccccc2OC1.C1=Cc2ccccc2OC1 | c1ccccc1.C1=Cc2cc3ccccc3cc2OC1 | c1ccccc1.c1ccsc1.C1=Cc2cc3ccccc3cc2OC1 | Other | ClCCl.C(C)(=O)OCC.C1CCOC1.CCCCCC | null | 0.083333 | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1.Cc1ccc(C2=CC(C)(C)Oc3ccc(C=O)cc32)s1>ClCCl.C(C)(=O)OCC.C1CCOC1.CCCCCC>CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)s2)=CC(C)(C)O4)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f1adbd425794bcdbe2ae73da2aa8582 | CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)s2)=CC(C)(C)O4)cc1>>Cc1ccc(C2=CC(C)(C)Oc3cc4ccc(-c5ccc(C(=O)O)cc5)cc4cc32)s1 | C(C)OC(C1=CC=C(C=C1)C=1C=CC2=C(C=C3C(=CC(OC3=C2)(C)C)C=2SC(=CC2)C)C1)=O.C(C)OC(C1=CC=C(C=C1)C=1C=CC2=C(C=C3C(=CC(OC3=C2)(C)C)C=2SC(=CC2)C)C1)=O.[Li+].[OH-]>>CC1(OC2=CC3=C(C=C2C(=C1)C=1SC(=CC1)C)C=C(C=C3)C3=CC=C(C(=O)O)C=C3)C | CC[O:24][C:22]([c:21]1[cH:20][cH:19][c:18](-[c:17]2[cH:16][cH:15][c:14]3[cH:13][c:12]4[c:30]([cH:29][c:28]3[cH:27]2)[C:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[s:31]2)=[CH:7][C:8]([CH3:9])([CH3:10])[O:11]4)[cH:26][cH:25]1)=[O:23]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[O:11][c:12]3[cH:13][c:14]... | CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)s2)=CC(C)(C)O4)cc1 | Cc1ccc(C2=CC(C)(C)Oc3cc4ccc(-c5ccc(C(=O)O)cc5)cc4cc32)s1 | null | null | C1CCOC1.CO.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1=C(c2cccs2)c2cc3cc(-c4ccccc4)ccc3cc2OC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 20 | HOUR | To a solution of ethyl-4-[2,2-dimethyl-4-(5-methyl-thien-2-yl)-benzo[1,2-g]-chrom-3-en-7-yl]benzoate (Compound 11, 18 mg, 0.03 mmol) in methanol (0.5 mL) and THF (1 mL), was added LiOH in water (1M solution, 0.3 mL). The reaction mixture was stirred for 20 hours, the solvent was removed under reduced pressure, the resi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccsc1.C1=Cc2cc3ccccc3cc2OC1.c1ccccc1 | Other | C1CCOC1.CO.O | null | 20 | CCOC(=O)c1ccc(-c2ccc3cc4c(cc3c2)C(c2ccc(C)s2)=CC(C)(C)O4)cc1>C1CCOC1.CO.O>Cc1ccc(C2=CC(C)(C)Oc3cc4ccc(-c5ccc(C(=O)O)cc5)cc4cc32)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4ced6f59ef644dca80ccd38e6f9bbbd4 | CC1(C)CC(=O)c2cc(Br)ccc2S1.Cc1cccs1>>Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)s1 | CC=1SC=CC1.[Li]CCCC.CC1(SC2=CC=C(C=C2C(C1)=O)Br)C.CC1(SC2=CC=C(C=C2C(C1)=O)Br)C>>CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)Br)C | O=[C:6]1[CH2:7][C:8]([CH3:9])([CH3:10])[S:11][c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]21.[CH3:1][c:2]1[cH:3][cH:4][cH:5][s:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[S:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]32)[s:19]1 | CC1(C)CC(=O)c2cc(Br)ccc2S1.Cc1cccs1 | Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)s1 | null | null | C1CCOC1.CCOCC.CCCCCC | C-C Coupling | OtherReaction | f84382ad0d9b549d389850ff2313cc81c26d293462aad5600da17e5491470b86 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | C1=C(c2cccs2)c2ccccc2SC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#16:6]-[c:7]:[c:8]-1:[c:9].[#16;a:10]1:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1>>[C;D1;H3:4]-[C:3]1(-[C;D1;H3:5])-[#16:6]-[c:7]:[c:8](:[c:9])-[C;H0;D3;+0:1](-[c;H0;D3;+0:14]2:[#16;a:10]:[c:11]:[c:12]:[c:13]:2)=[CH;D2;+0:2]-1 | null | [] | null | null | null | null | To a cold (-78° C.) solution of 2-methylthiophene (1.2 g, 12.2 mmol) in THF (8 mL) was added n-BuLi in hexane (1.6M, 8.5 mL). The mixture was warmed to ambient temperature over 30 minutes. with stirring. The mixture was recooled to -78° C. and a solution of 2,2-dimethyl-6-bromo-thiochroman-4-one (Compound M, 1.4 g, 5.2... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCCS2.c1ccsc1 | c1ccsc1.C1=Cc2ccccc2SC1 | c1ccsc1.C1=Cc2ccccc2SC1 | HO- | C1CCOC1.CCOCC.CCCCCC | null | null | CC1(C)CC(=O)c2cc(Br)ccc2S1.Cc1cccs1>C1CCOC1.CCOCC.CCCCCC>Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cd5084750b36490791be0dc4f9686048 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)s1>>Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1 | CN(C)C=O.CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)Br)C.CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)Br)C.[Li]CCCC>>CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)C=O)C | CN(C)[CH:16]=[O:17].Br[c:15]1[cH:14][cH:13][c:12]2[c:19]([cH:18]1)[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[s:20]1)=[CH:7][C:8]([CH3:9])([CH3:10])[S:11]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][C:8]([CH3:9])([CH3:10])[S:11][c:12]3[cH:13][cH:14][c:15]([CH:16]=[O:17])[cH:18][c:19]32)[s:20]1 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)s1 | Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1 | null | null | C1CCOC1.CCCCCC | C-C Coupling | Bouveault aldehyde synthesis | 5e24dadaa092a277f2c69c11b9ad7aeee19678eeda8b9c0dcc303ef56c6ededb | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | C1=C(c2cccs2)c2ccccc2SC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6]=[C:7].C-N(-C)-[CH;D2;+0:8]=[O;D1;H0:9]>>[C:7]=[C:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[CH;D2;+0:8]=[O;D1;H0:9]):[c:2]:[c:3] | null | [] | null | null | 16 | HOUR | To a cold (-78° C.) solution of 2,2-dimethyl-4(2-methyl-thien-5-yl)-6-bromo-thiochrom-3-ene (Compound T, 430 mg, 1.2 mmol) in THF (12 mL) was added n-BuLi in hexane (1.6M solution, 1 mL). The mixture was gradually warmed to ambient temperature over 1 hour and recooled to -78° C. To this solution was added DMF (220 mg, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | C1=Cc2ccccc2SC1 | C1=Cc2ccccc2SC1 | c1ccsc1.C1=Cc2ccccc2SC1 | HBr | C1CCOC1.CCCCCC | null | 16 | CN(C)C=O.Cc1ccc(C2=CC(C)(C)Sc3ccc(Br)cc32)s1>C1CCOC1.CCCCCC>Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3162245e48fc4356bfa767714f3ab8d2 | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1.Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1>>CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)cc2)=CCC3(C)C)CC(OC)OC)cc1 | CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)C=O)C.CC1(SC2=CC=C(C=C2C(=C1)C1=CC=C(S1)C)C=O)C.C1CCOC1.C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.C(C)OP(=O)(OCC)C(CCC1=CC=C(C(=O)OCC)C=C1)(OC)OC.C(C)(C)[N-]C(C)C.[Li+].C1CCOC1.C1CCOC1>>COC(C/C(=C\C1=CC=C2C(CC=C(C2=C1)C1=CC=C(C=C1)C)(C)C)/C1=CC=C(C(=O)OCC)C=C1)OC | CCOP(=O)(OCC)[C:32]([CH2:31][CH2:10][c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:38][cH:37]1)([O:33][CH3:34])[O:35][CH3:36].CC1(C)S[c:15]2[cH:14][cH:13][c:12]([CH:11]=O)[cH:17][c:16]2[C:18]([c:19]2s[c:22]([CH3:23])[cH:24][cH:25]2)=[CH:26]1.Cc1sc(C2=[CH:27][C:28]([CH3:29])([CH3:30])Sc3ccc(C=O)cc32)[cH:20... | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1.Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1 | CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)cc2)=CCC3(C)C)CC(OC)OC)cc1 | null | null | null | C-C Coupling | OtherReaction | 4d8df3c30a19a191e5ad4dd5a5dc3e35b513964b9586121508e4d613b1cec956 | 9c861942995479bb448fe8b9ef3aa06b81c20455ba60385f8f2d8b0b55b502bc | C1=C(c2ccccc2)c2cc(/C=C/c3ccccc3)ccc2CC1 | C-C-O-P(=O)(-O-C-C)-[C;H0;D4;+0:1](-[#8:2]-[C;D1;H3:3])(-[#8:4]-[C;D1;H3:5])-[C:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10].C-C1(-C)-S-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14](-[CH;D2;+0:15]=O):[c:16]:[c:17]:2-[C:18](-[c;H0;D3;+0:19]2:[c:20]:[c:21]:[c;H0;D3;+0:22](-[C;D1;H3:23]):s:2)=[CH;D2;+0:24]-1.C-c1:[cH;D2;+0:25]:[cH;D2;+0... | null | [] | -5 | CELSIUS | null | null | To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 500 mg, 1.29 mmol) in THF (2.5 mL) was added fleshly prepared lithium diisopropylamide in THF(1.5 mmol). The mixture was allowed to warm to -5° C. over a period of 1 hour and 40 minutes. The reaction mixture was recool... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Ether.Ether.Monosulfide.Monosulfide | Ether.Ether | C1=Cc2ccccc2SC1.c1ccsc1.c1ccsc1.C1=Cc2ccccc2SC1 | c1ccccc1.C1=Cc2ccccc2CC1 | c1ccccc1.c1ccccc1.C1=Cc2ccccc2CC1 | Other | null | -5 | null | CCOC(=O)c1ccc(CCC(OC)(OC)P(=O)(OCC)OCC)cc1.Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1.Cc1ccc(C2=CC(C)(C)Sc3ccc(C=O)cc32)s1>>CCOC(=O)c1ccc(/C(=C/c2ccc3c(c2)C(c2ccc(C)cc2)=CCC3(C)C)CC(OC)OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-efe1cb2656924866b2ad6f8e5b445bf1 | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](OC(=O)c3ccccc3)[C@H](OCC[Si](C)(C)C)O[C@H](COC(=O)c3ccccc3)[C@H]2O[C@@H]2O[C@H](COC(=O)c3ccccc3)[C@H](O)[C@H](O)[C@H]2OC(=O)c2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@@H]1OCc1ccccc1.Cc1ccc(S(=O)(=O)O)cc1>>CC(=O)O[C@@H]1[C@H](O)[C@@H](OC(=O)c2ccccc2)[C@H](O[C@@H]2[C@H](O[C@@H]3O[C@@H](... | C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCC[Si](C)(C)C)O[C@@H]([C@H]([C@@H]1O[C@H]1[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@@H](O1)C)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](O)[C@@H](O)[C@H](O1)COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O.C1=CC=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCC[Si... | [OH:4][C@@H:5]1[C@H:6]([OH:7])[C@@H:8]([O:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C@H:18]([O:19][C@H:20]2[C@H:21]([O:22][C@@H:23]3[O:24][C@@H:25]([CH3:26])[C@@H:27]([O:28][CH2:29][c:30]4[cH:31][cH:32][cH:33][cH:34][cH:35]4)[C@@H:36]([O:37][CH2:38][c:39]4[cH:40][cH:41][cH:42][cH:43][cH:44]4)[C@@H:4... | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](OC(=O)c3ccccc3)[C@H](OCC[Si](C)(C)C)O[C@H](COC(=O)c3ccccc3)[C@H]2O[C@@H]2O[C@H](COC(=O)c3ccccc3)[C@H](O)[C@H](O)[C@H]2OC(=O)c2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@@H]1OCc1ccccc1.Cc1ccc(S(=O)(=O)O)cc1 | CC(=O)O[C@@H]1[C@H](O)[C@@H](OC(=O)c2ccccc2)[C@H](O[C@@H]2[C@H](O[C@@H]3O[C@@H](C)[C@@H](OCc4ccccc4)[C@@H](OCc4ccccc4)[C@@H]3OCc3ccccc3)[C@@H](OC(=O)c3ccccc3)[C@H](OCC[Si](C)(C)C)O[C@@H]2COC(=O)c2ccccc2)O[C@@H]1COC(=O)c1ccccc1 | null | C(C)N(CC)CC | C(C)(OCC)(OCC)OCC | Acylation | OtherReaction | fcf49b1f7ebc3275ffe630708c815b451b132721b87e96914ba0fab9daf0bcd6 | e1b42c857fbdd960f04ebb42cc75d8542548efb8b97960f541241ccea07e9f08 | O=C(OC[C@@H]1CC[C@@H](OC(=O)c2ccccc2)[C@H](O[C@@H]2[C@H](O[C@@H]3OC[C@@H](OCc4ccccc4)[C@@H](OCc4ccccc4)[C@@H]3OCc3ccccc3)[C@@H](OC(=O)c3ccccc3)CO[C@@H]2COC(=O)c2ccccc2)O1)c1ccccc1 | C-c1:c:c:c(-S(-O)(=O)=[O;H0;D1;+0:1]):c:c:1.[#8:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]>>[#8:2]-[C:3]-[C:4](-[O;H0;D2;+0:5]-[C:7](-[C;D1;H3:8])=[O;H0;D1;+0:1])-[C:6] | 89 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCC[Si](C)(C)C)O[C@@H]([C@@H]([C@@H]1O[C@H]1[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@@H](O1)C)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](O)[C@@H](OC(C)=O)[C@H](O1)COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired"... | null | null | 1 | HOUR | A solution of compound 10a (1.87 g), in a mixture of benzene (50 mL) and triethyl orthoacetate (50 mL), containing 4-toluenesulfonic acid (0.25 g) was stirred for 1 h at room temperature. The acid was then neutralized with a few drops of triethylamine, and the mixture evaporated to dryness. The residue was mixed with 8... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary alcohol | Ester | c1ccccc1 | null | C1CCOCC1.c1ccccc1.C1CCOCC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1.c1ccccc1.c1ccccc1 | TsOH.HO- | C(C)N(CC)CC.C(C)(OCC)(OCC)OCC | null | 1 | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](OC(=O)c3ccccc3)[C@H](OCC[Si](C)(C)C)O[C@H](COC(=O)c3ccccc3)[C@H]2O[C@@H]2O[C@H](COC(=O)c3ccccc3)[C@H](O)[C@H](O)[C@H]2OC(=O)c2ccccc2)[C@@H](OCc2ccccc2)[C@H](OCc2ccccc2)[C@@H]1OCc1ccccc1.Cc1ccc(S(=O)(=O)O)cc1>C(C)N(CC)CC.C(C)(OCC)(OCC)OCC>CC(=O)O[C@@H]1[C@H](O)[C@@H](OC(=O)c2ccccc2)[C@H](O... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-794405d5658443eaa2988d9f4b124f36 | CCC(CC)(CC)C([O-])([O-])[O-].CCCCCCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@@H]2O[C@H](COC(=O)c3ccccc3)[C@H](O)[C@H](O)[C@H]2OC(=O)c2ccccc2)[C@H](O[C@@H]2O[C@@H](C)[C@@H](OCc3ccccc3)[C@@H](OCc3ccccc3)[C@@H]2OCc2ccccc2)[C@H]1OC(=O)c1ccccc1>>CCCCCCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@@H]2O[C@H](COC(=O)c3ccccc3)... | C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCCCCCCCC)O[C@@H]([C@H]([C@@H]1O[C@H]1[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@@H](O1)C)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](O)[C@@H](O)[C@H](O1)COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O.C1=CC=CC=C1.C(C)C(C([O-])([O-])[O-])(CC)CC>>C(C1=CC=CC=... | CC[C:41](CC)(CC)[C:40]([O-])([O-])[O-:42].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C@@H:10]1[O:11][C@H:12]([CH2:13][O:14][C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C@@H:23]([O:24][C@@H:25]2[O:26][C@H:27]([CH2:28][O:29][C:30](=[O:31])[c:32]3[cH:33][cH:34][cH:35][cH:36][cH:37]3)[C@H:... | CCC(CC)(CC)C([O-])([O-])[O-].CCCCCCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@@H]2O[C@H](COC(=O)c3ccccc3)[C@H](O)[C@H](O)[C@H]2OC(=O)c2ccccc2)[C@H](O[C@@H]2O[C@@H](C)[C@@H](OCc3ccccc3)[C@@H](OCc3ccccc3)[C@@H]2OCc2ccccc2)[C@H]1OC(=O)c1ccccc1 | CCCCCCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@@H]2O[C@H](COC(=O)c3ccccc3)[C@H](OC(C)=O)[C@H](O)[C@H]2OC(=O)c2ccccc2)[C@H](O[C@@H]2O[C@@H](C)[C@@H](OCc3ccccc3)[C@@H](OCc3ccccc3)[C@@H]2OCc2ccccc2)[C@H]1OC(=O)c1ccccc1 | null | null | C(C)N(CC)CC | Acylation | OtherReaction | 959a87fd7ff99d445b5957c6cdcb595e35c7aeec865dcf9e1912a4cdfcb738f9 | 37f9d0c402085ae7a53dbce85561bce6850cbef4177e39b629509223b5de2bec | O=C(OC[C@@H]1CC[C@@H](OC(=O)c2ccccc2)[C@H](O[C@H]2[C@H](O[C@@H]3OC[C@@H](OCc4ccccc4)[C@@H](OCc4ccccc4)[C@@H]3OCc3ccccc3)[C@@H](OC(=O)c3ccccc3)CO[C@@H]2COC(=O)c2ccccc2)O1)c1ccccc1 | C-C-[C;H0;D4;+0:1](-C-C)(-C-C)-[C;H0;D4;+0:2](-[O-;H0;D1:3])(-[O-])-[O-].[#8:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[#8:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-[C;H0;D3;+0:2](-[CH3;D1;+0:1])=[O;H0;D1;+0:3])-[C:8] | 91.3 | [{"value": 91.3, "product": "C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OCCCCCCCC)O[C@@H]([C@H]([C@@H]1O[C@H]1[C@@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@@H](O1)C)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](O)[C@@H](OC(C)=O)[C@H](O1)COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": fals... | null | null | 1 | HOUR | Compound 22 (5 g) was dissolved a 1:1 mixture of benzene and triethylorthoacetate (110 mL), containing 4-toluenesulfonic acid (0.2 g), and the mixture was stirred for 1 h at room temperature. The acid was neutralized with triethylamine, and the mixture evaporated to dryness. The residue was dissolved in 80% aqueous ace... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ester | null | null | C1CCOCC1.c1ccccc1.C1CCOCC1.c1ccccc1.c1ccccc1.C1CCOCC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)N(CC)CC | null | 1 | CCC(CC)(CC)C([O-])([O-])[O-].CCCCCCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@@H]2O[C@H](COC(=O)c3ccccc3)[C@H](O)[C@H](O)[C@H]2OC(=O)c2ccccc2)[C@H](O[C@@H]2O[C@@H](C)[C@@H](OCc3ccccc3)[C@@H](OCc3ccccc3)[C@@H]2OCc2ccccc2)[C@H]1OC(=O)c1ccccc1>C(C)N(CC)CC>CCCCCCCCO[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](O[C@@H]2O[C@H](COC(=... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3c1efdc8bce441deb9547de62f031a43 | CCOC(=O)C(=O)C(=O)CBr.NC(N)=S>>CCOC(=O)C(=O)c1csc(N)n1 | BrCC(=O)C(C(=O)OCC)=O.NC(=S)N.C>>NC=1SC=C(N1)C(C(=O)OCC)=O | O=[C:8]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7])[CH2:9]Br.[S:10]=[C:11]([NH2:12])[NH2:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][s:10][c:11]([NH2:12])[n:13]1 | CCOC(=O)C(=O)C(=O)CBr.NC(N)=S | CCOC(=O)C(=O)c1csc(N)n1 | null | null | C(C)O.O | Aromatic Heterocycle Formation | OtherReaction | fc21718fc6c34ef0f7810d7a45f0bdf77020d387262946a716cf15410d587f78 | db280cf997d76bf766c7104c1640e8ac58d2371bbbc46e9b355c0b3f1661b931 | c1cscn1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](=[O;D1;H0:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[N;D1;H2:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[S;H0;D1;+0:12]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[s;H0;D2;+0:12]:[c;H0;D3;+0:10](-[N;D1;H2:9]):[n;H0;D2;+0:11]:1 | null | [] | null | null | 30 | MINUTE | 195 g of ethyl bromoacetylglyoxylate are added dropwise to a solution of 66 g of thiourea in 450 ml of water and 450 ml of ethanol at 5° and after the addition has ended, the mixture is stirred at room temperature for 30 minutes and at 50° for 30 minutes and, after adding active charcoal, the resulting reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone.Thiourea | Ketone | null | c1cscn1 | c1cscn1 | HBr | C(C)O.O | null | 0.5 | CCOC(=O)C(=O)C(=O)CBr.NC(N)=S>C(C)O.O>CCOC(=O)C(=O)c1csc(N)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0332df00e2284765af8a85ebe5acb072 | CCCCCCCCCCCCCCCCCCOCC(O)CO.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCCCCCCCCCCCCCOCC(O)COC(c1ccccc1)(c1ccccc1)c1ccccc1 | C(C)N(CC)CC.CCCCCCCCCCCCCCCCCCOCC(CO)O.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Cl.C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Cl>>C(CCCCCCCCCCCCCCCCC)OCC(O)COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([OH:22])[CH2:23][OH:24].Cl[C:25]([c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)([c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1)[c:38]1[cH:39][cH:40][cH:41][cH:42][cH:43... | CCCCCCCCCCCCCCCCCCOCC(O)CO.ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCCCCCCCCCCCCCOCC(O)COC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fb955127af596450632db904a0236d35e158107f202af7adbe96e225ff5ada1f | 5adfb0e9c2ca3c5afac2c4b206fb6fda83b92f44074f2a75e26f913c192bc169 | c1ccc(C(c2ccccc2)c2ccccc2)cc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[C:11]-[C:12]-[OH;D1;+0:13]>>[C:11]-[C:12]-[O;H0;D2;+0:13]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 93.7 | [{"value": 93.7, "product": "C(CCCCCCCCCCCCCCCCC)OCC(O)COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 15 | MINUTE | 51.69 Grams (150 mmol) of batylalcohol and 62.73 g (225 mmol) freshly recrystallized tritylchloride are dissolved at 35° C. in 350 ml methylene chloride. (Note: It is recommended that the tritylchloride be freshly recrystallized from halpasol, trademark for a petroleum ether fraction, b.p. 100°-120° C.). During 15 minu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 70 | 0.25 | CCCCCCCCCCCCCCCCCCOCC(O)CO.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>C(Cl)Cl>CCCCCCCCCCCCCCCCCCOCC(O)COC(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0fbef638aadc4bb99507ff04ced879c5 | N#Cc1c(Cl)c(Cl)c(Cl)c(Cl)c1C#N.Oc1ccccc1>>N#Cc1c(Cl)c(Cl)c(Oc2ccccc2)c(Cl)c1C#N | [OH-].[K+].ClC=1C(=C(C(=C(C1Cl)Cl)Cl)C#N)C#N.C1(=CC=CC=C1)O>>ClC=1C(=C(C(=C(C1OC1=CC=CC=C1)Cl)Cl)C#N)C#N | Cl[c:8]1[c:6]([Cl:7])[c:4]([Cl:5])[c:3]([C:2]#[N:1])[c:18]([C:19]#[N:20])[c:16]1[Cl:17].[OH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[N:1]#[C:2][c:3]1[c:4]([Cl:5])[c:6]([Cl:7])[c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([Cl:17])[c:18]1[C:19]#[N:20] | N#Cc1c(Cl)c(Cl)c(Cl)c(Cl)c1C#N.Oc1ccccc1 | N#Cc1c(Cl)c(Cl)c(Oc2ccccc2)c(Cl)c1C#N | null | null | O.CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[Cl;D1;H0:6]):[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[Cl;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:5](-[Cl;D1;H0:6]):[c:7] | null | [] | 60 | CELSIUS | 2 | HOUR | A solution of potassium hydroxide (11.2 parts) in water (22 parts) was added dropwise to a stirred solution of 3,4,5,6-tetra-chloro-1,2-dicyanobenzene (26.6 parts) and phenol (9.4 parts) in acetone (100 arts) at 0° C. The solution was stirred at 60° C. for 2 hours before pouring into water (500 parts). The aqueous mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | O.CC(=O)C | 60 | 2 | N#Cc1c(Cl)c(Cl)c(Cl)c(Cl)c1C#N.Oc1ccccc1>O.CC(=O)C>N#Cc1c(Cl)c(Cl)c(Oc2ccccc2)c(Cl)c1C#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-50d21924746f443faec1be54b17f257d | N#Cc1cccc([N+](=O)[O-])c1C#N.[O-]c1ccccc1>>N#Cc1cccc(Oc2ccccc2)c1C#N | C(#N)C1=C(C(=CC=C1)[N+](=O)[O-])C#N.[O-]C1=CC=CC=C1.[Na+].O>>C(#N)C1=C(C(=CC=C1)OC1=CC=CC=C1)C#N | O=[N+]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[c:15]1[C:16]#[N:17].[O-:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]1[C:16]#[N:17] | N#Cc1cccc([N+](=O)[O-])c1C#N.[O-]c1ccccc1 | N#Cc1cccc(Oc2ccccc2)c1C#N | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 72f1fa5687fc36895f215d2ab646fa7b585e6124008e858ad97313b6bab444fe | 5d154e9342b990e3d7c4ce2c6f7cc039bc2f1990cb4cb06dbac9dbddc28572dc | c1ccc(Oc2ccccc2)cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[O-;H0;D1:8]-[c:9](:[c:10]):[c:11]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:2]:[c:3] | 60 | [{"value": 60.0, "product": "C(#N)C1=C(C(=CC=C1)OC1=CC=CC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1,2-dicyano-3-nitrobenzene (2.77 parts) and sodium phenoxide (2.79 parts) in dimethylformamide (50 parts) was stirred at 120° C. for 2 hours. The reaction mixture was poured into water and extracted with diethyl ether (100 parts). The diethyl ether extract was washed with 5% aqueous potassium hydroxide so... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | CN(C=O)C | null | null | N#Cc1cccc([N+](=O)[O-])c1C#N.[O-]c1ccccc1>CN(C=O)C>N#Cc1cccc(Oc2ccccc2)c1C#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-690d3f8480e44e9f98c5d08baf524723 | N#Cc1ccc([N+](=O)[O-])cc1C#N.[O-]c1ccccc1>>N#Cc1ccc(Oc2ccccc2)cc1C#N | C(#N)C1=C(C=C(C=C1)[N+](=O)[O-])C#N.[O-]C1=CC=CC=C1.[Na+]>>C(#N)C1=C(C=C(C=C1)OC1=CC=CC=C1)C#N | O=[N+]([O-])[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[c:15]([C:16]#[N:17])[cH:14]1.[O-:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]1[C:16]#[N:17] | N#Cc1ccc([N+](=O)[O-])cc1C#N.[O-]c1ccccc1 | N#Cc1ccc(Oc2ccccc2)cc1C#N | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 72f1fa5687fc36895f215d2ab646fa7b585e6124008e858ad97313b6bab444fe | 5d154e9342b990e3d7c4ce2c6f7cc039bc2f1990cb4cb06dbac9dbddc28572dc | c1ccc(Oc2ccccc2)cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O-;H0;D1:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9] | 49 | [{"value": 49.0, "product": "C(#N)C1=C(C=C(C=C1)OC1=CC=CC=C1)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure of Example 35 was followed except that 1,2-dicyano-4-nitrobenzene (1.0 part) was used in place of the 1,2-dicyano-3-nitrobenzene, 1.0 parts instead of 2.79 parts of sodium phenoxide and 20 parts instead of 50 parts of dimethylformamide were used. 1,2-Dicyano-4-phenoxybenzene (0.6 parts, 49%) was obtained ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | CN(C=O)C | null | null | N#Cc1ccc([N+](=O)[O-])cc1C#N.[O-]c1ccccc1>CN(C=O)C>N#Cc1ccc(Oc2ccccc2)cc1C#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c395594dc1e40538a243005b001547e | c1ccc2cc3ccccc3cc2c1>>c1ccc2cc3ccccc3cc2c1 | C1=CC=CC2=CC3=CC=CC=C3C=C12.[K]>>C1=CC=CC2=CC3=CC=CC=C3C=C12.[K] | [cH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[cH:13][c:14]2[cH:15]1>>[cH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[cH:13][c:14]2[cH:15]1 | c1ccc2cc3ccccc3cc2c1 | c1ccc2cc3ccccc3cc2c1 | null | null | COCCOC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2cc3ccccc3cc2c1 | null | null | [] | null | null | 8 | HOUR | A potassium anthracene solution is prepared by adding about 17.8 gm of anthracene to about 500 ml of ethylene glycol dimethyl ether (monoglyme) in a flask in a glove box. A total of about 3.8 gm potassium metal is then added to the mixture. This composition gives a 5% by weight KAn solution. The mixture is then stirred... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2cc3ccccc3cc2c1 | null | COCCOC | null | 8 | c1ccc2cc3ccccc3cc2c1>COCCOC>c1ccc2cc3ccccc3cc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f9862849edd4f0d80d4a6085f88fd8d | c1ccc2c(c1)cnc1ccccc12>>c1ccc2c(c1)cnc1ccccc12 | C1=CC=CC2=NC=C3C=CC=CC3=C12.[K]>>C1=CC=CC2=NC=C3C=CC=CC3=C12.[K] | [cH:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[cH:8][n:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]21>>[cH:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[cH:8][n:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]21 | c1ccc2c(c1)cnc1ccccc12 | c1ccc2c(c1)cnc1ccccc12 | null | null | C(OC)COC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2c(c1)cnc1ccccc12 | null | null | [] | null | null | null | null | A potassium phenanthridine (radical-anion complex) solution is prepared by adding about 3.5 g phenanthridine and about 0.75 g potassium metal to about 20 ml of monoglyme yielding a red-colored product. A sample of PTFE, PFA and RO2800 each immersed for 3 minutes in this bath show surface discoloration indicative of che... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)cnc1ccccc12 | null | C(OC)COC | null | null | c1ccc2c(c1)cnc1ccccc12>C(OC)COC>c1ccc2c(c1)cnc1ccccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e5b29654fa7b4c0a9addc6161d045c21 | CC(C)=O.CCOC(=O)c1ccc(O)cc1>>CCCCC#CC#CCOc1ccc(C(=O)OCC)cc1 | OC1=CC=C(C(=O)OCC)C=C1.C([O-])([O-])=O.[K+].[K+].CC(=O)C>>C(C#CC#CCCCC)OC1=CC=C(C(=O)OCC)C=C1 | O=[C:2]([CH3:3])[CH3:8].[OH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]#[C:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][cH:21]1 | CC(C)=O.CCOC(=O)c1ccc(O)cc1 | CCCCC#CC#CCOc1ccc(C(=O)OCC)cc1 | null | null | CCCCCC.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | f664e238e6425ae5c9631abf45bf536009218ac0f59118ec1cf142df1d70a5bd | 9c689c7d119d59631c1411a738472fca9179a9bf1be9d1f598f75af39bf392ec | c1ccccc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[CH3;D1;+0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:8]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:9]-[C:10]#[C:11]-[C:12]#[C;H0;D2;+0:3]-[C:13]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 70 | [{"value": 70.0, "product": "C(C#CC#CCCCC)OC1=CC=C(C(=O)OCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a flask were placed 3.78 g (0.024 mole) of 1-chloro-2,4-nonadiyne thus obtained, 3.32 g (0.02 mole) of ethyl 4-hydroxybenzoate, 5.5 g (0.04 mole) of potassium carbonate, and 50 ml of acetone and the mixture was refluxed by heating for 11 hours. After allowing to cool the reaction mixture to room temperature, the rea... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic alcohol | Ether.Alkyne.Alkyne | null | null | c1ccccc1 | null | CCCCCC.C(C)(=O)OCC | null | null | CC(C)=O.CCOC(=O)c1ccc(O)cc1>CCCCCC.C(C)(=O)OCC>CCCCC#CC#CCOc1ccc(C(=O)OCC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a31f86da055a41eca836286b819df96e | CCO.O=C([O-])c1ccccc1.[OH-]>>CCCCC#CC#CCOc1ccc(C(=O)O)cc1 | C(C1=CC=CC=C1)(=O)[O-].C(C)O.Cl.[OH-].[K+]>>C(C#CC#CCCCC)OC1=CC=C(C(=O)O)C=C1 | O[CH2:1][CH3:4].[cH:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[O-:17])[cH:18][cH:19]1.[OH-:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]#[C:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]1 | CCO.O=C([O-])c1ccccc1.[OH-] | CCCCC#CC#CCOc1ccc(C(=O)O)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 45c8b8deb6d78d7d3bfb3977ca301c8a93cca9440480b7fc431e5832fa1978ef | a333956bef90c5319a53bfffa018bdc629e806d90ca76dd568ca90bf1da5c059 | c1ccccc1 | O-[CH2;D2;+0:1]-[CH3;D1;+0:2].[O-;H0;D1:3]-[C:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]:1.[OH-;D0:12]>>[C:13]#[C:14]-[CH2;D2;+0:2]-[C:15]-[C:16]-[CH3;D1;+0:1].[C:17]-[C:18]-[O;H0;D2;+0:12]-[c;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6](-[C:4](=[O;D1;H0:5])-[OH;D1;+0:3]):[c:11]:[c:10]:1 | 89.3 | [{"value": 89.3, "product": "C(C#CC#CCCCC)OC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 24 | HOUR | In a flask were placed 4.0 g (0.014 mole) of the benzoate derivative obtained and 18 ml of ethanol and while stirring the mixture at room temperature, an aqueous solution composed of 2.0 g (0.36 mole) of potassium hydroxide and 20 ml of water was added to the mixture. After stirring the mixture for 24 hours at 40° C. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid.Ether.Alkyne.Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O | 40 | 24 | CCO.O=C([O-])c1ccccc1.[OH-]>O>CCCCC#CC#CCOc1ccc(C(=O)O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-79a844ae48a5409c8f92ead50c3e3c88 | CCCCCCC[C@H](C)O.CCCCCCC[C@@H]1CC[C@@H]([SiH]2CCC(c3cc(F)c(O)c(F)c3)CC2)CC1>>CCCCCCC[C@@H]1CC[C@@H]([Si@@H]2CC[C@@H](c3cc(F)c(O[C@H](C)CCCCCCC)c(F)c3)CC2)CC1 | C(CCCCCC)[C@@H]1CC[C@H](CC1)[SiH]1CCC(CC1)C1=CC(=C(C(=C1)F)O)F.C[C@@H](CCCCCCC)O>>C(CCCCCC)[C@@H]1CC[C@H](CC1)[Si@@H]1CC[C@H](CC1)C1=CC(=C(C(=C1)F)O[C@@H](CCCCCCC)C)F | O[C@H:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH3:9].[OH:10][c:11]1[c:12]([F:13])[cH:14][c:15]([CH:16]2[CH2:17][CH2:18][SiH:19]([C@H:20]3[CH2:21][CH2:22][C@H:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32]3)[CH2:33][CH2:34]2)[cH:35][c:36]1[F:37]>>[CH3:1][CH2:2][CH2:3][CH2:4][... | CCCCCCC[C@H](C)O.CCCCCCC[C@@H]1CC[C@@H]([SiH]2CCC(c3cc(F)c(O)c(F)c3)CC2)CC1 | CCCCCCC[C@@H]1CC[C@@H]([Si@@H]2CC[C@@H](c3cc(F)c(O[C@H](C)CCCCCCC)c(F)c3)CC2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | aee3d691a6dfc6c8223fef7b9bb4e58ec7e16fbc345d424207a131929cdf1d03 | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc([C@H]2CC[Si@H](C3CCCCC3)CC2)cc1 | O-[C@@H;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C@@H;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | The general procedure of Example 1 was repeated using 4-(4-(trans-4-n-heptylcyclohexyl)-4-silacyclohexyl)-2,6-difluorophenol and (S)-2-nonanol, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[SiH]CC1.C1CCCCC1 | HO- | null | null | null | CCCCCCC[C@H](C)O.CCCCCCC[C@@H]1CC[C@@H]([SiH]2CCC(c3cc(F)c(O)c(F)c3)CC2)CC1>>CCCCCCC[C@@H]1CC[C@@H]([Si@@H]2CC[C@@H](c3cc(F)c(O[C@H](C)CCCCCCC)c(F)c3)CC2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72fab4fbc2a4453fa699034540dc6310 | CCCCCCC[C@@H](C)O.CCCCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1>>CCCCCCC[C@H](C)Oc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCCCCCC)CC3)cc2)cc1F | C(CCCCCC)[Si]1(CCC(CC1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)F)O)F)C1=CC=CC=C1.C[C@H](CCCCCCC)O>>C(CCCCCC)[Si@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)F)O[C@H](CCCCCCC)C)F | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:9])[OH:10].O[c:11]1[c:12]([F:13])[cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH:20]3[CH2:21][CH2:22][Si:23](c4ccccc4)([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32]3)[cH:33][cH:34]2)[cH:35][c:36]1[F:37]>>[CH3:1][CH2:2][CH2:3][CH2:... | CCCCCCC[C@@H](C)O.CCCCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1 | CCCCCCC[C@H](C)Oc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCCCCCC)CC3)cc2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 809cc6cbaf33982b4720f55cded0356f6de764cf5e5db5bd5ba5a6fc35b910b3 | 21afe9f346294bdbef38ab7f045ecca1c526b5e6b5f292b0e81878bf722d9d88 | c1ccc(-c2ccc(C3CC[SiH2]CC3)cc2)cc1 | O-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si;H0;D4;+0:10](-[C:11]-[C:12])(-c1:c:c:c:c:c:1)-[C:13]-[C:14].[C:15]-[C:16](-[C;D1;H3:17])-[OH;D1;+0:18]>>[C:15]-[C:16](-[C;D1;H3:17])-[O;H0;D2;+0:18]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si... | null | [] | null | null | null | null | The general procedure of Example 1 was repeated using 4-(4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)phenyl) -2,6-difluorophenol and (R)-2-nonanol, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol.Silyl protective group | Ether | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | c1ccccc1.C1CC[SiH]CC1 | c1ccccc1.c1ccccc1.C1CC[SiH]CC1 | HO- | null | null | null | CCCCCCC[C@@H](C)O.CCCCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1>>CCCCCCC[C@H](C)Oc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCCCCCC)CC3)cc2)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-89dee9eba1ca4a43a70edd6d797697e9 | CC(C)CC[C@@H]1CC[C@@H]([Si]2(c3ccccc3)CCC(c3cc(F)c(O)c(F)c3)CC2)CC1.CCCCCCCC[C@H](F)CO>>CCCCCCCC[C@@H](F)COc1c(F)cc([C@@H]2CC[Si@@H]([C@@H]3CC[C@@H](CCC(C)C)CC3)CC2)cc1F | CC(CC[C@@H]1CC[C@H](CC1)[Si]1(CCC(CC1)C1=CC(=C(C(=C1)F)O)F)C1=CC=CC=C1)C.F[C@H](CO)CCCCCCCC>>CC(CC[C@@H]1CC[C@H](CC1)[Si@@H]1CC[C@H](CC1)C1=CC(=C(C(=C1)F)OC[C@@H](CCCCCCCC)F)F)C | O[c:13]1[c:14]([F:15])[cH:16][c:17]([CH:18]2[CH2:19][CH2:20][Si:21](c3ccccc3)([C@H:22]3[CH2:23][CH2:24][C@H:25]([CH2:26][CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:31][CH2:32]3)[CH2:33][CH2:34]2)[cH:35][c:36]1[F:37].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([F:10])[CH2:11][OH:12]>>[CH3:1][CH2:2][CH2:3]... | CC(C)CC[C@@H]1CC[C@@H]([Si]2(c3ccccc3)CCC(c3cc(F)c(O)c(F)c3)CC2)CC1.CCCCCCCC[C@H](F)CO | CCCCCCCC[C@@H](F)COc1c(F)cc([C@@H]2CC[Si@@H]([C@@H]3CC[C@@H](CCC(C)C)CC3)CC2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a5292fab5f0c5a773b5fbfda54b35e9fb676959b0034c0d96967dd938e31a477 | 202a91f94e251f2f429ba648344f55c7e5385f24ffb4fef2f6620119aecefe69 | c1ccc([C@H]2CC[Si@H](C3CCCCC3)CC2)cc1 | O-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si;H0;D4;+0:10](-[C:11](-[C:12])-[C:13])(-c1:c:c:c:c:c:1)-[C:14]-[C:15].[C:16]-[C:17]-[OH;D1;+0:18]>>[C:16]-[C:17]-[O;H0;D2;+0:18]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si@H;D3;+0:10](-[C:11](... | null | [] | null | null | null | null | The general procedure of Example 1 was repeated using 4-(4-(trans-4-(3-methylbutyl)cyclohexyl)-4-phenyl-4-silacyclohexyl)-2,6-difluorophenol and (S)-2-fluoro-1-decanol, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol.Silyl protective group | Ether | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | c1ccccc1.C1CC[SiH]CC1 | c1ccccc1.C1CC[SiH]CC1.C1CCCCC1 | HO- | null | null | null | CC(C)CC[C@@H]1CC[C@@H]([Si]2(c3ccccc3)CCC(c3cc(F)c(O)c(F)c3)CC2)CC1.CCCCCCCC[C@H](F)CO>>CCCCCCCC[C@@H](F)COc1c(F)cc([C@@H]2CC[Si@@H]([C@@H]3CC[C@@H](CCC(C)C)CC3)CC2)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f51cb37f4fa54c6b91257cdc5aa7389e | CCCCCC[C@H](F)CO.CCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1>>CCCCCC[C@@H](F)COc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCC)CC3)cc2)cc1F | C(CC)[Si]1(CCC(CC1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)F)O)F)C1=CC=CC=C1.F[C@H](CO)CCCCCC>>C(CC)[Si@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)F)OC[C@@H](CCCCCC)F)F | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([F:8])[CH2:9][OH:10].O[c:11]1[c:12]([F:13])[cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH:20]3[CH2:21][CH2:22][Si:23](c4ccccc4)([CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28]3)[cH:29][cH:30]2)[cH:31][c:32]1[F:33]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([F:8])[CH2... | CCCCCC[C@H](F)CO.CCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1 | CCCCCC[C@@H](F)COc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCC)CC3)cc2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a5292fab5f0c5a773b5fbfda54b35e9fb676959b0034c0d96967dd938e31a477 | 202a91f94e251f2f429ba648344f55c7e5385f24ffb4fef2f6620119aecefe69 | c1ccc(-c2ccc(C3CC[SiH2]CC3)cc2)cc1 | O-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si;H0;D4;+0:10](-[C:11]-[C:12])(-c1:c:c:c:c:c:1)-[C:13]-[C:14].