2-[6-(4-溴苯氧基)己基]环氧乙烷-2-羧酸的合成、表征及放射性标记

Synthesis, characterization and radiolabelling of 2-[6-(4-bromophenoxy)hexyl]oxirane-2-carboxylic acid.

作者信息

Abbas H G, Younas M, Feinendegen L E

机构信息

Institute of Medicine, Research Centre, Jülich, F.R.G.

出版信息

Int J Rad Appl Instrum A. 1991;42(1):1-5. doi: 10.1016/0883-2889(91)90116-i.

DOI:10.1016/0883-2889(91)90116-i

PMID:1850392

Abstract

A method is described for the synthesis, purification and radiolabelling of 2-[6-(4-bromophenoxy)hexyl]-oxirane-2-carboxylic acid. For the synthesis of this new agent, 6-(4-bromophenoxy)hexylbromide (1), synthesized by the treatment of 4-bromophenol with 1,6-dibromohexane under basic conditions, was converted to diethyl 6-(4-bromophenoxy)hexylmalonate (2), which, on alkaline hydrolysis, yielded ethyl 6-(4-bromophenoxy)hexylmalonate (3). Ethyl 8-(4-bromophenoxy)-2-methyleneoctanoate (4), prepared from the monoester (3), was oxidized with m-chloroperbenzoic acid to yield ethyl 2-[6-(4-bromophenoxy)-hexyl]oxirane-2-carboxylate (5). The method of radiolabelling, based on the Cu(I)Cl-assisted nucleophilic exchange reaction, resulted in regioselective radiobromination with a 45% radiochemical yield.

摘要

描述了一种合成、纯化和放射性标记2-[6-(4-溴苯氧基)己基]-环氧乙烷-2-羧酸的方法。为了合成这种新试剂，在碱性条件下用1,6-二溴己烷处理4-溴苯酚合成的6-(4-溴苯氧基)己基溴(1)被转化为6-(4-溴苯氧基)己基丙二酸二乙酯(2)，其在碱性水解时生成6-(4-溴苯氧基)己基丙二酸乙酯(3)。由单酯(3)制备的8-(4-溴苯氧基)-2-亚甲基辛酸乙酯(4)用间氯过氧苯甲酸氧化，得到2-[6-(4-溴苯氧基)己基]环氧乙烷-2-羧酸乙酯(5)。基于Cu(I)Cl辅助亲核交换反应的放射性标记方法导致区域选择性放射性溴化，放射化学产率为45%。