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-c31cb9b44c404c10ba3aa533aa079e2b | ord-c740aad84a644a7b8f32246156b14223 | C=CCBr.COC(CNC(=O)OCc1ccccc1)OC>>C=CCN(CC(OC)OC)C(=O)OCc1ccccc1 | COC(CNC(OCC1=CC=CC=C1)=O)OC.C(C=C)Br.[OH-].[Na+]>>C(C=C)N(C(OCC1=CC=CC=C1)=O)CC(OC)OC | Br[CH2:3][CH:2]=[CH2:1].[NH:4]([CH2:5][CH:6]([O:7][CH3:8])[O:9][CH3:10])[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]([O:7][CH3:8])[O:9][CH3:10])[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=CCBr.COC(CNC(=O)OCc1ccccc1)OC | C=CCN(CC(OC)OC)C(=O)OCc1ccccc1 | null | [Cl-].C[N+](CCCC)(CCCC)CCCC | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9f7a278cd5a191722d3eecc8371d7231da3fad2a3edd5ef5de754861b04320e0 | 98c73e1c03b612cc551f19f8f11205127745c589dc895b7127fa7c2738e6ad4e | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8](-[C:9]-[C:10])-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3] | null | [] | 16 | CELSIUS | 15 | MINUTE | The solution of Example 4A in toluene (343 Kg) was charged to a 200-gallon reactor followed by addition of allyl bromide (41.5 Kg) and methyltributylammonium chloride (8.3 Kg). The mixture was stirred for 15 minutes, cooled to 16° C., and treated with 50% NaOH solution (296.9 Kg) slowly over 1 hour while maintaining th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester.Allyl | null | null | c1ccccc1 | HBr | [Cl-].C[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C | 16 | 0.25 | C=CCBr.COC(CNC(=O)OCc1ccccc1)OC>[Cl-].C[N+](CCCC)(CCCC)CCCC.C1(=CC=CC=C1)C>C=CCN(CC(OC)OC)C(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be69af70a02f441cb1e4ee650e3d1be1 | Cl.O=[N+]([O-])c1ccc(O)nc1>>O=[N+]([O-])c1cnc(O)c(Cl)c1 | Cl.OC1=NC=C(C=C1)[N+](=O)[O-].Cl(=O)(=O)[O-].[K+]>>ClC=1C(=NC=C(C1)[N+](=O)[O-])O | [ClH:10].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]([OH:8])[cH:9][cH:11]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]([OH:8])[c:9]([Cl:10])[cH:11]1 | Cl.O=[N+]([O-])c1ccc(O)nc1 | O=[N+]([O-])c1cnc(O)c(Cl)c1 | null | null | O | Functional Group Addition | Chlorination | 7c108e53aa6849672ac0ea1998cfd24df7835b0d1bc5738d16f4d561a472c88e | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccncc1 | [ClH;D0;+0:1].[O;D1;H1:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:7]:[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[O;D1;H1:2] | null | [] | 53 | CELSIUS | null | null | Concentrated hydrochloric acid (239 g) was added to 2-hydroxy-5-nitropyridine (40.0 g). The resulting slurry was heated to 53° C., and stirred until all the solids dissolved. To this was slowly added a solution of potassium chlorate (14.0 g) in water (250 g), while maintaining the temperature between 55° C. and 59° C. ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | null | O | 53 | null | Cl.O=[N+]([O-])c1ccc(O)nc1>O>O=[N+]([O-])c1cnc(O)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24b9af19f3274d65838d2f2d70249021 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc(O)c(Cl)c1>>O=[N+]([O-])c1cnc(Cl)c(Cl)c1 | ClC=1C(=NC=C(C1)[N+](=O)[O-])O.C(C)#N.P(=O)(Cl)(Cl)Cl>>ClC1=NC=C(C=C1Cl)[N+](=O)[O-] | O=P(Cl)(Cl)[Cl:8].O[c:7]1[n:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:11][c:9]1[Cl:10]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11]1 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc(O)c(Cl)c1 | O=[N+]([O-])c1cnc(Cl)c(Cl)c1 | null | null | O | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | ab85b19a1f19bdb0596b983dc6471067aedf5e7b894e737e6d16cd077bd81b42 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccncc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[Cl;D1;H0:6]):[c:7]>>[Cl;D1;H0:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[#7;a:3]:[c:4] | null | [] | 80 | CELSIUS | 15 | HOUR | A mixture of 3-chloro-2-hydroxy-5-nitropyridine (36.0 g), acetonitrile (72 mL), and phosphorus oxychloride (37.5 g) was heated to 80° C. The reaction was then stirred at this temperature for about 15 hours. After cooling the reaction to 40° C., water (27 g) was added, while maintaining the temperature below 70° C. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | O | 80 | 15 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc(O)c(Cl)c1>O>O=[N+]([O-])c1cnc(Cl)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91f95e92dd7a4fe2822edbf52379784b | C1CCOC1.CCO.O.O=[N+]([O-])c1cnc(Cl)c(Cl)c1>>COC(CNc1cnc(Cl)c(Cl)c1)OC | O.C(C)O.C(C)(=O)O.O1CCCC1.ClC1=NC=C(C=C1Cl)[N+](=O)[O-].O1CCCC1.O.O1CCCC1>>ClC=1C=C(C=NC1Cl)NCC(OC)OC | C1OC[CH2:4][CH2:3]1.[CH2:1]([OH:2])[CH3:15].[OH2:14].O=[N+:5]([O-])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]([Cl:12])[cH:13]1>>[CH3:1][O:2][CH:3]([CH2:4][NH:5][c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]([Cl:12])[cH:13]1)[O:14][CH3:15] | C1CCOC1.CCO.O.O=[N+]([O-])c1cnc(Cl)c(Cl)c1 | COC(CNc1cnc(Cl)c(Cl)c1)OC | null | [Ni] | null | Functional Group Interconversion | OtherReaction | 014d6ca251b8ba0e733c2f491062a655d830ddf64271d45cafa3a45c0fd52127 | 3ed6b38eecfee7e072e331a82bda5766bcb18507b27b96753f96232209a5a65c | c1ccncc1 | C1-O-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-1.O=[N+;H0;D3:3](-[O-])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[CH3;D1;+0:9]-[CH2;D2;+0:10]-[OH;D1;+0:11].[OH2;D0;+0:12]>>[CH3;D1;+0:9]-[O;H0;D2;+0:12]-[CH;D3;+0:2](-[CH2;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[O;H0;D2;+0:11]-[CH3;D1;+0:10] | null | [] | null | null | 1 | HOUR | To a Parr bottle was charged Raney Nickel (10.1 g), water (40.0 g), tetrahydrofuran (166.3 g), ethanol (32.0 g) and acetic acid (2.5 g). A solution of 2,3-dichloro-5-nitropyridine (40.0 g) in tetrahydrofuran (40.1 g) was added to the Parr bottle in four portions and the mixture was hydrogenated at 40 psi and 35° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group.Primary alcohol | Ether.Ether.Secondary amine | C1CCOC1 | null | c1ccncc1 | HO- | [Ni] | null | 1 | C1CCOC1.CCO.O.O=[N+]([O-])c1cnc(Cl)c(Cl)c1>[Ni]>COC(CNc1cnc(Cl)c(Cl)c1)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9fab65ac8a284ff0bbf886a608c6fe83 | C=CCBr.COC(CNc1cnc(Cl)c(Cl)c1)OC>>C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1 | O.ClC=1C=C(C=NC1Cl)NCC(OC)OC.C(C=C)Br.[OH-].[Na+]>>C(C=C)N(CC(OC)OC)C=1C=NC(=C(C1)Cl)Cl | Br[CH2:3][CH:2]=[CH2:1].[NH:4]([CH2:5][CH:6]([O:7][CH3:8])[O:9][CH3:10])[c:11]1[cH:12][n:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]([O:7][CH3:8])[O:9][CH3:10])[c:11]1[cH:12][n:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1 | C=CCBr.COC(CNc1cnc(Cl)c(Cl)c1)OC | C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1 | null | [Cl-].C[N+](CCCC)(CCCC)CCCC | C(C)(C)(C)OC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f41840cb514801a9cb1d5daa03acb2d980295bce2299a2397b84c433eee890b2 | 17be7e5233143f3f5efba3e4456f48662a03854e74790b373fce106317c9bff2 | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11] | null | [] | 30 | CELSIUS | 24 | HOUR | To a mixture of (5,6-dichloro-pyridin-3-yl)-(2,2-dimethoxy-ethyl)-amine (190 g), allyl bromide (137.4 g), and methyl tributyl ammonium chloride (23.8 g) in methyl tert-butyl ether (1140 mL) was added 50% aqueous sodium hydroxide (665 mL). This was then stirred at 25-35° C. for about 24 hours. Then water (375 g) and met... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine.Allyl | null | null | c1ccncc1 | HBr | [Cl-].C[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC | 30 | 24 | C=CCBr.COC(CNc1cnc(Cl)c(Cl)c1)OC>[Cl-].C[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC>C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7ff3b8e8a66d40b8b0c76e7b059df3a8 | N[C@H](CO)c1ccccc1>>OC[C@@H](NO)c1ccccc1 | C1=CC=C(C=C1)[C@@H](CO)N.C(C1=CC=C(C=C1)OC)=O.ClC=1C=C(C(=O)OO)C=CC1.O1CCCC1>>ON[C@H](CO)C1=CC=CC=C1 | [OH:1][CH2:2][C@@H:3]([NH2:4])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[OH:1][CH2:2][C@@H:3]([NH:4][OH:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | N[C@H](CO)c1ccccc1 | OC[C@@H](NO)c1ccccc1 | null | null | C(C)(C)(C)OC | Oxidation | OtherReaction | 36bc010da50cb853d290455d74b81c6b7d705bd6d778962ba74a6651f739ef2a | bf2c27da79ae400add70fd2a0037e750b0b23f205d57f49d26532209823c4bae | c1ccccc1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[c:4]>>[C:1]-[C:2](-[c:4])-[NH;D2;+0:3]-[O;D1;H1:5] | null | [] | 0 | CELSIUS | 3 | HOUR | A solution of (S)-phenylglycinol (15 g) and p-anisaldehyde (16.4 g) in methyl tert-butyl ether (150 mL) was heated to reflux, with a Dean-Stark trap attached, for about 3 hours. Tetrahydrofuran (60 mL) was added and the mixture cooled to 0° C. To this was added a solution of m-chloroperoxybenzoic acid (29.8 g) in methy... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | null | null | c1ccccc1 | Other | C(C)(C)(C)OC | 0 | 3 | N[C@H](CO)c1ccccc1>C(C)(C)(C)OC>OC[C@@H](NO)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0b64ee6af274a6b84d05e1bcbe933c0 | C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1>>C=CCN(CC=O)c1cnc(Cl)c(Cl)c1 | C(C=C)N(CC(OC)OC)C=1C=NC(=C(C1)Cl)Cl.ClCCl.Cl>>C(C=C)N(C=1C=NC(=C(C1)Cl)Cl)CC=O | CO[CH:6]([CH2:5][N:4]([CH2:3][CH:2]=[CH2:1])[c:8]1[cH:9][n:10][c:11]([Cl:12])[c:13]([Cl:14])[cH:15]1)[O:7]C>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]=[O:7])[c:8]1[cH:9][n:10][c:11]([Cl:12])[c:13]([Cl:14])[cH:15]1 | C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1 | C=CCN(CC=O)c1cnc(Cl)c(Cl)c1 | null | null | O1CCCC1.O | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccncc1 | C-O-[CH;D3;+0:1](-[C:2]-[#7:3])-[O;H0;D2;+0:4]-C>>[#7:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | 15 | CELSIUS | 4 | HOUR | A solution of allyl-(5,6-dichloro-pyridin-3-yl)-(2,2-dimethoxy-ethyl)-amine (57.2 g) in tetrahydrofuran (443 g) was cooled to 10° C. A solution of concentrated hydrochloric acid (136 g) in water (114 g) was slowly added, maintaining the temperature below 20° C. The reaction was then stirred at 15° C. for about 4 hours.... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccncc1 | HO- | O1CCCC1.O | 15 | 4 | C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1>O1CCCC1.O>C=CCN(CC=O)c1cnc(Cl)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5034aacce47f4791ad7e311d6c37aec7 | N[C@@H]1CN(c2cnc(Cl)c(Cl)c2)C[C@@H]1CO>>Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl | N[C@H]1[C@H](CN(C1)C=1C=NC(=C(C1)Cl)Cl)CO.S(=O)(Cl)Cl.O>>ClC=1C=C(C=NC1Cl)N1C[C@@H]2CN[C@@H]2C1 | O[CH2:8][C@H:7]1[CH2:6][N:5]([c:4]2[cH:3][c:2]([Cl:1])[c:14]([Cl:15])[n:13][cH:12]2)[CH2:11][C@H:10]1[NH2:9]>>[Cl:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][C@@H:7]3[CH2:8][NH:9][C@@H:10]3[CH2:11]2)[cH:12][n:13][c:14]1[Cl:15] | N[C@@H]1CN(c2cnc(Cl)c(Cl)c2)C[C@@H]1CO | Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl | null | null | COCCOC.CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 5d35acc0b8f3b4b621b508209e76a9ce91ed7a09bd17af2e1e1b4523596d0b15 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1cncc(N2C[C@@H]3CN[C@@H]3C2)c1 | O-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-[C:6]-1-[NH2;D1;+0:7]>>[#7:4]1-[C:5]-[C:6]2-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-2-[C:3]-1 | null | [] | 50 | CELSIUS | 3 | HOUR | (3S,4S)-[4-Amino-1-(5,6-dichloro-pyridin-3-yl)-pyrrolidin-3-yl]-methanol (10 g) was suspended in 1,2-dimethoxyethane (100 mL) and N-methylpyrrolidinone (15 mL). The mixture was heated to 50° C. and then a solution of thionyl chloride (7.9 g) in 1,2-dimethoxyethane (35 mL) was slowly added, while maintaining the tempera... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | C1[NH]C[C@H]2NC[C@@H]12 | c1ccncc1.C1[NH]C[C@H]2NC[C@@H]12 | HO- | COCCOC.CN1C(CCC1)=O | 50 | 3 | N[C@@H]1CN(c2cnc(Cl)c(Cl)c2)C[C@@H]1CO>COCCOC.CN1C(CCC1)=O>Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d9279f1bac24f4d8604ee19c121c8b1 | CCOC(=O)C1CCCNC1.ClCCBr>>CCOC(=O)C1CCN(CCCl)CC1 | C(=O)([O-])[O-].[K+].[K+].N1CC(C(=O)OCC)CCC1.BrCCCl.CC(=O)C>>ClCCN1CCC(CC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:14][CH2:13][NH:9][CH2:8]1.Br[CH2:10][CH2:11][Cl:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][N:9]([CH2:10][CH2:11][Cl:12])[CH2:13][CH2:14]1 | CCOC(=O)C1CCCNC1.ClCCBr | CCOC(=O)C1CCN(CCCl)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 988a4dcba3f18ab40acf6397559fedcf7162a3958adc1dd35699195a758e5373 | e09591825c4808efe257024fb4bbe3690a7cda9ee664fef9727988761bae5b4a | C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8]1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-[NH;D2;+0:12]-[CH2;D2;+0:13]-1>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8]1-[CH2;D2;+0:10]-[C:11]-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3])-[CH2;D2;+0:13]-[CH2;D2;+0:9]-1 | 38.6 | [{"value": 38.6, "product": "ClCCN1CCC(CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of ethyl nipecotate (20.0 mL, 130 mmol) in acetone (180 mL) was added 1-bromo-2-chloroethane (21.6 mL, 260 mmol) followed by anhydrous K2CO3 (27.12 g, 196 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (75 mL) and extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Ester.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HBr | null | null | 24 | CCOC(=O)C1CCCNC1.ClCCBr>>CCOC(=O)C1CCN(CCCl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-76a37454e8034072be96957a325b7d0d | CCOC(=O)C1CCN(CCCl)CC1>>CCOC(=O)C12CCN(CC1)CC2 | ClCCN1CCC(CC1)C(=O)OCC.[Li+].CC(C)[N-]C(C)C>>N12CCC(CC1)(CC2)C(=O)OCC | Cl[CH2:13][CH2:12][N:9]1[CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:11][CH2:10]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]12[CH2:7][CH2:8][N:9]([CH2:10][CH2:11]1)[CH2:12][CH2:13]2 | CCOC(=O)C1CCN(CCCl)CC1 | CCOC(=O)C12CCN(CC1)CC2 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 2bd49a075b6994fff65e60c771472506f6f3684189e4249374b018412fdadf79 | e2072b513d16b3f8a4f047ad38a1d6ba3729e124ecb5f77bb47b58b6d8e00ecf | C1CN2CCC1CC2 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3]1-[C:4]-[C:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10])-[C:11]-[C:12]-1>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:6]12-[C:5]-[C:4]-[#7:3](-[C:2]-[CH2;D2;+0:1]-1)-[C:12]-[C:11]-2 | 95.7 | [{"value": 95.7, "product": "N12CCC(CC1)(CC2)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "N12CCC(CC1)(CC2)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl 1-(2-chloroethyl)-4-piperidinecarboxylate (20.42 g, 92.9 mmol) in THF (600 mL) was cooled to −50° C. under Ar. LDA (2.0 M in heptane/THF/ethyl benzene, 70 mL, 140 mmol) was slowly added to the solution at −50° C. over 25 min. The reaction was allowed to warm up to room temperature over 16 h. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | C1CC[NH]CC1 | C1CN2CCC1CC2 | C1CN2CCC1CC2 | HCl | C1CCOC1 | null | null | CCOC(=O)C1CCN(CCCl)CC1>C1CCOC1>CCOC(=O)C12CCN(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41beb49bbcac4cda9b59d6f424b24278 | CCOC(=O)C12CCN(CC1)CC2.[Li][c]1ccccc1>>OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | C1(=CC=CC=C1)[Li].N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2 | O([C:2](=[O:1])[C:15]12[CH2:16][CH2:17][N:18]([CH2:3][CH2:20]1)[CH2:21][CH2:22]2)[CH2:5][CH3:6].[Li][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:19][CH2:20]1)[CH2:21][CH2:22]2 | CCOC(=O)C12CCN(CC1)CC2.[Li][c]1ccccc1 | OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | a6d1beaf85332741c51057f17811c02a62b32807d2718650e00959e3e7e6e99e | d0784a3c81eac322a309102e03de8be1dab5a811461f48355f7f61ab49bc6e8f | c1ccc(C(c2ccccc2)C23CCN(CC2)CC3)cc1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-O-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]12-[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10]-1)-[CH2;D2;+0:11]-[CH2;D2;+0:12]-2.[Li]-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[OH;D1;+0:4]-[C;H0;D4;+0:3](-[c;H0;D3;+0:11]1:[c:18]:[cH;D2;+0:2]:[cH;D2;+0:1]:[c:19]:[c:20]:1)(-[c;H0;D3;+0:13](:[c:14]:[... | 32.7 | [{"value": 32.7, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of phenyllithium (1.5-1.7 M in 70 cyclohexane/30 ether, 20.0 mL, 32 mmol) was chilled down to −30° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (1.51 g, 8.23 mmol) in THF (20 mL) was slowly added to the reaction mixture at −30° C. over 25 min. The reaction was allowed to warm up to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amine.Aryl lithium | Tertiary alcohol.Tertiary amine | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | Li | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.[Li][c]1ccccc1>C1CCOC1>OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4baac701ad1747d0b121f583695158bc | BrCCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCC1=CC=CC=C1>>[Br-].OC(C12CC[N+](CC1)(CC2)CCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[Br:31].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:27][CH2:28]1)[CH2:29][CH2:30]2>>[OH:1][C: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:... | BrCCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCc3ccccc3)(CC1)CC2.[Br-] | null | null | CS(=O)C.CC#N.C(Cl)Cl.CO | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(CC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[c:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 48.6 | [{"value": 48.6, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.5, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | To a solution of 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0775 g, 0.264 mmol) in CH3CN/DCM/MeOH (2 mL/2 mL/1 mL) was added (2-bromoethyl)benzene (0.38 mL, 2.78 mmol). The solution was allowed to stir at room temperature for 4 days and then concentrated under vacuum to give a white solid. This residue was dissol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CS(=O)C.CC#N.C(Cl)Cl.CO | null | 96 | BrCCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CS(=O)C.CC#N.C(Cl)Cl.CO>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-995230ee17df496999c27d34a78626e4 | BrCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.CC#N.C1(=CC=CC=C1)OCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][O:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[Br:32].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:28][CH2:29]1)[CH2:30][CH2:31]2>>[OH:1][C: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:1... | BrCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] | null | null | CCCCCC.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 68.1 | [{"value": 67.6, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | To a solution of 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.055 0 g, 0.187 mmol) in 2 CH3CN/3 CHCl3 (2.5 mL) was added 2-bromoethyl phenyl ether (0.06 0 g, 0.29 mmol). The solution was stirred at 60° C. for 16 h. The reaction was cooled down to room temperature and then diluted with ethyl acetate and hexane causi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CCCCCC.C(C)(=O)OCC | 60 | 16 | BrCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CCCCCC.C(C)(=O)OCC>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eccd176fbcc0421fbb81fc3ffbef8a5f | BrCC1CC1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3CC3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCC1CC1>>[Br-].C1(CC1)C[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH:20]1[CH2:21][CH2:22]1)[Br:27].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:23][CH2:24]1)[CH2:25][CH2:26]2>>[OH:1][C: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)[C:15]12[CH2:16][CH2:... | BrCC1CC1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3CC3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[N+](CC4CC4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]1-[C:4]-[C:5]-1.[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C:11]-[C:12]>>[Br-;H0;D0:1].[C:6]-[C:7]-[N+;H0;D4:8](-[CH2;D2;+0:2]-[C:3]1-[C:4]-[C:5]-1)(-[C:9]-[C:10])-[C:11]-[C:12] | 11,174.5 | [{"value": 39.9, "product": "[Br-].C1(CC1)C[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11174.5, "product": "[Br-].C1(CC1)C[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0552 g, 0.188 mmol) in 2 CH3CN/3 CHCl3 (2.5 mL) was added (bromomethyl) cyclopropane (0.025 mL, 0.257 mmol). The solution was heated at 60° C. for 16 h, cooled down to room temperature and the solvents evaporated under vacuum. The residue was taken up in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | C1CC1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | 60 | null | BrCC1CC1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3CC3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e17fd00705204c30a0cb972fadafa940 | O=C(CBr)c1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>O=C(C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1ccccc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCC(=O)C1=CC=CC=C1>>[Br-].OC(C12CC[N+](CC1)(CC2)CC(C2=CC=CC=C2)=O)(C2=CC=CC=C2)C2=CC=CC=C2 | [O:1]=[C:2]([CH2:3][Br:32])[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1.[N:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)([CH2:22][CH2:23]1)[CH2:24][CH2:25]2>>[O:1]=[C:2]([CH2:3][N+:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12]... | O=C(CBr)c1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | O=C(C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1ccccc1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 52967c6c525f6fd449388f2f21be62ee27cce2784f49d80eefef6fdd2bffd668 | 9b4d821c54deb0cc19603ec7f579dca6c7b9d0b891b757664ed6185aa11a3daf | O=C(C[N+]12CCC(C(c3ccccc3)c3ccccc3)(CC1)CC2)c1ccccc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5].[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C:11]-[C:12]>>[Br-;H0;D0:1].[C:6]-[C:7]-[N+;H0;D4:8](-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5])(-[C:9]-[C:10])-[C:11]-[C:12] | 43.1 | [{"value": 43.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CC(C2=CC=CC=C2)=O)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CC(C2=CC=CC=C2)=O)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0567 g, 0.193 mmol) and 2-bromo-1-phenylethanone (0.0487 g, 0.245 mmol) in 2 CH3CN/3 CHCl3 (2.5 mL) were reacted to give the desired product (0.0410 g, 43.0%). EI-MS m/z 412(M+) Rt (1.90 min).
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Tertiary amine | Ketone | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | O=C(CBr)c1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>O=C(C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1ccccc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9d737449d1245a0a41492d3ccef342a | BrCCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.C1(=CC=CC=C1)OCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[Br:33].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:29][CH2:30]1)[CH2:31][CH2:32]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:... | BrCCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 86 | [{"value": 86.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.045 g, 0.153 mmol) and 3-bromopropyl phenyl ether (0.035 mL, 0.222 mmol) in 2 CH3CN/3 CHCl3 (3.0 mL) were reacted to give the desired product (0.0662 g, 86.0%). EI-MS m/z 428(M+) Rt (1.97 min).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de214945cab1473d9f877d108e9051bc | BrCCCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCCOc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.C1(=CC=CC=C1)OCCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH... | BrCCCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCCOc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 64.9 | [{"value": 64.9, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.3, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCCOC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0604 g, 0.206 mmol) and 4-bromobutyl phenyl ether (0.106 g, 0.463 mmol) in 2 CH3CN/3 CHCl3 (5.0 mL) were reacted to give the desired product (0.0649 g, 64.9%). EI-MS m/z 442(M+) Rt (2.13 min).
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCCOc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCCOc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-545c51543b6041fdbc453cda79339b85 | BrCCOC1CCCCO1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOC3CCCCO3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOC1OCCCC1>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2OCCCC2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][O:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27]1)[Br:32].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:28][CH2:29]1)[CH2:30][CH2:31]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:12][... | BrCCOC1CCCCO1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOC3CCCCO3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[N+](CCOC4CCCCO4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 31.6 | [{"value": 31.6, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2OCCCC2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2OCCCC2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0696 g, 0.237 mmol) and 2-[(2-bromoethyl)oxy]tetrahydro-2H-pyran (0.080 mL, 0.529 mmol) in 2 CH3CN/3 CHCl3 (5.0 mL) were reacted to give the desired product (0.0348 g, 31.6%). EI-MS m/z 422(M+) Rt (1.85 min).
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1CCOCC1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOC1CCCCO1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOC3CCCCO3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-019d6a562a5d48b2881352e438f6c0e5 | BrCCCCOCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCCOCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.C1(=CC=CC=C1)COCCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCCOCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][CH2:22][O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[Br:35].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:31][CH2:32]1)[CH2:33][CH2:34]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[c... | BrCCCCOCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCCOCc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 48.3 | [{"value": 48.3, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCCOCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCCOCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0646 g, 0.220 mmol) and 4-bromobutyl phenylmethyl ether (0.090 mL, 0.472 mmol) in 2 CH3CN/3 CHCl3 (5.0 mL) were reacted to give the desired product (0.0531 g, 48.3%). EI-MS m/z 456(M+) Rt (2.09 min).
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCCOCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCCOCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c74f7e464dd9443498d224e9f1ebe27f | BrCCCOCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.C1(=CC=CC=C1)COCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH... | BrCCCOCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOCc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 55.2 | [{"value": 55.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.9, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0677 g, 0.231 mmol) and 3-bromopropyl phenylmethyl ether (0.070 mL, 0.396 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0663 g, 55.2%). EI-MS m/z 442(M+) Rt (2.23 min).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5fca3d9e23d4fc4968430762cb29c69 | BrCCOc1ccc(Br)cc1Br.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOc3ccc(Br)cc3Br)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrC1=C(C=CC(=C1)Br)OCCBr>>[Br-].BrC1=C(C=CC(=C1)Br)OCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][O:21][c:22]1[cH:23][cH:24][c:25]([Br:26])[cH:27][c:28]1[Br:29])[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:1... | BrCCOc1ccc(Br)cc1Br.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOc3ccc(Br)cc3Br)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 52.6 | [{"value": 43.8, "product": "[Br-].BrC1=C(C=CC(=C1)Br)OCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.6, "product": "[Br-].BrC1=C(C=CC(=C1)Br)OCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0557 g, 0.190 mmol) and 2-bromoethyl 2,4-dibromophenyl ether (0.110 g, 0.306 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0525 g, 43.8%). EI-MS m/z 572(M+) Rt (2.26 min).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOc1ccc(Br)cc1Br.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOc3ccc(Br)cc3Br)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12f08366578049c6a7cda4ac3ff1b1ce | BrCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCBr)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCBr>>[Br-].BrCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][CH2:21][Br:22])[Br:27].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:23][CH2:24]1)[CH2:25][CH2:26]2>>[OH:1][C: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)[C:15]12[CH2:16][CH2:17... | BrCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCBr)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 43.1 | [{"value": 43.1, "product": "[Br-].BrCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.0, "product": "[Br-].BrCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0979 g, 0.334 mmol) and 1,3-dibromopropane (0.35 mL, 3.448 mmol) in 2 CH3CN/3 CHCl3 (15.0 mL) were reacted to give the desired product (0.0712 g, 43.1%). EI-MS m/z 415(M+) Rt (1.79 min).