[C:15]-[C:16]-[OH;D1;+0:17]>>[C:15]-[C:16]-[O;H0;D2;+0:17]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si@H;D3;+0:10](-[C:11]-[C:12])-[... | null | [] | null | null | null | null | The general procedure of Example 1 was repeated using 4-(4-(4-n-propyl-4-phenyl-4-silacyclohexyl)phenyl) -2,6-difluorophenol and (S)-2-fluoro-1-octanol, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol.Silyl protective group | Ether | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | c1ccccc1.C1CC[SiH]CC1 | c1ccccc1.c1ccccc1.C1CC[SiH]CC1 | HO- | null | null | null | CCCCCC[C@H](F)CO.CCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1>>CCCCCC[C@@H](F)COc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCC)CC3)cc2)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4163a4ffca54f15a71dce74978d3a8a | CCCCCCCC[C@H](F)CO.CCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1>>CCCCCCCC[C@@H](F)COc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCCCC)CC3)cc2)cc1F | C(CCCC)[Si]1(CCC(CC1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)F)O)F)C1=CC=CC=C1.F[C@H](CO)CCCCCCCC>>C(CCCC)[Si@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)F)OC[C@@H](CCCCCCCC)F)F | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([F:10])[CH2:11][OH:12].O[c:13]1[c:14]([F:15])[cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([CH:22]3[CH2:23][CH2:24][Si:25](c4ccccc4)([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32]3)[cH:33][cH:34]2)[cH:35][c:36]1[F:37]>>[CH3:1][CH2:2][CH2:3][CH2:4][... | CCCCCCCC[C@H](F)CO.CCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1 | CCCCCCCC[C@@H](F)COc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCCCC)CC3)cc2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a5292fab5f0c5a773b5fbfda54b35e9fb676959b0034c0d96967dd938e31a477 | 202a91f94e251f2f429ba648344f55c7e5385f24ffb4fef2f6620119aecefe69 | c1ccc(-c2ccc(C3CC[SiH2]CC3)cc2)cc1 | O-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si;H0;D4;+0:10](-[C:11]-[C:12])(-c1:c:c:c:c:c:1)-[C:13]-[C:14].[C:15]-[C:16]-[OH;D1;+0:17]>>[C:15]-[C:16]-[O;H0;D2;+0:17]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si@H;D3;+0:10](-[C:11]-[C:12])-[... | null | [] | null | null | null | null | The general procedure of Example 1 was repeated using 4-(4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)phenyl) -2,6-difluorophenol and (S)-2-fluoro-1-decanol, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol.Silyl protective group | Ether | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | c1ccccc1.C1CC[SiH]CC1 | c1ccccc1.c1ccccc1.C1CC[SiH]CC1 | HO- | null | null | null | CCCCCCCC[C@H](F)CO.CCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1>>CCCCCCCC[C@@H](F)COc1c(F)cc(-c2ccc([C@@H]3CC[Si@@H](CCCCC)CC3)cc2)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-88408290ebb7421ba1638c2e701191bf | CCCCCCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1.CCCCCC[C@@H](F)CO>>CCCCCCCCC[Si@@H]1CC[C@@H](c2ccc(-c3cc(F)c(OC[C@@H](F)CCCCCC)c(F)c3)cc2)CC1 | C(CCCCCCCC)[Si]1(CCC(CC1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)F)O)F)C1=CC=CC=C1.F[C@@H](CO)CCCCCC>>C(CCCCCCCC)[Si@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)F)OC[C@H](CCCCCC)F)F | O[c:22]1[c:20]([F:21])[cH:19][c:18](-[c:17]2[cH:16][cH:15][c:14]([CH:13]3[CH2:12][CH2:11][Si:10](c4ccccc4)([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:39][CH2:38]3)[cH:37][cH:36]2)[cH:35][c:33]1[F:34].[OH:23][CH2:24][C@H:25]([F:26])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>>[CH3:1][CH2:2... | CCCCCCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1.CCCCCC[C@@H](F)CO | CCCCCCCCC[Si@@H]1CC[C@@H](c2ccc(-c3cc(F)c(OC[C@@H](F)CCCCCC)c(F)c3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a5292fab5f0c5a773b5fbfda54b35e9fb676959b0034c0d96967dd938e31a477 | 202a91f94e251f2f429ba648344f55c7e5385f24ffb4fef2f6620119aecefe69 | c1ccc(-c2ccc(C3CC[SiH2]CC3)cc2)cc1 | O-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si;H0;D4;+0:10](-[C:11]-[C:12])(-c1:c:c:c:c:c:1)-[C:13]-[C:14].[C:15]-[C:16]-[OH;D1;+0:17]>>[C:15]-[C:16]-[O;H0;D2;+0:17]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]-[C:9]-[Si@@H;D3;+0:10](-[C:11]-[C:12])-... | null | [] | null | null | null | null | The general procedure of Example 1 was repeated using 4-(4-(4-n-nonyl-4-phenyl-4-silacyclohexyl)phenyl) -2,6-difluorophenol and (R)-2-fluoro-1-octanol, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol.Silyl protective group | Ether | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCCCCCCC[Si]1(c2ccccc2)CCC(c2ccc(-c3cc(F)c(O)c(F)c3)cc2)CC1.CCCCCC[C@@H](F)CO>>CCCCCCCCC[Si@@H]1CC[C@@H](c2ccc(-c3cc(F)c(OC[C@@H](F)CCCCCC)c(F)c3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-46318b77785946d0ac36cbc991b8c83d | CCCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CN(C)C=O>>CCCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(CC(C)CC)c(F)c2)CC1 | FC(S(=O)(=O)OC1=C(C=C(C=C1F)C1CC[Si](CC1)(C1=CC=CC=C1)CCCCCCC)F)(F)F.[Cl-].[Li+].CN(C=O)C>>C(CCCCCC)[Si]1(CCC(CC1)C1=CC(=C(C(=C1)F)CC(CC)C)F)C1=CC=CC=C1 | O=S(=O)(O[c:22]1[c:20]([F:21])[cH:19][c:18]([CH:17]2[CH2:16][CH2:15][Si:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[CH2:32][CH2:31]2)[cH:26][c:28]1[F:29])[C:24](F)(F)F.O=[CH:23]N([CH3:25])[CH3:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Si:8]1([c:9]2[cH:1... | CCCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CN(C)C=O | CCCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(CC(C)CC)c(F)c2)CC1 | 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.[Cl-].[Zn+2].[Cl-] | C1CCOC1 | C-C Coupling | OtherReaction | 03c091a4a3125c65fb4307c32f8bf6b7df53fc73226da1ed2bbe4c712d9c2a30 | b9402c4017906dbf23f20649295d19208f580adfc6186cd5f88f29f18e65c8d8 | c1ccc(C2CC[SiH](c3ccccc3)CC2)cc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:2]1:[c:3](-[F;D1;H0:4]):[c:5]:[c;H0;D3;+0:6](-[C:7](-[C:8])-[C:9]):[cH;D2;+0:10]:[c;H0;D3;+0:11]:1-[F;D1;H0:12].O=[CH;D2;+0:13]-N(-[CH3;D1;+0:14])-[CH3;D1;+0:15]>>[C:8]-[C:7](-[c;H0;D3;+0:6]1:[c:5]:[c:3](-[F;D1;H0:4]):[c;H0;D3;+0:2](-[CH2;D2;+0:13]-[CH;D3;+0:1](-[CH3;D1;... | 140.1 | [{"value": 70.0, "product": "C(CCCCCC)[Si]1(CCC(CC1)C1=CC(=C(C(=C1)F)CC(CC)C)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 140.1, "product": "C(CCCCCC)[Si]1(CCC(CC1)C1=CC(=C(C(=C1)F)CC(CC)C)F)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | 3.0 g (20 mmols) of (S)-1-bromo-2-methylbutane was dropped in a mixture of 0.5 g (21 mmols) of magnesium and 50 ml of THF to obtain a Grignard reagent. This reagent was dropped in 20 ml of a THF solution of 2.8 g (20 mmols) of zinc chloride to obtain an organizing reagent. Subsequently, the solution was dropped in a mi... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Aromatic halide.Tertiary amide | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | TfOH | 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.[Cl-].[Zn+2].[Cl-].C1CCOC1 | 50 | 8 | CCCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CN(C)C=O>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.[Cl-].[Zn+2].[Cl-].C1CCOC1>CCCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(CC(C)CC)c(F)c... |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-88bba747b04c4ea0a87b10994af1c1f6 | CCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CC[C@H](C)CBr>>CCCCC[Si@@H]1CC[C@@H](c2cc(F)c(C[C@@H](C)CC)c(F)c2)CC1 | BrC[C@H](CC)C.FC(S(=O)(=O)OC1=C(C=C(C=C1F)C1CC[Si](CC1)(C1=CC=CC=C1)CCCCC)F)(F)F>>C(CCCC)[Si@@H]1CC[C@H](CC1)C1=CC(=C(C(=C1)F)C[C@H](CC)C)F | O=S(=O)(O[c:14]1[c:12]([F:13])[cH:11][c:10]([CH:9]2[CH2:8][CH2:7][Si:6](c3ccccc3)([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:24][CH2:23]2)[cH:22][c:20]1[F:21])C(F)(F)F.Br[CH2:15][C@@H:16]([CH3:17])[CH2:18][CH3:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][Si@H:6]1[CH2:7][CH2:8][C@H:9]([c:10]2[cH:11][c:12]([F:13])[c:14]([CH2:1... | CCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CC[C@H](C)CBr | CCCCC[Si@@H]1CC[C@@H](c2cc(F)c(C[C@@H](C)CC)c(F)c2)CC1 | null | null | null | C-C Coupling | OtherReaction | 9935bdb83fbc880c2e9eb02eec45697ab84443ccaa012a08289b5e647b58c2bb | d420250488195ec0988f11ee19e589da2c0bbba7363b6c594fa4c059a9975431 | c1ccc(C2CC[SiH2]CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[F;D1;H0:10]):[c:11].[C:12]-[C:13]-[Si;H0;D4;+0:14](-[C:15]-[C:16])(-c1:c:c:c:c:c:1)-[C:17]-[C:18]>>[C:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[F;D1;H0:10])... | null | [] | null | null | null | null | The general procedure of Example 18 was repeated using (S)-1-bromo-2-methylbutane and (2,6-difluoro-4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary halide.Silyl protective group | null | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1 | TfOH.HBr | null | null | null | CCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CC[C@H](C)CBr>>CCCCC[Si@@H]1CC[C@@H](c2cc(F)c(C[C@@H](C)CC)c(F)c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5d28f4a4fee44bbab5a422500b71969d | CCCCCC[C@H](F)CBr.CCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1>>CCCCCC[C@H](F)Cc1c(F)cc([C@@H]2CC[Si@@H](CCC)CC2)cc1F | BrC[C@H](CCCCCC)F.FC(S(=O)(=O)OC1=C(C=C(C=C1F)C1CC[Si](CC1)(C1=CC=CC=C1)CCC)F)(F)F>>C(CC)[Si@@H]1CC[C@H](CC1)C1=CC(=C(C(=C1)F)C[C@H](CCCCCC)F)F | Br[CH2:9][C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[F:8].O=S(=O)(O[c:10]1[c:11]([F:12])[cH:13][c:14]([CH:15]2[CH2:16][CH2:17][Si:18](c3ccccc3)([CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23]2)[cH:24][c:25]1[F:26])C(F)(F)F>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@H:7]([F:8])[CH2:9][c:10]1[c:11]([F:12])[cH:13][c:... | CCCCCC[C@H](F)CBr.CCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1 | CCCCCC[C@H](F)Cc1c(F)cc([C@@H]2CC[Si@@H](CCC)CC2)cc1F | null | null | null | C-C Coupling | OtherReaction | 9935bdb83fbc880c2e9eb02eec45697ab84443ccaa012a08289b5e647b58c2bb | d420250488195ec0988f11ee19e589da2c0bbba7363b6c594fa4c059a9975431 | c1ccc(C2CC[SiH2]CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[F;D1;H0:4].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[F;D1;H0:10]):[c:11].[C:12]-[C:13]-[Si;H0;D4;+0:14](-[C:15]-[C:16])(-c1:c:c:c:c:c:1)-[C:17]-[C:18]>>[C:3]-[C:2](-[F;D1;H0:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[F;D1;H0:10])... | null | [] | null | null | null | null | The general procedure of Example 18 was repeated using (S)-1-bromo-2-fluorooctane and (2,6-difluoro-4-(4-n-propyl-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary halide.Silyl protective group | null | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | c1ccccc1.C1CC[SiH]CC1 | c1ccccc1.C1CC[SiH]CC1 | TfOH.HBr | null | null | null | CCCCCC[C@H](F)CBr.CCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1>>CCCCCC[C@H](F)Cc1c(F)cc([C@@H]2CC[Si@@H](CCC)CC2)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bed1a545f80b47caa1fbca1069b3c17a | C=CCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CCCCCC[C@@H](F)CBr>>C=CCCC[Si@@H]1CC[C@@H](c2cc(F)c(C[C@H](F)CCCCCC)c(F)c2)CC1 | BrC[C@@H](CCCCCC)F.FC(S(=O)(=O)OC1=C(C=C(C=C1F)C1CC[Si](CC1)(C1=CC=CC=C1)CCCC=C)F)(F)F>>C(CCC=C)[Si@@H]1CC[C@H](CC1)C1=CC(=C(C(=C1)F)C[C@@H](CCCCCC)F)F | O=S(=O)(O[c:14]1[c:12]([F:13])[cH:11][c:10]([CH:9]2[CH2:8][CH2:7][Si:6](c3ccccc3)([CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])[CH2:28][CH2:27]2)[cH:26][c:24]1[F:25])C(F)(F)F.Br[CH2:15][C@H:16]([F:17])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][Si@H:6]1[CH2:7][CH2:8][C@H:9]([c:10]2[cH:1... | C=CCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CCCCCC[C@@H](F)CBr | C=CCCC[Si@@H]1CC[C@@H](c2cc(F)c(C[C@H](F)CCCCCC)c(F)c2)CC1 | null | null | null | C-C Coupling | OtherReaction | 9935bdb83fbc880c2e9eb02eec45697ab84443ccaa012a08289b5e647b58c2bb | d420250488195ec0988f11ee19e589da2c0bbba7363b6c594fa4c059a9975431 | c1ccc(C2CC[SiH2]CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[F;D1;H0:4].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[F;D1;H0:10]):[c:11].[C:12]-[C:13]-[Si;H0;D4;+0:14](-[C:15]-[C:16])(-c1:c:c:c:c:c:1)-[C:17]-[C:18]>>[C:3]-[C:2](-[F;D1;H0:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[F;D1;H0:10])... | null | [] | null | null | null | null | The general procedure of Example 18 was repeated-using (R)-1-bromo-2-fluorooctane and (2,6-difluoro-4-(4-(4-pentenyl)-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary halide.Silyl protective group | null | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1 | TfOH.HBr | null | null | null | C=CCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1.CCCCCC[C@@H](F)CBr>>C=CCCC[Si@@H]1CC[C@@H](c2cc(F)c(C[C@H](F)CCCCCC)c(F)c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b51b9188153b4471b5d5fb0de0258451 | CCCCCC[C@@H](F)CBr.COCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1>>CCCCCC[C@@H](F)Cc1c(F)cc([C@@H]2CC[Si@@H](CCCCCOC)CC2)cc1F | BrC[C@@H](CCCCCC)F.FC(S(=O)(=O)OC1=C(C=C(C=C1F)C1CC[Si](CC1)(C1=CC=CC=C1)CCCCCOC)F)(F)F>>COCCCCC[Si@@H]1CC[C@H](CC1)C1=CC(=C(C(=C1)F)C[C@@H](CCCCCC)F)F | Br[CH2:9][C@@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[F:8].O=S(=O)(O[c:10]1[c:11]([F:12])[cH:13][c:14]([CH:15]2[CH2:16][CH2:17][Si:18](c3ccccc3)([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH2:26][CH2:27]2)[cH:28][c:29]1[F:30])C(F)(F)F>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([F:8])[CH2:9... | CCCCCC[C@@H](F)CBr.COCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1 | CCCCCC[C@@H](F)Cc1c(F)cc([C@@H]2CC[Si@@H](CCCCCOC)CC2)cc1F | null | null | null | C-C Coupling | OtherReaction | 9935bdb83fbc880c2e9eb02eec45697ab84443ccaa012a08289b5e647b58c2bb | d420250488195ec0988f11ee19e589da2c0bbba7363b6c594fa4c059a9975431 | c1ccc(C2CC[SiH2]CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[F;D1;H0:4].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[F;D1;H0:10]):[c:11].[C:12]-[C:13]-[Si;H0;D4;+0:14](-[C:15]-[C:16])(-c1:c:c:c:c:c:1)-[C:17]-[C:18]>>[C:3]-[C:2](-[F;D1;H0:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[c:6](-[F;D1;H0:7]):[c:8]):[c:9](-[F;D1;H0:10])... | null | [] | null | null | null | null | The general procedure of Example 18 was repeated using (R)-1-bromo-2-fluorooctane and (2,6-difluoro-4-(4-(5-methoxypentyl)-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary halide.Silyl protective group | null | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | c1ccccc1.C1CC[SiH]CC1 | c1ccccc1.C1CC[SiH]CC1 | TfOH.HBr | null | null | null | CCCCCC[C@@H](F)CBr.COCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1>>CCCCCC[C@@H](F)Cc1c(F)cc([C@@H]2CC[Si@@H](CCCCCOC)CC2)cc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd9da67525c44e2d8824e7d3320b62e1 | CCCCC[Si]1(c2ccccc2)CCC([C@@H]2CC[C@@H](c3ccc(OS(=O)(=O)C(F)(F)F)cc3)CC2)CC1.CC[C@H](C)CBr>>CCCCC[Si@@H]1CC[C@@H]([C@@H]2CC[C@@H](c3ccc(C[C@@H](C)CC)cc3)CC2)CC1 | BrC[C@H](CC)C.FC(S(=O)(=O)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C1CC[Si](CC1)(C1=CC=CC=C1)CCCCC)(F)F>>C(CCCC)[Si@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C[C@H](CC)C | O=S(=O)(O[c:17]1[cH:16][cH:15][c:14]([C@H:13]2[CH2:12][CH2:11][C@H:10]([CH:9]3[CH2:8][CH2:7][Si:6](c4ccccc4)([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:28][CH2:27]3)[CH2:26][CH2:25]2)[cH:24][cH:23]1)C(F)(F)F.Br[CH2:18][C@@H:19]([CH3:20])[CH2:21][CH3:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][Si@H:6]1[CH2:7][CH2:8][C@H:9]([... | CCCCC[Si]1(c2ccccc2)CCC([C@@H]2CC[C@@H](c3ccc(OS(=O)(=O)C(F)(F)F)cc3)CC2)CC1.CC[C@H](C)CBr | CCCCC[Si@@H]1CC[C@@H]([C@@H]2CC[C@@H](c3ccc(C[C@@H](C)CC)cc3)CC2)CC1 | null | null | null | C-C Coupling | OtherReaction | 9935bdb83fbc880c2e9eb02eec45697ab84443ccaa012a08289b5e647b58c2bb | d420250488195ec0988f11ee19e589da2c0bbba7363b6c594fa4c059a9975431 | c1ccc([C@H]2CC[C@H](C3CC[SiH2]CC3)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[C:10]-[C:11]-[Si;H0;D4;+0:12](-[C:13]-[C:14])(-c1:c:c:c:c:c:1)-[C:15]-[C:16]>>[C:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[C:10]-[C:11]-[Si@@H;D3;+0:12](-[C:13]-[C:14])-[C:15... | null | [] | null | null | null | null | The general procedure of Example 18 was repeated using (S)-1-bromo-2-methylbutane and (4-(trans-4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)cyclohexyl)phenyl) trifluoromethanesulfonate, thereby obtaining the intended compound.
Conditions: See reaction.notes.procedure_details.
