【结 构 式】 |
【分子编号】18612 【品名】(6R,8aS)-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol 【CA登记号】 |
【 分 子 式 】C16H19NO3 【 分 子 量 】273.3318 【元素组成】C 70.31% H 7.01% N 5.12% O 17.56% |
合成路线1
该中间体在本合成路线中的序号:(IV)Alkylation of potassium phthalimide (I) with an excess of 1,8-dibromooctane (II) in refluxing acetone afforded N-(8-bromooctyl)phthalimide (III). This was condensed with 6-O-demethylgalanthamine (IV) in the presence of Et3N in boiling acetonitrile to give phthalimidooctyl compound (V). Finally, reaction with N-bromosuccinimide in the presence of azobisisobutyronitrile provided the iminium bromide.
【1】 Mary, A.; Renko, D.Z.; Guillou, C.; Thal, C.; Potent acetylcholinesterase inhibitors: Design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series. Bioorg Med Chem 1998, 6, 10, 1835. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 10926 | (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)potassium | C8H4KNO2 | 详情 | 详情 | |
(II) | 18610 | 1,8-dibromooctane | 4549-32-0 | C8H16Br2 | 详情 | 详情 |
(III) | 18611 | 2-(8-bromooctyl)-1H-isoindole-1,3(2H)-dione | 17702-83-9 | C16H20BrNO2 | 详情 | 详情 |
(IV) | 18612 | (6R,8aS)-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol | C16H19NO3 | 详情 | 详情 | |
(V) | 18613 | 2-[8-[(6R,8aS)-6-hydroxy-3-methoxy-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11(12H)-yl]octyl]-1H-isoindole-1,3(2H)-dione | C32H38N2O5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(IV)Alkylation of potassium phthalimide (I) with an excess of 1,10-dibromodecane (II) in refluxing acetone afforded N-(10-bromodecyl)phthalimide (III). This was condensed with 6-O-demethylgalanthamine (IV) in the presence of Et3N in boiling acetonitrile to give phthalimidodecyl compound (V). Finally, reaction with N-bromosuccinimide in the presence of azobisisobutyronitrile provided the iminium bromide.
【1】 Mary, A.; Renko, D.Z.; Guillou, C.; Thal, C.; Potent acetylcholinesterase inhibitors: Design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series. Bioorg Med Chem 1998, 6, 10, 1835. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 10929 | 3-Ethyl-7-methyl-3,7-diazabicyclo[3.3.1]nonan-9-one | C10H18N2O | 详情 | 详情 | |
(II) | 18615 | 1,10-dibromodecane | 4101-68-2 | C10H20Br2 | 详情 | 详情 |
(III) | 18616 | 2-(10-bromodecyl)-1H-isoindole-1,3(2H)-dione | 24566-80-1 | C18H24BrNO2 | 详情 | 详情 |
(IV) | 18612 | (6R,8aS)-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol | C16H19NO3 | 详情 | 详情 | |
(V) | 18618 | 2-[10-[(6R,8aS)-6-hydroxy-3-methoxy-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11(12H)-yl]decyl]-1H-isoindole-1,3(2H)-dione | C34H42N2O5 | 详情 | 详情 |