(E)-4-(4-bromophenoxy)-2-butenyl acetate -Drug Synthesis Database

【结构式】

【分子编号】48863

【品名】(E)-4-(4-bromophenoxy)-2-butenyl acetate

【CA登记号】

【分子式】C₁₂H₁₃BrO₃

【分子量】285.13742

【元素组成】C 50.55% H 4.6% Br 28.02% O 16.83%

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：(XIV)

Alternatively, intermediate (VI) can be obtained as follows: 1,4-Dichloro-2-butene (I) is condensed with p-bromophenol (XII) by means of Cs2CO3 in acetonitrile to give compound (XIII), which is then converted into acetate (XIV) after treatment with ammonium tetrabutyl acetate in refluxing acetone. Saponification of (XIV) with NaOH in MeOH affords alcohol (XV), which is then subjected to Claisen rearrangement by refluxing in ethyl orthoacetate in propionic acid to provide ester (XVI). Reduction of (XVI) with LiAlH4 Et2O gives alcohol (XVII), which is finally condensed with 4-bromophenyltributyl tin (XVIII) by means of Pd(PPh3)4 and LiCl in toluene.

参考文献中间体

合成目标

【1】 Guilbaud, N.; Atassi, G.; Le Diguarher, T.; Bonnet, J.; Sabatini, M.; Casara, P.; Chollet, A.-M.; Pierre, A.; Tucker, G. (ADIR et Cie.); Carboxylic and hydroxamic acid cpds. inhibiting metalloproteases, method for preparing same and pharmaceutical compsns. containing them. EP 1091937; FR 2780402; WO 0000473 .

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)	32186	(E)-1,4-dichloro-2-butene	110-57-6	C₄H₆Cl₂	详情	详情
(VI)	48857	ethyl 3-[[(4'-bromo[1,1'-biphenyl]-4-yl)oxy]methyl]-4-pentenoate		C₂₀H₂₁BrO₃	详情	详情
(XII)	25313	4-bromophenol	106-41-2	C₆H₅BrO	详情	详情
(XIII)	48862	1-bromo-4-[[(E)-4-chloro-2-butenyl]oxy]benzene; 4-bromophenyl (E)-4-chloro-2-butenyl ether		C₁₀H₁₀BrClO	详情	详情
(XIV)	48863	(E)-4-(4-bromophenoxy)-2-butenyl acetate		C₁₂H₁₃BrO₃	详情	详情
(XV)	48864	(E)-4-(4-bromophenoxy)-2-buten-1-ol		C₁₀H₁₁BrO₂	详情	详情
(XVI)	48865	ethyl 3-[(4-bromophenoxy)methyl]-4-pentenoate		C₁₄H₁₇BrO₃	详情	详情
(XVII)	48866	3-[(4-bromophenoxy)methyl]-4-penten-1-ol		C₁₂H₁₅BrO₂	详情	详情
(XVIII)	48867	(4-bromophenyl)(tributyl)stannane		C₁₈H₃₁BrSn	详情	详情

Extended Information