3-fluoro-4-methylbenzonitrile -Drug Synthesis Database

【结构式】

【分子编号】45510

【品名】3-fluoro-4-methylbenzonitrile

【CA登记号】170572-49-3

【分子式】C₈H₆FN

【分子量】135.1407832

【元素组成】C 71.1% H 4.48% F 14.06% N 10.36%

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：(I)

Benzylic bromination of 3-fluoro-4-methylbenzaldehyde (I) using N-bromosuccinimide afforded bromide (II), which was converted to phosphonate (III) by reaction with triethyl phosphite. Horner-Emmons condensation of phosphonate (III) with monoprotected fumaraldehyde (IV) produced the diene acetal (V), which was then hydrolyzed to aldehyde (VI) with aqueous HCl.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; del Fresno, M.; Rabasseda, X.; CS-758. Drugs Fut 2003, 28, 3, 217.
【2】 Nakamura, Y.; Konosu, T.; Oida, S.; et al.; Synthesis and in vitro antifungal activities of novel triazole antifungal agent CS-758. Chem Pharm Bull 2001, 49, 12, 1647.
【4】 Mori, M.; Oida, S.; Uchida, T.; Nakagawa, A.; Kounosu, T.; Ohya, T. (Sankyo Co., Ltd.); Triazole antifungal agents. JP 2002161035 .
【5】 Mori, M.; Oida, S.; Konosu, T.; Uchida, T.; Ohya, S.; Nakagawa, A. (Sankyo Co., Ltd.); Triazole derivs. having antifungal activity. EP 1083175; JP 2001348384; JP 2002114782; US 6337403; US 6391903 .
【3】 Oida, S.; Mori, M.; nakamura, Y.; Habuki, S.; Kuwahara, S.; Somada, A.; Harada, Y.; Uchida, T.; Konosu, T.; R-120758, a novel triazole antifungal agent: Synthesis and structure-activity relationship. 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1087.

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)	45510	3-fluoro-4-methylbenzonitrile	170572-49-3	C₈H₆FN	详情	详情
(II)	45511	4-(bromomethyl)-3-fluorobenzonitrile		C₈H₅BrFN	详情	详情
(III)	45512	diethyl 4-cyano-2-fluorobenzylphosphonate		C₁₂H₁₅FNO₃P	详情	详情
(IV)	45513	(E)-4,4-dimethoxy-2-butenal	4093-49-6	C₆H₁₀O₃	详情	详情
(V)	45514	4-[(1E,3E)-5,5-dimethoxy-1,3-pentadienyl]-3-fluorobenzonitrile		C₁₄H₁₄FNO₂	详情	详情
(VI)	45515	3-fluoro-4-[(1E,3E)-5-oxo-1,3-pentadienyl]benzonitrile		C₁₂H₈FNO	详情	详情

Extended Information