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCBr)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f78c396aec84650930b152e60b939e1 | BrCC1CCCOC1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3CCCCO3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCC1COCCC1.CC#N>>[Br-].OC(C12CC[N+](CC1)(CC2)CC2OCCCC2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH:20]1[CH2:21][CH2:22][CH2:23][O:25][CH2:24]1)[Br:30].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:26][CH2:27]1)[CH2:28][CH2:29]2>>[OH:1][C: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... | BrCC1CCCOC1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3CCCCO3)(CC1)CC2.[Br-] | null | null | null | Functional Group Interconversion | OtherReaction | c250656f88769ba0db4acfd50296f0204cc82a304156bb4421985cb9aee457e4 | 75045b4719bb0f5d807ecf6f80483dc8c5f46632e33aaaca613bb090acc82365 | c1ccc(C(c2ccccc2)C23CC[N+](CC4CCCCO4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[CH;D3;+0:3]1-[C:4]-[C:5]-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:8]-1.[C:9]-[C:10]-[N;H0;D3;+0:11](-[C:12]-[C:13])-[C:14]-[C:15]>>[Br-;H0;D0:1].[C:9]-[C:10]-[N+;H0;D4:11](-[CH2;D2;+0:2]-[CH;D3;+0:3]1-[C:4]-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:8]-[O;H0;D2;+0:7]-1)(-[C:12]-[C:13])-[C:14]-[C:15] | 50.8 | [{"value": 50.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CC2OCCCC2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0677 g, 0.231 mmol) and 3-(bromomethyl)tetrahydro-2H-pyran (0.050 mL, 0.390 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0508 g, 50.8%). EI-MS m/z 392(M+) Rt (1.84 min).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Tertiary amine | Ether | C1CCOCC1.C1CN2CCC1CC2 | C1CCOCC1.C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1CCOCC1.C1C[NH+]2CCC1CC2 | null | null | null | null | BrCC1CCCOC1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3CCCCO3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-243da4e74c72457ebfcc457abec0d338 | BrCC1OCCO1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3OCCO3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCC1OCCO1>>[Br-].O1C(OCC1)C[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH:20]1[O:21][CH2:22][CH2:23][O:24]1)[Br:29].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[OH:1][C: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)[C:15]12[... | BrCC1OCCO1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3OCCO3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[N+](CC4OCCO4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]1-[#8:4]-[C:5]-[C:6]-[#8:7]-1.[C:8]-[C:9]-[N;H0;D3;+0:10](-[C:11]-[C:12])-[C:13]-[C:14]>>[Br-;H0;D0:1].[C:8]-[C:9]-[N+;H0;D4:10](-[CH2;D2;+0:2]-[C:3]1-[#8:4]-[C:5]-[C:6]-[#8:7]-1)(-[C:11]-[C:12])-[C:13]-[C:14] | 12.4 | [{"value": 12.4, "product": "[Br-].O1C(OCC1)C[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.4, "product": "[Br-].O1C(OCC1)C[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0574 g, 0.196 mmol) and 2-(bromomethyl)-1,3-dioxolane (0.040 mL, 0.386 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0112 g, 12.4%). EI-MS m/z 380(M+) Rt (1.64 min).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | C1COCO1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCC1OCCO1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CC3OCCO3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33f2b33e61364cfc8141f2389cc929ac | CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCC>>[Br-].C(C)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH3:1][CH2:2][Br:25].[N:3]12[CH2:4][CH2:5][C:6]([C:7]([OH:8])([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)([CH2:21][CH2:22]1)[CH2:23][CH2:24]2>>[CH3:1][CH2:2][N+:3]12[CH2:4][CH2:5][C:6]([C:7]([OH:8])([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:15]3[cH:16][cH:17][cH:18][cH:1... | CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C;D1;H3:3].[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7]-[C:8])-[C:9]-[C:10]>>[Br-;H0;D0:1].[C:4]-[C:5]-[N+;H0;D4:6](-[CH2;D2;+0:2]-[C;D1;H3:3])(-[C:7]-[C:8])-[C:9]-[C:10] | 54.9 | [{"value": 54.9, "product": "[Br-].C(C)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.5, "product": "[Br-].C(C)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0581 g, 0.198 mmol) and bromoethane (0.030 mL, 0.402 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0434 g, 54.9%). EI-MS m/z 322(M+) Rt (1.56 min).
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-422480ede4c74cc6a11e3d5d62b06b44 | CCCCCCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CCCCCCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCCCCCCC>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCCCCCCC)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][Br:32].[N:10]12[CH2:11][CH2:12][C:13]([C:14]([OH:15])([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)([CH2:28][CH2:29]1)[CH2:30][CH2:31]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N+:10]12[CH2... | CCCCCCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CCCCCCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 45.8 | [{"value": 45.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCCCCCCC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.5, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCCCCCCC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0561 g, 0.191 mmol) and 1-bromononane (0.055 mL, 0.288 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0435 g, 45.8%). EI-MS m/z 420(M+) Rt (2.34 min).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | CCCCCCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>CCCCCCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ddff3183e884720a924a859430299ba | C=CCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>C=CCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCC=C>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCC=C)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][Br:28].[N:6]12[CH2:7][CH2:8][C:9]([C:10]([OH:11])([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)([CH2:24][CH2:25]1)[CH2:26][CH2:27]2>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][N+:6]12[CH2:7][CH2:8][C:9]([C:10]([OH:11])([c:12]3[cH:13][cH:14][cH:15][... | C=CCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | C=CCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4]-[C:5]=[C;D1;H2:6].[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C:12]-[C:13]>>[Br-;H0;D0:1].[C:7]-[C:8]-[N+;H0;D4:9](-[CH2;D2;+0:2]-[C:3]-[C:4]-[C:5]=[C;D1;H2:6])(-[C:10]-[C:11])-[C:12]-[C:13] | 88.6 | [{"value": 88.6, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCC=C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCC=C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0608 g, 0.207 mmol) and 5-bromo-1-pentene (0.045 mL, 0.380 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0806 g, 88.6%). EI-MS m/z 362(M+) Rt (1.88 min).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | C=CCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>C=CCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d6ef788b1cc43fa81d5184ba1ae968f | OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2.OCCBr>>OCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCO>>[Br-].OC(C12CC[N+](CC1)(CC2)CCO)(C2=CC=CC=C2)C2=CC=CC=C2 | [N:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)([CH2:22][CH2:23]1)[CH2:24][CH2:25]2.[OH:1][CH2:2][CH2:3][Br:26]>>[OH:1][CH2:2][CH2:3][N+:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]3[cH:17][cH:1... | OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2.OCCBr | OCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[O;D1;H1:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[O;D1;H1:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 60.1 | [{"value": 60.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCO)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.6, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCO)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0638 g, 0.217 mmol) and 2-bromoethanol (0.035 mL, 0.494 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0541 g, 60.1%). EI-MS m/z 338(M+) Rt (1.42 min).
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2.OCCBr>CC#N>OCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-80b15873140f4d7aab08e719ed82a2af | C=CCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>C=CCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCCC=C>>[Br-].C(CCCC=C)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:29].[N:7]12[CH2:8][CH2:9][C:10]([C:11]([OH:12])([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)([CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][N+:7]12[CH2:8][CH2:9][C:10]([C:11]([OH:12])([c:13]3[cH:14... | C=CCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | C=CCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 67.1 | [{"value": 67.1, "product": "[Br-].C(CCCC=C)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "[Br-].C(CCCC=C)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0637 g, 0.217 mmol) and 6-bromo-1-hexene (0.050 mL, 0.373 mmol) in 2 CH3CN/3 CHCl3 (5.0 mL) were reacted to give the desired product (0.0664 g, 67.1%). EI-MS m/z 376(M+) Rt (1.90 min).
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | C=CCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>C=CCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f840d5f79b2c4d3289099e8d066d7bb2 | CBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrC>>[Br-].OC(C12CC[N+](CC1)(CC2)C)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][Br:24].[N:2]12[CH2:3][CH2:4][C:5]([C:6]([OH:7])([c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)([CH2:20][CH2:21]1)[CH2:22][CH2:23]2>>[CH3:1][N+:2]12[CH2:3][CH2:4][C:5]([C:6]([OH:7])([c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)([CH2... | CBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 4f219f8d05883cff5f9b3c02dabd46d48403e261e4b1908a6bde1cc75217ab51 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH3;D1;+0:2].[C:3]-[C:4]-[N;H0;D3;+0:5](-[C:6]-[C:7])-[C:8]-[C:9]>>[Br-;H0;D0:1].[C:3]-[C:4]-[N+;H0;D4:5](-[CH3;D1;+0:2])(-[C:6]-[C:7])-[C:8]-[C:9] | 88 | [{"value": 88.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0638 g, 0.217 mmol) and bromomethane (2.0 M in t-Butylmethyl ether, 0.250 mL, 0.500 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0739 g, 88.0%). EI-MS m/z 308(M+) Rt (1.58 min).
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | CBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c66fb74f1244c4a9004d316c6e63c7f | COCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>COCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.COCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOC)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][O:2][CH2:3][CH2:4][Br:27].[N:5]12[CH2:6][CH2:7][C:8]([C:9]([OH:10])([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)([CH2:23][CH2:24]1)[CH2:25][CH2:26]2>>[CH3:1][O:2][CH2:3][CH2:4][N+:5]12[CH2:6][CH2:7][C:8]([C:9]([OH:10])([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17... | COCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | COCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 42.8 | [{"value": 42.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.4, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0597 g, 0.203 mmol) and 2-bromoethyl methyl ether (0.030 mL, 0.319 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0372 g, 42.8%). EI-MS m/z 352(M+) Rt (1.69 min).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | COCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>COCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a28a4e28ce0549069ad4357821f0ad95 | O=C1c2ccccc2C(=O)N1CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>O=C1c2ccccc2C(=O)N1CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCN1C(C2=CC=CC=C2C1=O)=O>>[Br-].O=C1N(C(C2=CC=CC=C12)=O)CC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][Br:36].[N:14]12[CH2:15][CH2:16][C:17]([C:18]([OH:19])([c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)([CH2:32][CH2:33]1)[CH2:34][CH2:35]2>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](... | O=C1c2ccccc2C(=O)N1CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | O=C1c2ccccc2C(=O)N1CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | O=C1c2ccccc2C(=O)N1CC[N+]12CCC(C(c3ccccc3)c3ccccc3)(CC1)CC2 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[#7:4](-[C:5]=[O;D1;H0:6])-[C:7]=[O;D1;H0:8].[C:9]-[C:10]-[N;H0;D3;+0:11](-[C:12]-[C:13])-[C:14]-[C:15]>>[Br-;H0;D0:1].[C:9]-[C:10]-[N+;H0;D4:11](-[CH2;D2;+0:2]-[C:3]-[#7:4](-[C:5]=[O;D1;H0:6])-[C:7]=[O;D1;H0:8])(-[C:12]-[C:13])-[C:14]-[C:15] | 51.8 | [{"value": 51.8, "product": "[Br-].O=C1N(C(C2=CC=CC=C12)=O)CC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.6, "product": "[Br-].O=C1N(C(C2=CC=CC=C12)=O)CC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0916 g, 0.312 mmol) and 2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione (0.130 g, 0.512 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted give the desired product (0.0881 g, 51.8%). EI-MS m/z 467(M+) Rt (1.91 min).
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccc2c(c1)C[NH]C2.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | O=C1c2ccccc2C(=O)N1CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>O=C1c2ccccc2C(=O)N1CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aba5bddc494a41f2b0c72f5c1b5aae04 | O=C1c2ccccc2C(=O)N1CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>O=C1c2ccccc2C(=O)N1CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCN1C(C2=CC=CC=C2C1=O)=O>>[Br-].O=C1N(C(C2=CC=CC=C12)=O)CCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][Br:37].[N:15]12[CH2:16][CH2:17][C:18]([C:19]([OH:20])([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)([CH2:33][CH2:34]1)[CH2:35][CH2:36]2>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8... | O=C1c2ccccc2C(=O)N1CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | O=C1c2ccccc2C(=O)N1CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | O=C1c2ccccc2C(=O)N1CCC[N+]12CCC(C(c3ccccc3)c3ccccc3)(CC1)CC2 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11] | 82.4 | [{"value": 82.4, "product": "[Br-].O=C1N(C(C2=CC=CC=C12)=O)CCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "[Br-].O=C1N(C(C2=CC=CC=C12)=O)CCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0861 g, 0.293 mmol) and 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione (0.118 g, 0.440 mmol) in 2 CH3CN/3 CHCl3 (5.0 mL) were reacted to give the desired product (0.1319 g, 82.4%). EI-MS m/z 481(M+) Rt (1.90 min).
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccc2c(c1)C[NH]C2.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | O=C1c2ccccc2C(=O)N1CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>O=C1c2ccccc2C(=O)N1CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f98bd1102bbc4cc99c0b4705f77a43df | BrCCCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCC1=CC=CC=C1>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[Br:32].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:28][CH2:29]1)[CH2:30][CH2:31]2>>[OH:1][C: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... | BrCCCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(CCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 72.2 | [{"value": 72.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0625 g, 0.213 mmol) and (3-bromopropyl)benzene (0.050 mL, 0.329 mmol) in 2 CH3CN/3 CHCl3 (5.0 mL) were reacted to give the desired product (0.0722 g, 72.2%). EI-MS m/z 412(M+) Rt (2.01 min).
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4eb67cd9587a40c89902c12cb89f0bf6 | COCCOCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>COCCOCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOCCOC>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOCCOC)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][Br:30].[N:8]12[CH2:9][CH2:10][C:11]([C:12]([OH:13])([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)([CH2:26][CH2:27]1)[CH2:28][CH2:29]2>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N+:8]12[CH2:9][CH2:10][C:11]([C:12]([OH:13])([c:14... | COCCOCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | COCCOCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:8]-[C:9])(-[C:10]-[C:11])-[C:6]-[C:5].[Br-;H0;D0:4] | 78.8 | [{"value": 78.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCCOC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCCOC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0665 g, 0.227 mmol) and 1-bromo-2-{[2-(methyloxy)ethyl]oxy}ethane (0.05 5 mL, 0.405 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0843 g, 78.8%). EI-MS m/z 396(M+) Rt (1.64 min).
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | COCCOCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>COCCOCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e05a86bfbca41518bccbbbdcc3e93cd | CCOC(=O)CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CCOC(=O)CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCC(=O)OCC>>[Br-].C(C)OC(CCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][Br:31].[N:9]12[CH2:10][CH2:11][C:12]([C:13]([OH:14])([c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)([CH2:27][CH2:28]1)[CH2:29][CH2:30]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][N+:9]12[CH2:10][CH2:11][C:12]([C:... | CCOC(=O)CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CCOC(=O)CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[CH2;D2;+0:6]-[Br;H0;D1;+0:7].[C:8]-[C:9]-[N;H0;D3;+0:10](-[C:11]-[C:12])-[C:13]-[C:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[CH2;D2;+0:6]-[N+;H0;D4:10](-[C:9]-[C:8])(-[C:11]-[C:12])-[C:13]-[C:14].[Br-;H0;D0:7] | 57.9 | [{"value": 57.9, "product": "[Br-].C(C)OC(CCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.5, "product": "[Br-].C(C)OC(CCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0679 g, 0.231 mmol) and ethyl 4-bromobutanoate (0.055 mL, 0.524 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0637 g, 57.9%). EI-MS m/z 408(M+) Rt (1.80 min).
