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【结 构 式】 
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【分子编号】31392 【品名】2-(2-fluorophenyl)-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene 【CA登记号】 |
【 分 子 式 】C17H17F 【 分 子 量 】240.3203832 【元素组成】C 84.96% H 7.13% F 7.91% |
合成路线1
该中间体在本合成路线中的序号：(VI)Friedel-Crafts condensation of 2-fluorobiphenyl (I) with glutaric anhydride (II) in the presence of AlCl3 gave ketoacid (III). Reduction of the ketonic group of (III) with triethylsilane in trifluoroacetic acid afforded biphenylpentanoic acid (IV), which was cyclized to the benzosuberone derivative (V) using polyphosphoric acid. Ketone reduction of (IV) by means of triethylsilane and trifluoroacetic acid provided the benzocycloheptene (VI), which was further oxidized to the isomeric ketone (VII) with chromic acid. Finally, condensation of (VII) with 5-fluoroisatin (VIII) in the presence of KOH yielded the target tetracyclic system.
| 【1】 Suzuki, F.; Nakasato, Y.; Tsumuki, H.; Ohmori, K.; Nakajima, H.; Tamura, T.; Sato, S. (Kyowa Hakko Kogyo Co., Ltd.); Tetracyclic cpds.. US 5371225; WO 9322286 . |
| 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) | 31388 | 2-fluoro-1,1'-biphenyl | 321-60-8 | C12H9F | 详情 | 详情 |
| (II) | 15512 | Glutaric Anhydride; dihydro-2H-pyran-2,6(3H)-dione | 108-55-4 | C5H6O3 | 详情 | 详情 |
| (III) | 31389 | 5-(2'-fluoro[1,1'-biphenyl]-4-yl)-5-oxopentanoic acid | C17H15FO3 | 详情 | 详情 | |
| (IV) | 31390 | 5-(2'-fluoro[1,1'-biphenyl]-4-yl)pentanoic acid | C17H17FO2 | 详情 | 详情 | |
| (V) | 31391 | 3-(2-fluorophenyl)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one | C17H15FO | 详情 | 详情 | |
| (VI) | 31392 | 2-(2-fluorophenyl)-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene | C17H17F | 详情 | 详情 | |
| (VII) | 31393 | 2-(2-fluorophenyl)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one | C17H15FO | 详情 | 详情 | |
| (VIII) | 21552 | 5-fluoro-1H-indole-2,3-dione | 443-69-6 | C8H4FNO2 | 详情 | 详情 |