Workup: obtaining the intended compound | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary halide.Silyl protective group | null | c1ccccc1.C1CC[Si]CC1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1 | C1CC[SiH]CC1.C1CCCCC1.c1ccccc1 | TfOH.HBr | null | null | null | CCCCC[Si]1(c2ccccc2)CCC([C@@H]2CC[C@@H](c3ccc(OS(=O)(=O)C(F)(F)F)cc3)CC2)CC1.CC[C@H](C)CBr>>CCCCC[Si@@H]1CC[C@@H]([C@@H]2CC[C@@H](c3ccc(C[C@@H](C)CC)cc3)CC2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-185154b6627f4f909d32b9149fae48a3 | CCCCCCC[Si]1(c2ccccc2)CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCCCC[Si]1(c2ccccc2)CCC(C=O)CC1 | O.C(CCCCCC)[Si]1(CCC(CC1)=O)C1=CC=CC=C1.CC(C)([O-])C.[K+].[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(CCCCCC)[Si]1(CCC(CC1)C=O)C1=CC=CC=C1 | O=[C:17]1[CH2:16][CH2:15][Si:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:21][CH2:20]1.C[O:19][CH2:18][P+](c1ccccc1)(c1ccccc1)c1ccccc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Si:8]1([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16][CH:17]([CH... | CCCCCCC[Si]1(c2ccccc2)CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCCCC[Si]1(c2ccccc2)CCC(C=O)CC1 | null | null | C1CCOC1 | Acylation | OtherReaction | c1dcb58ebddab5be167e16eb629a1f11185def4238747797e7b1efdec4476674 | 43cbfec1f077c493b72a12008b2b079b7808ea096be066fc071cb46dfa7e38c3 | c1ccc([SiH]2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[CH2;D2;+0:2]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[C;H0;D3;+0:3]1-[C:4]-[C:5]-[#14:6]-[C:7]-[C:8]-1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[CH;D3;+0:3]1-[C:4]-[C:5]-[#14:6]-[C:7]-[C:8]-1 | null | [] | null | null | 2 | HOUR | 12 g of potassium t-butoxide was added to a mixture of 35 g of methoxymethyltriphenylphosphonium chloride and 200 ml of THF to prepare an orange ylide solution. A solution of 28 g of 4-n-heptyl-4-phenyl-4-silacyclohexanone in 50 ml of THF was added to the solution. After agitation for 2 hours at room temperature, the m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Aldehyde | C1CC[Si]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CC[Si]CC1 | c1ccccc1.C1CC[Si]CC1 | HO- | C1CCOC1 | null | 2 | CCCCCCC[Si]1(c2ccccc2)CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1CCOC1>CCCCCCC[Si]1(c2ccccc2)CCC(C=O)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cbb6a7ae64f8437f8e6e1b614d3b6cc8 | CCC[Si]1(c2ccccc2)CCC(=O)CC1.C[Si](C)(C)c1c(F)cc(Cl)cc1F.FC=C(F)c1c(F)cc(Br)cc1F>>CCC[Si@@H]1CC[C@@H](c2cc(F)c(-c3cc(F)c(C(F)=CF)c(F)c3)c(F)c2)CC1 | C(CC)[Si]1(CCC(CC1)=O)C1=CC=CC=C1.ClC1=CC(=C(C(=C1)F)[Si](C)(C)C)F.BrC1=CC(=C(C(=C1)F)C(=CF)F)F>>C(CC)[Si@@H]1CC[C@H](CC1)C1=CC(=C(C(=C1)F)C1=CC(=C(C(=C1)F)C(=CF)F)F)F | O=[C:7]1[CH2:6][CH2:5][Si:4](c2ccccc2)([CH2:3][CH2:2][CH3:1])[CH2:29][CH2:28]1.C[Si](C)(C)[c:12]1[c:10]([F:11])[cH:9][c:8](Cl)[cH:27][c:25]1[F:26].Br[c:13]1[cH:14][c:15]([F:16])[c:17]([C:18]([F:19])=[CH:20][F:21])[c:22]([F:23])[cH:24]1>>[CH3:1][CH2:2][CH2:3][Si@H:4]1[CH2:5][CH2:6][C@H:7]([c:8]2[cH:9][c:10]([F:11])[c:12... | CCC[Si]1(c2ccccc2)CCC(=O)CC1.C[Si](C)(C)c1c(F)cc(Cl)cc1F.FC=C(F)c1c(F)cc(Br)cc1F | CCC[Si@@H]1CC[C@@H](c2cc(F)c(-c3cc(F)c(C(F)=CF)c(F)c3)c(F)c2)CC1 | null | null | null | C-C Coupling | OtherReaction | c114e67971514a88461e2e58fce64858a0bdce70abbdd49913ab406bbb19d98c | ffa4885e784fbba7b2d1b68c3217b6b2d1f3e81903fca40b04b6a0bfa9819f5b | c1ccc(-c2ccc(C3CC[SiH2]CC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-[Si](-C)(-C)-[c;H0;D3;+0:6]1:[c:7](-[F;D1;H0:8]):[c:9]:[c;H0;D3;+0:10](-Cl):[c:11]:[c:12]:1-[F;D1;H0:13].O=[C;H0;D3;+0:14]1-[C:15]-[C:16]-[Si;H0;D4;+0:17](-[C:18]-[C:19])(-c2:c:c:c:c:c:2)-[C:20]-[C:21]-1>>[C:19]-[C:18]-[Si@@H;D3;+0:17]1-[C:16]-[C:15]-[C@@H;D3;+0:14](-[c;H0;... | null | [] | null | null | null | null | The general procedure of Example 35 was repeated using 4-propyl-4-phenyl-4-silacyclohexanone instead of 4-pentyl-4-phenyl-4-silacyclohexanone, 4-chloro-2,6-difluorophenyltrimethylsilane instead of 4-chlorophenyltrimethylsilane, and 4-bromo-2,6-difluoro-1-(1,2-difluorovinyl)benzene instead of 4-bromo-2,6-difluoro-1-(2,2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ketone.Silyl protective group.Silyl protective group | null | C1CC[Si]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | HCl.Br- | null | null | null | CCC[Si]1(c2ccccc2)CCC(=O)CC1.C[Si](C)(C)c1c(F)cc(Cl)cc1F.FC=C(F)c1c(F)cc(Br)cc1F>>CCC[Si@@H]1CC[C@@H](c2cc(F)c(-c3cc(F)c(C(F)=CF)c(F)c3)c(F)c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db385b2cb2e1457ba6d59349cf5dd028 | CCC[Si]1(c2ccccc2)CCC(=O)CC1.Fc1cc(Br)cc(F)c1C(Cl)=CCl>>CCC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(C(Cl)=CCl)cc3)cc2)CC1 | C(CC)[Si]1(CCC(CC1)=O)C1=CC=CC=C1.BrC1=CC(=C(C(=C1)F)C(=CCl)Cl)F>>C(CC)[Si@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=CCl)Cl | O=[C:7]1[CH2:6][CH2:5][Si:4]([CH2:3][CH2:2][CH3:1])([c:8]2[cH:9][cH:10][cH:11][cH:22][cH:23]2)[CH2:25][CH2:24]1.F[c:14]1[cH:13][c:12](Br)[cH:21][c:20](F)[c:15]1[C:16]([Cl:17])=[CH:18][Cl:19]>>[CH3:1][CH2:2][CH2:3][Si@H:4]1[CH2:5][CH2:6][C@H:7]([c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]([Cl:17])=[CH:1... | CCC[Si]1(c2ccccc2)CCC(=O)CC1.Fc1cc(Br)cc(F)c1C(Cl)=CCl | CCC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(C(Cl)=CCl)cc3)cc2)CC1 | null | null | null | C-C Coupling | OtherReaction | e5a5e1b56e7e83a5893b45a40f0605d07ed1404a9592ebd9676fc9599dabfb43 | b146dd937aa0b965d252e29e46cb395580fb8e88eaea95ea17e75722afccf9e0 | c1ccc(-c2ccc(C3CC[SiH2]CC3)cc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-F):[c:4](-[C:5](-[Cl;D1;H0:6])=[C:7]-[Cl;D1;H0:8]):[c;H0;D3;+0:9](-F):[c:10]:1.O=[C;H0;D3;+0:11]1-[C:12]-[C:13]-[Si;H0;D4;+0:14](-[C:15]-[C:16])(-[c;H0;D3;+0:17]2:[c:18]:[c:19]:[cH;D2;+0:20]:[c:21]:[c:22]:2)-[C:23]-[C:24]-1>>[C:16]-[C:15]-[Si@@H;D3;+0:14]1-[C:13]-[C:12]-[C@@H;D3... | null | [] | null | null | null | null | The general procedure of Example 35 was repeated using 4-propyl-4-phenyl-4-silacyclohexanone instead of 4-pentyl-4-phenyl-4-silacyclohexanone, and 4-bromo-2,6-difluoro-1-(1,2-dichlorovinyl)benzene instead of 4-bromo-2,6-difluoro-1-(2,2-difluorovinyloxy)benzene, thereby obtaining the intended compound.
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ketone.Silyl protective group | null | C1CC[Si]CC1.c1ccccc1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | Br- | null | null | null | CCC[Si]1(c2ccccc2)CCC(=O)CC1.Fc1cc(Br)cc(F)c1C(Cl)=CCl>>CCC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(C(Cl)=CCl)cc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a5876763371f4e2ba7a63c3d5338778c | CCC[Si]1(c2ccccc2)CCC(=O)CC1.FC(F)=C(F)Oc1ccc(Br)cc1F>>CCC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(OC(F)=C(F)F)c(F)c3)c(F)c2)CC1 | C(CC)[Si]1(CCC(CC1)=O)C1=CC=CC=C1.BrC1=CC(=C(C=C1)OC(=C(F)F)F)F>>C(CC)[Si@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)C1=CC(=C(C=C1)OC(=C(F)F)F)F)F | O=[C:7]1[CH2:6][CH2:5][Si:4]([CH2:3][CH2:2][CH3:1])([c:8]2[cH:9][cH:10][cH:11][cH:25][cH:27]2)[CH2:29][CH2:28]1.Br[c:12]1[cH:13][cH:14][c:15]([O:16][C:17]([F:18])=[C:19]([F:20])[F:26])[c:22]([F:23])[cH:24]1>>[CH3:1][CH2:2][CH2:3][Si@H:4]1[CH2:5][CH2:6][C@H:7]([c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([O:16... | CCC[Si]1(c2ccccc2)CCC(=O)CC1.FC(F)=C(F)Oc1ccc(Br)cc1F | CCC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(OC(F)=C(F)F)c(F)c3)c(F)c2)CC1 | null | null | null | C-C Coupling | OtherReaction | 6f04de024a67d2a26a3667e5b045e4864d6247c6202f07b467c3cb8fa4ffbb98 | 864d2f8b04ae13e79a3a6c1bfcb289b3655c2f5da11e73d36f080ee429520f30 | c1ccc(-c2ccc(C3CC[SiH2]CC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](-[F;D1;H0:8])=[C;H0;D3;+0:9](-[F;D1;H0:10])-[F;H0;D1;+0:11].O=[C;H0;D3;+0:12]1-[C:13]-[C:14]-[Si;H0;D4;+0:15](-[C:16]-[C:17])(-[c;H0;D3;+0:18]2:[c:19]:[cH;D2;+0:20]:[cH;D2;+0:21]:[c:22]:[c:23]:2)-[C:24]-[C:25]-1>>[#8:6]-[C:7](-[F;D1;H0:8])=[C;H0;D3;+0:9](-[F;D1;H... | null | [] | null | null | null | null | The general procedure of Example 36 was repeated using 4-propyl-4-phenyl-4-silacyclohexanone instead of 4-pentyl-4-phenyl-4-silacyclohexanone and 4-bromo-2-fluoro-1-(1,2,2-trifluorovinyloxy)benzene instead of 4-bromo-2,6-difluoro-1-(1,2,2-trifluorovinyl)benzene, thereby obtaining the intended compound.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkenyl halide.Alkenyl halide.Ketone.Silyl protective group | Aromatic halide.Alkenyl halide.Alkenyl halide | C1CC[Si]CC1.c1ccccc1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | Br- | null | null | null | CCC[Si]1(c2ccccc2)CCC(=O)CC1.FC(F)=C(F)Oc1ccc(Br)cc1F>>CCC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(OC(F)=C(F)F)c(F)c3)c(F)c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-af2f9c6c94004dd4808d0d3c80050cd2 | CC(C)CC[Si]1(c2ccccc2)CCC(=O)CC1.FC=C(F)c1ccc(Br)cc1>>CC(C)CC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(C(F)=CF)cc3)cc2)CC1 | CC(CC[Si]1(CCC(CC1)=O)C1=CC=CC=C1)C.BrC1=CC=C(C=C1)C(=CF)F>>CC(CC[Si@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C(=CF)F)C | O=[C:9]1[CH2:8][CH2:7][Si:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])([c:10]2[cH:11][cH:12][cH:13][cH:24][cH:25]2)[CH2:27][CH2:26]1.Br[c:14]1[cH:15][cH:16][c:17]([C:18]([F:19])=[CH:20][F:21])[cH:22][cH:23]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][Si@H:6]1[CH2:7][CH2:8][C@H:9]([c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:1... | CC(C)CC[Si]1(c2ccccc2)CCC(=O)CC1.FC=C(F)c1ccc(Br)cc1 | CC(C)CC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(C(F)=CF)cc3)cc2)CC1 | null | null | null | C-C Coupling | OtherReaction | 098880bfd8f7afe666b60d7968549bf369df250cbe13cb8c09602db1f7ee1559 | a055f5efd8bd9aebeee0fb3fc3b65cf76f24d02d8a6769b9bc6367b666f3a717 | c1ccc(-c2ccc(C3CC[SiH2]CC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[Si;H0;D4;+0:9](-[C:10]-[C:11])(-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[cH;D2;+0:15]:[c:16]:[c:17]:2)-[C:18]-[C:19]-1>>[C:11]-[C:10]-[Si@H;D3;+0:9]1-[C:8]-[C:7]-[C@H;D3;+0:6](-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[c;H0;D3;+0:15](-[c;H0;D3;+0:1](:[c:2]:[c:3]):... | null | [] | null | null | null | null | The general procedure of Example 35 was repeated using 4-(3-methylbutyl)-4-phenyl-4-silacyclohexanone instead of 4-pentyl-4-phenyl-4-silacyclohexanone and 4-bromo-1-(1,2-difluorovinyl)benzene instead of 4-bromo-2,6-difluoro-1-(2,2-difluorovinyloxy)benzene, thereby obtaining the intended compound.
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Silyl protective group | null | C1CC[Si]CC1.c1ccccc1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | C1CC[SiH]CC1.c1ccccc1.c1ccccc1 | Br- | null | null | null | CC(C)CC[Si]1(c2ccccc2)CCC(=O)CC1.FC=C(F)c1ccc(Br)cc1>>CC(C)CC[Si@@H]1CC[C@@H](c2ccc(-c3ccc(C(F)=CF)cc3)cc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-60ff9b3f88b74fb89fc2c3b2f2e968f6 | CCCCC[Si]1(c2ccccc2)CCC(C2CCC(=O)CC2)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCCCC[Si]1(c2ccccc2)CCC(C2CCC(C=O)CC2)CC1 | O.C(CCCC)[Si]1(CCC(CC1)C1CCC(CC1)=O)C1=CC=CC=C1.CC(C)([O-])C.[K+].[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(CCCC)[Si]1(CCC(CC1)C1CCC(CC1)C=O)C1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][Si:6]1([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][CH:15]([CH:16]2[CH2:17][CH2:18][C:19](=[O:21])[CH2:22][CH2:23]2)[CH2:24][CH2:25]1.CO[CH2:20][P+](c1ccccc1)(c1ccccc1)c1ccccc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][Si:6]1([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][... | CCCCC[Si]1(c2ccccc2)CCC(C2CCC(=O)CC2)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CCCCC[Si]1(c2ccccc2)CCC(C2CCC(C=O)CC2)CC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 326b81bec99b6e51af5a3a99e6338cf4b53775fec14ad82e34348f151bd89729 | 81ab61909aa1d0d77dde97eb1979cacb3b8aefd3e55c088ab4b0fb0fb14e9b18 | c1ccc([SiH]2CCC(C3CCCCC3)CC2)cc1 | C-O-[CH2;D2;+0:1]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C:2]-[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6]-[C:7]>>[C:2]-[C:3]-[CH;D3;+0:4](-[CH;D2;+0:1]=[O;H0;D1;+0:5])-[C:6]-[C:7] | null | [] | null | null | 2 | HOUR | 12 g of potassium t-butoxide was added to a mixture of 35 g of methoxymethyltriphenylphosphonium chloride and 200 ml of THF to prepare an orange ylide solution. A solution of 34 g of 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)cyclohexanone in 50 ml of THF was added to the ylide solution and agitated at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Aldehyde | C1CCCCC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccccc1.C1CC[Si]CC1.C1CCCCC1 | HO- | C1CCOC1 | null | 2 | CCCCC[Si]1(c2ccccc2)CCC(C2CCC(=O)CC2)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1CCOC1>CCCCC[Si]1(c2ccccc2)CCC(C2CCC(C=O)CC2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7af0ec22991e44728c4339cf7a4c117a | CCC[Si]1(c2ccccc2)CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>CCC[Si]1(c2ccccc2)CCC(C=O)CC1 | O.C(CC)[Si]1(CCC(CC1)=O)C1=CC=CC=C1.CC(C)([O-])C.[K+].[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(CC)[Si]1(CCC(CC1)C=O)C1=CC=CC=C1 | [CH3:1][CH2:2][CH2:3][Si:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][C:13](=[O:15])[CH2:16][CH2:17]1.CO[CH2:14][P+](c1ccccc1)(c1ccccc1)c1ccccc1>>[CH3:1][CH2:2][CH2:3][Si:4]1([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][CH:13]([CH:14]=[O:15])[CH2:16][CH2:17]1 | CCC[Si]1(c2ccccc2)CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | CCC[Si]1(c2ccccc2)CCC(C=O)CC1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | b5dbbbf509c3d46617f9e4b550ff3fc938df5015b3348da4ae36c4b9d1e5bc71 | 81ab61909aa1d0d77dde97eb1979cacb3b8aefd3e55c088ab4b0fb0fb14e9b18 | c1ccc([SiH]2CCCCC2)cc1 | C-O-[CH2;D2;+0:1]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[O;H0;D1;+0:2]=[C;H0;D3;+0:3]1-[C:4]-[C:5]-[#14:6]-[C:7]-[C:8]-1>>[O;H0;D1;+0:2]=[CH;D2;+0:1]-[CH;D3;+0:3]1-[C:4]-[C:5]-[#14:6]-[C:7]-[C:8]-1 | null | [] | null | null | 2 | HOUR | 12 g of potassium t-butoxide was added to a mixture of 35 g of methoxymethyltriphenylphosphonium chloride and 200 ml of THF to prepare an orange ylide solution. A solution of 23 g of 4-n-propyl-4-phenyl-4-silacyclohexanone in 50 ml of THF was added to the ylide solution and agitated at room temperature for 2 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Aldehyde | C1CC[Si]CC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CC[Si]CC1 | c1ccccc1.C1CC[Si]CC1 | HO- | C1CCOC1 | null | 2 | CCC[Si]1(c2ccccc2)CCC(=O)CC1.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1CCOC1>CCC[Si]1(c2ccccc2)CCC(C=O)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c8bd279ef8414749819522d3b3ae0914 | Cc1ccc(C(C)C)c2c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)O2>>Cc1ccc(C(C)C)c2c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)O2 | CC1=C2C(=C(C=C1)C(C)C)OC(=O)C3=C(C=CC(=C3OC(=O)C4=C(C=CC(=C4OC2=O)C(C)C)C)C(C)C)C.CBr>>CC1=C2C(=C(C=C1)C(C)C)OC(=O)C3=C(C=CC(=C3OC(=O)C4=C(C=CC(=C4OC2=O)C(C)C)C)C(C)C)C.CBr | [CH3:3][c:4]1[cH:5][cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[c:11]2[c:12]1[C:13](=[O:14])[O:15][c:16]1[c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22][c:23]([CH3:24])[c:25]1[C:26](=[O:27])[O:28][c:29]1[c:30]([CH:31]([CH3:32])[CH3:33])[cH:34][cH:35][c:36]([CH3:37])[c:38]1[C:39](=[O:40])[O:41]2>>[CH3:3][c:4]1[cH:5][cH:6][c:7](... | Cc1ccc(C(C)C)c2c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)O2 | Cc1ccc(C(C)C)c2c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)O2 | null | null | CC(C)(CC(C)C)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1Oc2ccccc2C(=O)Oc2ccccc2C(=O)Oc2ccccc21 | null | null | [] | null | null | 2 | HOUR | Tri-o-thymotide (25 g) was dissolved in 2,2,4-trimethylpentane (50 ml) at 100° C. and the hot solution was introduced into the high pressure autoclave. Methyl bromide was added to the autoclave until a pressure of 200 bar was reached. The high pressure autoclave was then kept for 2 hours at 110° C. and the solution was... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)COc1ccccc1COc1ccccc1CO2 | null | CC(C)(CC(C)C)C | null | 2 | Cc1ccc(C(C)C)c2c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)O2>CC(C)(CC(C)C)C>Cc1ccc(C(C)C)c2c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)Oc1c(C(C)C)ccc(C)c1C(=O)O2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4ada581c5e0b46f1931dbf7d4b1bd141 | Oc1ccc(O)cc1>>Oc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.C>>C1(O)=CC=C(O)C=C1.C | [OH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]1>>[OH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]1 | Oc1ccc(O)cc1 | Oc1ccc(O)cc1 | null | null | C(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 2 | HOUR | Hydroquinone (30 g) was dissolved in n-propanol (70 ml) at 70° C. The hot solution was introduced into the high pressure autoclave. The solution was subjected to compressed methane of 300 bar. The high pressure autoclave was kept for 2 h at 80° C. The solution was then cooled down to room temperature within 5 days. The... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(CC)O | null | 2 | Oc1ccc(O)cc1>C(CC)O>Oc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aa734d00cb9b4ff0af6b2f40ea427a91 | Oc1ccc(O)cc1>>Oc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.S(F)(F)(F)(F)(F)F>>C1(O)=CC=C(O)C=C1.S(F)(F)(F)(F)(F)F | [OH:8][c:9]1[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]1>>[OH:8][c:9]1[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]1 | Oc1ccc(O)cc1 | Oc1ccc(O)cc1 | null | null | C(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 2 | HOUR | Hydroquinone (30 g) was dissolved in n-propanol (70 ml) at 70° C. The hot solution was introduced into the high pressure autoclave. The solution was subjected to compressed sulphur hexafluoride of 300 bar. The high pressure autoclave was kept for 2 h at 80° C. The solution was then cooled down to room temperature withi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(CC)O | null | 2 | Oc1ccc(O)cc1>C(CC)O>Oc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4244cb2df0c84297bc02dcca716b6e6e | Oc1ccc(O)cc1>>Oc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.CCC>>C1(O)=CC=C(O)C=C1.CCC | [OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | Oc1ccc(O)cc1 | Oc1ccc(O)cc1 | null | null | C(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 2 | HOUR | Hydroquinone (30 g) was dissolved in n-propanol (70 ml at 70° C. The hot solution was introduced into the high pressure autoclave. The solution was subjected to compressed propane of 300 bar. The high pressure autoclave was kept for 2 h at 80° C. The solution was then cooled down to room temperature within 5 days. The ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(CC)O | null | 2 | Oc1ccc(O)cc1>C(CC)O>Oc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32522ad5fd5f43f794fa986ba7a13f31 | Oc1ccc(O)cc1>>Oc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.CC>>C1(O)=CC=C(O)C=C1.CC | [OH:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>>[OH:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1 | Oc1ccc(O)cc1 | Oc1ccc(O)cc1 | null | null | C(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 2 | HOUR | Hydroquinone (30 g) was dissolved in n-propanol (70 ml) at 70° C. The hot solution was introduced into the high pressure autoclave. The solution was subjected to compressed ethane of 300 bar. The high pressure autoclave was kept for 2 h at 80° C. The solution was then cooled down to room temperature within 5 days. The ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(CC)O | null | 2 | Oc1ccc(O)cc1>C(CC)O>Oc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-598e5ea1d2164dab8e306d31809079d4 | Oc1ccc(O)cc1>>Oc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.C(=O)=O>>C1(O)=CC=C(O)C=C1.C(=O)=O | [OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | Oc1ccc(O)cc1 | Oc1ccc(O)cc1 | null | null | C(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 2 | HOUR | Hydroquinone (30 g) was dissolved in n-propanol (70 ml) at 70° C. The hot solution was introduced into the high pressure autoclave. The solution was subjected to compressed carbon dioxide of 300 bar. The high pressure autoclave was kept for 2 h at 80° C. Then the solution was cooled down to room temperature within 5 da... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(CC)O | null | 2 | Oc1ccc(O)cc1>C(CC)O>Oc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a356fccaf3a4cd788213f325b73548d | Oc1ccc(O)cc1>>Oc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.C1CO1>>C1(O)=CC=C(O)C=C1.C1CO1 | [OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | Oc1ccc(O)cc1 | Oc1ccc(O)cc1 | null | null | C(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 2 | HOUR | Hydroquinone (30 g) was dissolved in n-propanol (70 ml) at 70° C. The hot solution was introduced into the high pressure autoclave. The solution was subjected to compressed ethylene oxide of 300 bar. The high pressure autoclave was kept for 2 h at 80° C. The solution was then cooled down to room temperature within 5 da... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(CC)O | null | 2 | Oc1ccc(O)cc1>C(CC)O>Oc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aee401aa610948b4ba9849d385e0dbc0 | Oc1ccc(O)cc1>>Oc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.C1CC1>>C1(O)=CC=C(O)C=C1.C1CC1 | [OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | Oc1ccc(O)cc1 | Oc1ccc(O)cc1 | null | null | C(CC)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 2 | HOUR | Hydroquinone (30 g) was dissolved in n-propanol (70 ml) at 70° C. The hot solution was introduced into the high pressure autoclave. The solution was subjected to compressed cyclopropane of 300 bar. The high pressure autoclave was kept for 2 h at 80° C. The solution was then cooled down to room temperature within 5 days... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(CC)O | null | 2 | Oc1ccc(O)cc1>C(CC)O>Oc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-73f99bd74f564708835c9ff95325d839 | NC(N)=O>>NC(N)=O | NC(=O)N.CC(C)(C)C>>NC(=O)N.CC(C)(C)C | [NH2:6][C:7]([NH2:8])=[O:9]>>[NH2:6][C:7]([NH2:8])=[O:9] | NC(N)=O | NC(N)=O | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 4 g urea were dissolved in 12 ml ethanol at 60° C. The solution was then placed in a high pressure autoclave and subjected to a neopentane pressure of 150 bar. The solution was cooled down from 60° C. to room temperature within 48 h. The solution with h/g crystals was removed from the autoclave, filtered and the h/g cr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | NC(N)=O>C(C)O>NC(N)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6524f1bde06c4fafba21ea58a8da26cd | NC(N)=S>>NC(N)=S | NC(=S)N.CC(C)(C)C>>NC(=S)N.CC(C)(C)C | [NH2:6][C:7]([NH2:8])=[S:9]>>[NH2:6][C:7]([NH2:8])=[S:9] | NC(N)=S | NC(N)=S | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 4 g thiourea were dissolved in 20 ml ethanol at 60° C. The solution was then placed in a high pressure autoclave and subjected to a neopentane pressure of 150 bar. The solution was cooled down to room temperature within 60 h. The solution with h/g crystals was removed from the autoclave, filtered and the h/g crystals w... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | NC(N)=S>C(C)O>NC(N)=S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-40b377d619b3445095890b35e71e45d2 | CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1>>CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(O)CC[C@@H]32)C1 | C(C)(=O)OC1CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)=O.[BH4-].[Na+]>>C(C)(=O)OC1CC2=CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)O | [CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][CH2:7][C@@:8]2([CH3:9])[C:10](=[CH:11][CH2:12][C@@H:13]3[C@@H:14]2[CH2:15][CH2:16][C@:17]2([CH3:18])[C:19](=[O:20])[CH2:21][CH2:22][C@@H:23]32)[CH2:24]1>>[CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][CH2:7][C@@:8]2([CH3:9])[C:10](=[CH:11][CH2:12][C@@H:13]3[C@@H:14]2[CH2:15][CH2:16][C@:... | CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1 | CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(O)CC[C@@H]32)C1 | null | null | CCO.O | Reduction | Reduction of ketone to secondary alcohol | f5bb2c1fe53d23865825cb224f0859293c61a7ae7516db2de3f6029aa775144a | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | C1=C2CCCCC2[C@H]2CCC3CCC[C@H]3[C@@H]2C1 | [C:1]-[C:2]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-[C;H0;D3;+0:7]-1=[O;H0;D1;+0:8]>>[C:1]-[C:2]1(-[C;D1;H3:3])-[C:4]-[C:5]-[C:6]-[CH;D3;+0:7]-1-[OH;D1;+0:8] | null | [] | null | null | null | null | To a solution of 100 mg. (0.303 mmol) of 3-acetoxy-androst-5-en-17-one in 3 ml EtOH at -10° C., was added 22.9 mg (0.606 mmol) of sodium borohydride with stirring. After the reaction mixture was stirred for one and 1/2 hours, the mixture was diluted with 10 ml water, the ethanol solvent removed under vacuum, and the re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | C1=C2CCCC[C@@H]2[C@H]2CC[C@@H]3CCC[C@H]3[C@@H]2C1 | null | CCO.O | null | null | CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]32)C1>CCO.O>CC(=O)OC1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(O)CC[C@@H]32)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5c5e1fcc0a6a453590b1c97dc343fa23 | CCOC(=O)C(F)(F)F.NCCNCCN>>O=C(NCCNCCNC(=O)C(F)(F)F)C(F)(F)F | C(C)OC(C(F)(F)F)=O.NCCNCCN>>FC(C(=O)NCCNCCNC(C(F)(F)F)=O)(F)F | [O:1]=[C:10]([O:11][CH2:16][CH3:2])[C:12]([F:13])([F:15])[F:18].[NH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][NH2:9]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[C:12]([F:13])([F:14])[F:15])[C:16]([F:17])([F:18])[F:19] | CCOC(=O)C(F)(F)F.NCCNCCN | O=C(NCCNCCNC(=O)C(F)(F)F)C(F)(F)F | null | null | O1CCCC1 | Acylation | OtherReaction | b625191471eb9ee640b46807cd399a1dc960d9a809383d32cb7311288f4bfd6e | 05ddf5d02f266550a590a539b30bfe90243aa9068306e48b8caecad7b17f8b15 | null | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;H0;D1;+0:9].[C:10]-[C:11]-[NH2;D1;+0:12].[C:13]-[C:14]-[NH2;D1;+0:15]>>[C:13]-[C:14]-[NH;D2;+0:15]-[C;H0;D3;+0:4](=[O;H0;D1;+0:3])-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;D1;H0:16])-[F;D1;H0:8].[C:10]-[C:11... | null | [] | null | null | 8 | HOUR | 113.3 g (790 mmol) of trifluoroacetic acid ethyl ester is instilled in a solution of 41.14 g (390 mmol) of 1,4,7-triazaheptane in 350 ml of tetrahydrofuran at 0° C. and under nitrogen. It is allowed to stir overnight at room temperature, concentrated by evaporation in a vacuum. The remaining oil is crystallized from he... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ester.Primary amine.Primary amine | Trifluoro group.Trifluoro group.Secondary amide.Secondary amide | null | null | null | Other | O1CCCC1 | null | 8 | CCOC(=O)C(F)(F)F.NCCNCCN>O1CCCC1>O=C(NCCNCCNC(=O)C(F)(F)F)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c8da16698d84ca89d17a28beea2d3de | O=C(O)COc1ccc(Cl)cc1Cl>>O=C(O)COc1ccc(Cl)cc1Cl | COC=1C(=CC=C(C1C(=O)O)Cl)Cl.ClC1=C(OCC(=O)O)C=CC(=C1)Cl.COC=1C(=CC=C(C1C(=O)O)Cl)Cl>>ClC1=C(OCC(=O)O)C=CC(=C1)Cl.COC=1C(=CC=C(C1C(=O)O)Cl)Cl | [O:14]=[C:15]([OH:16])[CH2:17][O:18][c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][c:25]1[Cl:26]>>[O:14]=[C:15]([OH:16])[CH2:17][O:18][c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][c:25]1[Cl:26] | O=C(O)COc1ccc(Cl)cc1Cl | O=C(O)COc1ccc(Cl)cc1Cl | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | 85 | CELSIUS | null | null | In another example, a dispersion or emulsion of 30% by weight 2,4-dichlorophenoxy acetic acid (2,4-D) and 70% by weight dicamba is prepared in water, at a concentration of 45% by weight of the 2,4-D and dicamba mixture. Thirty grams of the 2,4-D/dicamba mixture is added to a 50 ml (milliliter) beaker, and while this mi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | O | 85 | null | O=C(O)COc1ccc(Cl)cc1Cl>O>O=C(O)COc1ccc(Cl)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a412429988a4f6d803dc50ce52e1efd | C#Cc1ccc(O)cc1.C1=COCCC1>>C=Cc1ccc(O)cc1.C=Cc1ccc(OC2CCCCO2)cc1 | C([O-])([O-])=O.[Na+].[Na+].O1CCCC=C1.S(O)(O)(=O)=O.C#CC1=CC=C(C=C1)O>>O1C(CCCC1)OC1=CC=C(C=C)C=C1.OC1=CC=C(C=C)C=C1 | [c:6]1([OH:7])[cH:8][cH:9][c:12]([C:11]#[CH:10])[cH:13][cH:14]1.[CH:17]1=[CH:18][CH2:19][CH2:23][CH2:20][O:22]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]1.[CH2:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][O:22]2)[cH:23][cH:24]1 | C#Cc1ccc(O)cc1.C1=COCCC1 | C=Cc1ccc(O)cc1.C=Cc1ccc(OC2CCCCO2)cc1 | null | null | O.C(OC)COC | Aromatic Heterocycle Formation | OtherReaction | 5378c931b4094956c2bc8eaa49a31f294816697aa15dc03425df62a4b779ccbd | 08b65a8b52f629ca4576b2fd96d4829ea6c544ea572ecdde798ba191baa585ef | c1ccc(OC2CCCCO2)cc1.c1ccccc1 | [CH2;D2;+0:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[CH;D1;+0:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[O;D1;H1:13]):[c:14]:[cH;D2;+0:15]:1>>[CH2;D1;+0:7]=[CH;D2;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[c:16](-[#8:17]-[CH;D3;+0:5]2-[CH2;D2;+0:6]-[CH2;D... | null | [] | null | null | 15 | HOUR | Poly(p-hydroxystyrene) (weight average molecular weight: 9,600) in an amount of 9 g was dissolved in 100 ml of dimethoxyethane, and thereto 12.6 g of 3,4-dihydro-2H-pyran and 0.5 ml of sulfuric acid were added. This solution was stirred for 15 hours at 30°-40° C. After the reaction was completed, the reaction solution ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol.Alkyne | Ether.Ether.Aromatic alcohol.Vinyl.Vinyl | c1ccccc1.C1=COCCC1 | c1ccccc1.c1ccccc1.C1CCOCC1 | c1ccccc1.c1ccccc1.C1CCOCC1 | Other | O.C(OC)COC | null | 15 | C#Cc1ccc(O)cc1.C1=COCCC1>O.C(OC)COC>C=Cc1ccc(O)cc1.C=Cc1ccc(OC2CCCCO2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-71f52937412841d2816b018d6d494dfa | C=CC(=O)OC1CCCCO1>>C=CC(=O)OC1CCCCO1 | O.C(C=C)(=O)OC1OCCCC1.C(C(=C)C)(=O)OC.N(=NC(C#N)(C)C)C(C#N)(C)C>>C(C=C)(=O)OC1OCCCC1.C(C(=C)C)(=O)OC | [CH2:8]=[CH:9][C:10](=[O:11])[O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1>>[CH2:8]=[CH:9][C:10](=[O:11])[O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1 | C=CC(=O)OC1CCCCO1 | C=CC(=O)OC1CCCCO1 | null | null | COCC(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1CCOCC1 | null | null | [] | null | null | 8 | HOUR | In 80 g of propylene glycol monomethyl ether were dissolved 78 g (0.5 mole) of tetrahydropyranyl acrylate and 42 g (0.5 mole) of methyl methacrylate, and 3 g of azobisisobutyronitrile was added thereto, after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction tempera... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCOCC1 | null | COCC(C)O | null | 8 | C=CC(=O)OC1CCCCO1>COCC(C)O>C=CC(=O)OC1CCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a955b85440dc450e8071495d57560dc1 | C=Cc1ccc(OC(C)(C)C)cc1>>C#Cc1ccc(O)cc1 | C(C)(=O)OCC.C(C)(C)(C)OC1=CC=C(C=C)C=C1.N(=NC(C#N)(C)C)C(C#N)(C)C.S(O)(O)(=O)=O>>C#CC1=CC=C(C=C1)O | CC(C)(C)[O:7][c:6]1[cH:5][cH:4][c:3]([CH:2]=[CH2:1])[cH:9][cH:8]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]1 | C=Cc1ccc(OC(C)(C)C)cc1 | C#Cc1ccc(O)cc1 | null | null | COCC(C)O | Miscellaneous | OtherReaction | e11b50561923199f63afb23b7d200eac717436c4f1fbe653d693cd5f6b3b0ea4 | 37703de57c19a2d438444946f0487f2945caff11aae6e15905d4b1aca14883ea | c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[CH;D2;+0:6]=[CH2;D1;+0:7]):[c:8]:[c:9]:1>>[CH;D1;+0:7]#[C;H0;D2;+0:6]-[c:5]1:[c:4]:[c:3]:[c:2](-[OH;D1;+0:1]):[c:9]:[c:8]:1 | null | [] | null | null | 8 | HOUR | In 80 g of propylene glycol monomethyl ether was dissolved 88 g of p-t-butoxystyrene, and then, 2 g of azobisisobutyronitrile was added to the solution, after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C. After the polymerization, ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Vinyl | Aromatic alcohol.Alkyne | null | null | c1ccccc1 | Other | COCC(C)O | null | 8 | C=Cc1ccc(OC(C)(C)C)cc1>COCC(C)O>C#Cc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-213aa3293583470397546ec060f9017a | C=C(C)C(=O)OCCN=C=O.Nc1ccc(O)cc1>>C=C(C)C(=O)OCCNC(=O)Nc1ccc(O)cc1 | C(C(=C)C)(=O)OCCN=C=O.NC1=CC=C(C=C1)O>>OC1=CC=C(C=C1)NC(NCCOC(C(=C)C)=O)=O | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][N:9]=[C:10]=[O:11].[NH2:12][c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([OH:17])[cH:18][cH:19]1 | C=C(C)C(=O)OCCN=C=O.Nc1ccc(O)cc1 | C=C(C)C(=O)OCCNC(=O)Nc1ccc(O)cc1 | null | null | O1CCOCC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccccc1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 2 | HOUR | Methacryloyloxyethylisocyanate and 4-aminophenol were added to dioxane solvent, and stirred for 2 hours to obtain 2-(N'-(4-hydroxyphenyl)ureido)ethylmethacrylate (hereinafter referred to simply as "Compound 1").
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1 | null | O1CCOCC1 | null | 2 | C=C(C)C(=O)OCCN=C=O.Nc1ccc(O)cc1>O1CCOCC1>C=C(C)C(=O)OCCNC(=O)Nc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8b5f7f2703854551b27afadeac0bb0b6 | Nc1ccc(O)cc1.O=C=Nc1ccccc1>>O=C(Nc1ccccc1)Nc1ccc(O)cc1 | C1(=CC=CC=C1)N=C=O.NC1=CC=C(C=C1)O>>C1(=CC=CC=C1)NC(NC1=CC=C(C=C1)O)=O | [NH2:10][c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1 | Nc1ccc(O)cc1.O=C=Nc1ccccc1 | O=C(Nc1ccccc1)Nc1ccc(O)cc1 | null | null | O1CCOCC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 2 | HOUR | Phenyl isocyanate and 4-aminophenol were added to dioxane solvent, and stirred for 2 hours to obtain 4-(N'-phenylureido)phenol (hereinafter, referred to simply as "Compound 8").
