【结 构 式】 |
【分子编号】11622 【品名】1-(2,3-Dihydro-1H-inden-2-yl)-1-ethanone 【CA登记号】 |
【 分 子 式 】C11H12O 【 分 子 量 】160.21568 【元素组成】C 82.46% H 7.55% O 9.99% |
合成路线1
该中间体在本合成路线中的序号:(IV)A new synthesis of atipamezole has been described: The cyclization of alpha,alpha'-dibromo-o-xylene (I) with acetylacetone (II) by means of NaOH and tetrabutylammonium bromide in toluene/water at 80 C under phase-transfer conditions gives the unstable diacetyl derivative (III), which presumably undergoes cleavage to afford 2-acetylindane (IV). The alkylation of (IV) with ethyl iodide and potassium tert-butoxide yields 2-acetyl-2-ethylindane (V), which is brominated with Br2 to give 2-(bromoacetyl)-2-ethylindane (VI). Finally, this compound is cyclized with formamide at 160 C [some 2-ethyl-2-(4-oxazolyl)indane is also formed but is easily eliminated]; the cyclization can also be carried out with formamidine in liquid ammonia.
【1】 Wong, W.C.; Gluchowski, C.; A concise synthesis of atipamezole. Synthesis 1995, 2, 2, 139. |
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) | 11619 | 2,2-Bis(bromomethyl)indane | C11H12Br2 | 详情 | 详情 | |
(II) | 11620 | 2,4-Pentanedione;acetylacetone | 123-54-6 | C5H8O2 | 详情 | 详情 |
(III) | 11621 | 1-(2-Acetyl-2,3-dihydro-1H-inden-2-yl)-1-ethanone | C13H14O2 | 详情 | 详情 | |
(IV) | 11622 | 1-(2,3-Dihydro-1H-inden-2-yl)-1-ethanone | C11H12O | 详情 | 详情 | |
(V) | 11612 | 1-(2-Ethyl-2,3-dihydro-1H-inden-2-yl)-1-ethanone | C13H16O | 详情 | 详情 | |
(VI) | 11613 | 2-Bromo-1-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-1-ethanone | C13H15BrO | 详情 | 详情 |