dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e88b6018253240189f556b5baaee75e8 | C#CCOC1CCCCO1.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1>>CC(C)(C)C(=O)Nc1cc2c(O)n(C#CCOC3CCCCO3)cnc-2n1 | C(C#C)OC1OCCCC1.IN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O.C(C#C)OC1OCCCC1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>>O1C(CCCC1)OCC#CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O | [CH:14]#[C:15][CH2:16][O:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][O:23]1.I[n:13]1[c:11]([OH:12])[c:10]2[cH:9][c:8]([NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[n:27][c:26]-2[n:25][cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]2[c:11]([OH:12])[n:13]([C:14]#[C:15][CH2:16][O:17][CH:1... | C#CCOC1CCCCO1.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1 | CC(C)(C)C(=O)Nc1cc2c(O)n(C#CCOC3CCCCO3)cnc-2n1 | null | [Pd](Cl)Cl | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2f759f114767b91e2231d010a7bf2c8670481fd3eb71a70def1ce9d9314ff239 | 0ff14f8ed0439469fe0912bb971ad27399d5e9d291750b4a0bb5781f426b3afa | C(#Cn1cnc2nccc-2c1)COC1CCCCO1 | I-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[#7;a:5])-[c:6]:[c:7]:1-[O;D1;H1:8].[C:9]-[C:10]#[CH;D1;+0:11]>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2]:[n;H0;D3;+0:1](-[C;H0;D2;+0:11]#[C:10]-[C:9]):[c:7](-[O;D1;H1:8]):[c:6]-1 | null | [] | null | null | 12 | HOUR | A mixture of 14.6 g of 3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 7.6 g of 2-(2-propynyloxy)-tetrahydropyran, 798 mg (10%) of palladium chloride, 2.36 g (20%) of triphenyl phosphine, 428 mg (5%) of cuprous iodide, 45 ml of triethyl amine and 700 ml of acetonitrile is heated at reflux under nitrogen for 1... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | c1cc2cncnc2[nH]1 | c1cc2cncnc2[nH]1 | c1cc2cncnc2[nH]1.C1CCOCC1 | HI | [Pd](Cl)Cl.C(C)#N | null | 12 | C#CCOC1CCCCO1.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1>[Pd](Cl)Cl.C(C)#N>CC(C)(C)C(=O)Nc1cc2c(O)n(C#CCOC3CCCCO3)cnc-2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-68835ea9559e4264a057fa5856eb6da6 | CC(C)(C)C(=O)Nc1cc2c(O)n(C#CCOC3CCCCO3)cnc-2n1>>CC(C)(C)C(=O)Nc1cc2c(O)n(C=CCOC3CCCCO3)cnc-2n1 | O1C(CCCC1)OCC#CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O.CO.N1=CC=CC2=CC=CC=C12.[H][H]>>O1C(CCCC1)OCC=CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]2[c:11]([OH:12])[n:13]([C:14]#[C:15][CH2:16][O:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:23]3)[cH:24][n:25][c:26]-2[n:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]2[c:11]([OH:12])[n:13]([CH:14]=[CH:15][CH2:16][O:17][CH:18... | CC(C)(C)C(=O)Nc1cc2c(O)n(C#CCOC3CCCCO3)cnc-2n1 | CC(C)(C)C(=O)Nc1cc2c(O)n(C=CCOC3CCCCO3)cnc-2n1 | null | [Pd] | C(Cl)(Cl)Cl.CCOCC | Reduction | Hydrogenation (triple to double) | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | C(=Cn1cnc2nccc-2c1)COC1CCCCO1 | [#7;a:1]:[c:2]:[#7;a:3](-[C;H0;D2;+0:4]#[C;H0;D2;+0:5]-[C:6]-[#8:7]):[c:8]>>[#7;a:1]:[c:2]:[#7;a:3](-[CH;D2;+0:4]=[CH;D2;+0:5]-[C:6]-[#8:7]):[c:8] | null | [] | null | null | null | null | A mixture of 2 g of 3-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 40 ml of methanol, 20 ml of chloroform, 40 mg of 5% palladium on barium sulfate, and 40 mg of synthetic quinoline is stirred under 1 atmosphere hydrogen pressure for 40 min. The solvent then is removed by ev... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1cc2cncnc2[nH]1.C1CCOCC1 | null | [Pd].C(Cl)(Cl)Cl.CCOCC | null | null | CC(C)(C)C(=O)Nc1cc2c(O)n(C#CCOC3CCCCO3)cnc-2n1>[Pd].C(Cl)(Cl)Cl.CCOCC>CC(C)(C)C(=O)Nc1cc2c(O)n(C=CCOC3CCCCO3)cnc-2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f4b94ff8ba9e4c06ac8d51b313e46253 | CC(C)(C)C(=O)Nc1cc2c(O)n(C=CCOC3CCCCO3)cnc-2n1.CCOC(=O)CC[C@H](NC(=O)c1ccc(I)cc1)C(=O)OCC>>CCOC(=O)CC[C@H](NC(=O)c1ccc(C(=Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)COC2CCCCO2)cc1)C(=O)OCC | O1C(CCCC1)OCC=CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O.IC1=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C1.CC1=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C.IC1=CC=C(C(=O)N[C@@H](CCC(=O)[O-])C(=O)OCC)C=C1>>O1C(CCCC1)OCC(=CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O)C2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2 | [CH:16](=[CH:17][n:18]1[cH:19][n:20][c:21]2[n:22][c:23]([NH:24][C:25](=[O:26])[C:27]([CH3:28])([CH3:29])[CH3:30])[cH:31][c:32]-2[c:33]1[OH:34])[CH2:35][O:36][CH:37]1[CH2:38][CH2:39][CH2:40][CH2:41][O:42]1.I[c:15]1[cH:14][cH:13][c:12]([C:10]([NH:9][C@@H:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:45](=[O:46])[O... | CC(C)(C)C(=O)Nc1cc2c(O)n(C=CCOC3CCCCO3)cnc-2n1.CCOC(=O)CC[C@H](NC(=O)c1ccc(I)cc1)C(=O)OCC | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(=Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)COC2CCCCO2)cc1)C(=O)OCC | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)#N.C(C)N(CC)CC | C-C Coupling | OtherReaction | ce3f42a910b3127aad0a3268e34d71bbd746e6540dbbe4cd945674b3fdabe8ab | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | C(=C(COC1CCCCO1)c1ccccc1)n1cnc2nccc-2c1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]-[C:7]=[CH;D2;+0:8]-[C:9]-[#8:10]>>[#7;a:6]-[C:7]=[C;H0;D3;+0:8](-[C:9]-[#8:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 12 | HOUR | A mixture containing 3.48 g of 3-(3-tetrahydropyr-2-yloxyprop-1-en-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 3.12g (1.2 equiv.) of diethyl N-(4-iodobenzoyl)glutamate, 546 mg (20%) of tris-(2-methylphenyl)phosphine, 201 mg (10%) of palladium acetate and 85.5 mg (5%) of cuprous iodide in 15 ml of triethyla... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cc2cncnc2[nH]1.C1CCOCC1 | HI | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)#N.C(C)N(CC)CC | null | 12 | CC(C)(C)C(=O)Nc1cc2c(O)n(C=CCOC3CCCCO3)cnc-2n1.CCOC(=O)CC[C@H](NC(=O)c1ccc(I)cc1)C(=O)OCC>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)#N.C(C)N(CC)CC>CCOC(=O)CC[C@H](NC(=O)c1ccc(C(=Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)COC2CCCCO2)cc1)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-60b4f2f7c4364d6ea701f73a82cf4b0f | C#C[Si](C)(C)C.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1>>CC(C)(C)C(=O)Nc1cc2c(O)n(C#C[Si](C)(C)C)cnc-2n1 | IN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O.C[Si](C)(C)C#C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>>C[Si](C)(C)C#CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O | [CH:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19].I[n:13]1[c:11]([OH:12])[c:10]2[cH:9][c:8]([NH:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])[n:23][c:22]-2[n:21][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]2[c:11]([OH:12])[n:13]([C:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][n... | C#C[Si](C)(C)C.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1 | CC(C)(C)C(=O)Nc1cc2c(O)n(C#C[Si](C)(C)C)cnc-2n1 | null | [Pd](Cl)Cl | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 2f759f114767b91e2231d010a7bf2c8670481fd3eb71a70def1ce9d9314ff239 | 0ff14f8ed0439469fe0912bb971ad27399d5e9d291750b4a0bb5781f426b3afa | c1cc2c[nH]cnc-2n1 | I-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[#7;a:5])-[c:6]:[c:7]:1-[O;D1;H1:8].[C;D1;H3:9]-[#14:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C:13]#[CH;D1;+0:14]>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2]:[n;H0;D3;+0:1](-[C;H0;D2;+0:14]#[C:13]-[#14:10](-[C;D1;H3:9])(-[C;D1;H3:11])-[C;D1;H3:12]):[c:7](-[O;D1;H1:8]):[c:6]-1 | null | [] | null | null | null | null | A mixture of 2.0 g of 3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 1.2 g. of trimethylsilylacetylene, 0.1 g of palladium chloride, 0.23 g of triphenylphosphine, 0.06 g of cuprous iodide, and 2.6 g of triethylamine in 100 mL of acetonitrile is heated in a sealed tube for 1.5 hours at 50° C. and then at refl... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Alkyne | c1cc2cncnc2[nH]1 | c1cc2cncnc2[nH]1 | c1cc2cncnc2[nH]1 | HI | [Pd](Cl)Cl.C(C)#N | null | null | C#C[Si](C)(C)C.CC(C)(C)C(=O)Nc1cc2c(O)n(I)cnc-2n1>[Pd](Cl)Cl.C(C)#N>CC(C)(C)C(=O)Nc1cc2c(O)n(C#C[Si](C)(C)C)cnc-2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-733afb349588418397c28c2bf0f606c4 | CC(C)(C)C(=O)Nc1cc2c(O)n(C#C[Si](C)(C)C)cnc-2n1>>C#Cn1cnc2nc(NC(=O)C(C)(C)C)cc-2c1O | C[Si](C)(C)C#CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(#C)N1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O | C[Si](C)(C)[C:1]#[C:2][n:3]1[cH:4][n:5][c:6]2[n:7][c:8]([NH:9][C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][c:17]-2[c:18]1[OH:19]>>[CH:1]#[C:2][n:3]1[cH:4][n:5][c:6]2[n:7][c:8]([NH:9][C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][c:17]-2[c:18]1[OH:19] | CC(C)(C)C(=O)Nc1cc2c(O)n(C#C[Si](C)(C)C)cnc-2n1 | C#Cn1cnc2nc(NC(=O)C(C)(C)C)cc-2c1O | null | null | O1CCCC1 | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1cc2c[nH]cnc-2n1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[#7;a:3]>>[#7;a:3]-[C:2]#[CH;D1;+0:1] | null | [] | null | null | 5 | MINUTE | To a solution of 1.5 g of 3-trimethylsilylethynyl--4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine in 100 mL of anhydrous tetrahydrofuran cooled to 0° C. are added under nitrogen 4.75 mL of 1M tetrabutylammonium fluoride in anhydrous tetrahydrofuran. After 5 minutes, the reaction mixture is allowed to attain room tem... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1cc2cncnc2[nH]1 | Other | O1CCCC1 | null | 0.083333 | CC(C)(C)C(=O)Nc1cc2c(O)n(C#C[Si](C)(C)C)cnc-2n1>O1CCCC1>C#Cn1cnc2nc(NC(=O)C(C)(C)C)cc-2c1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4bb92475c2714241b96d0051b037ece5 | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(=Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)COC2CCCCO2)cc1)C(=O)OCC>>CCOC(=O)CC[C@H](NC(=O)c1ccc(C(COC2CCCCO2)Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)cc1)C(=O)OCC | O1C(CCCC1)OCC(=CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O)C2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2>>O1C(CCCC1)OCC(CN1C=NC=2C(=C1O)C=C(N2)NC(C(C)(C)C)=O)C2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([C:16]([CH2:17][O:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][O:24]2)=[CH:25][n:26]2[cH:27][n:28][c:29]3[n:30][c:31]([NH:32][C:33](=[O:34])[C:35]([CH3:36])([CH3:37])[CH3:38])[cH:39][c:40]-3[c:41]2[OH:42])[cH:43][cH:44... | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(=Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)COC2CCCCO2)cc1)C(=O)OCC | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(COC2CCCCO2)Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)cc1)C(=O)OCC | null | [Pt](=O)=O | C(C)(=O)O.CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(C(COC2CCCCO2)Cn2cnc3nccc-3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3](-[CH;D2;+0:4]=[C;H0;D3;+0:5](-[C:6]-[#8:7])-[c:8](:[c:9]):[c:10]):[c:11]>>[#7;a:1]:[c:2]:[#7;a:3](-[CH2;D2;+0:4]-[CH;D3;+0:5](-[C:6]-[#8:7])-[c:8](:[c:9]):[c:10]):[c:11] | null | [] | null | null | null | null | A solution of 1.16 g of diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidin-3-yl)prop-2-en-2-yl}benzoyl]glutamate and 174 mg (20%) of amorphous platinum (IV) oxide in 150 ml of glacial acetic acid is hydrogenated for 10 hours at 50 psi. The reaction mixture is diluted with 50 ml ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1CCOCC1.c1cc2cncnc2[nH]1 | null | [Pt](=O)=O.C(C)(=O)O.CO | null | null | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(=Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)COC2CCCCO2)cc1)C(=O)OCC>[Pt](=O)=O.C(C)(=O)O.CO>CCOC(=O)CC[C@H](NC(=O)c1ccc(C(COC2CCCCO2)Cn2cnc3nc(NC(=O)C(C)(C)C)cc-3c2O)cc1)C(=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-906733f298d349598a10f27ec82e8d53 | CC(C)=CC(SC(C=C(C)C)c1ccccc1)c1ccccc1>>CC1(C)CCSc2ccccc21 | C1(=CC=CC=C1)C(C=C(C)C)SC(C=C(C)C)C1=CC=CC=C1.C1(=CC=CC=C1)C(C=C(C)C)SC(C=C(C)C)C1=CC=CC=C1.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3.P(O)(O)(O)=O.C1=CC=CC=C1>>CC1(CCSC2=CC=CC=C12)C | CC(C)=CC([S:6][CH:5](c1ccccc1)[CH:4]=[C:2]([CH3:1])[CH3:3])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][S:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | CC(C)=CC(SC(C=C(C)C)c1ccccc1)c1ccccc1 | CC1(C)CCSc2ccccc21 | null | null | null | Miscellaneous | OtherReaction | 17747e57fe02c662d03eeec5e5a2e4cf099e136b9c4b178418ec017c976c4880 | 04aedd72d47e3929bd14c1ad18abeeed4729294a1bf9373b286439de2d28df92 | c1ccc2c(c1)CCCS2 | C-C(-C)=C-C(-[S;H0;D2;+0:1]-[CH;D3;+0:2](-[CH;D2;+0:3]=[C;H0;D3;+0:4](-[C;D1;H3:5])-[C;D1;H3:6])-c1:c:c:c:c:c:1)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[c:11]:[cH;D2;+0:12]:1>>[C;D1;H3:5]-[C;H0;D4;+0:4]1(-[C;D1;H3:6])-[CH2;D2;+0:3]-[CH2;D2;+0:2]-[S;H0;D2;+0:1]-[c;H0;D3;+0:7]2:[c:8]:[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:12]:2-1 | null | [] | null | null | 20 | HOUR | To a solution of 15.48g (86.824 mmol) of phenyl-3-methylbut-2-enylsulfide (Compound 60) in 160ml benzene were added successively 12.6g (88.767mmol) of phosphorus pentoxide and 11 ml of 85% phosphoric acid. This solution was refluxed with vigorous stirring under argon for 20 hours, then cooled to room temperature. The s... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | Other | null | null | 20 | CC(C)=CC(SC(C=C(C)C)c1ccccc1)c1ccccc1>>CC1(C)CCSc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-96350377ef0540789eec3b3c750eb3d6 | CC(=O)Cl.CC1(C)CCSc2ccccc21>>CC(=O)c1ccc2c(c1)C(C)(C)CCS2 | CC1(CCSC2=CC=CC=C12)C.CC1(CCSC2=CC=CC=C12)C.C(C)(=O)Cl.O.Cl>>CC1(CCSC2=CC=C(C=C12)C(C)=O)C | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][S:15]2>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][S:15]2 | CC(=O)Cl.CC1(C)CCSc2ccccc21 | CC(=O)c1ccc2c(c1)C(C)(C)CCS2 | null | null | C1=CC=CC=C1 | C-C Coupling | Friedel-Crafts acylation | 30000e9ca7973a4d33543508f12d2b7c4f487848b11ac645b8fbc477f5926434 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2c(c1)CCCS2 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | 12 | HOUR | A solution of 14.3g (80.21 mmol) of 4,4-dimethylthiochroman (Compound 61) and 6.76g (86.12 mmol) of acetyl chloride in 65 ml benzene was cooled in an ice bath and treated dropwise with 26.712g (102.54 mmol) of stannic chloride. The mixture was stirred at room temperature for 12 hours, then treated with 65 ml water and ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | HCl | C1=CC=CC=C1 | null | 12 | CC(=O)Cl.CC1(C)CCSc2ccccc21>C1=CC=CC=C1>CC(=O)c1ccc2c(c1)C(C)(C)CCS2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9c32ed92dd3d4d46bcb3d11e63e1b46e | CC(=O)c1ccc2c(c1)C(C)(C)CCS2>>C#Cc1ccc2c(c1)C(C)(C)CCS2 | C(C)(C)NC(C)C.P(=O)(OCC)(OCC)Cl.C(C)(C)[N-]C(C)C.[Li+].CC1(CCSC2=CC=C(C=C12)C(C)=O)C.CC1(CCSC2=CC=C(C=C12)C(C)=O)C.C(CCC)[Li].C(C)(C)NC(C)C.C(CCC)[Li]>>CC1(CCSC2=CC=C(C=C12)C#C)C | O=[C:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][S:14]2>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][S:14]2 | CC(=O)c1ccc2c(c1)C(C)(C)CCS2 | C#Cc1ccc2c(c1)C(C)(C)CCS2 | null | null | CCCCCC.O1CCCC1 | Functional Group Interconversion | OtherReaction | df4f03d2116228d20bc5d8403092a8dd982f38312b775d7fadf08d78c364384d | 70d06bbe4d921df55900f4b8f7e6e878b9de0b1a93bf34dcf81c33c29d9b3281 | c1ccc2c(c1)CCCS2 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[CH;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | -78 | CELSIUS | 1 | HOUR | To a solution of 1.441 g (14.2405 mmol) of diisopropylamine in 30 ml dry tetrahydrofuran under argon at -78 degrees C. was added dropwise 9 ml of 1.6 M (14.4 mmol) n-butyl lithium in hexane. After stirring this solution at -78 degrees C. for 1 hour, it was treated dropwise with a solution of 2.95 g (13.389 mmol) of 4,4... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkyne | null | null | c1ccc2c(c1)CCCS2 | HO- | CCCCCC.O1CCCC1 | -78 | 1 | CC(=O)c1ccc2c(c1)C(C)(C)CCS2>CCCCCC.O1CCCC1>C#Cc1ccc2c(c1)C(C)(C)CCS2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3d9d382e9f8f4afa9b0c7a2622b789ae | C#C[Si](C)(C)C.Cc1cc2c(cc1Br)C(C)(C)CCS2>>Cc1cc2c(cc1C#C[Si](C)(C)C)C(C)(C)CCS2 | CC1(CCSC2=CC(=C(C=C12)Br)C)C.CC1(CCSC2=CC(=C(C=C12)Br)C)C.C[Si](C)(C)C#C>>CC1(CCSC2=CC(=C(C=C12)C#C[Si](C)(C)C)C)C | [CH:8]#[C:9][Si:10]([CH3:11])([CH3:12])[CH3:13].Br[c:7]1[c:2]([CH3:1])[cH:3][c:4]2[c:5]([cH:6]1)[C:14]([CH3:15])([CH3:16])[CH2:17][CH2:18][S:19]2>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[C:8]#[C:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[C:14]([CH3:15])([CH3:16])[CH2:17][CH2:18][S:19]2 | C#C[Si](C)(C)C.Cc1cc2c(cc1Br)C(C)(C)CCS2 | Cc1cc2c(cc1C#C[Si](C)(C)C)C(C)(C)CCS2 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd+2] | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 75ff6039cbc5d1f725e4edefe2b102acf00802e47106a77cfc4f5a03c5a8f94b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)CCCS2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[C;D1;H3:7]-[#14:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C:11]#[CH;D1;+0:12]>>[C;D1;H3:7]-[#14:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C:11]#[C;H0;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6] | null | [] | 85 | CELSIUS | 15 | HOUR | A mixture of 624 mg (3.0 mmol) of 4,4,7-trimethyl-6-bromothiochroman (Compound 66) 314 mg (3.2 mmol) of trimethylsilyl acetylene, 40 mg (0.21 mmol) of cuprous iodide, 80 mg (0.11 mmol) of bis (triphenylphosphin) palladium (II) chloride and 1 ml of triethylamine was degassed under nitrogen and heated in a sealed tube at... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | HBr | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd+2].C(C)N(CC)CC | 85 | 15 | C#C[Si](C)(C)C.Cc1cc2c(cc1Br)C(C)(C)CCS2>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd+2].C(C)N(CC)CC>Cc1cc2c(cc1C#C[Si](C)(C)C)C(C)(C)CCS2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c6412dfebb444e2990d8e868c7d27f9b | Cc1cc2c(cc1C#C[Si](C)(C)C)C(C)(C)CCS2>>C#Cc1cc2c(cc1C)SCCC2(C)C | C[Si](C)(C)C#CC=1C=C2C(CCSC2=CC1C)(C)C.CC1(CCSC2=CC(=C(C=C12)C#C[Si](C)(C)C)C)C.[OH-].[K+]>>CC1(CCSC2=CC(=C(C=C12)C#C)C)C | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH3:9])[S:10][CH2:11][CH2:12][C:13]2([CH3:14])[CH3:15]>>[CH:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH3:9])[S:10][CH2:11][CH2:12][C:13]2([CH3:14])[CH3:15] | Cc1cc2c(cc1C#C[Si](C)(C)C)C(C)(C)CCS2 | C#Cc1cc2c(cc1C)SCCC2(C)C | null | null | C(C)(C)O | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc2c(c1)CCCS2 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | null | [] | null | null | 16 | HOUR | A mixture of 380 mg (1.69 mmol of trimethylsilyl (4,4,7-trimethyl-thiochroman-6-yl) ethyne, (Compound 67) 4 ml of isopropanol and 2.5 ml of aqueous 1N potassium hydroxide was degassed under nitrogen and stirred at room temperature for 16 h. The mixture was concentrated under vacuum and extracted with 2×10 ml of ether. ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccc2c(c1)CCCS2 | Other | C(C)(C)O | null | 16 | Cc1cc2c(cc1C#C[Si](C)(C)C)C(C)(C)CCS2>C(C)(C)O>C#Cc1cc2c(cc1C)SCCC2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-097dd43f94c04983b56bf26afb022512 | CC(C)=CC(=O)Sc1ccc(Br)cc1>>CC1(C)CC(=O)Sc2ccc(Br)cc21 | CC(=CC(=O)SC1=CC=C(C=C1)Br)C.[Cl-].[Al+3].[Cl-].[Cl-].CC(=CC(=O)SC1=CC=C(C=C1)Br)C>>CC1(CC(SC2=CC=C(C=C12)Br)=O)C | [CH3:1][C:2]([CH3:3])=[CH:4][C:5](=[O:6])[S:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[S:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]21 | CC(C)=CC(=O)Sc1ccc(Br)cc1 | CC1(C)CC(=O)Sc2ccc(Br)cc21 | null | null | [Cl-].[Na+].O.C(Cl)Cl | C-C Coupling | OtherReaction | 7798c6e176a7f028b9d886487c33de5391e3a6df54b34bedbe336b108755f5f6 | 008e5428c97983096daee005b9f466e3a6a99ee4ea8c97203bdc8e8fb3e881f7 | O=C1CCc2ccccc2S1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#16:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#16:7]-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12] | null | [] | null | null | 72 | HOUR | To a stirred, ice-cooled suspension of 15.9 g (119 mmol) of aluminum chloride in 140 ml of methylene chloride was added under nitrogen, a solution of 21.64 g (79.9 mmol) of S-(4-bromophenyl) 3,3-dimethyl-thioacrylate (Compound 69) in 100 ml of methylene chloride. The mixture was then stirred at room temperature for 72 ... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Carbo-thioester | c1ccccc1 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | null | [Cl-].[Na+].O.C(Cl)Cl | null | 72 | CC(C)=CC(=O)Sc1ccc(Br)cc1>[Cl-].[Na+].O.C(Cl)Cl>CC1(C)CC(=O)Sc2ccc(Br)cc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0ec6951958484f6ea4aba6784e537f20 | CC1(C)CC(=O)Sc2ccc(Br)cc21.CC1(C)CC(=O)Sc2ccc(Br)cc21>>CC(C)(O)CC(C)(C)c1cc(Br)ccc1S | Cl(=O)(=O)(=O)[O-].[Li+].C[Mg]Br.CCOCC.OS(=O)(=O)O.CC1(CC(SC2=CC=C(C=C12)Br)=O)C.CC1(CC(SC2=CC=C(C=C12)Br)=O)C>>BrC1=CC(=C(C=C1)S)C(CC(C)(O)C)(C)C | CC1([CH3:1])CC(=O)Sc2ccc(Br)cc21.[C:2]1(=[O:4])[CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[S:16]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]1[SH:16] | CC1(C)CC(=O)Sc2ccc(Br)cc21.CC1(C)CC(=O)Sc2ccc(Br)cc21 | CC(C)(O)CC(C)(C)c1cc(Br)ccc1S | null | null | null | C-C Coupling | OtherReaction | 9aaf93948966c0059aa47d6cf36fa3996b34e14cee1d6eb565eb4d1fba390aaf | a9b00035e28ea4f98b659dbf52a161e5323c7a50a9e1fcecd47c0627e66eb6dd | c1ccccc1 | Br-c1:c:c:c2:c(:c:1)-C(-C)(-[CH3;D1;+0:1])-C-C(=O)-S-2.[O;H0;D1;+0:2]=[C;H0;D3;+0:3]1-[C:4]-[C:5]-[c:6]:[c:7](:[c:8])-[S;H0;D2;+0:9]-1>>[C;D1;H3:10]-[C;H0;D4;+0:3](-[CH3;D1;+0:1])(-[OH;D1;+0:2])-[C:4]-[C:5]-[c:6]:[c:7](-[SH;D1;+0:9]):[c:8] | null | [] | null | null | null | null | To 3.49 g (32.8 mmol) of lithium perchlorate was added under argon 35 ml of 3.0M (105 mmol) methyl magnesium bromide in ether. The above mixture was treated dropwise with stirring with a solution of 2.961 g (10.926 mmol) of 4,4-dimethyl-6-bromo-2-oxo-thiochroman (Compound 70) and the reaction mixture was then heated at... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbo-thioester.Carbo-thioester | Tertiary alcohol.Aromatic thiol | c1ccc2c(c1)CCCS2.c1ccc2c(c1)CCCS2 | null | c1ccccc1 | HBr | null | null | null | CC1(C)CC(=O)Sc2ccc(Br)cc21.CC1(C)CC(=O)Sc2ccc(Br)cc21>>CC(C)(O)CC(C)(C)c1cc(Br)ccc1S |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3b023fa40f894243abce5a27de4b2fb6 | CC(C)(O)CC(C)(C)c1cc(Br)ccc1S>>CC1(C)CC(C)(C)c2cc(Br)ccc2S1 | BrC1=CC(=C(C=C1)S)C(CC(C)(O)C)(C)C.BrC1=CC(=C(C=C1)S)C(CC(C)(O)C)(C)C.OS(=O)(=O)O>>CC1(SC2=CC=C(C=C2C(C1)(C)C)Br)C | O[C:2]([CH3:1])([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[SH:15]>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[S:15]1 | CC(C)(O)CC(C)(C)c1cc(Br)ccc1S | CC1(C)CC(C)(C)c2cc(Br)ccc2S1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | aabb035ad6b1c7bf2fc4c433589845997e6de24946e274a69282c44ba9ac5716 | d27c27c55a7a9aed1e1b8ad0a4889e0d3ee7d5cd231d778f88c9844538c6315f | c1ccc2c(c1)CCCS2 | O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4]-[C:5]-[c:6]:[c:7](-[SH;D1;+0:8]):[c:9]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[C;D1;H3:3])-[C:4]-[C:5]-[c:6]:[c:7](:[c:9])-[S;H0;D2;+0:8]-1 | null | [] | null | null | null | null | A mixture of 500 mg (1.49 mmol) of 4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol (Compound 71) and 8 ml of 20 percent aqueous H2SO4 was heated at reflux for 24 h. The mixture was extracted with hexanes the organic extracts were combined and washed successively with water, saturated NaHCO3, water again, saturate... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Aromatic thiol | Monosulfide | null | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | HO- | null | null | null | CC(C)(O)CC(C)(C)c1cc(Br)ccc1S>>CC1(C)CC(C)(C)c2cc(Br)ccc2S1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4c3949980b3e41958aed662fc5a1a3e0 | C#C[Si](C)(C)C.CC1(C)CC(C)(C)c2cc(Br)ccc2S1>>CC1(C)CC(C)(C)c2cc(C#C[Si](C)(C)C)ccc2S1 | CC1(SC2=CC=C(C=C2C(C1)(C)C)Br)C.CC1(SC2=CC=C(C=C2C(C1)(C)C)Br)C.C[Si](C)(C)C#C.C[Si](C)(C)C#C>>CC1(SC2=CC=C(C=C2C(C1)(C)C)C#C[Si](C)(C)C)C | [CH:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16].Br[c:10]1[cH:9][c:8]2[c:19]([cH:18][cH:17]1)[S:20][C:2]([CH3:1])([CH3:3])[CH2:4][C:5]2([CH3:6])[CH3:7]>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[c:8]2[cH:9][c:10]([C:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18][c:19]2[S:20]1 | C#C[Si](C)(C)C.CC1(C)CC(C)(C)c2cc(Br)ccc2S1 | CC1(C)CC(C)(C)c2cc(C#C[Si](C)(C)C)ccc2S1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 75ff6039cbc5d1f725e4edefe2b102acf00802e47106a77cfc4f5a03c5a8f94b | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)CCCS2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[CH;D1;+0:11]>>[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 100 | CELSIUS | 24 | HOUR | A solution of 600 mg (2.11 mmol) of 2,2,4,4-tetramethyl-6-bromothiochroman (Compound 72) in 1.5 ml of triethylamine was placed in a heavy-walled tube and degassed and then treated under argon with 1.4 g (14.3 mmol) of trimethylsilylacetylene and a powdered mixture of 75 mg (0.39 mmol) of cuprous iodide and 150 mg (0.21... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | c1ccc2c(c1)CCCS2 | HBr | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC | 100 | 24 | C#C[Si](C)(C)C.CC1(C)CC(C)(C)c2cc(Br)ccc2S1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>CC1(C)CC(C)(C)c2cc(C#C[Si](C)(C)C)ccc2S1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fd81178d17144eccb85427ba5786701d | CC1(C)CC(C)(C)c2cc(C#C[Si](C)(C)C)ccc2S1>>C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2 | CC1(SC2=CC=C(C=C2C(C1)(C)C)C#C[Si](C)(C)C)C.[OH-].[K+]>>CC1(SC2=CC=C(C=C2C(C1)(C)C)C#C)C | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][C:13]([CH3:14])([CH3:15])[S:16]2>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][C:13]([CH3:14])([CH3:15])[S:16]2 | CC1(C)CC(C)(C)c2cc(C#C[Si](C)(C)C)ccc2S1 | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2 | null | null | C(C)(C)O | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc2c(c1)CCCS2 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | null | [] | null | null | 20 | HOUR | To a solution of 527.6 mg (1.75 mmol) of 2,2,4,4-tetramethyl-6-trimethylsilyl-ethynylthiochroman (Compound 73) in 4 ml of isopropanol was added, under argon, 4 ml of 1N KOH solution. The reaction mixture was stirred at room temperature for 20 h and the isopropanol was then removed under vacuum. The residue was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccc2c(c1)CCCS2 | Other | C(C)(C)O | null | 20 | CC1(C)CC(C)(C)c2cc(C#C[Si](C)(C)C)ccc2S1>C(C)(C)O>C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6c3ee84e636a4a4683f03212d22a0466 | C=C(C)C(COP(=O)([O-])[O-])(c1ccccc1)c1ccccc1.C=C(C)C(COP(=O)([O-])[O-])(c1ccccc1)c1ccccc1.Oc1ccccc1>>CC1(C)CCOc2ccccc21 | C1(=CC=CC=C1)O.P(=O)(OCC(C(=C)C)(C1=CC=CC=C1)C1=CC=CC=C1)([O-])[O-].P(=O)(OCC(C(=C)C)(C1=CC=CC=C1)C1=CC=CC=C1)([O-])[O-]>>CC1(CCOC2=CC=CC=C12)C | CC(C(COP(=O)([O-])[O-])(c1ccccc1)c1ccccc1)=[CH2:1].C[C:4]([C:2](c1ccccc1)(c1ccccc1)[CH2:3]OP(=O)([O-])[O-])=[CH2:5].[OH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | C=C(C)C(COP(=O)([O-])[O-])(c1ccccc1)c1ccccc1.C=C(C)C(COP(=O)([O-])[O-])(c1ccccc1)c1ccccc1.Oc1ccccc1 | CC1(C)CCOc2ccccc21 | null | null | C(=S)=S | Heteroatom Alkylation and Arylation | OtherReaction | 1fa0d945ac8f369a904dee8571d71ca2d737ad79aee847bc2ace7d59c60a59e6 | 8d227405e51f25e30cac82fc09e6bc03a44973463e1abd462d2a90cda8b5e97e | c1ccc2c(c1)CCCO2 | C-C(=[CH2;D1;+0:1])-C(-C-O-P(=O)(-[O-])-[O-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.C-[C;H0;D3;+0:2](=[CH2;D1;+0:3])-[C;H0;D4;+0:4](-[CH2;D2;+0:5]-O-P(=O)(-[O-])-[O-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[OH;D1;+0:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[CH3;D1;+0:1]-[C;H0;D4;+0:4]1(-[CH3;D1;+0:5])-[CH2;D2;+0:2]-[CH2;D2;+0:... | null | [] | 0 | CELSIUS | 0.5 | HOUR | To a dry, ice-cooled flask containing 34.95g (0.134 mol) of stannic chloride was added quickly under argon 63.0g (0.669 mol) of phenol. The mixture was stirred at 0 degrees C. for 0.5 hour and then treated with 43.0g (0.135 mol) of diphenyl-3-methyl-3-buten-1-yl phosphate (Compound 75), followed by a 5 ml carbon disulf... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Vinyl.Vinyl | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | HO- | C(=S)=S | 0 | 0.5 | C=C(C)C(COP(=O)([O-])[O-])(c1ccccc1)c1ccccc1.C=C(C)C(COP(=O)([O-])[O-])(c1ccccc1)c1ccccc1.Oc1ccccc1>C(=S)=S>CC1(C)CCOc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5f176039deb740b6a1362543c95ff2fb | CC(=O)Cl.CC1(C)CCOc2ccccc21>>CC(=O)c1ccc2c(c1)C(C)(C)CCO2 | [Cl-].[Al+3].[Cl-].[Cl-].CC1(CCOC2=CC=CC=C12)C.CC1(CCOC2=CC=CC=C12)C.C(C)(=O)Cl.Cl>>CC1(CCOC2=CC=C(C=C12)C(C)=O)C | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][O:15]2>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][O:15]2 | CC(=O)Cl.CC1(C)CCOc2ccccc21 | CC(=O)c1ccc2c(c1)C(C)(C)CCO2 | null | null | CCOCC.[N+](=O)([O-])C | C-C Coupling | Friedel-Crafts acylation | 638470e28b39a3831ba1cc18812a4a3c900caa75183eda12e0a014574a67f433 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2c(c1)CCCO2 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | 5.5 | HOUR | To a stirred solution 7.94 g (48.9425 mmol) of 4,4-dimethylchroman (Compound 76) in 70 ml of nitromethane was added under argon 4.0 g (50.96 mmol) of acetyl chloride followed by 6.8 g (51 mmol) of aluminum chloride. This was stirred at room temperature for 5.5 hours and then cooled in an ice bath and treated slowly wit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | HCl | CCOCC.[N+](=O)([O-])C | null | 5.5 | CC(=O)Cl.CC1(C)CCOc2ccccc21>CCOCC.[N+](=O)([O-])C>CC(=O)c1ccc2c(c1)C(C)(C)CCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ba3e58b15e064002855b866cd5171510 | CC(=O)c1ccc2c(c1)C(C)(C)CCO2>>C#Cc1ccc2c(c1)C(C)(C)CCO2 | P(=O)(OCC)(OCC)Cl.C(C)(C)[N-]C(C)C.[Li+].C(CCC)[Li].C(C)(C)NC(C)C.C(CCC)[Li].CC1(CCOC2=CC=C(C=C12)C(C)=O)C.CC1(CCOC2=CC=C(C=C12)C(C)=O)C>>CC1(CCOC2=CC=C(C=C12)C#C)C | O=[C:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][O:14]2>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][O:14]2 | CC(=O)c1ccc2c(c1)C(C)(C)CCO2 | C#Cc1ccc2c(c1)C(C)(C)CCO2 | null | null | CCCCCC.O1CCCC1 | Functional Group Interconversion | OtherReaction | df4f03d2116228d20bc5d8403092a8dd982f38312b775d7fadf08d78c364384d | 70d06bbe4d921df55900f4b8f7e6e878b9de0b1a93bf34dcf81c33c29d9b3281 | c1ccc2c(c1)CCCO2 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[CH;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | 78 | CELSIUS | 1 | HOUR | To a solution of 2.47 g (24.41 mmol) of diisopropylamine in 40 ml dry tetrahydrofuran under argon at 31 78 degrees C was added dropwise 15.2 ml of 1.6M (24.32 mmol) n-butyl lithium in hexane. This mixture was stirred at 31 78 degrees C. for 1 hour and then treated dropwise with a solution of 4.98 g (24.38 mmol) of 4,4-... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkyne | null | null | c1ccc2c(c1)CCCO2 | HO- | CCCCCC.O1CCCC1 | 78 | 1 | CC(=O)c1ccc2c(c1)C(C)(C)CCO2>CCCCCC.O1CCCC1>C#Cc1ccc2c(c1)C(C)(C)CCO2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-71093b2e470a4e1d97851b4d87f2732a | CC(C)=CC(=O)Oc1ccccc1>>CC1(C)CC(=O)Oc2ccccc21 | CC(=CC(=O)OC1=CC=CC=C1)C.CC(=CC(=O)OC1=CC=CC=C1)C.[Cl-].[Al+3].[Cl-].[Cl-]>>CC1(CC(OC2=CC=CC=C12)=O)C | [CH3:1][C:2]([CH3:3])=[CH:4][C:5](=[O:6])[O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[O:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21 | CC(C)=CC(=O)Oc1ccccc1 | CC1(C)CC(=O)Oc2ccccc21 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | b1ca5a0f576c8c6a3aa21c580a85630a897c9683b185fae225d50532a19957b4 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | O=C1CCc2ccccc2O1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12] | null | [] | null | null | 42 | HOUR | To a stirred, ice-cooled suspension of 10.4 g (78 mmol) of aluminum chloride in 160 ml of methylene chloride was added slowly under argon a solution of 7 g (39.8 mmol) of phenyl 3,3-dimethylacrylate (Compound 81) in 40 ml of methylene chloride. The cooling bath was removed and the mixture stirred for a further 42 h. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | c1ccccc1 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | null | C(Cl)Cl | null | 42 | CC(C)=CC(=O)Oc1ccccc1>C(Cl)Cl>CC1(C)CC(=O)Oc2ccccc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bd19b92dd3104e8c9e26eeaeb7ba0bf2 | CC(C)(O)CC(C)(C)c1ccccc1O>>CC1(C)CC(C)(C)c2ccccc2O1 | CC(CC(C)(O)C)(C)C1=C(C=CC=C1)O.CC(CC(C)(O)C)(C)C1=C(C=CC=C1)O.OS(=O)(=O)O>>CC1(OC2=CC=CC=C2C(C1)(C)C)C | O[C:2]([CH3:1])([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]([CH3:6])([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[O:14]1 | CC(C)(O)CC(C)(C)c1ccccc1O | CC1(C)CC(C)(C)c2ccccc2O1 | null | null | O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | d9641bb5951ac69cb502f22192c733e934905d219b37bbb10d6e5f44cdc5c184 | 0a70c59834af648d4da9cf9d3918e25f9a9a23c33d84d8cfdfd64980b339bbb3 | c1ccc2c(c1)CCCO2 | O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4]-[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[C;D1;H3:3])-[C:4]-[C:5]-[c:6]:[c:7](:[c:9])-[O;H0;D2;+0:8]-1 | null | [] | null | null | 72 | HOUR | A Mixture of 2.98 g (14.3 mmol) of 2-(1,1,3-trimethyl-3-hydroxybutyl) phenol (Compound 83) and 40 ml of 20% aqueous H2SO4 was heated at reflux, under nitrogen, for 4 h. The mixture was stirred at room temperature for a further 72 h and then diluted with 50 ml of water. The mixture was extracted with 3×20 ml of hexanes.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | HO- | O | null | 72 | CC(C)(O)CC(C)(C)c1ccccc1O>O>CC1(C)CC(C)(C)c2ccccc2O1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-964ba96c58d94d2ea992b45e7a732b3b | CC(=O)Cl.CC1(C)CC(C)(C)c2ccccc2O1.CC1(C)CC(C)(C)c2ccccc2O1>>CC(=O)c1ccc2c(c1)C(C)(C)CC(C)(C)O2 | CC1(OC2=CC=CC=C2C(C1)(C)C)C.CC1(OC2=CC=CC=C2C(C1)(C)C)C.[Cl-].[Al+3].[Cl-].[Cl-].C(C)(=O)Cl>>CC1(OC2=CC=C(C=C2C(C1)(C)C)C(C)=O)C | Cl[C:2]([CH3:1])=[O:3].c1ccc2c(c1)O[C:10]([CH3:11])([CH3:12])[CH2:13][C:14]2([CH3:15])[CH3:16].CC1(C)CC(C)(C)[O:17][c:7]2[cH:6][cH:5][cH:4][cH:9][c:8]21>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][C:14]([CH3:15])([CH3:16])[O:17]2 | CC(=O)Cl.CC1(C)CC(C)(C)c2ccccc2O1.CC1(C)CC(C)(C)c2ccccc2O1 | CC(=O)c1ccc2c(c1)C(C)(C)CC(C)(C)O2 | null | null | [N+](=O)([O-])C | C-C Coupling | OtherReaction | 1d6669ea8e523939356eee428ed568e240013a9c015b85bc4a78168bc34f55f4 | a3916129802117871fa78d56772f1be9c1c5d4bafb02314df0e93b4e352ec853 | c1ccc2c(c1)CCCO2 | C-C1(-C)-C-C(-C)(-C)-[c;H0;D3;+0:1]2:[c:2]:[cH;D2;+0:3]:[c:4]:[c:5]:[c:6]:2-[O;H0;D2;+0:7]-1.Cl-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;D1;H0:10].[C;D1;H3:11]-[C;H0;D4;+0:12]1(-[C;D1;H3:13])-O-c2:c:c:c:c:c:2-[C;H0;D4;+0:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C:17]-1>>[C;D1;H3:11]-[C;H0;D4;+0:12]1(-[C;D1;H3:13])-[C:17]-[C;H0;D4;+0:... | null | [] | null | null | 16 | HOUR | To an ice bath cooled solution of 2 g (10.53 mmol) of 2,2,4,4-tetramethylchroman (Compound 84) in 25 ml of nitromethane was added, under nitrogen, 941 mg (11.99 mmol) of acetyl chloride followed by 1.59 g (11.92) mmol) of aluminum chloride. The cooling bath was then removed and the mixture stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Ether | Ketone.Ether | c1ccc2c(c1)CCCO2.c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | HCl | [N+](=O)([O-])C | null | 16 | CC(=O)Cl.CC1(C)CC(C)(C)c2ccccc2O1.CC1(C)CC(C)(C)c2ccccc2O1>[N+](=O)([O-])C>CC(=O)c1ccc2c(c1)C(C)(C)CC(C)(C)O2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b04cdc9bba80470aa3364e2940bee852 | CC(=O)c1ccc2c(c1)C(C)(C)CC(C)(C)O2>>C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)O2 | C(C)OP(=O)(OCC)Cl.C(C)(C)NC(C)C.C(CCC)[Li].CC1(OC2=CC=C(C=C2C(C1)(C)C)C(C)=O)C.CC1(OC2=CC=C(C=C2C(C1)(C)C)C(C)=O)C.C(C)(C)[N-]C(C)C.[Li+].C(CCC)[Li].C(C)(C)NC(C)C>>CC1(OC2=CC=C(C=C2C(C1)(C)C)C#C)C | O=[C:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][C:13]([CH3:14])([CH3:15])[O:16]2>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][C:13]([CH3:14])([CH3:15])[O:16]2 | CC(=O)c1ccc2c(c1)C(C)(C)CC(C)(C)O2 | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)O2 | null | null | CCCCCC.C1CCOC1 | Functional Group Interconversion | OtherReaction | df4f03d2116228d20bc5d8403092a8dd982f38312b775d7fadf08d78c364384d | 70d06bbe4d921df55900f4b8f7e6e878b9de0b1a93bf34dcf81c33c29d9b3281 | c1ccc2c(c1)CCCO2 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[CH;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | -78 | CELSIUS | 40 | MINUTE | To a cooled (-78 degrees C.) solution of 522 mg (5.17 mmol) of diisopropylamine in 8 ml of dry THF was added slowly, under nitrogen, 3.23 ml of 1.6 M (5.17 mmol) n-butyl lithium in hexane. The mixture was stirred at -78 degrees C. for 40 minutes and then treated with a solution of 1.24 g (5.17 mmol) of 2,2,4,4-tetramet... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkyne | null | null | c1ccc2c(c1)CCCO2 | HO- | CCCCCC.C1CCOC1 | -78 | 0.666667 | CC(=O)c1ccc2c(c1)C(C)(C)CC(C)(C)O2>CCCCCC.C1CCOC1>C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)O2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8a77678c1c0d40678a7ca530c2333364 | Cc1ccc(C(C)(C)CC(C)(C)O)c(O)c1>>Cc1ccc2c(c1)OC(C)(C)CC2(C)C | CC(CC(C)(O)C)(C)C1=C(C=C(C=C1)C)O.CC(CC(C)(O)C)(C)C1=C(C=C(C=C1)C)O.S(O)(O)(=O)=O>>CC1(OC2=CC(=CC=C2C(C1)(C)C)C)C | O[C:9]([CH3:10])([CH3:11])[CH2:12][C:13]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:7][c:6]1[OH:8])([CH3:14])[CH3:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[O:8][C:9]([CH3:10])([CH3:11])[CH2:12][C:13]2([CH3:14])[CH3:15] | Cc1ccc(C(C)(C)CC(C)(C)O)c(O)c1 | Cc1ccc2c(c1)OC(C)(C)CC2(C)C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether (intramolecular) | d9641bb5951ac69cb502f22192c733e934905d219b37bbb10d6e5f44cdc5c184 | 0a70c59834af648d4da9cf9d3918e25f9a9a23c33d84d8cfdfd64980b339bbb3 | c1ccc2c(c1)CCCO2 | O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4]-[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[C;D1;H3:3])-[C:4]-[C:5]-[c:6]:[c:7](:[c:9])-[O;H0;D2;+0:8]-1 | null | [] | null | null | null | null | To 2.16 g (11.7 mmol) of 2-(1,1,3-trimethyl-3-hydroxybutyl) 5-methyl-phenol (Compound 88) was added under nitrogen 50 ml of 20% aqueous sulfuric acid. The reaction mixture was heated at reflux for 13 h and then cooled. The organic layer was separated and the aqueous layer was extracted with ether. The organic extracts ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Aromatic alcohol | Ether | null | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | HO- | null | null | null | Cc1ccc(C(C)(C)CC(C)(C)O)c(O)c1>>Cc1ccc2c(c1)OC(C)(C)CC2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c5fd59f9b15f4b71be7ea5f13a3755da | CC(=O)Cl.Cc1ccc2c(c1)OC(C)(C)CC2(C)C>>CC(=O)c1cc2c(cc1C)OC(C)(C)CC2(C)C | [Cl-].[Al+3].[Cl-].[Cl-].CC1(OC2=CC(=CC=C2C(C1)(C)C)C)C.CC1(OC2=CC(=CC=C2C(C1)(C)C)C)C.Cl.C(C)(=O)Cl>>CC1(OC2=CC(=C(C=C2C(C1)(C)C)C(C)=O)C)C | Cl[C:2]([CH3:1])=[O:3].[cH:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[CH3:10])[O:11][C:12]([CH3:13])([CH3:14])[CH2:15][C:16]2([CH3:17])[CH3:18]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[CH3:10])[O:11][C:12]([CH3:13])([CH3:14])[CH2:15][C:16]2([CH3:17])[CH3:18] | CC(=O)Cl.Cc1ccc2c(c1)OC(C)(C)CC2(C)C | CC(=O)c1cc2c(cc1C)OC(C)(C)CC2(C)C | null | null | CCOCC.O.[N+](=O)([O-])C | C-C Coupling | Friedel-Crafts acylation | 638470e28b39a3831ba1cc18812a4a3c900caa75183eda12e0a014574a67f433 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2c(c1)CCCO2 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | null | null | 14 | HOUR | To an ice-bath cooled solution of 1.96 g (9.6 mmol) of 2,2,4,4,7-pentamethyl-chroman (Compound 89) in 30 ml of nitromethane was added under argon 1.059 g (13.5 mmol) of acetyl chloride followed by 1.9 g (14.3 mmol) of aluminum chloride. The reaction mixture was stirred at room temperature for 14 h and then cooled in an... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2 | HCl | CCOCC.O.[N+](=O)([O-])C | null | 14 | CC(=O)Cl.Cc1ccc2c(c1)OC(C)(C)CC2(C)C>CCOCC.O.[N+](=O)([O-])C>CC(=O)c1cc2c(cc1C)OC(C)(C)CC2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8ab7f252cbf94f38a7c5fa1c66be5d0f | CC(=O)c1cc2c(cc1C)OC(C)(C)CC2(C)C>>C#Cc1cc2c(cc1C)OC(C)(C)CC2(C)C | C(C)(C)NC(C)C.CC1(OC2=CC(=C(C=C2C(C1)(C)C)C(C)=O)C)C.CC1(OC2=CC(=C(C=C2C(C1)(C)C)C(C)=O)C)C.C(C)(C)[N-]C(C)C.[Li+].P(=O)(OCC)(OCC)Cl.[Li]CCCC.Cl.