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【结 构 式】

【分子编号】31390

【品名】5-(2'-fluoro[1,1'-biphenyl]-4-yl)pentanoic acid

【CA登记号】

【 分 子 式 】C17H17FO2

【 分 子 量 】272.3191832

【元素组成】C 74.98% H 6.29% F 6.98% O 11.75%

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:(IV)

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
Extended Information