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | CCOC(=O)CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>CCOC(=O)CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfd412060c6344eb95f0afe2468f1c7b | CCOC(=O)C12CCN(CC1)CC2.[Li][c]1cccs1>>OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2 | S1C(=CC=C1)[Li].N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C=2SC=CC2)C=2SC=CC2 | O([C:2](=[O:1])[C:13]12[CH2:14][CH2:15][N:16]([CH2:8][CH2:18]1)[CH2:19][CH2:20]2)[CH2:9][CH3:10].[Li][c:3]1[cH:4][cH:5][cH:6][s:7]1>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:14][CH2:15][N:16]([CH2:17][CH2:18]1)[CH2:19][CH2:20]2 | CCOC(=O)C12CCN(CC1)CC2.[Li][c]1cccs1 | OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 7b98b58fe6a65cd66d96bc209bf655938f2905da698f57787d2ae46902152e85 | d0784a3c81eac322a309102e03de8be1dab5a811461f48355f7f61ab49bc6e8f | c1csc(C(c2cccs2)C23CCN(CC2)CC3)c1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-O-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]12-[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10]-1)-[CH2;D2;+0:11]-[CH2;D2;+0:12]-2.[Li]-[c;H0;D3;+0:13]1:[#16;a:14]:[c:15]:[c:16]:[c:17]:1>>[OH;D1;+0:4]-[C;H0;D4;+0:3](-[c;H0;D3;+0:13]1:[#16;a:14]:[c:15]:[c:16]:[c:17]:1)(-[c;H0;D3;+0:11]1:[#16;a:18]:[c:19]:... | 59.5 | [{"value": 59.5, "product": "N12CCC(CC1)(CC2)C(O)(C=2SC=CC2)C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.5, "product": "N12CCC(CC1)(CC2)C(O)(C=2SC=CC2)C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-thienyllithium (1.0M in THF, 9.10 mL, 9.10 mmol) was chilled down to −30° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.4196 g, 2.289 mmol) in THF (8 mL) was slowly added to the reaction mixture over 20 min. The reaction was allowed to warm up to room temperature over 16 h. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amine.Aryl lithium | Tertiary alcohol.Tertiary amine | c1ccsc1.C1CN2CCC1CC2 | c1ccsc1.c1ccsc1.C1CN2CCC1CC2 | c1ccsc1.c1ccsc1.C1CN2CCC1CC2 | HO-.Li | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.[Li][c]1cccs1>C1CCOC1>OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5faa1e540e0c42608c1ae0357ebc6da3 | BrCCOc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2>>OC(c1cccs1)(c1cccs1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C=2SC=CC2)C=2SC=CC2.C1(=CC=CC=C1)OCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2 | [CH2:17]([CH2:18][O:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[Br:30].[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:14][CH2:15][N:16]([CH2:26][CH2:27]1)[CH2:28][CH2:29]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:14][CH2:... | BrCCOc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2 | OC(c1cccs1)(c1cccs1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] | null | null | CO | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCC[N+]23CCC(C(c4cccs4)c4cccs4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 74.7 | [{"value": 74.7, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.5, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol (0.0693 g, 0.227 mmol) and 2-bromoethyl phenyl ether (0.056 g, 0.279 mmol) in 1 MeOH/1 CHCl3 (3.0 mL) were reacted to give the desired product (0.0822 g, 74.7%). EI-MS m/z 426(M+) Rt (2.00 min).
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccsc1.c1ccsc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CO | null | null | BrCCOc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2>CO>OC(c1cccs1)(c1cccs1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-54f80564a4f54826b8c950069ea4fd25 | BrCCCOc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2>>OC(c1cccs1)(c1cccs1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C=2SC=CC2)C=2SC=CC2.C1(=CC=CC=C1)OCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2 | [CH2:17]([CH2:18][CH2:19][O:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[Br:31].[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:14][CH2:15][N:16]([CH2:27][CH2:28]1)[CH2:29][CH2:30]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:... | BrCCCOc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2 | OC(c1cccs1)(c1cccs1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] | null | null | CO | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4cccs4)c4cccs4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 45.5 | [{"value": 45.4, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.5, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol (0.0578 g, 0.189 mmol) and 3-bromopropyl phenyl ether (0.033 mL, 0.209 mmol) in 1 MeOH/1 CHCl3 (4.0 mL) were reacted to give the desired product (0.0448 g, 45.4%). EI-MS m/z 440(M+) Rt (1.94 min).
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccsc1.c1ccsc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CO | null | null | BrCCCOc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2>CO>OC(c1cccs1)(c1cccs1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18615591e7224aed81e93c6949289383 | BrCCc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2>>OC(c1cccs1)(c1cccs1)C12CC[N+](CCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C=2SC=CC2)C=2SC=CC2.BrCCC1=CC=CC=C1>>[Br-].OC(C12CC[N+](CC1)(CC2)CCC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2 | [CH2:17]([CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[Br:29].[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:14][CH2:15][N:16]([CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:14][CH2:15][N+... | BrCCc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2 | OC(c1cccs1)(c1cccs1)C12CC[N+](CCc3ccccc3)(CC1)CC2.[Br-] | null | null | CO | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(CC[N+]23CCC(C(c4cccs4)c4cccs4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[c:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 3,792.8 | [{"value": 48.9, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3792.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol (0.0658 g, 0.215 mmol) and (2-bromoethyl)benzene (0.050 mL, 0.366 mmol) in 1 MeOH/1 CHCl3 (4.0 mL) were reacted to give the desired product (0.051 4 g, 48.9%). EI-MS m/z 410(M+) Rt (1.83 min).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccsc1.c1ccsc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CO | null | null | BrCCc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2>CO>OC(c1cccs1)(c1cccs1)C12CC[N+](CCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79b302f8ae414f61bf1c49f84a070992 | BrCCCc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2>>OC(c1cccs1)(c1cccs1)C12CC[N+](CCCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C=2SC=CC2)C=2SC=CC2.BrCCCC1=CC=CC=C1>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2 | [CH2:17]([CH2:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[Br:30].[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:14][CH2:15][N:16]([CH2:26][CH2:27]1)[CH2:28][CH2:29]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][s:7]1)([c:8]1[cH:9][cH:10][cH:11][s:12]1)[C:13]12[CH2:14][CH... | BrCCCc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2 | OC(c1cccs1)(c1cccs1)C12CC[N+](CCCc3ccccc3)(CC1)CC2.[Br-] | null | null | CO | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(CCC[N+]23CCC(C(c4cccs4)c4cccs4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 62.3 | [{"value": 62.3, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.3, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol (0.0688 g, 0.225 mmol) and (3-bromopropyl)benzene (0.070 mL, 0.460 mmol) in 1 MeOH/1 CHCl3 (4.0 mL) were reacted to give the desired product (0.0685 g, 62.3%). EI-MS m/z 424(M+) Rt (1.97 min).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccsc1.c1ccsc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CO | null | null | BrCCCc1ccccc1.OC(c1cccs1)(c1cccs1)C12CCN(CC1)CC2>CO>OC(c1cccs1)(c1cccs1)C12CC[N+](CCCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3dcb0f0e983d476ab3b35211f538f30f | Brc1ccsc1.CCOC(=O)C12CCN(CC1)CC2.[Li][CH2]CCC>>CCCC[N+]12CCC(C(O)(c3ccsc3)c3ccsc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(=O)OCC.C(CCC)[Li].BrC1=CSC=C1>>[Br-].C(CCC)[N+]12CCC(CC1)(CC2)C(C2=CSC=C2)(C2=CSC=C2)O | [c:11]1([Br:25])[cH:12][cH:13][s:14][cH:15]1.O([C:9]([C:8]12[CH2:7][CH2:6][N:5]([CH2:22][CH2:21]1)[CH2:24][CH2:17]2)=[O:10])[CH2:20][CH3:16].[Li][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][N+:5]12[CH2:6][CH2:7][C:8]([C:9]([OH:10])([c:11]3[cH:12][cH:13][s:14][cH:15]3)[c:16]3[cH:17][cH:18][s:19][cH:20]3)([... | Brc1ccsc1.CCOC(=O)C12CCN(CC1)CC2.[Li][CH2]CCC | CCCC[N+]12CCC(C(O)(c3ccsc3)c3ccsc3)(CC1)CC2.[Br-] | null | null | CS(=O)C.C1CCOC1.CCOCC.C(C)OCC | Aromatic Heterocycle Formation | OtherReaction | 93bb7afb789cac4882b3ae98e56f8dce01e065dd69b51910e0fb416029c3180c | 66bbd788cf7d4ac2e2187955f80930ff697faa25d594fa103967e0d7a395c4c6 | c1cc(C(c2ccsc2)C23CC[NH+](CC2)CC3)cs1 | [Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1.[CH3;D1;+0:7]-[CH2;D2;+0:8]-O-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C;H0;D4;+0:11]12-[C:12]-[C:13]-[N;H0;D3;+0:14](-[C:15]-[C:16]-1)-[CH2;D2;+0:17]-[CH2;D2;+0:18]-2.[C:19]-[C:20]-[CH2;D2;+0:21]-[Li]>>[Br-;H0;D0:1].[C:19]-[C:20]-[CH2;D2;+0:21]-[N+;H0;D4:14]12-[C:... | 9.4 | [{"value": 9.4, "product": "[Br-].C(CCC)[N+]12CCC(CC1)(CC2)C(C2=CSC=C2)(C2=CSC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.4, "product": "[Br-].C(CCC)[N+]12CCC(CC1)(CC2)C(C2=CSC=C2)(C2=CSC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of n-Butyl lithium (2.5M in hexanes, 5.0 mL, 12.5 mmol) was chilled to −78° C. under Ar. 3-Bromothiophene (1.15 mL, 12.3 mmol) dissolved in ethyl ether (4.0 mL) was slowly added to the reaction mixture. The reaction was stirred for 30 min and then ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.7640 g, 4.16... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Tertiary amine.Alkyl lithium | Tertiary alcohol | c1ccsc1.C1CN2CCC1CC2 | c1ccsc1.c1ccsc1.C1C[NH+]2CCC1CC2 | c1ccsc1.c1ccsc1.C1C[NH+]2CCC1CC2 | HO-.Li | CS(=O)C.C1CCOC1.CCOCC.C(C)OCC | null | 0.5 | Brc1ccsc1.CCOC(=O)C12CCN(CC1)CC2.[Li][CH2]CCC>CS(=O)C.C1CCOC1.CCOCC.C(C)OCC>CCCC[N+]12CCC(C(O)(c3ccsc3)c3ccsc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-971f23f050a44da2bf7265f69b3b618a | BrCCOc1ccccc1.OC(c1ccsc1)(c1ccsc1)C12CCN(CC1)CC2>>OC(c1ccsc1)(c1ccsc1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CSC=C2)C2=CSC=C2.C1(=CC=CC=C1)OCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C2=CSC=C2)C2=CSC=C2 | [CH2:17]([CH2:18][O:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[Br:30].[OH:1][C:2]([c:3]1[cH:4][cH:5][s:6][cH:7]1)([c:8]1[cH:9][cH:10][s:11][cH:12]1)[C:13]12[CH2:14][CH2:15][N:16]([CH2:26][CH2:27]1)[CH2:28][CH2:29]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][s:6][cH:7]1)([c:8]1[cH:9][cH:10][s:11][cH:12]1)[C:13]12[CH2:14][CH2:... | BrCCOc1ccccc1.OC(c1ccsc1)(c1ccsc1)C12CCN(CC1)CC2 | OC(c1ccsc1)(c1ccsc1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] | null | null | CO | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCC[N+]23CCC(C(c4ccsc4)c4ccsc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 54.5 | [{"value": 54.5, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C2=CSC=C2)C2=CSC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.3, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C2=CSC=C2)C2=CSC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(di-3-thienyl)methanol (0.0787 g, 0.258 mmol) and 2-bromoethyl phenyl ether (0.0839 g, 0.417 mmol) in 2 MeOH/3 CHCl3/2 CH3CN (5.0 mL) were reacted to give the desired product (0.0709 g, 54.5%). EI-MS m/z 426(M+) Rt (1.85 min).
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccsc1.c1ccsc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CO | null | null | BrCCOc1ccccc1.OC(c1ccsc1)(c1ccsc1)C12CCN(CC1)CC2>CO>OC(c1ccsc1)(c1ccsc1)C12CC[N+](CCOc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c58e7719e2947228f7f1ba1f63e9b3e | BrCCCOc1ccccc1.OC(c1ccsc1)(c1ccsc1)C12CCN(CC1)CC2>>OC(c1ccsc1)(c1ccsc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CSC=C2)C2=CSC=C2.C1(=CC=CC=C1)OCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CSC=C2)C2=CSC=C2 | [CH2:17]([CH2:18][CH2:19][O:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[Br:31].[OH:1][C:2]([c:3]1[cH:4][cH:5][s:6][cH:7]1)([c:8]1[cH:9][cH:10][s:11][cH:12]1)[C:13]12[CH2:14][CH2:15][N:16]([CH2:27][CH2:28]1)[CH2:29][CH2:30]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][s:6][cH:7]1)([c:8]1[cH:9][cH:10][s:11][cH:12]1)[C:13]12[CH2:... | BrCCCOc1ccccc1.OC(c1ccsc1)(c1ccsc1)C12CCN(CC1)CC2 | OC(c1ccsc1)(c1ccsc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] | null | null | CO | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccsc4)c4ccsc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 44.7 | [{"value": 44.7, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CSC=C2)C2=CSC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.6, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CSC=C2)C2=CSC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4-yl(di-3-thienyl)methanol (0.0808 g, 0.264 mmol) and 3-bromopropyl phenyl ether (0.070 mL, 0.444 mmol) in 2 MeOH/3 CHCl3/2 CH3CN (5.0 mL) were reacted to give the desired product (0.0613 g, 44.7%). EI-MS m/z 440(M+) Rt (2.05 min).
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccsc1.c1ccsc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CO | null | null | BrCCCOc1ccccc1.OC(c1ccsc1)(c1ccsc1)C12CCN(CC1)CC2>CO>OC(c1ccsc1)(c1ccsc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ffa8d6da89ce4e088caa6f56f08216ff | CCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCC>>[Br-].C(CCC)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH3:1][CH2:2][CH2:3][CH2:4][Br:27].[N:5]12[CH2:6][CH2:7][C:8]([C:9]([OH:10])([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)([CH2:23][CH2:24]1)[CH2:25][CH2:26]2>>[CH3:1][CH2:2][CH2:3][CH2:4][N+:5]12[CH2:6][CH2:7][C:8]([C:9]([OH:10])([c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[... | CCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 70.7 | [{"value": 70.7, "product": "[Br-].C(CCC)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.0, "product": "[Br-].C(CCC)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0496 g, 0.169 mmol) and 1-bromobutane (0.030 mL, 0.279 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0509 g, 70.7%). EI-MS m/z 350(M+) Rt (1.83 min).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | CCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>CCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd55fe7a8f634633a9ae7a0f0afdbfc9 | CCCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CCCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCCCC>>[Br-].C(CCCCC)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:29].[N:7]12[CH2:8][CH2:9][C:10]([C:11]([OH:12])([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)([CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N+:7]12[CH2:8][CH2:9][C:10]([C:11]([OH:12])([c:13]3[cH:14... | CCCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CCCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 73 | [{"value": 73.0, "product": "[Br-].C(CCCCC)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "[Br-].C(CCCCC)[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0498 g, 0.170 mmol) and 1-bromohexane (0.040 mL, 0.285 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0562 g, 73.0%). EI-MS m/z 378(M+) Rt (2.09 min).
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | CCCCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>CCCCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e415d81417e942aca724ca551c413cb4 | CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCC>>[Br-].OC(C12CC[N+](CC1)(CC2)CCC)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][CH2:2][CH2:3][Br:26].[N:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)([CH2:22][CH2:23]1)[CH2:24][CH2:25]2>>[CH3:1][CH2:2][CH2:3][N+:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]3[cH:17][cH... | CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C;D1;H3:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C;D1;H3:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 75.1 | [{"value": 75.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0518 g, 0.176 mmol) and 1-bromopropane (0.030 mL, 0.330 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0548 g, 75.1%). EI-MS m/z 336(M+) Rt (1.97 min).
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | CCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>CCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d2e1633250949b888d409e2c88104af | COc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>COc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=C(C=CC=C1)OC>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][CH2:12][Br:35].[N:13]12[CH2:14][CH2:15][C:16]([C:17]([OH:18])([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)([CH2:31][CH2:32]1)[CH2:33][CH2:34]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][... | COc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | COc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11] | 73.5 | [{"value": 73.5, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0467 g, 0.159 mmol) and 1-[(3-bromopropyl)oxy]-2-(methyloxy)benzene (0.0541 g, 0.221 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0625 g, 73.5%). EI-MS m/z 458(M+) Rt (1.96 min).