[Li]CCCC>>CC1(OC2=CC(=C(C=C2C(C1)(C)C)C#C)C)C | O=[C:2]([CH3:1])[c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH3:9])[O:10][C:11]([CH3:12])([CH3:13])[CH2:14][C:15]2([CH3:16])[CH3:17]>>[CH:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH3:9])[O:10][C:11]([CH3:12])([CH3:13])[CH2:14][C:15]2([CH3:16])[CH3:17] | CC(=O)c1cc2c(cc1C)OC(C)(C)CC2(C)C | C#Cc1cc2c(cc1C)OC(C)(C)CC2(C)C | null | null | C1CCOC1.O.CCCCCC | Functional Group Interconversion | OtherReaction | df4f03d2116228d20bc5d8403092a8dd982f38312b775d7fadf08d78c364384d | 70d06bbe4d921df55900f4b8f7e6e878b9de0b1a93bf34dcf81c33c29d9b3281 | c1ccc2c(c1)CCCO2 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[CH;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | -78 | CELSIUS | 45 | MINUTE | To a solution of 455 mg (4.5 mmol) of disopropylamine in 5 ml of dry THF at -78 degrees C. was added under argon 3 ml of 1.5 M n-BuLi in hexane. The mixture was stirred at -78 degrees C. for a further 45 min and then treated with a solution of 1.07 g (4.3 mmol) of 2,2,4,4,7-pentamethyl-6-acetyl-chroman (Compound 90) in... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkyne | null | null | c1ccc2c(c1)CCCO2 | HO- | C1CCOC1.O.CCCCCC | -78 | 0.75 | CC(=O)c1cc2c(cc1C)OC(C)(C)CC2(C)C>C1CCOC1.O.CCCCCC>C#Cc1cc2c(cc1C)OC(C)(C)CC2(C)C |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6b77fd970be54f8dbe3fb67395b6565b | CC(C)=CC(=O)Cl.Nc1ccc(Br)cc1>>CC(C)=CC(=O)Nc1ccc(Br)cc1 | CCCCCC.CC(=CC(=O)Cl)C.BrC1=CC=C(N)C=C1>>BrC1=CC=C(C=C1)NC(C=C(C)C)=O | Cl[C:5]([CH:4]=[C:2]([CH3:1])[CH3:3])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[CH3:1][C:2]([CH3:3])=[CH:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1 | CC(C)=CC(=O)Cl.Nc1ccc(Br)cc1 | CC(C)=CC(=O)Nc1ccc(Br)cc1 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4](-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 2 | HOUR | To a solution of 9.48 g (80 mmol) of 3,3-dimethylacryloyl chloride in 200 ml of dry THF was added with vigorous shaking a solution of 13.76 g (80 mmol) of 4-bromoaniline in 300 ml of dry THF. The mixture was stood at room temperature for 2 h and then treated with 80 g of ice followed by 200 ml of hexane. The organic la... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | C1CCOC1 | null | 2 | CC(C)=CC(=O)Cl.Nc1ccc(Br)cc1>C1CCOC1>CC(C)=CC(=O)Nc1ccc(Br)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6cb26ad1fba64b678a6b1a50558d49a1 | CC(C)=CC(=O)Nc1ccc(Br)cc1>>CC1(C)CC(=O)Nc2ccc(Br)cc21 | BrC1=CC=C(C=C1)NC(C=C(C)C)=O.BrC1=CC=C(C=C1)NC(C=C(C)C)=O.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Al+3].[Cl-].[Cl-]>>CC1(CC(NC2=CC=C(C=C12)Br)=O)C | [CH3:1][C:2]([CH3:3])=[CH:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]21 | CC(C)=CC(=O)Nc1ccc(Br)cc1 | CC1(C)CC(=O)Nc2ccc(Br)cc21 | null | null | null | C-C Coupling | OtherReaction | aea010e81c6715af41577808b3395b1a500e0b61256ebfb3a34fc3616fdf9072 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1CCc2ccccc2N1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12] | null | [] | 130 | CELSIUS | 16 | HOUR | To 6.7 g (26.02 mmol) of molten N-(4-bromophenyl)3,3-dimethylacrylamide (Compound 92) (heated to 135 degrees C.) was added 4.15 g (31.09) of aluminum chloride over 25 min. The reaction mixture was stirred at 130 degrees C. for 16 h and then treated with a further 1 g (7.5 mmol) of aluminum chloride. The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | null | null | 130 | 16 | CC(C)=CC(=O)Nc1ccc(Br)cc1>>CC1(C)CC(=O)Nc2ccc(Br)cc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d6ef274af24b45559d2457755ce4ee72 | CC1(C)CC(=O)Nc2ccc(Br)cc21>>CC1(C)CCNc2ccc(Br)cc21 | [H-].[Al+3].[Li+].[H-].[H-].[H-].CC1(CC(NC2=CC=C(C=C12)Br)=O)C.CC1(CC(NC2=CC=C(C=C12)Br)=O)C>>CC1(CCNC2=CC=C(C=C12)Br)C | O=[C:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[c:13]2[c:7]([cH:8][cH:9][c:10]([Br:11])[cH:12]2)[NH:6]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][NH:6][c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]21 | CC1(C)CC(=O)Nc2ccc(Br)cc21 | CC1(C)CCNc2ccc(Br)cc21 | null | null | C1CCOC1.CCOCC | Reduction | Reduction of secondary amides to amines | 788a8d0e853f94332dfbb9ba2e19be4ef643430c4f1cc6825c96cd2edba7148d | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc2c(c1)CCCN2 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | null | [] | null | null | null | null | To 23.5 ml of 1.0 M (23.5 mmol) lithium aluminum hydride in THF, heated to reflux under nitrogen, was added to solution of 4.95 g (19.48 mmol) of 4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline (Compound 93) in 50 ml of dry THF and 100 ml of dry ether via a double-ended needle. The mixture was heated at reflux f... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | Other | C1CCOC1.CCOCC | null | null | CC1(C)CC(=O)Nc2ccc(Br)cc21>C1CCOC1.CCOCC>CC1(C)CCNc2ccc(Br)cc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-093606782439496bbfe40e499def95b8 | C#C[Si](C)(C)C.CC1(C)CCNc2ccc(Br)cc21>>CC1(C)CCNc2ccc(C#C[Si](C)(C)C)cc21 | C[Si](C)(C)C#C.CC1(CCNC2=CC=C(C=C12)Br)C.CC1(CCNC2=CC=C(C=C12)Br)C.C(Cl)Cl>>CC1(CCNC2=CC=C(C=C12)C#C[Si](C)(C)C)C | [CH:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16].Br[c:10]1[cH:9][cH:8][c:7]2[c:18]([cH:17]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][NH:6]2>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][NH:6][c:7]2[cH:8][cH:9][c:10]([C:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][c:18]21 | C#C[Si](C)(C)C.CC1(C)CCNc2ccc(Br)cc21 | CC1(C)CCNc2ccc(C#C[Si](C)(C)C)cc21 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 49d7204f9037d5c527ab7f8fcbc5304c9323062fd2df2bf1de26f30069687930 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)CCCN2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[CH;D1;+0:11]>>[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 50 | CELSIUS | 48 | HOUR | A solution of 1.608 g (6.7 mmol) of 4,4-dimethyl-6-bromo-1,2,3,4-tetrahydroquinoline (Compound 94) in 1.5 ml of triethylamine in a heavy-walled tube was degassed under argon and then treated with 75 mg (0.39 mmol) of cuprous iodide and 150 mg (0.21 mmol) of bis(triphenylphosphine) palladium (II) chloride. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | HBr | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC | 50 | 48 | C#C[Si](C)(C)C.CC1(C)CCNc2ccc(Br)cc21>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>CC1(C)CCNc2ccc(C#C[Si](C)(C)C)cc21 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-413684e85ed6442a83d777131c638b39 | CC1(C)CCNc2ccc(C#C[Si](C)(C)C)cc21>>C#Cc1ccc2c(c1)C(C)(C)CCN2 | CC1(CCNC2=CC=C(C=C12)C#C[Si](C)(C)C)C.CC1(CCNC2=CC=C(C=C12)C#C[Si](C)(C)C)C.[OH-].[K+]>>CC1(CCNC2=CC=C(C=C12)C#C)C | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][NH:14]2>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])([CH3:11])[CH2:12][CH2:13][NH:14]2 | CC1(C)CCNc2ccc(C#C[Si](C)(C)C)cc21 | C#Cc1ccc2c(c1)C(C)(C)CCN2 | null | null | C(C)(C)O | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc2c(c1)CCCN2 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | null | [] | null | null | 36 | HOUR | To a solution of 569 mg (2.21 mmol) of 4,4-dimethyl-6-trimethylsilylethynyl-1,2,3,4-tetrahydroquinoline (Compound 95) in 3 ml of isopropanol was added, under argon, 1 ml of 1N aqueous KOH solution. The reaction mixture was stirred at room temperature for 36 h and the isopropanol was removed under vacuum. The residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccc2c(c1)CCCN2 | Other | C(C)(C)O | null | 36 | CC1(C)CCNc2ccc(C#C[Si](C)(C)C)cc21>C(C)(C)O>C#Cc1ccc2c(c1)C(C)(C)CCN2 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-788057af86b945868d94596518452f80 | CCO.O=C(O)c1ccc(I)cc1>>CCOC(=O)c1ccc(I)cc1 | IC1=CC=C(C(=O)O)C=C1.C(C)O.S(=O)(Cl)Cl>>C(C)OC(C1=CC=C(C=C1)I)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([I:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([I:10])[cH:11][cH:12]1 | CCO.O=C(O)c1ccc(I)cc1 | CCOC(=O)c1ccc(I)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a suspension of 10 g (40.32 mmol) of 4-iodobenzoic acid in 100 ml absolute ethanol was added 2 ml thionyl chloride and the mixture was then heated at reflux for 3 hours. Solvent was removed in vacuo and the residue was dissolved in 100 ml ether. The ether solution was washed with saturated NaHCO3 and saturated NaCl ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.O=C(O)c1ccc(I)cc1>>CCOC(=O)c1ccc(I)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-8a817766383541e695f1bd93a0b40edf | CCO.O=C(O)c1ccc(Cl)nc1>>CCOC(=O)c1ccc(Cl)nc1 | ClC1=NC=C(C(=O)O)C=C1.C(C)O.C1(CCCCC1)N=C=NC1CCCCC1.CN(C)C1=NC=CC=C1>>ClC1=NC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[n:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[n:11][cH:12]1 | CCO.O=C(O)c1ccc(Cl)nc1 | CCOC(=O)c1ccc(Cl)nc1 | null | null | C(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C;D1;H3:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | A mixture of 15.75 g (0.1 mol) 6-chloronicotinic acid, 6.9 g (0.15 mol) ethanol, 22.7 g (0.11 mol) dicyclohexylcarbodiimide and 3.7 g dimethylaminopyridine in 200 ml methylene chloride was heated at reflux for 2 hours. The mixture was allowed to cool, solvent removed in vacuo and the residue subjected to flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | null | CCO.O=C(O)c1ccc(Cl)nc1>C(Cl)Cl>CCOC(=O)c1ccc(Cl)nc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-df4dd9f6709d4060bb9662c908f9c9e0 | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2.CCOC(=O)c1ccc(Cl)nc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)S3)nc1 | CC1(SC2=CC=C(C=C2C(C1)(C)C)C#C)C.CC1(SC2=CC=C(C=C2C(C1)(C)C)C#C)C.ClC1=NC=C(C(=O)OCC)C=C1.ClC1=NC=C(C(=O)OCC)C=C1>>CC1(SC2=CC=C(C=C2C(C1)(C)C)C#CC1=NC=C(C(=O)OCC)C=C1)C | [CH:10]#[C:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([CH3:19])([CH3:20])[CH2:21][C:22]([CH3:23])([CH3:24])[S:25]2.Cl[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:27][n:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]... | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2.CCOC(=O)c1ccc(Cl)nc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)S3)nc1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccn1)c1ccc2c(c1)CCCS2 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:8]-[C:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 55 | CELSIUS | 60 | HOUR | A solution of 232 mg (1.01 mmol) of 2,2,4,4-tetramethyl-6-ethynylthiochroman (Compound 3) and 190 mg (1.03 mmol) of ethyl 6-chloro-nicotinate (Compound 98) in 2 ml of triethylamine was placed in a heavy-walled glass tube, degassed, placed under argon and then treated with a powdered mixture of 53 mg (0.28 mmol) of cupr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCCS2 | HCl | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC | 55 | 60 | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2.CCOC(=O)c1ccc(Cl)nc1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)S3)nc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-63143f8bc47845178483dc51a00282c1 | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)O2.CCOC(=O)c1ccc(Cl)nc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)O3)nc1 | CC1(OC2=CC=C(C=C2C(C1)(C)C)C#C)C.CC1(OC2=CC=C(C=C2C(C1)(C)C)C#C)C.ClC1=NC=C(C(=O)OCC)C=C1.ClC1=NC=C(C(=O)OCC)C=C1>>CC1(OC2=CC=C(C=C2C(C1)(C)C)C#CC1=NC=C(C(=O)OCC)C=C1)C | [CH:10]#[C:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([CH3:19])([CH3:20])[CH2:21][C:22]([CH3:23])([CH3:24])[O:25]2.Cl[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:27][n:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]... | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)O2.CCOC(=O)c1ccc(Cl)nc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)O3)nc1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccn1)c1ccc2c(c1)CCCO2 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:8]-[C:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 55 | CELSIUS | 80 | HOUR | A solution of 233 mg (1.09 mmol) of 2,2,4,4-tetramethyl-6-ethynylchroman (Compound 5) and 209 mg (1.09 mmol) of ethyl 6-chloronicotinate (Compound 98) in 1 ml of triethylamine was degassed and then treated under argon with a powdered mixture of 50 mg (0.26 mmol) of cuprous iodide and 100 mg (0.14 mmol) of bis(triphenyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2c(c1)CCCO2 | HCl | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC | 55 | 80 | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)O2.CCOC(=O)c1ccc(Cl)nc1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)O3)nc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-91b8bb89ed7c42379155d02f724bb0c7 | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2.CCOC(=O)c1ccc(I)cc1>>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)S3)cc1 | CC1(SC2=CC=C(C=C2C(C1)(C)C)C#C)C.CC1(SC2=CC=C(C=C2C(C1)(C)C)C#C)C.IC1=CC=C(C(=O)OCC)C=C1.IC1=CC=C(C(=O)OCC)C=C1>>CC1(SC2=CC=C(C=C2C(C1)(C)C)C#CC1=CC=C(C(=O)OCC)C=C1)C | [CH:10]#[C:11][c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[C:18]([CH3:19])([CH3:20])[CH2:21][C:22]([CH3:23])([CH3:24])[S:25]2.I[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:27][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][cH:14][c:15]3[c:16]([cH:17]2)[C:18]... | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2.CCOC(=O)c1ccc(I)cc1 | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)S3)cc1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccc2c(c1)CCCS2)c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:8]-[C:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 40 | HOUR | A solution of 110.7 mg (0.481 mmol) of 2,2,4,4,-tetramethyl-6-ethynylthiochroman (Compound 3) and 142.3 mg (0.516 mmol) of ethyl 4-iodobenzoate (Compound 97) in 2 ml of triethylamine was placed in a heavy walled glass tube and degassed under argon. The mixture was then treated with a finely ground mixture of 42 mg (0.2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCCS2 | HI | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC | null | 40 | C#Cc1ccc2c(c1)C(C)(C)CC(C)(C)S2.CCOC(=O)c1ccc(I)cc1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(C)(C)S3)cc1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-268b5629ab3849f890d911d8df2bb683 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-fa96c0a11fd64fd4b77113a1be91640b | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-c81bab83314a47db87e8b8809ef91417 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-01e7218d0d9042f6bb980d3c55b949be | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-15f1bac3436146ea94022d35f164d4f5 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-64828f6c8da24f54941fe2a4518be318 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-039db69849d0448baa4933c8edcbfd3d | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | [B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-2996dfdd337244988de62e12bd857f58 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccccc1P(c2ccccc2)c3ccccc3 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-98740ba1c61e42afbf7f7d12f038bff6 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-] | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-d3bf215cf76441e4922064905afd536f | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-d873f030d895438099c6eddf52b36838 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1cc2ccc3cccnc3c2nc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-a04c4ae6f7834ea98dbd4f1d508ee6ee | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-749bbb237d814fc2a5e26e3d398dad8c | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-3315fc7c2c4346b38f7327abd20f4727 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-714db71d31474721b0d116c1531517da | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-54b9a7cd21a44d239130a5392901a794 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-14f33e924ede436686e3bb3ff049880c | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-496079031890470ca91ea1e08184e87e | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-3aeaaaa9d1cb4451935d5a3f1001577e | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | [B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-83cbd14a71fe499885cdb990576dd464 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccccc1P(c2ccccc2)c3ccccc3 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-076a73e767944927bf34e7ae507da5e2 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-] | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-d0b9063e2d014144bdfdc54e3fe28d5b | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-f05a3a67e19e4c0994dc6bb3ecf61cc0 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1cc2ccc3cccnc3c2nc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-4abcb5a3c1fc4044843c5fd90ceba179 