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【结 构 式】 
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【分子编号】11614 【品名】1,2-Bis(bromomethyl)benzene; alpha,alpha'-Dibromo-o-xylene 【CA登记号】91-13-4 |
【 分 子 式 】C8H8Br2 【 分 子 量 】263.95952 【元素组成】C 36.4% H 3.05% Br 60.54% |
合成路线1
该中间体在本合成路线中的序号：(III)This compound can be obtained in two different ways: 1) The bromination of 1-(2-ethylindan-2-yl)-1-ethanone (I) with Br2 in ether gives 2-bromo-1-(2-ethylindan-2-yl)-1-ethanone (II), which is then cyclized with formamide by heating at 170-80 C. 2) The cyclization of alpha,alpha'-dibromo-o-xylene (III) with 4-penten-2-one (IV) by means of tetrabutylammonium hydroxide in toluene at 100 C gives 1-(2-vinylindan-2-yl)-1-ethanone (V), which is brominated with Br2 in dichloromethane to yield 2-bromo-1-(2-vinylindan-2-yl)-1-ethanone (VI). The cyclization of (VI) with formamide at 160 C as before affords 4-(2-vinylindan-2-yl)-1H-imidazole (VII), which is finally hydrogenated with H2 over Pd/C in ethanol.
| 【1】 Graziano, M.P.; Maxham, C.P.; Malbon, C.C.; Purified rat hepatic beta2-adrenergic receptor: Structural similarities in the rat fat cell beta1-adrenergic receptor. J Biol Chem 1985, 260, 7665-74. |
| 【2】 Karjalainen, A.L.; Karjalainen, A.J. (Orion Pharma); 4(5)-Substd. imidazole derivs., and intermediates and processes for their preparation. EP 0247764; US 4933359 . |
| 【3】 Karjalainen, A.J.; Virtanen, R.E.; Kurkela, K.O.A.; Karjalainen, A. (Orion Pharma); Substd. imidazole derivs. and their preparation and use. AU 8550083; EP 0183492; EP 0310745; ES 8704462; ES 8801248; GB 2167408; JP 1986143366 . |
| 【4】 Prous, J.; Castaner, J.; Atipamezole. Drugs Fut 1990, 15, 5, 448. |
| 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) | 11612 | 1-(2-Ethyl-2,3-dihydro-1H-inden-2-yl)-1-ethanone | C13H16O | 详情 | 详情 | |
| (II) | 11613 | 2-Bromo-1-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-1-ethanone | C13H15BrO | 详情 | 详情 | |
| (III) | 11614 | 1,2-Bis(bromomethyl)benzene; alpha,alpha'-Dibromo-o-xylene | 91-13-4 | C8H8Br2 | 详情 | 详情 |
| (IV) | 11615 | 4-Penten-2-one | C5H8O | 详情 | 详情 | |
| (V) | 11616 | 1-(2-Vinyl-2,3-dihydro-1H-inden-2-yl)-1-ethanone | C13H14O | 详情 | 详情 | |
| (VI) | 11617 | 2-Bromo-1-(2-vinyl-2,3-dihydro-1H-inden-2-yl)-1-ethanone | C13H13BrO | 详情 | 详情 | |
| (VII) | 11618 | 4-(2-Vinyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole | C14H14N2 | 详情 | 详情 |