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | COc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>COc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-569f43f1167a408da33be69a4bb986c6 | OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2.Oc1ccccc1OCCCBr>>Oc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=C(C=CC=C1)O>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)O)(C2=CC=CC=C2)C2=CC=CC=C2 | [N:12]12[CH2:13][CH2:14][C:15]([C:16]([OH:17])([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)([CH2:30][CH2:31]1)[CH2:32][CH2:33]2.[OH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][CH2:11][Br:34]>>[OH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][CH2:11... | OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2.Oc1ccccc1OCCCBr | Oc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 75 | [{"value": 75.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)O)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)O)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0505 g, 0.172 mmol) and 2-[(3-bromopropyl)oxy]phenol (0.0547 g, 0.236 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0675 g, 75.0%). EI-MS m/z 444(M+) Rt (1.91 min).
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2.Oc1ccccc1OCCCBr>CC#N>Oc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c9819f0d63ff406c9ec0ae489e040a95 | BrCCCOc1ccc2ccccc2c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc4ccccc4c3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.C1=C(C=CC2=CC=CC=C12)OCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC1=CC=CC=C1C=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[cH:32]1)[Br:37].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:33][CH2:34]1)[CH2:35][CH2:36]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8... | BrCCCOc1ccc2ccccc2c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc4ccccc4c3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[N+](CCCOc4ccc5ccccc5c4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 63.7 | [{"value": 63.7, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC1=CC=CC=C1C=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC1=CC=CC=C1C=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0472 g, 0.160 mmol) and 3-bromopropyl 2-naphthalenyl ether (0.0618 g, 0.233 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0567 g, 63.7%). EI-MS m/z 478(M+) Rt (2.22 min).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccc2ccccc2c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc4ccccc4c3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b37f44a004549439dfa519a6a73739e | Clc1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(Cl)c3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.ClC=1C=C(C=CC1)OCCCBr>>[Br-].ClC=1C=C(C=CC1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]1)[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH... | Clc1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(Cl)c3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 74.4 | [{"value": 74.4, "product": "[Br-].ClC=1C=C(C=CC1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "[Br-].ClC=1C=C(C=CC1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0479 g, 0.163 mmol) and 3-bromopropyl 3-chlorophenyl ether (0.0552 g, 0.221 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0655 g, 74.4%). EI-MS m/z 462(M+) Rt (2.17 min).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | Clc1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(Cl)c3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0efd0556ec545679e1831747e879aad | BrCCCOc1ccc(Br)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(Br)cc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=CC=C(C=C1)Br>>[Br-].BrC1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][c:26]([Br:27])[cH:28][cH:29]1)[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH... | BrCCCOc1ccc(Br)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(Br)cc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 75.4 | [{"value": 75.4, "product": "[Br-].BrC1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.4, "product": "[Br-].BrC1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0486 g, 0.165 mmol) and 4-bromophenyl 3-bromopropyl ether (0.0630 g, 0.214 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0731 g, 75.4%). EI-MS m/z 506(M+) Rt (2.18 min).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccc(Br)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(Br)cc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94d23a24ee9446ed9f0dfe3890712622 | O=[N+]([O-])c1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>O=[N+]([O-])c1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.[N+](=O)([O-])C1=CC=C(C=C1)OCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)[N+](=O)[O-])(C2=CC=CC=C2)C2=CC=CC=C2 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Br:36])[cH:34][cH:35]1.[N:12]12[CH2:13][CH2:14][C:15]([C:16]([OH:17])([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][C... | O=[N+]([O-])c1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | O=[N+]([O-])c1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 67 | [{"value": 67.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)[N+](=O)[O-])(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)[N+](=O)[O-])(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0468 g, 0.159 mmol) and 3-bromopropyl 4-nitrophenyl ether (0.0550 g, 0.211 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0590 g, 67.0%). EI-MS m/z 473(M+) Rt (2.06 min).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | O=[N+]([O-])c1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>O=[N+]([O-])c1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84bf056e9f2e48368471471482ffa588 | BrCCCOc1ccccc1OCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3OCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=C(C=CC=C1)OCC1=CC=CC=C1>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)OCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1[O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[Br:41].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:37][CH2:38]1)[CH2:39][CH2:40]2>>[OH:1][C:2]([c:3]1[... | BrCCCOc1ccccc1OCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3OCc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COc2ccccc2OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 71.4 | [{"value": 71.4, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)OCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)OCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0492 g, 0.168 mmol) and 1-[(3-bromopropyl)oxy]-2-[(phenylmethyl)oxy]benzene (0.0706 g, 0.220 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0735 g, 71.4%). EI-MS m/z 533(M+) Rt (2.25 mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccccc1OCc1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3OCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e941b5511de4dc9a6a4023515d9aaa7 | BrCCCOc1ccccc1Br.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3Br)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=C(C=CC=C1)Br>>[Br-].BrC1=C(C=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1[Br:29])[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:1... | BrCCCOc1ccccc1Br.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3Br)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 74.8 | [{"value": 74.8, "product": "[Br-].BrC1=C(C=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.3, "product": "[Br-].BrC1=C(C=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0472 g, 0.161 mmol) and 2-bromophenyl 3-bromopropyl ether (0.0648 g, 0.220 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0703 g, 74.8%). EI-MS m/z 507(M+) Rt (2.18 min).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccccc1Br.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3Br)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f7a0d2b328b4ab98dc03cfb546b6567 | BrCCCOc1ccc(OCc2ccccc2)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(OCc4ccccc4)cc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=CC=C(C=C1)OCC1=CC=CC=C1>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)OCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][c:26]([O:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[cH:35][cH:36]1)[Br:41].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:37][CH2:38]1)[CH2:39][CH2:40]2>>[OH:1][C:2]([c:3]... | BrCCCOc1ccc(OCc2ccccc2)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(OCc4ccccc4)cc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COc2ccc(OCCC[N+]34CCC(C(c5ccccc5)c5ccccc5)(CC3)CC4)cc2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 83.3 | [{"value": 83.3, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)OCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)OCC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0479 g, 0.163 mmol) and 1-[(3-bromopropyl)oxy]-4-[(phenylmethyl)oxy]benzene (0.0730 g, 0.227 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0833 g, 83.3%). EI-MS m/z 534(M+) Rt (2.31 mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccc(OCc2ccccc2)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(OCc4ccccc4)cc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-950f911a66794d80b4f95ff98cf5582c | COCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>COCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.COCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][Br:28].[N:6]12[CH2:7][CH2:8][C:9]([C:10]([OH:11])([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)([CH2:24][CH2:25]1)[CH2:26][CH2:27]2>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N+:6]12[CH2:7][CH2:8][C:9]([C:10]([OH:11])([c:12]3[cH:13][cH:14][cH:15][cH:1... | COCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | COCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 86.1 | [{"value": 86.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0632 g, 0.215 mmol) and 3-bromopropyl methyl ether (0.0461 g, 0.301 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0826 g, 86.0%). EI-MS m/z 366(M+) Rt (1.55 min).
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | COCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>COCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97dfc7ff7c754b50a69b372f177ad995 | C=CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>C=CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCC=C>>[Br-].OC(C12CC[N+](CC1)(CC2)CC=C)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH2:1]=[CH:2][CH2:3][Br:26].[N:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)([CH2:22][CH2:23]1)[CH2:24][CH2:25]2>>[CH2:1]=[CH:2][CH2:3][N+:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]3[cH:17][cH... | C=CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | C=CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | d09a56d2afbdd2e5718e534e0d17df4608190d35dfa32e1a5e198fa2031ba8f1 | 180734a17ce97a3891189f3918b4a57acce5242a1c390aec6e4e15882fd77a79 | c1ccc(C(c2ccccc2)C23CC[NH+](CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]=[C;D1;H2:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]=[C;D1;H2:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 79.8 | [{"value": 79.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CC=C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CC=C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0577 g, 0.197 mmol) and 3-bromo-1-propene (0.025 mL, 0.289 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0646 g, 79.8%). EI-MS m/z 334(M+) Rt (1.54 min).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | Allyl | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | C=CCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>C=CC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35f859b94e6346748dd11651bbddf1c7 | COc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>COc1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=CC=C(C=C1)OC>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][Br:35])[cH:33][cH:34]1.[N:11]12[CH2:12][CH2:13][C:14]([C:15]([OH:16])([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)([CH2:29][CH2:30]1)[CH2:31][CH2:32]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:... | COc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | COc1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 77.8 | [{"value": 77.5, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=C(C=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0483 g, 0.164 mmol) and 1-[(3-bromopropyl)oxy]-4-(methyloxy)benzene (0.052 g, 0.21 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0687 g, 77.5%). EI-MS m/z 458(M+) Rt (2.03 min).
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | COc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>COc1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-566378bf37d544efa5523c9047480c61 | CCOC(=O)C12CCN(CC1)CC2.Fc1cc[c]([Mg][Br])cc1>>OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2 | FC1=CC=C(C=C1)[Mg]Br.N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)F)C2=CC=C(C=C2)F | O([C:2](=[O:1])[C:17]12[CH2:18][CH2:19][N:20]([CH2:12][CH2:22]1)[CH2:23][CH2:24]2)[CH2:11][CH3:10].[Br][Mg][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1>>[OH:1][C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)([c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1)[C:17]12[CH2:18][CH2:19][N:20]([CH2:21][CH2:22]1)[CH2:23][CH... | CCOC(=O)C12CCN(CC1)CC2.Fc1cc[c]([Mg][Br])cc1 | OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | fd3e8c1cfc57b2c7712d8187f33262dfcfe80df5f1888717b811e4a78494948a | b445477ea8e5ca1facb860b4766e96514240a7932015b93af713ffe513ccc370 | c1ccc(C(c2ccccc2)C23CCN(CC2)CC3)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH3;D1;+0:6]-[CH2;D2;+0:7]-O-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10]12-[C:11]-[C:12]-[N;H0;D3;+0:13](-[C:14]-[C:15]-1)-[CH2;D2;+0:16]-[CH2;D2;+0:17]-2>>[F;D1;H0:18]-[c:19]1:[c:20]:[c:21]:[c;H0;D3;+0:6](-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:... | 88.9 | [{"value": 88.9, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)F)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)F)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-fluorophenylmagnesiumbromide (1.0 M in THF, 4.4 mL, 4.4 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1973 g, 1.08 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperature and t... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Tertiary amine | Aromatic halide.Tertiary alcohol.Tertiary amine | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | Br-.Mg | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.Fc1cc[c]([Mg][Br])cc1>C1CCOC1>OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb8eedb7725a4b6291c6692a0c587464 | BrCCCOc1ccccc1.OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2>>OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)F)C2=CC=C(C=C2)F.C1(=CC=CC=C1)OCCCBr>>[Br-].FC1=CC=C(C=C1)C(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(O)C2=CC=C(C=C2)F | [CH2:21]([CH2:22][CH2:23][O:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[Br:35].[OH:1][C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)([c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1)[C:17]12[CH2:18][CH2:19][N:20]([CH2:31][CH2:32]1)[CH2:33][CH2:34]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)([c:1... | BrCCCOc1ccccc1.OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2 | OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 65.4 | [{"value": 65.2, "product": "[Br-].FC1=CC=C(C=C1)C(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(O)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "[Br-].FC1=CC=C(C=C1)C(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(O)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl[bis(4-fluorophenyl)]methanol (0.0538 g, 0.163 mmol) and 3-bromopropyl phenyl ether (0.0386 mL, 0.245 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.058 g, 65.2%). EI-MS m/z 464(M+) Rt (2.16 min).
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccccc1.OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2>CC#N>OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CC[N+](CCCOc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c955ba82ef2c4285a04b1094ed5e1717 | BrCCOCc1ccccc1.OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2>>OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)F)C2=CC=C(C=C2)F.C1(=CC=CC=C1)COCCBr>>[Br-].FC1=CC=C(C=C1)C(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(O)C2=CC=C(C=C2)F | [CH2:21]([CH2:22][O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[Br:35].[OH:1][C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)([c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1)[C:17]12[CH2:18][CH2:19][N:20]([CH2:31][CH2:32]1)[CH2:33][CH2:34]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)([c:1... | BrCCOCc1ccccc1.OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2 | OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 66.3 | [{"value": 66.1, "product": "[Br-].FC1=CC=C(C=C1)C(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(O)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "[Br-].FC1=CC=C(C=C1)C(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(O)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl[bis(4-fluorophenyl)]methanol (0.0489 g, 0.148 mmol) and 2-bromoethyl phenylmethyl ether (0.0352 mL, 0.222 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0534 g, 66.1%). EI-MS m/z 464(M+) Rt (1.99 min).
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOCc1ccccc1.OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CCN(CC1)CC2>CC#N>OC(c1ccc(F)cc1)(c1ccc(F)cc1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8efe6b5dfc84309ab6be20983a98ab2 | CCOC(=O)C12CCN(CC1)CC2.COc1ccc[c]([Mg][Br])c1>>COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1 | COC=1C=C(C=CC1)[Mg]Br.N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC | [C:8](=[O:9])([O:15][CH2:14][CH3:13])[C:18]12[CH2:19][CH2:20][N:21]([CH2:10][CH2:23]1)[CH2:24][CH2:25]2.[Br][Mg][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]([OH:9])([c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17]2)[C:18]23[CH2:19][CH2:20][N:21]([CH2:22][... | CCOC(=O)C12CCN(CC1)CC2.COc1ccc[c]([Mg][Br])c1 | COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 409bdbd467bcfabab9c88745e89b7dfe92d1563bc4fc2d6c65216990622bafe1 | 756cff41d8fd571671874e8db19cfa05bd64ad8d65a329d1a73967c00e752fae | c1ccc(C(c2ccccc2)C23CCN(CC2)CC3)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH3;D1;+0:6]-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[C:11]12-[C:12]-[C:13]-[N;H0;D3;+0:14](-[C:15]-[C:16]-1)-[CH2;D2;+0:17]-[CH2;D2;+0:18]-2>>[C;D1;H3:19]-[O;H0;D2;+0:8]-[c;H0;D3;+0:7]1:[c:20]:[c;H0;D3;+0:17](-[C;H0;D4;+0:9](-[OH;D1;+0:10])(-[c;... | 92.9 | [{"value": 92.9, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(methyloxy)phenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1608 g, 0.877 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Tertiary amine | Ether.Tertiary alcohol.Tertiary amine | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | Br-.Mg | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.COc1ccc[c]([Mg][Br])c1>C1CCOC1>COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb16e12fa46541238c5e9d145b5488ff | BrCCCOc1ccccc1.COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1>>COc1cccc(C(O)(c2cccc(OC)c2)C23CC[N+](CCCOc4ccccc4)(CC2)CC3)c1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC.C1(=CC=CC=C1)OCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC | [CH2:22]([CH2:23][CH2:24][O:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[Br:37].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]([OH:9])([c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17]2)[C:18]23[CH2:19][CH2:20][N:21]([CH2:32][CH2:33]2)[CH2:34][CH2:35]3)[cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:... | BrCCCOc1ccccc1.COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1 | COc1cccc(C(O)(c2cccc(OC)c2)C23CC[N+](CCCOc4ccccc4)(CC2)CC3)c1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 33.2 | [{"value": 33.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC=CC=C2)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl{bis[3-(methyloxy)phenyl]}methanol (0.0506 g, 0.143 mmol) and 3-bromopropyl phenyl ether (0.0338 mL, 0.214 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.027 g, 33.2%). EI-MS m/z 488(M+) Rt (2.02 min).