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-3646d2adc6594cf58c47dcf81bb96194 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-edd18fbaef9e4aefbdfa671a3a538296 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-abe7279d16ce4b098964ac7a32957785 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-da7f5371c67a4aba8fa7823c6f802521 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-9910a16faee0401ea0538392be5dad81 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-b19af635309b426797bc8886e409bd8a | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-6a7177f9c52d4a3eab8bddcc1aebb6e1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | [B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-1b49ec5f9b284ff1a1a0b9006e48ec55 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccccc1P(c2ccccc2)c3ccccc3 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-d560178d1d62499ea17700ba128cd064 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-] | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-6c0d11e56efd4829895533cb0a7e0bb9 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-bbb8a98a95df4c53b55a2d548e0b3319 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1cc2ccc3cccnc3c2nc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-27d74db70f024daca00a793a73b106bd | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-c69520efa98f4cf1a2e508bf197389c5 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-dea4c62ef9b04abbb50ae4714624c4f8 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-cbc221e748a241d79a69fccbc4a9a86e | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-45a6d236ed2c489a95bf181273228ba8 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-f1878e25cd174fc19a012690d71a341b | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-86e1aba7f287472ab5011469f615e063 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-d26dbd693bfe4f539ea4025c6f891d3c | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | [B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-ec198f10c6b54c69a55df9579fdfe8d7 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccccc1P(c2ccccc2)c3ccccc3 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-cd7480ef50fb4667b553bb6aa842fa7d | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-] | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-79fb01b428084f0abbf6732d602bd211 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-8ded12783f644b7d9d2cfbc9c5a27d5b | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1cc2ccc3cccnc3c2nc1 | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-fad5b04a99eb4e54bd675e634380c5ff | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C | Cc1ccccc1 | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.Cc1ccccc1 | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.Cc1ccccc1>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-908f60ae11374d9781a45aebc2d3da52 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-4eecde1a13b9483b9b39152b407bb80b | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-90e4154252bb4259b420235d8ad32459 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-d4bcee2598eb43d9a0f56efeb9f9b7d0 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-bdb5fdf52126448d9c5520d49d027708 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-e3906835aa8f470e929acdd90809a695 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-6f5a514f400c425c852e36bf2039d7ee | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | [B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.[B-](F)(F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-e176c4131c5943bba40ff877a2a85b79 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1ccccc1P(c2ccccc2)c3ccccc3 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1ccccc1P(c2ccccc2)c3ccccc3.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-8ffba729b25e40b0a2fe135e8449174c | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-] | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CC(C)(C)[O-].[K+].CC1=CC(=C(C(=C1)C)N2C=C[N+](=C2)C3=C(C=C(C=C3C)C)C)C.[Cl-].CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-e6815de2054c42cea8e81cd3c1cba50b | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.CN(C)c1ccccc1c2ccccc2P(C3CCCCC3)C4CCCCC4.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-4b5782904a014c9fbd65a5ca303bf47f | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | c1cc2ccc3cccnc3c2nc1 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.c1cc2ccc3cccnc3c2nc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-8f2de4d875324efeaff0b0db009f4afd | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.F[C:1](F)(F)S(=[O:30])([O:34][c:33]1[cH:14][cH:13][cH:12][cH:11][cH:32]1)=[O:38]>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25]... | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 2a9a1b3e68be0503d570bab2e98f28be18d0a929b3a09d20ff6198a3915301b6 | 852485e10e7686869539835249e914b9929f0612a04542a2db4929e2f4452c1d | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | F-[C;H0;D4;+0:1](-F)(-F)-S(=[O;H0;D1;+0:2])(=[O;H0;D1;+0:3])-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1.[C;D1;H2:11]=[CH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H2:11]=[C;H0;D3;+0:12](-[c:13](:[c:14]):[c:15])-[c:16](:[c:17]):[c:18].[C;D1;H3:19]-[O;H0;D2;+0:2]-[c:20]1:[c:21]:[c:... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Triflate.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.O=S(=O)(Oc1ccccc1)C(F)(F)F>CCN(CC)CC.O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-2f3b353791224a5e8c728712369a0147 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1 | CN(C)C=O | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.FC(F)(F)c1ccc(N2CP(c3ccccc3)CN(c3ccc(C(F)(F)F)cc3)CP(c3ccccc3)C2)cc1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-8cbd9c3811214ee7973259a8b5fee219 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2 | CN(C)C=O | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.FC(F)(F)C(C=C1)=CC=C1N2CP(C3CCCCC3)CN(C4=CC=C(C(F)(F)F)C=C4)CP(C5CCCCC5)C2.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-43b322e6affe4a8caeef5b28a5f92100 | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1 | CN(C)C=O | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.CC(C)(C)P1CN(C2=CC=C(C(F)(F)F)C=C2)CP(C(C)(C)C)CN(C3=CC=C(C(F)(F)F)C=C3)C1.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
ord_dataset-0316886541d9435489859c2ad7edc863 | ord-d0e73775f0b04c0dbd9fc011b7a038af | C=Cc1ccccc1.Ic1ccccc1>>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | C=Cc1ccccc1.c1ccc(cc1)I>>COc1cc(OC)cc(OC)c1.C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1 | [CH2:15]=[CH:16][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.I[c:33]1[cH:32][cH:1][cH:40][cH:37][cH:36]1>>[CH:1](=[CH:2]/[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)\[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[CH2:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:29][O:30]... | C=Cc1ccccc1.Ic1ccccc1 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 | CCN(CC)CC | C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4 | CN(C)C=O | Aromatic Heterocycle Formation | Heck terminal vinyl | 87942ebd0c4e9d22481d1ede8665c868dd2cefe94eb63a5ecee60c2f5d1a29e2 | b413d32c039c1306ae73738879382e3661dd723f900f84dc1362dca9e8516744 | C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1.[C;D1;H2:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:12]-[c:13]1:[cH;D2;+0:6]:[c;H0;D3;+0:1](-[#8:14]-[C;D1;H3:15]):[c:2]:[c;H0;D3;+0:3](-[#8:16]-[C;D1;H3:17]):[cH;D2;+0:4]:1.[C;D1;H2:7]=[C;H0;D3;+0:8](-[c:18](:[c:19]):[c:20])-[c:9](:[c:10]):[... | null | [] | 85 | CELSIUS | 16 | HOUR | Environment: GLOVE_BOX Environment details: nitrogen atmosphere | null | null | Aromatic halide.Vinyl | Ether.Ether.Ether.Vinyl | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | I- | CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CN(C)C=O | 85 | 16 | C=Cc1ccccc1.Ic1ccccc1>CCN(CC)CC.C1=CC=C(C=C1)P(CCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.CN(C)C=O>C(=C/c1ccccc1)\c1ccccc1.C=C(c1ccccc1)c1ccccc1.COc1cc(OC)cc(OC)c1 |
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