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【结 构 式】

【分子编号】11618

【品名】4-(2-Vinyl-2,3-dihydro-1H-inden-2-yl)-1H-imidazole

【CA登记号】

【 分 子 式 】C14H14N2

【 分 子 量 】210.27864

【元素组成】C 79.97% H 6.71% N 13.32%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

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
Extended Information