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccccc1.COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1>CC#N>COc1cccc(C(O)(c2cccc(OC)c2)C23CC[N+](CCCOc4ccccc4)(CC2)CC3)c1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4da0403fa7f14fb6b2ef8fd5288bd592 | BrCCOCc1ccccc1.COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1>>COc1cccc(C(O)(c2cccc(OC)c2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)c1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC.C1(=CC=CC=C1)COCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC | [CH2:22]([CH2:23][O:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[Br:37].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]([OH:9])([c:10]2[cH:11][cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17]2)[C:18]23[CH2:19][CH2:20][N:21]([CH2:32][CH2:33]2)[CH2:34][CH2:35]3)[cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:... | BrCCOCc1ccccc1.COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1 | COc1cccc(C(O)(c2cccc(OC)c2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)c1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 33.8 | [{"value": 33.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC(=CC=C2)OC)C2=CC(=CC=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl {bis[3-(methyloxy)phenyl]}methanol (0.0538 g, 0.152 mmol) and 2-bromoethyl phenylmethyl ether (0.0361 mL, 0.228 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0292 g, 33.8%). EI-MS m/z 488(M+) Rt (2.03 min)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOCc1ccccc1.COc1cccc(C(O)(c2cccc(OC)c2)C23CCN(CC2)CC3)c1>CC#N>COc1cccc(C(O)(c2cccc(OC)c2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)c1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e746f90ebe61427490bb4048ac73cd6c | CCOC(=O)C12CCN(CC1)CC2.COc1cc[c]([Mg][Br])cc1>>COc1ccc(C(O)(c2ccc(OC)cc2)C23CCN(CC2)CC3)cc1 | COC1=CC=C(C=C1)[Mg]Br.N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC | [CH3:1][CH2:3][O:2][C:7](=[O:8])[C:17]12[CH2:18][CH2:19][N:20]([CH2:9][CH2:22]1)[CH2:23][CH2:24]2.[Br][Mg][c:6]1[cH:5][cH:4][c:12]([O:13][CH3:14])[cH:26][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[C:17]23[CH2:18][CH2:19][N:20]([CH2:21][CH2:22]2)... | CCOC(=O)C12CCN(CC1)CC2.COc1cc[c]([Mg][Br])cc1 | COc1ccc(C(O)(c2ccc(OC)cc2)C23CCN(CC2)CC3)cc1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | e8d4490293bfbd8598fd5ab48ac7bf08c299ebf75acb7f130627b70c271734dd | b38fbba258263d0ec501cac372df31e7a8146d92f935715b8366a9b6362b216e | c1ccc(C(c2ccccc2)C23CCN(CC2)CC3)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[#8:5]-[C;D1;H3:6]):[cH;D2;+0:7]:[c:8]:1.[CH3;D1;+0:9]-[CH2;D2;+0:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[C:14]12-[C:15]-[C:16]-[N;H0;D3;+0:17](-[C:18]-[C:19]-1)-[CH2;D2;+0:20]-[CH2;D2;+0:21]-2>>[C;D1;H3:6]-[#8:5]-[c;H0;D3;+0:4]1:[c:22]:[c:23]:... | 89.2 | [{"value": 89.0, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-(methyloxy)phenylmagnesiumbromide (0.5 M in THF, 6.5 mL, 3.25 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1587 g, 0.866 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Ether.Tertiary amine | Ether.Ether.Tertiary alcohol.Tertiary amine | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | Br-.Mg | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.COc1cc[c]([Mg][Br])cc1>C1CCOC1>COc1ccc(C(O)(c2ccc(OC)cc2)C23CCN(CC2)CC3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0820f68160c444088565c6a86c8ec4dc | BrCCOCc1ccccc1.COc1ccc(C(O)(c2ccc(OC)cc2)C23CCN(CC2)CC3)cc1>>COc1ccc(C(O)(c2ccc(OC)cc2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)cc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC.C1(=CC=CC=C1)COCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC | [CH2:21]([CH2:22][O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[Br:37].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[C:17]23[CH2:18][CH2:19][N:20]([CH2:31][CH2:32]2)[CH2:33][CH2:34]3)[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH... | BrCCOCc1ccccc1.COc1ccc(C(O)(c2ccc(OC)cc2)C23CCN(CC2)CC3)cc1 | COc1ccc(C(O)(c2ccc(OC)cc2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)cc1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 46.7 | [{"value": 46.7, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.7, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl{bis[4-(methyloxy)phenyl]}methanol (0.0498 g, 0.141 mmol) and 2-bromoethyl phenylmethyl ether (0.0334 mL, 0.211 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0374 g, 46.7%). EI-MS m/z 488(M+) Rt (1.94 min).... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOCc1ccccc1.COc1ccc(C(O)(c2ccc(OC)cc2)C23CCN(CC2)CC3)cc1>CC#N>COc1ccc(C(O)(c2ccc(OC)cc2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc6c0b11e9a9404d8d06af211e7a6c21 | CCOC(=O)C12CCN(CC1)CC2.Fc1ccc[c]([Mg][Br])c1>>OC(c1cccc(F)c1)(c1cccc(F)c1)C12CCN(CC1)CC2 | FC=1C=C(C=CC1)[Mg]Br.N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)F)C2=CC(=CC=C2)F | O([C:2](=[O:1])[C:17]12[CH2:18][CH2:19][N:20]([CH2:10][CH2:22]1)[CH2:23][CH2:24]2)[CH2:11][CH3:12].[Br][Mg][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[cH:9]1>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[cH:9]1)([c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]1)[C:17]12[CH2:18][CH2:19][N:20]([CH2:21][CH2:22]1)[CH2:23][CH... | CCOC(=O)C12CCN(CC1)CC2.Fc1ccc[c]([Mg][Br])c1 | OC(c1cccc(F)c1)(c1cccc(F)c1)C12CCN(CC1)CC2 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | fd3e8c1cfc57b2c7712d8187f33262dfcfe80df5f1888717b811e4a78494948a | b445477ea8e5ca1facb860b4766e96514240a7932015b93af713ffe513ccc370 | c1ccc(C(c2ccccc2)C23CCN(CC2)CC3)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH3;D1;+0:6]-[CH2;D2;+0:7]-O-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[C:10]12-[C:11]-[C:12]-[N;H0;D3;+0:13](-[C:14]-[C:15]-1)-[CH2;D2;+0:16]-[CH2;D2;+0:17]-2>>[OH;D1;+0:9]-[C;H0;D4;+0:8](-[c;H0;D3;+0:16]1:[c:18]:[c:19]:[c:20]:[cH;D2;+0:6]:[cH;D2;+0:7]:1)(-[c;H0;D3;+0:1](:[c:2... | 76.7 | [{"value": 76.7, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)F)C2=CC(=CC=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)F)C2=CC(=CC=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-fluorophenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1756 g, 0.958 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Tertiary amine | Aromatic halide.Tertiary alcohol.Tertiary amine | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | Br-.Mg | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.Fc1ccc[c]([Mg][Br])c1>C1CCOC1>OC(c1cccc(F)c1)(c1cccc(F)c1)C12CCN(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee4d714b54bd4eafa6bb5b4e9c639701 | BrCCOCc1ccccc1.OC(c1cccc(F)c1)(c1cccc(F)c1)C12CCN(CC1)CC2>>OC(c1cccc(F)c1)(c1cccc(F)c1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)F)C2=CC(=CC=C2)F.C1(=CC=CC=C1)COCCBr>>[Br-].FC=1C=C(C=CC1)C(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(O)C2=CC(=CC=C2)F | [CH2:21]([CH2:22][O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[Br:35].[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[cH:9]1)([c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]1)[C:17]12[CH2:18][CH2:19][N:20]([CH2:31][CH2:32]1)[CH2:33][CH2:34]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[cH:9]1)([c:1... | BrCCOCc1ccccc1.OC(c1cccc(F)c1)(c1cccc(F)c1)C12CCN(CC1)CC2 | OC(c1cccc(F)c1)(c1cccc(F)c1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 43.2 | [{"value": 43.2, "product": "[Br-].FC=1C=C(C=CC1)C(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(O)C2=CC(=CC=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.2, "product": "[Br-].FC=1C=C(C=CC1)C(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(O)C2=CC(=CC=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl[bis(3-fluorophenyl)]methanol (0.0507 g, 0.154 mmol) and 2-bromoethyl phenylmethyl ether (0.0365 mL, 0.230 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0362 g, 43.2%). EI-MS m/z 464(M+) Rt (2.02 min).
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOCc1ccccc1.OC(c1cccc(F)c1)(c1cccc(F)c1)C12CCN(CC1)CC2>CC#N>OC(c1cccc(F)c1)(c1cccc(F)c1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-127f06aa4fd943f5bc20ab4e2d682fbf | CCOC(=O)C12CCN(CC1)CC2.Cc1ccc[c]([Mg][Br])c1>>Cc1cccc(C(O)(c2cccc(C)c2)C23CCN(CC2)CC3)c1 | CC=1C=C(C=CC1)[Mg]Br.N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)C)C2=CC(=CC=C2)C | O([C:7](=[O:8])[C:16]12[CH2:17][CH2:18][N:19]([CH2:5][CH2:21]1)[CH2:22][CH2:23]2)[CH2:12][CH3:11].[Br][Mg][c:9]1[cH:10][cH:4][cH:3][c:2]([CH3:1])[cH:15]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][cH:12][c:13]([CH3:14])[cH:15]2)[C:16]23[CH2:17][CH2:18][N:19]([CH2:20][CH2:21]2)[CH2:22][CH2:... | CCOC(=O)C12CCN(CC1)CC2.Cc1ccc[c]([Mg][Br])c1 | Cc1cccc(C(O)(c2cccc(C)c2)C23CCN(CC2)CC3)c1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | ee54e3895eabb2d58961e5eef1e17c89ac466338d4a3f3e9e6c5d7ecbb403557 | 86699f3430ab47d59e6b5700fdac59e8de3d70ed63f18e2ca2dc71019642ab75 | c1ccc(C(c2ccccc2)C23CCN(CC2)CC3)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c:4]:[c;H0;D3;+0:5](-[C;D1;H3:6]):[cH;D2;+0:7]:1.[CH3;D1;+0:8]-[CH2;D2;+0:9]-O-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12]12-[C:13]-[C:14]-[N;H0;D3;+0:15](-[C:16]-[C:17]-1)-[CH2;D2;+0:18]-[CH2;D2;+0:19]-2>>[C;D1;H3:20]-[c:21]1:[cH;D2;+0:9]:[cH;D2;+0:8]:[cH;D2;+0:2]:[c;H... | 69.4 | [{"value": 69.4, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)C)C2=CC(=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.4, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)C)C2=CC(=CC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-methylphenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1484 g, 0.810 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Tertiary amine | Tertiary alcohol.Tertiary amine | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | Br-.Mg | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.Cc1ccc[c]([Mg][Br])c1>C1CCOC1>Cc1cccc(C(O)(c2cccc(C)c2)C23CCN(CC2)CC3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-120573c21a7f407c84bf65575e9f9c31 | BrCCOCc1ccccc1.Cc1cccc(C(O)(c2cccc(C)c2)C23CCN(CC2)CC3)c1>>Cc1cccc(C(O)(c2cccc(C)c2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)c1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC(=CC=C2)C)C2=CC(=CC=C2)C.C1(=CC=CC=C1)COCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC(=CC=C2)C)C2=CC(=CC=C2)C | [CH2:20]([CH2:21][O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1)[Br:35].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][cH:12][c:13]([CH3:14])[cH:15]2)[C:16]23[CH2:17][CH2:18][N:19]([CH2:30][CH2:31]2)[CH2:32][CH2:33]3)[cH:34]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2... | BrCCOCc1ccccc1.Cc1cccc(C(O)(c2cccc(C)c2)C23CCN(CC2)CC3)c1 | Cc1cccc(C(O)(c2cccc(C)c2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)c1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 11 | [{"value": 11.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC(=CC=C2)C)C2=CC(=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC(=CC=C2)C)C2=CC(=CC=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 4, 1-azabicyclo[2.2.2]oct-4yl[bis(3-methylphenyl)]methanol (0.0496 g, 0.154 mmol) and 2-bromoethyl phenylmethyl ether (0.0364 mL, 0.230 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0091 g, 11.0%). EI-MS m/z 456(M+) Rt (2.20 min).
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOCc1ccccc1.Cc1cccc(C(O)(c2cccc(C)c2)C23CCN(CC2)CC3)c1>CC#N>Cc1cccc(C(O)(c2cccc(C)c2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)c1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b19057c82554cb5a67198f6c2efb19e | CCOC(=O)C12CCN(CC1)CC2.Cc1cc[c]([Mg][Br])cc1>>Cc1ccc(C(O)(c2ccc(C)cc2)C23CCN(CC2)CC3)cc1 | CC1=CC=C(C=C1)[Mg]Br.N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)C)C2=CC=C(C=C2)C | O([CH2:2][CH3:1])[C:6](=[O:7])[C:15]12[CH2:16][CH2:17][N:18]([CH2:8][CH2:20]1)[CH2:21][CH2:22]2.[Br][Mg][c:5]1[cH:4][cH:3][c:11]([CH3:12])[cH:24][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([OH:7])([c:8]2[cH:9][cH:10][c:11]([CH3:12])[cH:13][cH:14]2)[C:15]23[CH2:16][CH2:17][N:18]([CH2:19][CH2:20]2)[CH2:21][CH2:22]3)[c... | CCOC(=O)C12CCN(CC1)CC2.Cc1cc[c]([Mg][Br])cc1 | Cc1ccc(C(O)(c2ccc(C)cc2)C23CCN(CC2)CC3)cc1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | ee54e3895eabb2d58961e5eef1e17c89ac466338d4a3f3e9e6c5d7ecbb403557 | 86699f3430ab47d59e6b5700fdac59e8de3d70ed63f18e2ca2dc71019642ab75 | c1ccc(C(c2ccccc2)C23CCN(CC2)CC3)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[C;D1;H3:5]):[cH;D2;+0:6]:[c:7]:1.[C;D1;H3:8]-[CH2;D2;+0:9]-O-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:12]12-[C:13]-[C:14]-[N;H0;D3;+0:15](-[C:16]-[C:17]-1)-[CH2;D2;+0:18]-[CH2;D2;+0:19]-2>>[C;D1;H3:5]-[c;H0;D3;+0:4]1:[c:20]:[c:21]:[c;H0;D3;+0:18](-[C;H0;D4;+0:10... | 86.6 | [{"value": 86.6, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)C)C2=CC=C(C=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.6, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)C)C2=CC=C(C=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-methylphenylmagnesiumbromide (1.0 M in THF, 3.3 mL, 3.3 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1509 g, 0.823 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester.Tertiary amine | Tertiary alcohol.Tertiary amine | c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | c1ccccc1.c1ccccc1.C1CN2CCC1CC2 | Br-.Mg | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.Cc1cc[c]([Mg][Br])cc1>C1CCOC1>Cc1ccc(C(O)(c2ccc(C)cc2)C23CCN(CC2)CC3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a43493cd76749e6862807cb1cb9fe62 | BrCCOCc1ccccc1.Cc1ccc(C(O)(c2ccc(C)cc2)C23CCN(CC2)CC3)cc1>>Cc1ccc(C(O)(c2ccc(C)cc2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)cc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=C(C=C2)C)C2=CC=C(C=C2)C.C1(=CC=CC=C1)COCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC=C(C=C2)C)C2=CC=C(C=C2)C | [CH2:19]([CH2:20][O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[Br:35].[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([OH:7])([c:8]2[cH:9][cH:10][c:11]([CH3:12])[cH:13][cH:14]2)[C:15]23[CH2:16][CH2:17][N:18]([CH2:29][CH2:30]2)[CH2:31][CH2:32]3)[cH:33][cH:34]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([OH:7])([c:8]2[cH:9]... | BrCCOCc1ccccc1.Cc1ccc(C(O)(c2ccc(C)cc2)C23CCN(CC2)CC3)cc1 | Cc1ccc(C(O)(c2ccc(C)cc2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)cc1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 53.2 | [{"value": 53.1, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC=C(C=C2)C)C2=CC=C(C=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC=C(C=C2)C)C2=CC=C(C=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl[bis(4-methylphenyl)]methanol (0.0525 g, 0.163 mmol) and 2-bromoethyl phenylmethyl ether (0.0387 mL, 0.245 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0465 g, 53.1%). EI-MS m/z 456(M+) Rt (2.09 min).