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1 | null | O1CCOCC1 | null | 2 | Nc1ccc(O)cc1.O=C=Nc1ccccc1>O1CCOCC1>O=C(Nc1ccccc1)Nc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-57f6a6d0eb6f4093927d8288234b69ac | C=C(C)C(=O)Cl.Oc1ccc(O)cc1>>C=C(C)C(=O)O.Oc1ccc(O)cc1 | C1(O)=CC=C(O)C=C1.C(C(=C)C)(=O)Cl>>C(C(=C)C)(=O)O.C1(O)=CC=C(O)C=C1 | Cl[C:4]([C:2](=[CH2:1])[CH3:3])=[O:5].[OH:6][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]1>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[OH:6].[OH:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]1 | C=C(C)C(=O)Cl.Oc1ccc(O)cc1 | C=C(C)C(=O)O.Oc1ccc(O)cc1 | null | null | N1=CC=CC=C1.CC(=O)C | Acylation | OtherReaction | fa15a26725f3d7e3dbe40835b07ac461304d6268bf396ddbd52cb3a4976f0754 | aa9c1c62acf29afcbc56fa3bdafb58308a151bd2fd599222061f5d0a6084da45 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[C;D1;H2:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H2:4]=[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:6].[O;D1;H1:12]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | null | [] | 0 | CELSIUS | 3 | HOUR | 350 g of hydroquinone was dissolved in 2.5 kg of acetone and 500 ml of pyridine. After cooling to 0° C., 313.5 g of methacryloyl chloride was added dropwise, with the reaction temperature maintained at 0° to 5° C. Stirring was then carried out for 3 hours at the same temperature. After stirring for one more hour at roo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Carboxylic acid.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | N1=CC=CC=C1.CC(=O)C | 0 | 3 | C=C(C)C(=O)Cl.Oc1ccc(O)cc1>N1=CC=CC=C1.CC(=O)C>C=C(C)C(=O)O.Oc1ccc(O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4650456a153c455f9e0bb76bdb3d8e53 | CCO.F[P-](F)(F)(F)(F)F.O.O.OCC1(CO)C=CN=C(c2ccccn2)C1.[NH4+].c1ccc(-c2ccccn2)nc1>>F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.O=C(O)c1ccnc(-c2cc(C(=O)O)ccn2)c1.c1ccc(-c2ccccn2)nc1.c1ccc(-c2ccccn2)nc1 | OCC1(CC(=NC=C1)C1=NC=CC=C1)CO.O.O.[Ru+2].N1=C(C=CC=C1)C1=NC=CC=C1.C(C)O.F[P-](F)(F)(F)(F)F.[NH4+]>>F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.N1=C(C=C(C=C1)C(=O)O)C1=NC=CC(=C1)C(=O)O.N1=C(C=CC=C1)C1=NC=CC=C1.N1=C(C=CC=C1)C1=NC=CC=C1.[Ru+2] | O[CH2:46][CH3:47].[F:1][P-:2]([F:4])([F:5])([F:11])([F:12])[F:14].[OH2:28].[OH2:17].[OH:15][CH2:16][C:18]1([CH2:30][OH:27])[CH:19]=[CH:20][N:21]=[C:49]([c:50]2[cH:51][cH:52][cH:53][cH:54][n:55]2)[CH2:48]1.[NH4+:31].[cH:34]1[cH:35][cH:36][c:37](-[c:38]2[cH:39][cH:40][cH:41][cH:42][n:43]2)[n:44][cH:45]1>>[F:1][P-:2]([F:3... | CCO.F[P-](F)(F)(F)(F)F.O.O.OCC1(CO)C=CN=C(c2ccccn2)C1.[NH4+].c1ccc(-c2ccccn2)nc1 | F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.O=C(O)c1ccnc(-c2cc(C(=O)O)ccn2)c1.c1ccc(-c2ccccn2)nc1.c1ccc(-c2ccccn2)nc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 5a6ceb2e8225efa74b59c461575b600758dfd349566cf25377c7dc9aa664c3a5 | 0ab36b352c6d9efbf7a7ea16b337e32920a59106c18b96b4a8eb37adbc2d17f4 | c1ccc(-c2ccccn2)nc1.c1ccc(-c2ccccn2)nc1.c1ccc(-c2ccccn2)nc1 | O-[CH2;D2;+0:1]-[CH3;D1;+0:2].[F;D1;H0:3]-[P-;H0;D6:4](-[F;D1;H0:5])(-[F;D1;H0:6])(-[F;H0;D1;+0:7])(-[F;H0;D1;+0:8])-[F;H0;D1;+0:9].[NH4+;D0:10].[OH2;D0;+0:11].[OH2;D0;+0:12].[OH;D1;+0:13]-[CH2;D2;+0:14]-[C;H0;D4;+0:15]1(-[CH2;D2;+0:16]-[OH;D1;+0:17])-[CH2;D2;+0:18]-[C;H0;D3;+0:19](-[c;H0;D3;+0:20](:[#7;a:21]:[c:22]):[... | null | [] | null | null | null | null | 4,4'-Diethoxycarbonyl-2,2'-bipyridine was prepared from 2,2-bipyridine-4,'dicarboxylic acid by the method of Sprintschink et al. (J. Amer. Chem. Soc. 99, 4947 (1977)). The diethyl ester (100 mg) was dissolved in anhydrous diethyl ether (35 ml). Lithium aluminum hydride (100 mg) was added, and following a 30 minute incu... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine.Primary alcohol.Primary alcohol.Primary alcohol | Carboxylic acid.Carboxylic acid | C1=CN=CCC1 | c1ccncc1.c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1.c1ccncc1.c1ccncc1.c1ccncc1.c1ccncc1 | HO- | null | null | null | CCO.F[P-](F)(F)(F)(F)F.O.O.OCC1(CO)C=CN=C(c2ccccn2)C1.[NH4+].c1ccc(-c2ccccn2)nc1>>F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.O=C(O)c1ccnc(-c2cc(C(=O)O)ccn2)c1.c1ccc(-c2ccccn2)nc1.c1ccc(-c2ccccn2)nc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-989c68d91dfc4d74a9b62cfdff0165f9 | O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21>>O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | ON1C(CCC1=O)=O.OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12.NCCC1=CC=C(C=C1)O.C([O-])(O)=O.C(C)[NH+](CC)CC>>OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12.NCCC1=CC=C(C=C1)O | [O:11]=[C:12]([OH:13])[CH2:14][CH2:15][CH2:16][CH2:17][C@@H:18]1[S:19][CH2:20][C@@H:21]2[NH:22][C:23](=[O:24])[NH:25][C@H:26]12>>[O:11]=[C:12]([OH:13])[CH2:14][CH2:15][CH2:16][CH2:17][C@@H:18]1[S:19][CH2:20][C@@H:21]2[NH:22][C:23](=[O:24])[NH:25][C@H:26]12 | O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1N[C@H]2CSC[C@H]2N1 | null | null | [] | 50 | CELSIUS | null | null | a solution of biotin-N-hydroxysuccinimide, 170 mg (0.5 mMoles), and tyramine (recrystallized from water), 68.5 mg (0.5 mMoles), in 25 ml dimethylformamide was treated with 10 ml of 1M triethylammonium bicarbonate, pH 7.5, and then heated at 50° C. for 3 hours.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1N[C@H]2CSC[C@H]2N1 | null | CN(C=O)C | 50 | null | O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21>CN(C=O)C>O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3da89dd6f0cf4b19a43b09c6563de2f4 | CCO.Cc1c(CC(=O)O)c(=O)oc2cc(O)ccc12>>CCOC(=O)Cc1c(C)c2ccc(O)cc2oc1=O | OC1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)O)C.S(O)(O)(=O)=O.C(C)O>>OC1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)OCC)C | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH2:6][c:7]1[c:8]([CH3:9])[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[o:17][c:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[c:8]([CH3:9])[c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[o:17][c:18]1=[O:19] | CCO.Cc1c(CC(=O)O)c(=O)oc2cc(O)ccc12 | CCOC(=O)Cc1c(C)c2ccc(O)cc2oc1=O | null | null | C(C)(=O)OCC | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=c1ccc2ccccc2o1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[c:5]:[#8;a:6].[C;D1;H3:7]-[C:8]-[OH;D1;+0:9]>>[#8;a:6]:[c:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8]-[C;D1;H3:7] | 92 | [{"value": 92.0, "product": "OC1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Hydroxy-4-methylcoumarin-3-acetic acid (1) (1 gm, 4.3 mmol) was suspended in anhydrous ethanol (15 mL), concentrated sulfuric acid (1.5 mL) was added and the mixture was heated at reflux for 1 hour. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with 5% NaHCO3 (5×50 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1coc2ccccc2c1 | HO- | C(C)(=O)OCC | null | null | CCO.Cc1c(CC(=O)O)c(=O)oc2cc(O)ccc12>C(C)(=O)OCC>CCOC(=O)Cc1c(C)c2ccc(O)cc2oc1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e05a904ddd240dbb2ba875f082acfe9 | CCOC(=O)Cc1c(C)c2ccc([C@@]3(C(C)=O)O[C@H](CO)[C@@](O)(C(C)=O)[C@@](O)(C(C)=O)[C@]3(O)C(C)=O)cc2oc1=O>>Cc1c(CC(=O)O)c(=O)oc2cc([C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)ccc12 | Cl.C(C)(=O)[C@]1([C@@]([C@]([C@](O[C@@H]1CO)(C1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)OCC)C)C(C)=O)(O)C(C)=O)(O)C(C)=O)O.[OH-].[K+]>>[C@@H]1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)C1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)O)C | CC[O:7][C:5]([CH2:4][c:3]1[c:2]([CH3:1])[c:27]2[c:11]([o:10][c:8]1=[O:9])[cH:12][c:13]([C@@:14]1(C(C)=O)[O:15][C@H:16]([CH2:17][OH:18])[C@:19](C(C)=O)([OH:20])[C@:21](C(C)=O)([OH:22])[C@@:23]1(C(C)=O)[OH:24])[cH:25][cH:26]2)=[O:6]>>[CH3:1][c:2]1[c:3]([CH2:4][C:5](=[O:6])[OH:7])[c:8](=[O:9])[o:10][c:11]2[cH:12][c:13]([C... | CCOC(=O)Cc1c(C)c2ccc([C@@]3(C(C)=O)O[C@H](CO)[C@@](O)(C(C)=O)[C@@](O)(C(C)=O)[C@]3(O)C(C)=O)cc2oc1=O | Cc1c(CC(=O)O)c(=O)oc2cc([C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)ccc12 | null | null | CO | Reduction | OtherReaction | fb3e5fd462bf1b5ce2c5fc31f921f1cbbb76f0851a61fd66ce072a143a52d47e | c582a9e0a544dcabf493471caa4cc703a6971b5e6e8eedc311d9366c7843c32b | O=c1ccc2ccc([C@H]3CCCCO3)cc2o1 | C-C(=O)-[C@;H0;D4;+0:1]1(-[O;D1;H1:2])-[C@@;H0;D4;+0:3](-C(-C)=O)(-[c:4](:[c:5]):[c:6]:[c:7]:[#8;a:8])-[#8:9]-[C:10](-[C:11])-[C@@;H0;D4;+0:12](-[O;D1;H1:13])(-C(-C)=O)-[C@@;H0;D4;+0:14]-1(-[O;D1;H1:15])-C(-C)=O.C-C-[O;H0;D2;+0:16]-[C:17](-[C:18])=[O;D1;H0:19]>>[#8;a:8]:[c:7]:[c:6]:[c:4](-[C@@H;D3;+0:3]1-[#8:9]-[C:10](... | 60.4 | [{"value": 60.0, "product": "[C@@H]1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)C1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.4, "product": "[C@@H]1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)C1=CC=C2C(=C(C(OC2=C1)=O)CC(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | 8 | HOUR | To a stirred solution of 7-(tetraacetyl-β-galactosyl)-4-methylcoumarin-3-acetic acid, ethyl ester (3) (422 mg, 0.712 mmol) in methanol was added 6.8M KOH (5 mL) and the solution was stirred overnight at room temperature. The solution was neutralized by the addition of 1N HCl and evaporated to dryness under reduced pres... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ketone.Ketone.Ester.Ether.Tertiary alcohol.Tertiary alcohol.Tertiary alcohol | Carboxylic acid.Ether.Secondary alcohol.Secondary alcohol.Secondary alcohol | C1CCOCC1 | C1CCOCC1 | c1coc2ccccc2c1.C1CCOCC1 | HO- | CO | null | 8 | CCOC(=O)Cc1c(C)c2ccc([C@@]3(C(C)=O)O[C@H](CO)[C@@](O)(C(C)=O)[C@@](O)(C(C)=O)[C@]3(O)C(C)=O)cc2oc1=O>CO>Cc1c(CC(=O)O)c(=O)oc2cc([C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)ccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2c4f86a4ef96422c818776439d737e2a | CC(C)[C@H](N)C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-]>>CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O | N[C@@H](CS)C(=O)O.N[C@@H](C(C)C)C(=O)O.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC=3C=CC=CC3)C(=O)[O-])C.[K+]>>CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CCC[C@@H](C(=O)O)N)C(=O)O)C | C[CH:12]([CH3:11])[C@H:13]([NH2:14])[C:15](=[O:16])[OH:17].c1ccc([CH2:10][C:8]([NH:7][C@H:6]2[C@H:5]3[S:4][C:2]([CH3:1])([CH3:3])[C@H:21]([C:22](=[O:23])[O-:24])[N:20]3[C:18]2=[O:19])=[O:9])cc1>>[CH3:1][C:2]1([CH3:3])[S:4][C@@H:5]2[C@H:6]([NH:7][C:8](=[O:9])[CH2:10][CH2:11][CH2:12][C@H:13]([NH2:14])[C:15](=[O:16])[OH:1... | CC(C)[C@H](N)C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-] | CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O | null | null | null | C-C Coupling | OtherReaction | b1c5a75836252e474a37fcf494cff25f4048b2f6fdb0bbc647b8a649fa439615 | 0a3570e04fbe6a3b2ffc12a820c50434dd728efb01bf353938ae9117a6d26a85 | O=C1C[C@H]2SCCN12 | C-[CH;D3;+0:1](-[CH3;D1;+0:2])-[C:3](-[N;D1;H2:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7].[O-;H0;D1:8]-[C:9](=[O;D1;H0:10])-[C:11]-[#7:12]-[C:13](=[O;D1;H0:14])-[C:15]-[#7:16]-[C:17](=[O;D1;H0:18])-[CH2;D2;+0:19]-c1:c:c:c:c:c:1>>[N;D1;H2:4]-[C:3](-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:19]-[C:17](=[O;D1;H0:18])-[#7:16]-[C:15]... | null | [] | null | null | null | null | The first two steps in the biosynthesis of penicillin in P. chrysogenum are the condensation of the three amino acids L-5-amino-5-carboxypentanoic acid (L-α-aminoadipic acid) (A), L-cysteine (C) and L-valine (V) into the tripeptide LLD-ACV, followed by cyclization of this tripeptide to form isopenicillin N. This compou... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | c1ccccc1 | null | C1CN2CC[C@H]2S1 | Other | null | null | null | CC(C)[C@H](N)C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)Cc3ccccc3)C(=O)N2[C@H]1C(=O)[O-]>>CC1(C)S[C@@H]2[C@H](NC(=O)CCC[C@H](N)C(=O)O)C(=O)N2[C@H]1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-674d9614a90647d78c6df6894988a158 | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O>>NC(=O)c1ccccc1 | P(=O)([O-])([O-])[O-].[K+].[K+].[K+].CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C=3C=CC=CC3)N)C(=O)O)C.CC(C)S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O.Cl.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C=3C=CC=CC3)N)C(=O)O)C>>C(C1=CC=CC=C1)(=O)N | CC1(C)S[C@@H]2[C@H](NC([C@H](N)c3ccccc3)=[O:3])C(=O)N2[C@H]1C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)[C@H:2]([NH2:1])[c:4]3[cH:5][cH:6][cH:7][cH:8][cH:9]3)C(=O)N2[C@H]1C(=O)O>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O | NC(=O)c1ccccc1 | null | null | C(C1=CC=CC=C1)#N.P(=O)([O-])([O-])[O-] | Miscellaneous | OtherReaction | 72cebb523f4574d529f48c8029f84b2d51d09e15e23a2fc4d8b7de6fd6ccff6f | 8ee66c8c2f1eae8d4e2c35a616107a57a494432dbe373748e089d0e1ffc1ed36 | c1ccccc1 | null | null | [] | null | null | 8 | HOUR | TG1/pNHJ10H and TG1/pNEJ20L were inoculated into 10 ml of 2×YT medium containing 50 μg/ml of ampicillin and incubated at 30° C. overnight (12 hours). 1 ml of the resultant culture was added to 100 ml of 2×YT medium (50 μg/ml of ampicillin, 0.1 g of CoCl2.6H2O/l). The mixture was incubated at 30° C. for 4 hours. IPTG wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Secondary amide.Secondary amide.Tertiary amide.Tertiary amide.Primary amine.Monosulfide.Monosulfide | Primary amide | c1ccccc1.C1CN2CC[C@H]2S1.C1CN2CC[C@H]2S1 | null | c1ccccc1 | Other | C(C1=CC=CC=C1)#N.P(=O)([O-])([O-])[O-] | null | 8 | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O.CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O>C(C1=CC=CC=C1)#N.P(=O)([O-])([O-])[O-]>NC(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-56ee7e03a5e84bf7aaab24c26d7d4d75 | CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O>>N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O | C(C)(=O)N[C@H]1C(O)O[C@@H]([C@H]([C@@H]1O)O)CO.P(=O)([O-])([O-])[O-]>>OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO | CC(=O)[NH:1][C@H:2]1[CH:3]([OH:4])[O:5][C@H:6]([CH2:7][OH:8])[C@@H:9]([OH:10])[C@@H:11]1[OH:12]>>[NH2:1][C@H:2]1[CH:3]([OH:4])[O:5][C@H:6]([CH2:7][OH:8])[C@@H:9]([OH:10])[C@@H:11]1[OH:12] | CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O | N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | C1CCOCC1 | C-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#8:5]>>[#8:5]-[C:4]-[C:2](-[NH2;D1;+0:1])-[C:3] | null | [] | null | null | 30 | MINUTE | The activity is determined by the following method. Namely, 0.3 ml of a 10% solution of N-acetyl-D-glucosamine is added as a substrate to 0.1 ml of a 200 mM phosphate buffer solution (pH 7.8). Next, 0.1 ml of an enzyme solution is further added thereto followed by incubation at 48° C. for 30 minutes. Then the D-glucosa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1CCOCC1 | HO- | null | null | 0.5 | CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O>>N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c0a3230366d04c2986114da6b17393e8 | CC(=C1C=CC=C1)c1ccccc1.c1ccc2c(c1)Cc1ccccc1-2>>CCc1cccc(C2C=CCC2)c1C1c2ccccc2-c2ccccc21 | C1=CC=CC=2C3=CC=CC=C3CC12.[Li].CC(=C1C=CC=C1)C1=CC=CC=C1.O>>C1(C=CCC1)C=1C(=C(C=CC1)CC)C1C2=CC=CC=C2C=2C=CC=CC12 | [CH3:1][C:2](=[C:3]1[CH:4]=[CH:5][CH:6]=[CH:12]1)[c:8]1[cH:7][cH:26][cH:11][cH:10][cH:9]1.[c:13]12[c:21]([cH:22][cH:23][cH:24][cH:25]1)-[c:20]1[c:15]([cH:16][cH:17][cH:18][cH:19]1)[CH2:14]2>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH:9]=[CH:10][CH2:11][CH2:12]2)[c:13]1[CH:14]1[c:15]2[cH:16][cH:17][cH:18][cH... | CC(=C1C=CC=C1)c1ccccc1.c1ccc2c(c1)Cc1ccccc1-2 | CCc1cccc(C2C=CCC2)c1C1c2ccccc2-c2ccccc21 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | c743bc6ef6344cf945aac3b91b50bd29646054343281431e62da1d80389a9ca9 | 3f717670d1fd4141debd5ac3d116184b7da41f3bd09ff882aae5bf8ce08bc3e3 | C1=CC(c2ccccc2C2c3ccccc3-c3ccccc32)CC1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[C;H0;D3;+0:3]1-[CH;D2;+0:4]=[CH;D2;+0:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-1)-[c;H0;D3;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1.[c:14]:[c:15]1:[c:16](:[c:17])-[c;H0;D3;+0:18]2:[c:19]:[c:20]:[c:21]:[cH;D2;+0:22]:[c;H0;D3;+0:23]:2-[CH2;D2;+0:24]-1>>[C;D1;H3:1]-[CH... | 84.2 | [{"value": 84.2, "product": "C1(C=CCC1)C=1C(=C(C=CC1)CC)C1C2=CC=CC=C2C=2C=CC=CC12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "C1(C=CCC1)C=1C(=C(C=CC1)CC)C1C2=CC=CC=C2C=2C=CC=CC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 67.8 mmol of lithiumfluorene in 50 cm3 of tetrahydrofuran is added to a solution of 11.4 g (67.8 mmol) of 6-methyl-6-phenyl-fulvene in 40 cm3 of tetrahydrofuran at room temperature. After the mixture had been stirred at room temperature for 2 hours, 60 cm3 of water were added. The substance which precipit... | 10.6084/m9.figshare.5104873.v1 | null | Conjugated diene | null | C1=CCC=C1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | c1ccccc1.C1=CCCC1.c1ccc2c(c1)Cc1ccccc12 | c1ccccc1.C1=CCCC1.c1ccc2c(c1)Cc1ccccc12 | null | O1CCCC1 | null | 2 | CC(=C1C=CC=C1)c1ccccc1.c1ccc2c(c1)Cc1ccccc1-2>O1CCCC1>CCc1cccc(C2C=CCC2)c1C1c2ccccc2-c2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1d2b61ecfe914348bdf9551b97784846 | C=C1C=CC(c2ccccc2)=C1c1ccccc1.c1ccc2c(c1)Cc1ccccc1-2>>C1=C(C(c2ccccc2)(c2ccccc2)C2c3ccccc3-c3ccccc32)CCC1 | C1(=CC=CC=C1)C1=C(C(C=C1)=C)C1=CC=CC=C1.CCCCCC.C(CCC)[Li].C1=CC=CC=2C3=CC=CC=C3CC12>>C1(=CCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1C2=CC=CC=C2C=2C=CC=CC12 | [CH2:1]=[C:31]1[C:3]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[C:2]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH:29]=[CH:30]1.[CH2:16]1[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2-[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]21>>[CH:1]1=[C:2]([C:3]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)([c:10]2[cH:11][cH:12][cH:13][cH:14][c... | C=C1C=CC(c2ccccc2)=C1c1ccccc1.c1ccc2c(c1)Cc1ccccc1-2 | C1=C(C(c2ccccc2)(c2ccccc2)C2c3ccccc3-c3ccccc32)CCC1 | null | null | O.O1CCCC1 | Functional Group Interconversion | OtherReaction | db434545cc634c4725772e24678ff57fdd6fb48694a318f9aa2481a3e5ea2f16 | ca6325c099d7c2b1d2ef7a2d73bc2cb7b6150d410376f4333461d24bfa1f9854 | C1=C(C(c2ccccc2)(c2ccccc2)C2c3ccccc3-c3ccccc32)CCC1 | [CH2;D1;+0:1]=[C;H0;D3;+0:2]1-[CH;D2;+0:3]=[CH;D2;+0:4]-[C;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])=[C;H0;D3;+0:11]-1-[c:12](:[c:13]):[c:14].[c:15]:[c:16]1:[c:17]-[c:18]:[c:19](:[c:20])-[CH2;D2;+0:21]-1>>[c:13]:[c:12](-[C;H0;D4;+0:11](-[C;H0;D3;+0:5]1=[CH;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4... | 42 | [{"value": 42.0, "product": "C1(=CCCC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1C2=CC=CC=C2C=2C=CC=CC12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | 12.3 cm3 (30.7 mmol) of a 2.5 molar hexane solution of n-butyllithium were slowly added to a solution of 5.10 g (30.7 mmol) of fluorene in 60 cm3 of tetrahydrofuran at room temperature. After 40 minutes, 7.07 g (30.7 mmol) of diphenylfulvene were added to the orange solution and the mixture was stirred overnight. 60 cm... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | C1=CCC=C1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | C1=CCCC1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | C1=CCCC1.c1ccccc1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | null | O.O1CCCC1 | null | 0.666667 | C=C1C=CC(c2ccccc2)=C1c1ccccc1.c1ccc2c(c1)Cc1ccccc1-2>O.O1CCCC1>C1=C(C(c2ccccc2)(c2ccccc2)C2c3ccccc3-c3ccccc32)CCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d0d762737d34c2080eeda70e521dbc7 | ClCc1ccccc1.O=c1ccc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc2o1>>O=c1ccc2cc(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(OCc3ccccc3)cc2o1 | C1=C2C(=CC(=C1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)OC(=O)C=C2.C(C1=CC=CC=C1)Cl.C([O-])([O-])=O.[K+].[K+].C1COCCOCCOCCOCCOCCO1.