5-(2'-fluoro[1,1'-biphenyl]-4-yl)pentanoic acid -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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