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOCc1ccccc1.Cc1ccc(C(O)(c2ccc(C)cc2)C23CCN(CC2)CC3)cc1>CC#N>Cc1ccc(C(O)(c2ccc(C)cc2)C23CC[N+](CCOCc4ccccc4)(CC2)CC3)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0527c1483c854b7fbfb284f389e22a47 | CCOC(=O)C12CCN(CC1)CC2.[Br][Mg][c]1ccc2ccccc2c1>>OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CCN(CC1)CC2 | C1=C(C=CC2=CC=CC=C12)[Mg]Br.N12CCC(CC1)(CC2)C(=O)OCC>>N12CCC(CC1)(CC2)C(O)(C2=CC1=CC=CC=C1C=C2)C2=CC1=CC=CC=C1C=C2 | O([C:2](=[O:1])[C:23]12[CH2:24][CH2:25][N:26]([CH2:27][CH2:28]1)[CH2:29][CH2:30]2)[CH2:13][CH3:19].[Br][Mg][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1>>[OH:1][C:2]([c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1)([c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22... | CCOC(=O)C12CCN(CC1)CC2.[Br][Mg][c]1ccc2ccccc2c1 | OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CCN(CC1)CC2 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | e646028fbabecb23ca4cf89e1dd4e595daeffd9083f9fd6ac973ce5284430292 | 0b91bc36d63c570fba02035c23fdcf278e8164647420394f29330caa2ac0d989 | c1ccc2cc(C(c3ccc4ccccc4c3)C34CCN(CC3)CC4)ccc2c1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-O-[CH2;D2;+0:10]-[CH3;D1;+0:11])(-[C:12])-[C:13]>>[C:6]-[C:7](-[C;H0;D4;+0:8](-[OH;D1;+0:9])(-[c;H0;D3;+0:10](:[c:14]:[c:15]):[c:16]:[c:17]:[c:18]:[cH;D2;+0:11]:[c:19]:[c:20])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])(-[C:12... | 77.3 | [{"value": 77.3, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC1=CC=CC=C1C=C2)C2=CC1=CC=CC=C1C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "N12CCC(CC1)(CC2)C(O)(C2=CC1=CC=CC=C1C=C2)C2=CC1=CC=CC=C1C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2-naphthalenyl)magnesiumbromide (0.5 M in THF, 6.5 mL, 3.25 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1597 g, 0.871 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperature a... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ester | Tertiary alcohol | c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccc2ccccc2c1.C1CN2CCC1CC2 | Br-.Mg | C1CCOC1 | null | null | CCOC(=O)C12CCN(CC1)CC2.[Br][Mg][c]1ccc2ccccc2c1>C1CCOC1>OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CCN(CC1)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f103f309c7840c2a61752374acb7265 | BrCCOCc1ccccc1.OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CCN(CC1)CC2>>OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC1=CC=CC=C1C=C2)C2=CC1=CC=CC=C1C=C2.C1(=CC=CC=C1)COCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC1=CC=CC=C1C=C2)C2=CC1=CC=CC=C1C=C2 | [CH2:27]([CH2:28][O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[Br:41].[OH:1][C:2]([c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12]1)([c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1)[C:23]12[CH2:24][CH2:25][N:26]([CH2:37][CH2:38]1)[CH2:39][CH2:40]2>>[OH:1][C:2]([c:3]1[... | BrCCOCc1ccccc1.OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CCN(CC1)CC2 | OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccc5ccccc5c4)c4ccc5ccccc5c4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 25 | [{"value": 25.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC1=CC=CC=C1C=C2)C2=CC1=CC=CC=C1C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC=CC=C2)(C2=CC1=CC=CC=C1C=C2)C2=CC1=CC=CC=C1C=C2", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(di-2-naphthalenyl)methanol (0.063.7 g, 0.162 mmol) and 2-bromoethyl phenylmethyl ether (0.0384 mL, 0.243 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0246 g, 25.0%). EI-MS m/z 528(M+) Rt (2.36 min).
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCOCc1ccccc1.OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CCN(CC1)CC2>CC#N>OC(c1ccc2ccccc2c1)(c1ccc2ccccc2c1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13672c8998514bb3af2628fa6027cc2b | BrCCCBr.Oc1ccccc1F>>Fc1ccccc1OCCCBr | C(=O)([O-])[O-].[Cs+].[Cs+].FC1=C(C=CC=C1)O.BrCCCBr>>FC1=C(C=CC=C1)OCCCBr | Br[CH2:9][CH2:10][CH2:11][Br:12].[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[OH:8]>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][CH2:11][Br:12] | BrCCCBr.Oc1ccccc1F | Fc1ccccc1OCCCBr | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 26.2 | [{"value": 26.2, "product": "FC1=C(C=CC=C1)OCCCBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.2, "product": "FC1=C(C=CC=C1)OCCCBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 2-fluorophenol (0.040 mL, 0.448 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.450 mL, 4.43 mmol) followed by Cs2CO3 (0.232 g, 0.713 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DC... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 24 | BrCCCBr.Oc1ccccc1F>C(C)#N>Fc1ccccc1OCCCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-996721d04d0946c597d8d350fa4e7851 | Fc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3F)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.FC1=C(C=CC=C1)OCCCBr>>[Br-].FC1=C(C=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1[F:29])[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11... | Fc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3F)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 68.3 | [{"value": 68.3, "product": "[Br-].FC1=C(C=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.3, "product": "[Br-].FC1=C(C=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0282 g, 0.0960 mmol) and 3-bromopropyl 2-fluorophenyl ether (0.0274 g, 0.118 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0345 g, 68.3%). EI-MS m/z 446(M+) Rt (1.96 min).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | Fc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccccc3F)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c9d9f2653bf24e0692556e82c34d4919 | BrCCCBr.Oc1cccc(F)c1>>Fc1cccc(OCCCBr)c1 | C(=O)([O-])[O-].[Cs+].[Cs+].FC=1C=C(C=CC1)O.BrCCCBr>>FC=1C=C(C=CC1)OCCCBr | Br[CH2:8][CH2:9][CH2:10][Br:11].[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:7])[cH:12]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][Br:11])[cH:12]1 | BrCCCBr.Oc1cccc(F)c1 | Fc1cccc(OCCCBr)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 13.2 | [{"value": 13.2, "product": "FC=1C=C(C=CC1)OCCCBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.1, "product": "FC=1C=C(C=CC1)OCCCBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 3-fluorophenol (0.040 mL, 0.448 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.450 mL, 4.43 mmol) followed by Cs2CO3 (0.246 g, 0.756 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DC... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 24 | BrCCCBr.Oc1cccc(F)c1>C(C)#N>Fc1cccc(OCCCBr)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de22f37ba3374b339525b9f6a60efc3a | Fc1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(F)c3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.FC=1C=C(C=CC1)OCCCBr>>[Br-].FC=1C=C(C=CC1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]1)[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:... | Fc1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(F)c3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 53.1 | [{"value": 53.1, "product": "[Br-].FC=1C=C(C=CC1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.9, "product": "[Br-].FC=1C=C(C=CC1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0137 g, 0.0467 mmol) and 3-bromopropyl 3-fluorophenyl ether (0.0137 g, 0.0588 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0130 g, 53.1%). EI-MS m/z 446(M+) Rt (2.03 min).
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | Fc1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(F)c3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bd1a67f8edb4a728cb38b9f655b88ba | BrCCCBr.Oc1ccc(F)cc1>>Fc1ccc(OCCCBr)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+].FC1=CC=C(C=C1)O.BrCCCBr>>FC1=CC=C(C=C1)OCCCBr | Br[CH2:7][CH2:8][CH2:9][Br:10].[F:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:11][cH:12]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][Br:10])[cH:11][cH:12]1 | BrCCCBr.Oc1ccc(F)cc1 | Fc1ccc(OCCCBr)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 14.7 | [{"value": 14.7, "product": "FC1=CC=C(C=C1)OCCCBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.7, "product": "FC1=CC=C(C=C1)OCCCBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 4-fluorophenol (0.0567 g, 0.506 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.520 mL, 5.12 mmol) followed by Cs2CO3 (0.252 g, 0.774 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DC... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 24 | BrCCCBr.Oc1ccc(F)cc1>C(C)#N>Fc1ccc(OCCCBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-48ade8c30c484a23b80e3c79327c64b9 | Fc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(F)cc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.FC1=CC=C(C=C1)OCCCBr>>[Br-].FC1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:... | Fc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(F)cc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 43.7 | [{"value": 43.7, "product": "[Br-].FC1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.7, "product": "[Br-].FC1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0182 g, 0.0621 mmol) and 3-bromopropyl 4-fluorophenyl ether (0.0173 g, 0.0742 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0143 g, 43.7%). EI-MS m/z 446(M+) Rt (1.96 min).
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | Fc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(F)cc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72579b1d11524729ad93d8d304dbdec5 | BrCCCBr.Oc1cccc(-c2ccccc2)c1>>BrCCCOc1cccc(-c2ccccc2)c1 | C(=O)([O-])[O-].[Cs+].[Cs+].C1(=CC(=CC=C1)O)C1=CC=CC=C1.BrCCCBr>>BrCCCOC=1C=C(C=CC1)C1=CC=CC=C1 | Br[CH2:4][CH2:3][CH2:2][Br:1].[OH:5][c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1>>[Br:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1 | BrCCCBr.Oc1cccc(-c2ccccc2)c1 | BrCCCOc1cccc(-c2ccccc2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 57.9 | [{"value": 57.8, "product": "BrCCCOC=1C=C(C=CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.9, "product": "BrCCCOC=1C=C(C=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 3-biphenylol (0.0574 g, 0.337 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.340 mL, 3.35 mmol) followed by Cs2CO3 (0.172 g, 0.529 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | 24 | BrCCCBr.Oc1cccc(-c2ccccc2)c1>C(C)#N>BrCCCOc1cccc(-c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa78ea82ad6b4a4493a6229e1d8d286b | BrCCCOc1cccc(-c2ccccc2)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(-c4ccccc4)c3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC=1C=C(C=CC1)C1=CC=CC=C1>>[Br-].C1(=CC(=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][cH:26][c:27](-[c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34]1)[Br:39].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:35][CH2:36]1)[CH2:37][CH2:38]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5]... | BrCCCOc1cccc(-c2ccccc2)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(-c4ccccc4)c3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(-c2cccc(OCCC[N+]34CCC(C(c5ccccc5)c5ccccc5)(CC3)CC4)c2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 70.6 | [{"value": 70.6, "product": "[Br-].C1(=CC(=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "[Br-].C1(=CC(=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0433 g, 0.148 mmol) and 3-biphenylyl 3-bromopropyl ether (0.0568 g, 0.196 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0610 g, 70.6%). EI-MS m/z 504(M+) Rt (2.37 min).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1cccc(-c2ccccc2)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3cccc(-c4ccccc4)c3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdc2cc7a381b49f38b70d46d2219fbf9 | BrCCCBr.Oc1ccc(-c2ccccc2)cc1>>BrCCCOc1ccc(-c2ccccc2)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+].C1(=CC=C(C=C1)O)C1=CC=CC=C1.BrCCCBr>>BrCCCOC1=CC=C(C=C1)C1=CC=CC=C1 | Br[CH2:4][CH2:3][CH2:2][Br:1].[OH:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[Br:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | BrCCCBr.Oc1ccc(-c2ccccc2)cc1 | BrCCCOc1ccc(-c2ccccc2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 64 | [{"value": 64.0, "product": "BrCCCOC1=CC=C(C=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.9, "product": "BrCCCOC1=CC=C(C=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-biphenylol (0.0514 g, 0.302 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.310 mL, 3.05 mmol) followed by Cs2CO3 (0.154 g, 0.472 mmol). The reaction mixture was stirred for 24h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | null | BrCCCBr.Oc1ccc(-c2ccccc2)cc1>C(C)#N>BrCCCOc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8704550a39c4ddc94114e575c1a2954 | BrCCCOc1ccc(-c2ccccc2)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(-c4ccccc4)cc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=CC=C(C=C1)C1=CC=CC=C1>>[Br-].C1(=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)C2=CC=CC=C2 | [CH2:19]([CH2:20][CH2:21][O:22][c:23]1[cH:24][cH:25][c:26](-[c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:33][cH:34]1)[Br:39].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:35][CH2:36]1)[CH2:37][CH2:38]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5]... | BrCCCOc1ccc(-c2ccccc2)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(-c4ccccc4)cc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(-c2ccc(OCCC[N+]34CCC(C(c5ccccc5)c5ccccc5)(CC3)CC4)cc2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 77.8 | [{"value": 75.2, "product": "[Br-].C1(=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "[Br-].C1(=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0437 g, 0.144 mmol) and 4-biphenylyl 3-bromopropyl ether (0.0562 g, 0.194 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0655 g, 75.2%). EI-MS m/z 504(M+) Rt (2.24 min).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | BrCCCOc1ccc(-c2ccccc2)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCCOc3ccc(-c4ccccc4)cc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb47d0baf7a2451a96f5133f6b686298 | BrCCCBr.O=[N+]([O-])c1cccc(O)c1>>O=[N+]([O-])c1cccc(OCCCBr)c1 | C(=O)([O-])[O-].[Cs+].[Cs+].[N+](=O)([O-])C=1C=C(C=CC1)O.BrCCCBr>>[N+](=O)([O-])C=1C=C(C=CC1)OCCCBr | Br[CH2:10][CH2:11][CH2:12][Br:13].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:14]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][Br:13])[cH:14]1 | BrCCCBr.O=[N+]([O-])c1cccc(O)c1 | O=[N+]([O-])c1cccc(OCCCBr)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 56.7 | [{"value": 56.6, "product": "[N+](=O)([O-])C=1C=C(C=CC1)OCCCBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.7, "product": "[N+](=O)([O-])C=1C=C(C=CC1)OCCCBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 3-nitrophenol (0.0689 g, 0.495 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.500 mL, 3.05 mmol) followed by Cs2CO3 (0.244 g, 0.748 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 24 | BrCCCBr.O=[N+]([O-])c1cccc(O)c1>C(C)#N>O=[N+]([O-])c1cccc(OCCCBr)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3efa776270464385bc7f1fde39b3b9f6 | O=[N+]([O-])c1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>O=[N+]([O-])c1cccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.[N+](=O)([O-])C=1C=C(C=CC1)OCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC(=CC=C2)[N+](=O)[O-])(C2=CC=CC=C2)C2=CC=CC=C2 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][Br:36])[cH:35]1.[N:13]12[CH2:14][CH2:15][C:16]([C:17]([OH:18])([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)([CH2:31][CH2:32]1)[CH2:33][CH2:34]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([... | O=[N+]([O-])c1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | O=[N+]([O-])c1cccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11] | 82.2 | [{"value": 82.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC(=CC=C2)[N+](=O)[O-])(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.2, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=CC(=CC=C2)[N+](=O)[O-])(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0608 g, 0.207 mmol) and 3-bromopropyl 3-nitrophenyl ether (0.0730 g, 0.281 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0942 g, 82.2%). EI-MS m/z 474(M+) Rt (2.04 min).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | O=[N+]([O-])c1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>O=[N+]([O-])c1cccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb7103a624a342a2ac98058fa5b9661d | BrCCCBr.Cc1ccccc1O>>Cc1ccccc1OCCCBr | C(=O)([O-])[O-].[Cs+].[Cs+].CC1=C(C=CC=C1)O.BrCCCBr>>CC1=C(C=CC=C1)OCCCBr | Br[CH2:9][CH2:10][CH2:11][Br:12].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[OH:8]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][CH2:11][Br:12] | BrCCCBr.Cc1ccccc1O | Cc1ccccc1OCCCBr | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 44.1 | [{"value": 44.1, "product": "CC1=C(C=CC=C1)OCCCBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.1, "product": "CC1=C(C=CC=C1)OCCCBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 2-methylphenol (0.0954 g, 0.924 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (1.00 mL, 9.85 mmol) followed by Cs2CO3 (0.469 g, 1.44 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted with DCM ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 24 | BrCCCBr.Cc1ccccc1O>C(C)#N>Cc1ccccc1OCCCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e12855d0143470ebc98d4e594fa9626 | Cc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>Cc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.CC1=C(C=CC=C1)OCCCBr>>[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)C)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][CH2:11][Br:34].[N:12]12[CH2:13][CH2:14][C:15]([C:16]([OH:17])([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][CH2:... | Cc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | Cc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 76.5 | [{"value": 76.5, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCCOC2=C(C=CC=C2)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0447 g, 0.152 mmol) and 3-bromopropyl 2-methylphenyl ether (0.0934 g, 0.407 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0586 g, 76.5%). EI-MS m/z 442(M+) Rt (2.17 min).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | Cc1ccccc1OCCCBr.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>Cc1ccccc1OCCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13a6f94b14c7421494d2718790e0f673 | CCN(CC)c1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CCN(CC)c1cccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC=1C=C(N(CC)CC)C=CC1>>[Br-].C(C)N(C=1C=C(C=CC1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)CC | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][CH2:14][Br:38])[cH:37]1.[N:15]12[CH2:16][CH2:17][C:18]([C:19]([OH:20])([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)([CH2:33][CH2:34]1)[CH2:35][CH2:36]2>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5]... | CCN(CC)c1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CCN(CC)c1cccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11] | 63 | [{"value": 63.0, "product": "[Br-].C(C)N(C=1C=C(C=CC1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0257 g, 0.0876 mmol) and 3-[(3-bromopropyl)oxy]-N,N-diethylaniline (0.0314 g, 0.110 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.032.0 g, 63.0%). EI-MS m/z 500(M+) Rt (1.58 min).