[I-].[K+]>>C(C1=CC=CC=C1)OC1=C(C=C2C=CC(OC2=C1)=O)OC1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | Cl[CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[O:1]=[c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([O:8][C@@H:9]3[O:10][C@H:11]([CH2:12][OH:13])[C@@H:14]([OH:15])[C@H:16]([OH:17])[C@H:18]3[OH:19])[c:20]([OH:21])[cH:29][c:30]2[o:31]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([O:8][CH:9]3[O:10][C@H:11]([CH2:12][OH:13])[C@@... | ClCc1ccccc1.O=c1ccc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc2o1 | O=c1ccc2cc(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(OCc3ccccc3)cc2o1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=c1ccc2cc(OC3CCCCO3)c(OCc3ccccc3)cc2o1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#8;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:10] | 86.4 | [{"value": 86.4, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C=CC(OC2=C1)=O)OC1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | Esculin (1.0 g), benzyl chloride (1.0 g), potassium carbonate (0.7 g), catalytic amounts of 18-crown-6-ether and potassium iodide, and dimethylformamide (40 ml) were placed in an eggplant-shaped flask (100 ml). The mixture was reacted while stirred at 60° C. for 8 hours. The reaction mixture was concentrated under redu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2occcc2c1.C1CCOCC1.c1ccccc1 | HCl | CN(C=O)C | 60 | 8 | ClCc1ccccc1.O=c1ccc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc2o1>CN(C=O)C>O=c1ccc2cc(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(OCc3ccccc3)cc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a927144cffe4757b1c0239ad6f9ed5a | CN(C)C=O.[N-]=[N+]=[N-].[N-]=[N+]=[N-]>>CNN=NCCN=NNC | BrCCBr.[N-]=[N+]=[N-].[Na+].CN(C)C=O.[Li]C.[N-]=[N+]=[N-]>>CNN=NCCN=NNC | CN(C=O)[CH3:1].[N-:7]=[N+:8]=[N-:9].[N-:2]=[N+:3]=[N-:4]>>[CH3:1][NH:2][N:3]=[N:4][CH2:5][CH2:6][N:7]=[N:8][NH:9][CH3:10] | CN(C)C=O.[N-]=[N+]=[N-].[N-]=[N+]=[N-] | CNN=NCCN=NNC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 31109ffc1f6ef08da8e6051f73f57d3e75645c4c6837008743f49a4704668091 | 94f1e96913ccfdd25d281c71f9eda6c1dd39067e35255001c10483f233cac504 | null | C-N(-[CH3;D1;+0:1])-C=O.[N-;H0;D1:2]=[N+;H0;D2:3]=[N-;H0;D1:4].[N-;H0;D1:5]=[N+;H0;D2:6]=[N-;H0;D1:7]>>[C;D1;H3:8]-[NH;D2;+0:4]-[N;H0;D2;+0:3]=[N;H0;D2;+0:2]-[C:9]-[C:10]-[N;H0;D2;+0:7]=[N;H0;D2;+0:6]-[NH;D2;+0:5]-[CH3;D1;+0:1] | 32 | [{"value": 32.0, "product": "CNN=NCCN=NNC", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | A flask is charged with 5.0 g (27 mmole) of 1,2-dibromoethane, 3.8 g (58 mmole) of sodium azide, and 50 ml of DMF. The mixture is heated at 50° C. with stirring under argon overnight. The mixture is worked up as described above, except that the azide solution is not evaporated down totally. When about 30 ml of solution... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Hydrazone.Hydrazone | null | null | null | Other | null | 50 | 8 | CN(C)C=O.[N-]=[N+]=[N-].[N-]=[N+]=[N-]>>CNN=NCCN=NNC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b61bb71ca3fc444f88d24d728812b5de | C=C(P(=O)(OC)OC)S(=O)(=O)OC.c1c[nH]cn1>>O=P(O)(O)C(Cn1ccnc1)S(=O)(=O)O | O.N1C=NC=C1.COP(=O)(C(=C)S(=O)(=O)OC)OC.Br[Si](C)(C)C>>N1(C=NC=C1)CC(S(=O)(=O)O)P(=O)(O)O | C[O:3][P:2](=[O:1])([O:4]C)[C:5](=[CH2:6])[S:12](=[O:13])(=[O:14])[O:15]C.[nH:7]1[cH:8][cH:9][n:10][cH:11]1>>[O:1]=[P:2]([OH:3])([OH:4])[CH:5]([CH2:6][n:7]1[cH:8][cH:9][n:10][cH:11]1)[S:12](=[O:13])(=[O:14])[OH:15] | C=C(P(=O)(OC)OC)S(=O)(=O)OC.c1c[nH]cn1 | O=P(O)(O)C(Cn1ccnc1)S(=O)(=O)O | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 174663545862e816dcca39da3824223f4ceedf633c2460516060f2d4a2a0484c | 9a626e72af92b4926e3e632773bc972f63cd9f1cf5e0e294f2aa92f80c10ca13 | c1c[nH]cn1 | C-[O;H0;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH2;D1;+0:6])-[#15:7](=[O;D1;H0:8])(-[O;H0;D2;+0:9]-C)-[O;H0;D2;+0:10]-C.[#7;a:11]1:[c:12]:[nH;D2;+0:13]:[c:14]:[c:15]:1>>[O;D1;H0:3]=[#16:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[CH;D3;+0:5](-[CH2;D2;+0:6]-[n;H0;D3;+0:13]1:[c:12]:[#7;a:11]:[c:15]:[c:14]:1)-... | null | [] | null | null | 2.5 | DAY | A mixture of 0.68 g (0.01 mole) of imidazole and 2.30 g (0.01 mole) of methyl 1-dimethoxyphosphinylethenesulfonate (U.S. Pat. No. 5,011,938 issued to Barnett et al. on Apr. 30, 1991) in 20 ml of chloroform is stirred at 20°-50° for one day. The reaction is cooled to room temperature, and 10.7 g (0.07 mole) of bromotrim... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | Other | C(Cl)(Cl)Cl | null | 60 | C=C(P(=O)(OC)OC)S(=O)(=O)OC.c1c[nH]cn1>C(Cl)(Cl)Cl>O=P(O)(O)C(Cn1ccnc1)S(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8cd4bb1e8724101af770fd96846b25d | O=P(O)(O)C(CNc1cccnc1)S(=O)(=O)O>>O=P(O)(O)C(CNC1CCCNC1)S(=O)(=O)O | P(=O)(O)(O)C(CNC=1C=NC=CC1)S(=O)(=O)O>>P(=O)(O)(O)C(CNC1CNCCC1)S(=O)(=O)O | [O:1]=[P:2]([OH:3])([OH:4])[CH:5]([CH2:6][NH:7][c:8]1[cH:9][cH:10][cH:11][n:12][cH:13]1)[S:14](=[O:15])(=[O:16])[OH:17]>>[O:1]=[P:2]([OH:3])([OH:4])[CH:5]([CH2:6][NH:7][CH:8]1[CH2:9][CH2:10][CH2:11][NH:12][CH2:13]1)[S:14](=[O:15])(=[O:16])[OH:17] | O=P(O)(O)C(CNc1cccnc1)S(=O)(=O)O | O=P(O)(O)C(CNC1CCCNC1)S(=O)(=O)O | null | [Pd] | O | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCNCC1 | [C:1]-[#7:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:1>>[C:1]-[#7:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-1 | null | [] | null | null | 2 | DAY | A mixture of 1 g of 1-phosphono-2-(3-pyridinylamino)ethanesulfonic acid and 0.5 g of palladium on charcoal catalyst in 50 ml of distilled water is hydrogenated on a Parr apparatus at 40 PSI for about 2 days. The catalyst is removed by filtration, and the filtrate is concentrated to a few mls. Ethanol is added slowly to... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | C1CCNCC1 | null | [Pd].O | null | 48 | O=P(O)(O)C(CNc1cccnc1)S(=O)(=O)O>[Pd].O>O=P(O)(O)C(CNC1CCCNC1)S(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f0adc11e00943cfa52c22b2a6fa6941 | N#CCC(P(=O)(O)O)S(=O)(=O)[O-]>>NCCC(P(=O)(O)O)S(=O)(=O)O | C(#N)CC(S(=O)(=O)[O-])P(=O)(O)O.[H][H]>>NCCC(S(=O)(=O)O)P(=O)(O)O | [N:1]#[C:2][CH2:3][CH:4]([P:5](=[O:6])([OH:7])[OH:8])[S:9](=[O:10])(=[O:11])[O-:12]>>[NH2:1][CH2:2][CH2:3][CH:4]([P:5](=[O:6])([OH:7])[OH:8])[S:9](=[O:10])(=[O:11])[OH:12] | N#CCC(P(=O)(O)O)S(=O)(=O)[O-] | NCCC(P(=O)(O)O)S(=O)(=O)O | null | [Rh] | N | Reduction | OtherReaction | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | null | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[C:3]-[C:4]-[#16:5](-[O-;H0;D1:6])(=[O;D1;H0:7])=[O;D1;H0:8]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4]-[#16:5](=[O;D1;H0:7])(=[O;D1;H0:8])-[OH;D1;+0:6] | null | [] | null | null | null | null | The hydrogenation of 2-cyano-1-phosphonoethanesulfonate is carried out using the hydrogenation technique of Freifelder (J. Am. Chem. Soc., 82, 2386 (1960)). The cyano compound (2.15 g; 0.01 mole) is placed in 20 ml of 10% methanolic ammonia. Rhodium on alumina (5%) catalyst (0.5 g) is added, and the mixture is hydrogen... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | [Rh].N | null | null | N#CCC(P(=O)(O)O)S(=O)(=O)[O-]>[Rh].N>NCCC(P(=O)(O)O)S(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4470e62e4a394eda811791ff8afc4223 | O=P(O)(O)C(Cc1ccccn1)S(=O)(=O)O>>O=P(O)(O)C(CC1CCCCN1)S(=O)(=O)O | P(=O)(O)(O)C(CC1=NC=CC=C1)S(=O)(=O)O>>P(=O)(O)(O)C(CC1NCCCC1)S(=O)(=O)O | [O:1]=[P:2]([OH:3])([OH:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][n:12]1)[S:13](=[O:14])(=[O:15])[OH:16]>>[O:1]=[P:2]([OH:3])([OH:4])[CH:5]([CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][NH:12]1)[S:13](=[O:14])(=[O:15])[OH:16] | O=P(O)(O)C(Cc1ccccn1)S(=O)(=O)O | O=P(O)(O)C(CC1CCCCN1)S(=O)(=O)O | null | [Pd] | O | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCNCC1 | [C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[n;H0;D2;+0:8]:1>>[C:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[NH;D2;+0:8]-1 | null | [] | null | null | 2 | DAY | A mixture of 1 g of 1-phosphono-2-(2-pyridinyl)ethanesulfonic acid and 0.5 g of palladium on charcoal catalyst in 50 ml of distilled water is hydrogenated on a Parr apparatus at 40 PSI for about 2 days. The catalyst is removed by filtration, and the filtrate is concentrated to a few mls. Ethanol is added slowly to prec... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | C1CCNCC1 | null | [Pd].O | null | 48 | O=P(O)(O)C(Cc1ccccn1)S(=O)(=O)O>[Pd].O>O=P(O)(O)C(CC1CCCCN1)S(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a3dd7bd8f8c04710b88cd5e838b3da7e | C=CC#N.CCOP(=O)(CS(=O)(=O)[O-])OCC>>CCOP(=O)(OCC)C(CCC#N)S(=O)(=O)[O-] | O.C(CCC)[Li].[Li+].C(C)OP(=O)(OCC)CS(=O)(=O)[O-].C(C=C)#N>>[Li+].C(#N)CCC(S(=O)(=O)[O-])P(=O)(OCC)OCC | [CH2:10]=[CH:11][C:12]#[N:13].[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH2:9][S:14](=[O:15])(=[O:16])[O-:17]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:10][CH2:11][C:12]#[N:13])[S:14](=[O:15])(=[O:16])[O-:17] | C=CC#N.CCOP(=O)(CS(=O)(=O)[O-])OCC | CCOP(=O)(OCC)C(CCC#N)S(=O)(=O)[O-] | null | null | C(C)(=O)O.C1CCOC1.O1CCCC1 | C-C Coupling | Michael addition | 33e48384816274b5aff616852dc4f14f9c75728889ba8232dee5d0bd480280d7 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | null | [#8:1]-[#15:2](-[#8:3])(=[O;D1;H0:4])-[CH2;D2;+0:5]-[#16:6](-[O;-;D1;H0:7])(=[O;D1;H0:8])=[O;D1;H0:9].[CH2;D1;+0:10]=[CH;D2;+0:11]-[C:12]#[N;D1;H0:13]>>[#8:1]-[#15:2](-[#8:3])(=[O;D1;H0:4])-[CH;D3;+0:5](-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[C:12]#[N;D1;H0:13])-[#16:6](-[O;-;D1;H0:7])(=[O;D1;H0:8])=[O;D1;H0:9] | null | [] | null | null | null | null | A suspension of 2.38 g (0.01 mole) of diethoxyphosphinylmethanesulfonate lithium salt (Carretero, et al.; Tetrahedron, 43, 5125 (1987)) in 50 ml of anhydrous tetrahydrofuran is stirred in a -40° bath under a dry nitrogen atmosphere. To this is added n-butyl lithium (4.4 ml of 2.5M solution in hexanes; 0.011 mole) via s... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | null | null | C(C)(=O)O.C1CCOC1.O1CCCC1 | null | null | C=CC#N.CCOP(=O)(CS(=O)(=O)[O-])OCC>C(C)(=O)O.C1CCOC1.O1CCCC1>CCOP(=O)(OCC)C(CCC#N)S(=O)(=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5f1b002fa6a34530a6058c7ef3ffccff | CCOP(=O)(OCC)C(CCC#N)S(=O)(=O)[O-]>>NCCCC(P(=O)(O)O)S(=O)(=O)O | [Li+].C(#N)CCC(S(=O)(=O)[O-])P(=O)(OCC)OCC.[H][H]>>NCCCC(S(=O)(=O)O)P(=O)(O)O | CC[O:8][P:6]([CH:5]([CH2:4][CH2:3][C:2]#[N:1])[S:10](=[O:11])(=[O:12])[O-:13])(=[O:7])[O:9]CC>>[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]([P:6](=[O:7])([OH:8])[OH:9])[S:10](=[O:11])(=[O:12])[OH:13] | CCOP(=O)(OCC)C(CCC#N)S(=O)(=O)[O-] | NCCCC(P(=O)(O)O)S(=O)(=O)O | null | [Rh] | N | Deprotection | OtherReaction | 3f4c343b8c82a475aab87f90bd36c86a4a5b1c43e2c8e4489a1dddde8344006b | 474cda33fc342096e88418c7d98019c0d3bbb3f77794901f9557701873e93896 | null | C-C-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[O;H0;D2;+0:4]-C-C)-[C:5](-[C:6]-[C:7]-[C;H0;D2;+0:8]#[N;H0;D1;+0:9])-[#16:10](-[O-;H0;D1:11])(=[O;D1;H0:12])=[O;D1;H0:13]>>[NH2;D1;+0:9]-[CH2;D2;+0:8]-[C:7]-[C:6]-[C:5](-[#15:2](=[O;D1;H0:3])(-[OH;D1;+0:1])-[OH;D1;+0:4])-[#16:10](=[O;D1;H0:12])(=[O;D1;H0:13])-[OH;D1;+0:11] | null | [] | null | null | null | null | The hydrogenation of 3-cyano-1-diethoxyphosphinylpropanesulfonic acid lithium salt is carried out using the hydrogenation technique of Freifelder (J. Am. Chem. Soc., 82, 2386 (1960)). The cyano compound (2.62 g; 0.01 mole) is placed in 20 ml of 10% methanolic ammonia. Rhodium on alumina (5%) catalyst (0.5 g) is added, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | Other | [Rh].N | null | null | CCOP(=O)(OCC)C(CCC#N)S(=O)(=O)[O-]>[Rh].N>NCCCC(P(=O)(O)O)S(=O)(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c441ac980b3c4b878d770f161b660243 | CC(=O)O.CCOP(=O)(OCC)C(Cc1cccnc1)S(=O)(=O)[O-]>>CCOP(=O)(OCC)C(O)(Cc1cccnc1)S(=O)(=O)[O-] | C(C)(=O)O.C(CCC)[Li].[Li+].C(C)OP(=O)(C(CC=1C=NC=CC1)S(=O)(=O)[O-])OCC>>[Li+].C(C)OP(=O)(C(CC=1C=NC=CC1)(S(=O)(=O)[O-])O)OCC | CC(=O)[OH:10].[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[CH:9]([CH2:11][c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1)[S:18](=[O:19])(=[O:20])[O-:21]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[C:9]([OH:10])([CH2:11][c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1)[S:18](=[O:19])(=[O:20])[O-:21] | CC(=O)O.CCOP(=O)(OCC)C(Cc1cccnc1)S(=O)(=O)[O-] | CCOP(=O)(OCC)C(O)(Cc1cccnc1)S(=O)(=O)[O-] | null | null | C1CCOC1.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 71168a9595deb1b70d04ab58a20e78fa3bd8eaefbc28d676e002d08001bb17dd | bffcd622760a679386af1df32ddf8f2ce219043eab021847724d1b23a2111cb8 | c1ccncc1 | C-C(=O)-[OH;D1;+0:1].[#7;a:2]:[c:3]:[c:4]-[C:5]-[CH;D3;+0:6](-[#15:7](-[#8:8])(-[#8:9])=[O;D1;H0:10])-[#16:11](-[O;-;D1;H0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#7;a:2]:[c:3]:[c:4]-[C:5]-[C;H0;D4;+0:6](-[OH;D1;+0:1])(-[#15:7](-[#8:8])(-[#8:9])=[O;D1;H0:10])-[#16:11](-[O;-;D1;H0:12])(=[O;D1;H0:13])=[O;D1;H0:14] | null | [] | null | null | null | null | A suspension of 3.29 g (0.01 mole) of 1-diethoxyphosphinyl-2-(3-pyridinyl)ethanesulfonic acid lithium salt (from part I of Example 16) in 50 ml of anhydrous tetrahydrofuran is stirred in a -40° bath under a dry nitrogen atmosphere. To this is added n-butyl lithium (4.4 ml of 2.5M solution in hexanes; 0.011 mole) via sy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Tertiary alcohol | null | null | c1ccncc1 | HO- | C1CCOC1.O1CCCC1 | null | null | CC(=O)O.CCOP(=O)(OCC)C(Cc1cccnc1)S(=O)(=O)[O-]>C1CCOC1.O1CCCC1>CCOP(=O)(OCC)C(O)(Cc1cccnc1)S(=O)(=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32d204e930f44b07bcd483b6190195d9 | N#Cc1ccc(CBr)cc1.O=C1NCCN1>>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | O.BrCC1=CC=C(C#N)C=C1.[H-].[Na+].N1C(NCC1)=O>>O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1 | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23]1.[NH:8]1[CH2:9][CH2:15][NH:11][C:21]1=[O:22]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]3)[C:21]2=[O:22])[cH:23][cH:24]1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1 | N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 39571f641692bae0ab2e4fb7e56baf0a046bbe68e5d15065d8f936b61702d85c | 04064b000c1f037cb6379c4a9b891971302bcd094d2302ea56061b3b37327222 | O=C1N(Cc2ccccc2)CCN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-1>>[C:11]-[c:12](:[c:13]):[cH;D2;+0:8]:[c:14]:[c:15]-[C:16]-[N;H0;D3;+0:7]1-[C:17]-[CH2;D2;+0:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:6]-1=[O;D1;H0:5] | null | [] | null | null | 1 | HOUR | To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea.Nitrile | C1CNCN1 | C1C[NH]C[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | Br- | CN(C=O)C | null | 1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1>CN(C=O)C>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fbaa285e651946388fecdcd4723f445c | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.BrCC=1C=C(C#N)C=CC1.[H-].[Na+]>>C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O | Br[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:27]1.[nH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[nH:24][c:25]1=[O:26]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:1... | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In a manner similar to Preparation 1 above, 2,3-dihydro4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, 2 mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chrom... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C=O)C | null | null | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C=O)C>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c77074e30c694112be26f331a27ce8b0 | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | Cl.C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.[H-].[Na+].BrCC=1C=C(C(=O)OC)C=CC1>>COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O | Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:29]1.[nH:11]1[c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[nH:26][c:27]1=[O:28]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][n:11]2[c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:... | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 25 | [{"value": 25.0, "product": "COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of NaH (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DM... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C)C=O | 50 | 0.5 | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C)C=O>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1a30227dd645430c9b19f043cd01f350 | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O.BrCC1=CC=C2C=CC(=CC2=C1)C#N>>C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O | Br[CH2:25][c:26]1[cH:27][cH:28][c:29]2[cH:30][cH:31][c:32]([C:33]#[N:34])[cH:35][c:36]2[cH:37]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[nH:24][c:38]2=[O:39])[cH:40]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6... | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1n(Cc2ccccc2)c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12]:1=[O;D1;H0:13] | null | [] | null | null | null | null | In a manner similar to Preparation 2 above, 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile was reacted with 7-(bromomethyl)-naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3) 8.05 (s,1), 7... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.c1c[nH]cn1 | HBr | null | null | null | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c24bf49608274542bccfffbad5927301 | CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O>>CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(S)Cc2ccccc2)C1=O | C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)OC(C)(C)C)CC(C)C)C=CC=C2)CC2=CC=CC=C2.Cl>>SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)OC(C)(C)C)CC(C)C)C=CC=C2)CC2=CC=CC=C2 | O=C(c1ccccc1)[S:27][CH:26]([C:24]([NH:23][CH:22]1[CH2:21][c:20]2[c:15]([cH:16][cH:17][cH:18][cH:19]2)[CH2:14][N:13]([CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:35]1=[O:36])=[O:25])[CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([C:... | CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O | CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(S)Cc2ccccc2)C1=O | null | null | CO | Reduction | OtherReaction | 3ad374f993c0dcc0c7bd535fc99990c89c5c9215cbb98c33afd4359fe55055ac | 18d802456fe85193570fdb3a00b25c8956a03b5a0210f708f961e42c1669d76e | O=C(CCc1ccccc1)NC1Cc2ccccc2CNC1=O | O=C(-[S;H0;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](=[O;D1;H0:9])-[#7:10])-c1:c:c:c:c:c:1>>[#7:10]-[C:8](=[O;D1;H0:9])-[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[SH;D1;+0:1] | null | [] | null | null | null | null | Combine 2-[4-(2-Benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid, tert-butyl ester (0.229 mmol) in degassed methanol (3 mL) and cool in an ice bath. Treat with degassed 1N aqueous lithium hydroxide (1.0 mL) and stir, allowing the ice bath to warm gradually ov... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Aliphatic thiol | c1ccccc1 | null | c1ccc2c(c1)CCC[NH]C2.c1ccccc1 | HO- | CO | null | null | CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O>CO>CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(S)Cc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76b9fb90e765478eb9f07bde4c5ac1d8 | C1COCCN1.CN1CCOCC1.O=C(Cl)CCl>>NC(=O)N1CCOCC1.O=C(O)CCl | ClCC(=O)Cl.CN1CCOCC1.N1CCOCC1>>N1(CCOCC1)C(=O)N.ClCC(=O)O | C1C[O:3]CC[NH:1]1.[CH3:2][N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1.Cl[C:11](=[O:10])[CH2:13][Cl:14]>>[NH2:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1.[O:10]=[C:11]([OH:12])[CH2:13][Cl:14] | C1COCCN1.CN1CCOCC1.O=C(Cl)CCl | NC(=O)N1CCOCC1.O=C(O)CCl | null | null | ClCCl | Acylation | OtherReaction | bc1a2ed06ff75a97b9a461dc10aef814e51a98c2e1e1e18952b7b36da763a0a1 | 336fa6aadcc2a5e69d7c6213ac4f0680f80a3515c515c1cee16e8672a05f4ab2 | C1COCCN1 | C1-C-[O;H0;D2;+0:1]-C-C-[NH;D2;+0:2]-1.Cl-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]-[Cl;D1;H0:6].[C:7]-[#7:8](-[CH3;D1;+0:9])-[C:10]>>[C:7]-[#7:8](-[C;H0;D3;+0:9](-[NH2;D1;+0:2])=[O;H0;D1;+0:1])-[C:10].[Cl;D1;H0:6]-[C:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[O;D1;H1:11] | null | [] | null | null | 1 | HOUR | Combine chloroacetyl chloride (2.00 mL, 25.0 mmol) and N-methylmorpholine (2.76 mL, 25.0 mmol) in dichloromethane (100 mL). Cool in an ice-bath. Add morpholine (2.19 mL, 25.0 mmol) and stir in the ice-bath for 1 hour. Warm to ambient temperature and stir for 1 hour. Extract with cold aqueous 5% sulfuric acid solution, ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carboxylic acid.Urea | C1COCCN1 | null | C1COCC[NH]1 | HCl | ClCCl | null | 1 | C1COCCN1.CN1CCOCC1.O=C(Cl)CCl>ClCCl>NC(=O)N1CCOCC1.O=C(O)CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5676a3bcc4df4c039dcca17382f31a6c | C=Cc1ccccc1CI.CC1(C)C2CCC13CS(=O)(=O)N(C(=O)CN=C(S(C)(=O)=O)S(C)(=O)=O)C3C2>>C=Cc1ccccc1CC(N=C(S(C)(=O)=O)S(C)(=O)=O)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C | ICC1=C(C=CC=C1)C=C.CS(=O)(=O)C(=NCC(=O)N1S(CC23C1CC(CC2)C3(C)C)(=O)=O)S(=O)(=O)C>>CS(=O)(=O)C(=NC(C(=O)N1S(CC23C1CC(CC2)C3(C)C)(=O)=O)CC3=C(C=CC=C3)C=C)S(=O)(=O)C | I[CH2:9][c:8]1[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]1.[CH2:10]([N:11]=[C:12]([S:13]([CH3:14])(=[O:15])=[O:16])[S:17]([CH3:18])(=[O:19])=[O:20])[C:21](=[O:22])[N:23]1[CH:24]2[CH2:25][CH:26]3[CH2:27][CH2:28][C:29]2([CH2:30][S:31]1(=[O:32])=[O:33])[C:34]3([CH3:35])[CH3:36]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH... | C=Cc1ccccc1CI.CC1(C)C2CCC13CS(=O)(=O)N(C(=O)CN=C(S(C)(=O)=O)S(C)(=O)=O)C3C2 | C=Cc1ccccc1CC(N=C(S(C)(=O)=O)S(C)(=O)=O)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C | null | null | null | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | O=C(CCc1ccccc1)N1C2CC3CCC2(C3)CS1(=O)=O | I-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[C;D1;H2:6].[#16:7]-[C:8](-[#16:9])=[#7:10]-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#7:14](-[#16:15])-[C:16]>>[#16:7]-[C:8](-[#16:9])=[#7:10]-[CH;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[C;D1;H2:6])-[C:12](=[O;D1;H0:13])-[#7:14](-[#16:15])-[C:16] | null | [] | null | null | null | null | In step c, the appropriate 1-iodomethyl-2-vinyl-benzene derivative of structure (3) is subjected to an addition, elimination reaction with 2-(bis-methylsulfonyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-ethanone (4) to give the corresponding 2-(bis-methylsulfonyl-methylenea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | C1CC23CS[NH]C2CC1C3.c1ccccc1 | HI | null | null | null | C=Cc1ccccc1CI.CC1(C)C2CCC13CS(=O)(=O)N(C(=O)CN=C(S(C)(=O)=O)S(C)(=O)=O)C3C2>>C=Cc1ccccc1CC(N=C(S(C)(=O)=O)S(C)(=O)=O)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6b603afd4cbc4c76bf70f00b9d99e734 | C=Cc1ccccc1CC(N=C(S(C)(=O)=O)S(C)(=O)=O)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C>>C=Cc1ccccc1CC(N)C(=O)O | Cl.CS(=O)(=O)C(=NC(C(=O)N1S(CC23C1CC(CC2)C3(C)C)(=O)=O)CC3=C(C=CC=C3)C=C)S(=O)(=O)C.O1CCCC1>>NC(C(=O)O)CC1=C(C=CC=C1)C=C | CC1(C)C2CCC13CS(=O)(=[O:14])N([C:12]([CH:10]([CH2:9][c:8]1[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]1)[N:11]=C(S(C)(=O)=O)S(C)(=O)=O)=[O:13])C3C2>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH:10]([NH2:11])[C:12](=[O:13])[OH:14] | C=Cc1ccccc1CC(N=C(S(C)(=O)=O)S(C)(=O)=O)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C | C=Cc1ccccc1CC(N)C(=O)O | null | null | null | Miscellaneous | OtherReaction | b49460996556343bbd25f4ba0b1c5ed2b5d29ae0d3b113a956e18b943e1f74f2 | e4f8c86e676002aebe6415b9b14da74851bd0341979d0c3ecd3831b4382b1334 | c1ccccc1 | C-C1(-C)-C2-C-C-C-13-C-S(=O)(=[O;H0;D1;+0:1])-N(-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C:5])-[N;H0;D2;+0:6]=C(-S(-C)(=O)=O)-S(-C)(=O)=O)-C-3-C-2>>[C:5]-[C:4](-[NH2;D1;+0:6])-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | For example, the appropriate 2-(bis-methylsulfonyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-3-(2-vinyl-phenyl)-propan-1-one derivative of structure (5) is treated with a suitable acid such as aqueous hydrochloric acid in a suitable organic solvent such as tetrahydrofuran. ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Sulfone.Sulfone | Carboxylic acid.Primary amine | C1CC23CSNC2CC1C3 | null | c1ccccc1 | HO- | null | null | null | C=Cc1ccccc1CC(N=C(S(C)(=O)=O)S(C)(=O)=O)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C>>C=Cc1ccccc1CC(N)C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb64b8ce0a9f4ad097d9d9c05791fc8a | O=C(O)Cc1ccccc1C(=O)O>>OCCc1ccccc1CO | [OH-].[Na+].C(CC=1C(C(=O)O)=CC=CC1)(=O)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>OCC1=C(C=CC=C1)CCO | O=[C:2]([OH:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=O)[OH:11]>>[OH:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][OH:11] | O=C(O)Cc1ccccc1C(=O)O | OCCc1ccccc1CO | null | null | O1CCCC1 | Reduction | OtherReaction | 7804636a44915b08795011f5b5c9502cacf9d283edb989cb64c46e705ab92b92 | d79eeaf40d12fc4bd25f20e3884e4444b3630e84e8a1d07d90aec9bcb6a34993 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]-[C:6]-[C;H0;D3;+0:7](=O)-[O;D1;H1:8]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]-[C:6]-[CH2;D2;+0:7]-[O;D1;H1:8] | 98,293.7 | [{"value": 98.0, "product": "OCC1=C(C=CC=C1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98293.7, "product": "OCC1=C(C=CC=C1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve homophthalic acid (22.2 g, 0.123 mmol) in tetrahydrofuran (250 mL) and add dropwise at room temperature to a slurry of lithium aluminum hydride (15.5 g, 0.407 mol) in tetrahydrofuran (500 mL). Heat at reflux for 18 hours, cool in an ice bath and carefully add, by dropwise addition, water (16 mL), followed by 5... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Primary alcohol.Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1 | null | null | O=C(O)Cc1ccccc1C(=O)O>O1CCCC1>OCCc1ccccc1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d530a516b02640fda96b3ced16ffaeab | CS(=O)(=O)Cl.OCCc1ccccc1CO>>CS(=O)(=O)OCCc1ccccc1CCl | S(=O)(=O)(C)Cl.[Cl-].[Li+].OCC1=C(C=CC=C1)CCO.N1=C(C=C(C=C1C)C)C>>ClCC1=C(C=CC=C1)CCOS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[Cl:15].O[CH2:14][c:13]1[c:8]([CH2:7][CH2:6][OH:5])[cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14][Cl:15] | CS(=O)(=O)Cl.OCCc1ccccc1CO | CS(=O)(=O)OCCc1ccccc1CCl | null | null | CN(C=O)C | Acylation | OtherReaction | cfee7c8a94ee06c62dfd420c5806cd959e012bddef0d55ab8ee06e19f19c9d4c | ef6a81b2d855eb909d9191d46bd5acf0ca0e48fcb85117bbef959bcc67284495 | c1ccccc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-[OH;D1;+0:7].[C;D1;H3:8]-[S;H0;D4;+0:9](-[Cl;H0;D1;+0:10])(=[O;D1;H0:11])=[O;D1;H0:12]>>[C;D1;H3:8]-[S;H0;D4;+0:9](=[O;D1;H0:11])(=[O;D1;H0:12])-[O;H0;D2;+0:7]-[C:6]-[C:5]-[c:4]:[c:2](-[CH2;D2;+0:1]-[Cl;H0;D1;+0:10]):[c:3] | 45 | [{"value": 45.0, "product": "ClCC1=C(C=CC=C1)CCOS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 4 | HOUR | Mix 2-(2-hydroxymethyl-phenyl)-ethanol (12.0 g, 78.8 mmol) and collidine (23 mL, 0.17 mol) and treat with lithium chloride (7.35 g, 0.173 mmol) in dimethylformamide (125 mL). Cool in an ice bath and treat, by dropwise addition, with mesyl chloride (13.4 mL). Stir at 0° C. for 4 hours, partition between ice water (300 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Sulfonyl halide | Mesylate.Primary halide | null | null | c1ccccc1 | HO- | CN(C=O)C | 0 | 4 | CS(=O)(=O)Cl.OCCc1ccccc1CO>CN(C=O)C>CS(=O)(=O)OCCc1ccccc1CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fc7f4a6b6ae94decb6730375d9ad1be0 | CS(=O)(=O)OCCc1ccccc1CCl>>C=Cc1ccccc1CCl | ClCC1=C(C=CC=C1)CCOS(=O)(=O)C.CC(C)([O-])C.[K+]>>ClCC1=C(C=CC=C1)C=C | CS(=O)(=O)O[CH2:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][Cl:10]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][Cl:10] | CS(=O)(=O)OCCc1ccccc1CCl | C=Cc1ccccc1CCl | null | null | CCOCC | Functional Group Interconversion | OtherReaction | cb4eeb0feeb0f4fdcaeadd89d8590ccda92f2bbb1e2b7b6f5750ebcbe3bb6183 | e5d3d01ff8985232ee1f8e827d0fa8d925f7725fab5f04beedb194c8308db390 | c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 82 | [{"value": 82.0, "product": "ClCC1=C(C=CC=C1)C=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "ClCC1=C(C=CC=C1)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -35 | CELSIUS | null | null | Dissolve methanesulfonic acid 2-(2-chloromethyl-phenyl)-ethyl ester (8.8 g, 35.4 mmol) in ether (80 mL) and cool to -35° C. Add potassium t-butoxide (10 g, 89 mmol) and stir for 30 minutes. Add water (50 mL) and ether (150 mL), extract, dry (Na2SO4) and purify by silica gel chromatography (2:3 methylene chloride/pentan... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Vinyl | null | null | c1ccccc1 | MsOH.HO- | CCOCC | -35 | null | CS(=O)(=O)OCCc1ccccc1CCl>CCOCC>C=Cc1ccccc1CCl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e62ed52d8b364ce5b8047d942697fb19 | C=Cc1ccccc1CCl.[I-]>>C=Cc1ccccc1CI | ClCC1=C(C=CC=C1)C=C.[I-].[Na+].O>>ICC1=C(C=CC=C1)C=C | Cl[CH2:9][c:8]1[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]1.[I-:10]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][I:10] | C=Cc1ccccc1CCl.[I-] | C=Cc1ccccc1CI | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[C;D1;H2:6].[I-;H0;D0:7]>>[C;D1;H2:6]=[C:5]-[c:4]:[c:2](-[CH2;D2;+0:1]-[I;H0;D1;+0:7]):[c:3] | 95 | [{"value": 95.0, "product": "ICC1=C(C=CC=C1)C=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve 1-chloromethyl-2-vinyl-benzene (4.0 g, 26 mmol) in acetone (100 mL) and add sodium iodide (4.5 g, 30 mmol). Heat at gentle reflux for 30 minutes. Cool, add water (150 mL) and extract with pentane (200 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound (95%).
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1ccccc1 | Other | CC(=O)C | null | null | C=Cc1ccccc1CCl.[I-]>CC(=O)C>C=Cc1ccccc1CI |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e02594bc80d0495fbf7697482e3af45c | C=Cc1ccccc1CI.CSC(=NCC(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C)SC>>C=Cc1ccccc1CC(N=C(SC)SC)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C | CN(C)P(=O)(N(C)C)N(C)C.C(CCC)[Li].CCCCCC.CSC(=NCC(=O)N1S(CC23C1CC(CC2)C3(C)C)(=O)=O)SC.ICC1=C(C=CC=C1)C=C>>CSC(=NC(C(=O)N1S(CC23C1CC(CC2)C3(C)C)(=O)=O)CC3=C(C=CC=C3)C=C)SC | I[CH2:9][c:8]1[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]1.[CH2:10]([N:11]=[C:12]([S:13][CH3:14])[S:15][CH3:16])[C:17](=[O:18])[N:19]1[CH:20]2[CH2:21][CH:22]3[CH2:23][CH2:24][C:25]2([CH2:26][S:27]1(=[O:28])=[O:29])[C:30]3([CH3:31])[CH3:32]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH:10]([N:11]=[C:12... | C=Cc1ccccc1CI.CSC(=NCC(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C)SC | C=Cc1ccccc1CC(N=C(SC)SC)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | O=C(CCc1ccccc1)N1C2CC3CCC2(C3)CS1(=O)=O | I-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[C;D1;H2:6].[#16:7]-[C:8](-[#16:9])=[#7:10]-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#7:14](-[#16:15])-[C:16]>>[#16:7]-[C:8](-[#16:9])=[#7:10]-[CH;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[C;D1;H2:6])-[C:12](=[O;D1;H0:13])-[#7:14](-[#16:15])-[C:16] | 43.5 | [{"value": 43.5, "product": "CSC(=NC(C(=O)N1S(CC23C1CC(CC2)C3(C)C)(=O)=O)CC3=C(C=CC=C3)C=C)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1.5 | HOUR | Dissolve 2-(bis-methylsulfanyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-ethanone (7.91 g, 21.0 mmol) in tetrahydrofuran (100 mL) and cool to -78° C. Treat, by dropwise addition, with 1.6M n-butyllithium in hexane (13.1 mL, 21 mmol). Stir for 1.5 hours, then add hexamethylp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | C1CC23CS[NH]C2CC1C3.c1ccccc1 | HI | O1CCCC1 | -78 | 1.5 | C=Cc1ccccc1CI.CSC(=NCC(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C)SC>O1CCCC1>C=Cc1ccccc1CC(N=C(SC)SC)C(=O)N1C2CC3CCC2(CS1(=O)=O)C3(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-327356c7969544e4a2e0c6dd10bf0943 | C=Cc1ccccc1CC(N)C(=O)O.CCOC(=O)N1C(=O)c2ccccc2C1=O>>C=Cc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O | NC(C(=O)O)CC1=C(C=CC=C1)C=C.C([O-])([O-])=O.[Na+].[Na+].C(=O)(OCC)N1C(C=2C(C1=O)=CC=CC2)=O>>O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)O)CC1=C(C=CC=C1)C=C | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH:10]([C:11](=[O:12])[OH:13])[NH2:14].CCOC(=O)N1[C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[C:23]1=[O:24]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH:10]([C:11](=[O:12])[OH:13])[N:14]1[C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][c... | C=Cc1ccccc1CC(N)C(=O)O.CCOC(=O)N1C(=O)c2ccccc2C1=O | C=Cc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O | null | null | O | Acylation | OtherReaction | dee4319fb5c05073dfe09fdcfc315b1d79c0b2e71d9dcd2bec537ad3e531713e | bd8b586242504a7a0d63516550627e0a235acd769462fa1476e6d9c6d91ef2e8 | O=C1c2ccccc2C(=O)N1CCc1ccccc1 | C-C-O-C(=O)-N1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:6])-[C;H0;D3;+0:7]-1=[O;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[O;D1;H1:14]>>[C:9]-[C:10](-[C:12](=[O;D1;H0:13])-[O;D1;H1:14])-[N;H0;D3;+0:11]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:6])-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 60.1 | [{"value": 60.1, "product": "O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)O)CC1=C(C=CC=C1)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Dissolve 2-amino-3-(2-vinyl-phenyl)-propionic acid (3.40 g) in water (75 mL) and add sodium carbonate (1.97 g, 18.6 mmol) and N-carbethoxyphthalimide (2.81 g, 12.8 mmol). Stir for 2.5 hours, wash with methylene chloride (200 mL), acidify to pH 1 with cold concentrated hydrochloric acid and extract with ethyl acetate (3... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Substituted dicarboximide.Substituted dicarboximide.Primary amine | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O | null | 2.5 | C=Cc1ccccc1CC(N)C(=O)O.CCOC(=O)N1C(=O)c2ccccc2C1=O>O>C=Cc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f82b850c17b44c82bd3c88a18c85d0b3 | C=Cc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O.C[Si](C)(C)CCO>>C=Cc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O | Cl.CN(CCCN=C=NCC)C.N1=CC=CC=C1.C[Si](CCO)(C)C.O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)O)CC1=C(C=CC=C1)C=C>>O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=C | O[C:11]([CH:10]([CH2:9][c:8]1[c:3]([CH:2]=[CH2:1])[cH:4][cH:5][cH:6][cH:7]1)[N:20]1[C:21](=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[C:29]1=[O:30])=[O:12].[OH:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH:10]([C:11](=[O:12])[O:13][CH2:14][CH... | C=Cc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O.C[Si](C)(C)CCO | C=Cc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | O=C1c2ccccc2C(=O)N1CCc1ccccc1 | 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]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[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] | 81 | [{"value": 81.0, "product": "O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.5, "product": "O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid (2.47 g, 7.69 mmol) in tetrahydrofuran (35 mL) and cool in an ice bath. Treat with pyridine (1.6 mL, 20 mmol) and 2-(trimethylsilyl)ethanol (2.3 mL, 16 mmol). Stir for 30 minutes and add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | C(C)(=O)OCC.O1CCCC1 | 0 | 0.5 | C=Cc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O.C[Si](C)(C)CCO>C(C)(=O)OCC.O1CCCC1>C=Cc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5c09177d7e64c599435165854334fd6 | C=Cc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O>>C[Si](C)(C)CCOC(=O)C(Cc1ccccc1C=O)N1C(=O)c2ccccc2C1=O | O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=C.O=[O+][O-]>>O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=O | C=[CH:18][c:17]1[c:12]([CH2:11][CH:10]([C:8]([O:7][CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4])=[O:9])[N:20]2[C:21](=[O:22])[c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]3[C:29]2=[O:30])[cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][C:8](=[O:9])[CH:10]([CH2:11][c:12]1[cH:13][cH:14][cH:15]... | C=Cc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O | C[Si](C)(C)CCOC(=O)C(Cc1ccccc1C=O)N1C(=O)c2ccccc2C1=O | null | null | CO.C(Cl)Cl | Oxidation | Alkene oxidation to aldehyde | d8a9b78d3268b1276aae5339f679b7d52c3239349ff909dd02d119f9b6b6fbf6 | 63e1c45bed9e5e455511d54aa776987c80b93229f60232b32aa30b9f700d26d1 | O=C1c2ccccc2C(=O)N1CCc1ccccc1 | C=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[O;D1;H0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester (2.61 g, 6.19 mmol) in methylene chloride (70 mL) and methanol (75 mL). Cool to -78° C. and treat with ozone until a blue color persists. Purge with nitrogen and add dimethylsulfide (7 mL) and pyridine (0.... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | Aldehyde | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | null | CO.C(Cl)Cl | -78 | null | C=Cc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O>CO.C(Cl)Cl>C[Si](C)(C)CCOC(=O)C(Cc1ccccc1C=O)N1C(=O)c2ccccc2C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-47a0518a349f4b378e32db04cdc4b810 | CC(C)C[C@H](N)C(=O)OC(C)(C)C.C[Si](C)(C)CCOC(=O)C(Cc1ccccc1C=O)N1C(=O)c2ccccc2C1=O>>CC(C)CC(NCc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C | C(#N)[BH3-].[Na+].C(#N)[BH3-].[Na+].Cl.C(C)(C)(C)OC([C@@H](N)CC(C)C)=O.O=C1N(C(C2=CC=CC=C12)=O)C(C(=O)OCC[Si](C)(C)C)CC1=C(C=CC=C1)C=O>>O=C1N(C(C2=CC=CC=C12)=O)C(CC1=C(CNC(C(=O)OC(C)(C)C)CC(C)C)C=CC=C1)C(=O)OCC[Si](C)(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH2:6])[C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42].O=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH2:14][CH:15]([C:16](=[O:17])[O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[N:25]1[C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34]1=[O:35]>>[C... | CC(C)C[C@H](N)C(=O)OC(C)(C)C.C[Si](C)(C)CCOC(=O)C(Cc1ccccc1C=O)N1C(=O)c2ccccc2C1=O | CC(C)CC(NCc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C | null | null | CO.O1CCCC1 | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C1c2ccccc2C(=O)N1CCc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[C@H;D3;+0:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15]>>[C:5]-[C:6]-[CH;D3;+0:7](-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15] | 63 | [{"value": 63.0, "product": "O=C1N(C(C2=CC=CC=C12)=O)C(CC1=C(CNC(C(=O)OC(C)(C)C)CC(C)C)C=CC=C1)C(=O)OCC[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "O=C1N(C(C2=CC=CC=C12)=O)C(CC1=C(CNC(C(=O)OC(C)(C)C)CC(C)C)C=CC=C1)C(=O)OCC[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 0.5 | HOUR | Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-formyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester (250 mg, 0.590 mmol) in methanol (15 mL) and treat with L-leucine tert-butyl ester hydrochloride (0.66 g, 3.0 mmol). Stir at room temperature for 2 hours with 3A molecular sieves, add sodium cyanoborohydr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | Other | CO.O1CCCC1 | null | 0.5 | CC(C)C[C@H](N)C(=O)OC(C)(C)C.C[Si](C)(C)CCOC(=O)C(Cc1ccccc1C=O)N1C(=O)c2ccccc2C1=O>CO.O1CCCC1>CC(C)CC(NCc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C |
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