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | CCN(CC)c1cccc(OCCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>CCN(CC)c1cccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e02fdf63b664ae7b3dd35125eae814d | BrCCCBr.N#Cc1ccc(O)cc1>>N#Cc1ccc(OCCCBr)cc1 | C(=O)([O-])[O-].[Cs+].[Cs+].OC1=CC=C(C#N)C=C1.BrCCCBr>>BrCCCOC1=CC=C(C#N)C=C1 | Br[CH2:8][CH2:9][CH2:10][Br:11].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:12][cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][Br:11])[cH:12][cH:13]1 | BrCCCBr.N#Cc1ccc(O)cc1 | N#Cc1ccc(OCCCBr)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 71.4 | [{"value": 71.4, "product": "BrCCCOC1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.2, "product": "BrCCCOC1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 4-hydroxybenzonitrile (0.109 g, 0.913 mmol) in acetonitrile (4 mL) was added 1,3-dibromopropane (0.930 mL, 9.16 mmol) followed by Cs2CO3 (0.439 g, 1.35 mmol). The reaction mixture was stirred for 24 h and then concentrated under vacuum. The resulting residue was treated with H2O (4 mL) and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 24 | BrCCCBr.N#Cc1ccc(O)cc1>C(C)#N>N#Cc1ccc(OCCCBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b15a483f74b44f88be5bbc611710f5ee | N#Cc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>N#Cc1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCCOC1=CC=C(C#N)C=C1>>[Br-].C(#N)C1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][Br:35])[cH:33][cH:34]1.[N:11]12[CH2:12][CH2:13][C:14]([C:15]([OH:16])([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)([CH2:29][CH2:30]1)[CH2:31][CH2:32]2>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10... | N#Cc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | N#Cc1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(OCCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[Br-;H0;D0:1].[C:5]-[C:6]-[N+;H0;D4:7](-[CH2;D2;+0:2]-[C:3]-[C:4])(-[C:8]-[C:9])-[C:10]-[C:11] | 76.9 | [{"value": 76.8, "product": "[Br-].C(#N)C1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "[Br-].C(#N)C1=CC=C(C=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.0520 g, 0.177 mmol) and 4-[(3-bromopropyl)oxy]benzonitrile (0.156 g, 0.652 mmol) in 2 CH3CN/3 CHCl3 (4.0 mL) were reacted to give the desired product (0.0726 g, 76.8%). EI-MS m/z 453(M+) Rt (1.86 min).
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | null | null | N#Cc1ccc(OCCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>N#Cc1ccc(OCCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c0b24f787e014589a3b8ee2ba1308fb4 | COc1cccc(CCl)c1.OCCO>>COc1cccc(COCCO)c1 | COC=1C=C(CCl)C=CC1.C(CO)O.[H-].[Na+].O.COC=1C=C(CCl)C=CC1>>COC=1C=C(C=CC1)COCCO | Cl[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13]1.[OH:9][CH2:10][CH2:11][OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9][CH2:10][CH2:11][OH:12])[cH:13]1 | COc1cccc(CCl)c1.OCCO | COc1cccc(COCCO)c1 | null | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-] | CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 42 | [{"value": 42.0, "product": "COC=1C=C(C=CC1)COCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.7, "product": "COC=1C=C(C=CC1)COCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | Ethylene glycol (0.084 mL, 1.5 mmol) was added to NaH (38 mg, 1.52 mmol, 95% in oil) in THF (3 mL) (caution: exotherm). m-Methoxybenzyl chloride (0.21 mL, 1.5 mmol) was added to the reaction, and the residual m-methoxybenzyl chloride was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HCl | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1 | 60 | null | COc1cccc(CCl)c1.OCCO>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1>COc1cccc(COCCO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6f680cf5c6c449ba65fff89cfe0e099 | COc1cccc(COCCO)c1.O=C1CCC(=O)N1Br>>COc1cccc(COCCBr)c1 | COC=1C=C(C=CC1)COCCO.BrN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCOCC1=CC(=CC=C1)OC | O[CH2:11][CH2:10][O:9][CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13]1.O=C1CCC(=O)N1[Br:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9][CH2:10][CH2:11][Br:12])[cH:13]1 | COc1cccc(COCCO)c1.O=C1CCC(=O)N1Br | COc1cccc(COCCBr)c1 | null | null | [Al].C(Cl)Cl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[Br;H0;D1;+0:4] | 104.3 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.3, "product": "BrCCOCC1=CC(=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of N-bromosuccinimide (272 mg, 1.53 mmol) in DCM (2.5 mL) was added resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL). The reaction was stirred at room temperature for 10 min. A solution of 2-({[3-(methyloxy)phenyl]methyl}oxy)ethanol (114 mg, 0.626 mmol) in DCM (1.5 mL) was added to... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | [Al].C(Cl)Cl | null | 0.166667 | COc1cccc(COCCO)c1.O=C1CCC(=O)N1Br>[Al].C(Cl)Cl>COc1cccc(COCCBr)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e38b6c5ffc4f4ea4b4691d315c8bef3f | COc1cccc(COCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>COc1cccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOCC1=CC(=CC=C1)OC>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC(=CC=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9][CH2:10][CH2:11][Br:35])[cH:34]1.[N:12]12[CH2:13][CH2:14][C:15]([C:16]([OH:17])([c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][O:9][CH2:1... | COc1cccc(COCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | COc1cccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] | null | null | CC#N | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 14 | [{"value": 14.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC(=CC=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOCC2=CC(=CC=C2)OC)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (30 mg, 0.102 mmol) was added to a solution of 1-{[(2-bromoethyl)oxy]methyl}-3-(methyloxy)benzene (35 mg, 0.143 mmol) in 2 CH3CN/3 CHCl3 (3 mL). The reaction was heated at 60° C. for 96 h. The reaction was concentrated, and the crude product was washed with EtOAc (3×1 mL) a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N | 60 | null | COc1cccc(COCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N>COc1cccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)c1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9168808fe24d4674af8f0a5dfdd7aee3 | CC(C)(C)c1ccc(COCCO)cc1.O=C1CCC(=O)N1Br>>CC(C)(C)c1ccc(COCCBr)cc1 | CC(C)(C)C1=CC=C(C=C1)COCCO.BrN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCOCC1=CC=C(C=C1)C(C)(C)C | O[CH2:12][CH2:11][O:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:15][cH:14]1.O=C1CCC(=O)N1[Br:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][O:10][CH2:11][CH2:12][Br:13])[cH:14][cH:15]1 | CC(C)(C)c1ccc(COCCO)cc1.O=C1CCC(=O)N1Br | CC(C)(C)c1ccc(COCCBr)cc1 | null | null | [Al].C(Cl)Cl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[Br;H0;D1;+0:4] | 50 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.0, "product": "BrCCOCC1=CC=C(C=C1)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.0, "product": "BrCCOCC1=CC=C(C=C1)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of N-bromosuccinimide (272 mg, 1.53 mmol) in DCM (2.5 mL) was added to resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL), and the reaction was stirred at rt for 10 min. A solution of 2-({[4-(1,1-dimethylethyl)phenyl]methyl}oxy)ethanol (160 mg, 0.768 mmol) in DCM (1.5 mL) was added t... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | [Al].C(Cl)Cl | null | 0.166667 | CC(C)(C)c1ccc(COCCO)cc1.O=C1CCC(=O)N1Br>[Al].C(Cl)Cl>CC(C)(C)c1ccc(COCCBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4684c190ef4244c8827b591a42265bdf | CC(C)(C)c1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CC(C)(C)c1ccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOCC1=CC=C(C=C1)C(C)(C)C>>[Br-].CC(C)(C)C1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][O:10][CH2:11][CH2:12][Br:37])[cH:35][cH:36]1.[N:13]12[CH2:14][CH2:15][C:16]([C:17]([OH:18])([c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)([CH2:31][CH2:32]1)[CH2:33][CH2:34]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:... | CC(C)(C)c1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CC(C)(C)c1ccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | null | null | CC#N.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 16 | [{"value": 16.0, "product": "[Br-].CC(C)(C)C1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.6, "product": "[Br-].CC(C)(C)C1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 60 | CELSIUS | null | null | 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (30 mg, 0.102 mmol) was added to a solution of 1-{[(2-bromoethyl)oxy]methyl}-4-(1,1-dimethylethyl)benzene (25 mg, 0.143 mmol) in 2:3 CH3CN /CHCl3 (3 mL), and the reaction was heated at 60° C. for 96 h. The reaction was concentrated, and the crude product was washed with EtO... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N.C(Cl)(Cl)Cl | 60 | null | CC(C)(C)c1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N.C(Cl)(Cl)Cl>CC(C)(C)c1ccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2105038183b5404480cfb84c7fefed18 | Fc1ccc(CBr)cc1.OCCO>>OCCOCc1ccc(F)cc1 | BrCC1=CC=C(C=C1)F.O.C(CO)O.[H-].[Na+].BrCC1=CC=C(C=C1)F>>FC1=CC=C(C=C1)COCCO | Br[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1.[OH:1][CH2:2][CH2:3][OH:4]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1 | Fc1ccc(CBr)cc1.OCCO | OCCOCc1ccc(F)cc1 | null | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-] | CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.0, "product": "FC1=CC=C(C=C1)COCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.8, "product": "FC1=CC=C(C=C1)COCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | Ethylene glycol (0.084 mL, 1.5 mmol) was added to NaH (38 mg, 1.52 mmol, 95% in oil) in THF (3 mL). 1-(Bromomethyl)-4-fluorobenzene (0.19 mL, 1.5 mmol) was added to the reaction, and the residual 1-(bromomethyl)-4-fluorobenzene was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1 | 60 | 4 | Fc1ccc(CBr)cc1.OCCO>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1>OCCOCc1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a30b3f3f1aa459588ef2c44354abdd1 | O=C1CCC(=O)N1Br.OCCOCc1ccc(F)cc1>>Fc1ccc(COCCBr)cc1 | FC1=CC=C(C=C1)COCCO.BrN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCOCC1=CC=C(C=C1)F | O=C1CCC(=O)N1[Br:10].O[CH2:9][CH2:8][O:7][CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:12][cH:11]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][O:7][CH2:8][CH2:9][Br:10])[cH:11][cH:12]1 | O=C1CCC(=O)N1Br.OCCOCc1ccc(F)cc1 | Fc1ccc(COCCBr)cc1 | null | null | [Al].C(Cl)Cl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[Br;H0;D1;+0:4] | 50 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.0, "product": "BrCCOCC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.9, "product": "BrCCOCC1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of N-bromosuccinimide (272 mg, 1.53 mmol) in DCM (2.5 mL) was added to resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL), and the reaction was stirred at rt for 10 min. A solution of 2-{[(4-fluorophenyl)methyl]oxy}ethanol (122 mg, 0.717 mmol) in DCM (1.5 mL) was added to the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | [Al].C(Cl)Cl | null | 0.166667 | O=C1CCC(=O)N1Br.OCCOCc1ccc(F)cc1>[Al].C(Cl)Cl>Fc1ccc(COCCBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34a17220bbf24f0883994ec45b18941c | Fc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(F)cc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOCC1=CC=C(C=C1)F>>[Br-].FC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][O:21][CH2:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1)[Br:34].[OH:1][C: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)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:... | Fc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(F)cc3)(CC1)CC2.[Br-] | null | null | CC#N.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 16.8 | [{"value": 16.0, "product": "[Br-].FC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.8, "product": "[Br-].FC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (30 mg, 0.102 mmol) was added to a solution of 1-{[(2-bromoethyl)oxy]methyl}-4-fluorobenzene (33 mg, 0.143 mmol) in 2:3 CH3CN/CHCl3 (3 mL), and the reaction was heated at 60° C. for 96 h. The reaction was concentrated, and the crude product was washed with EtOAc (3×1 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N.C(Cl)(Cl)Cl | 60 | null | Fc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N.C(Cl)(Cl)Cl>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(F)cc3)(CC1)CC2.[Br-] |
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