(2S)-1-[(2-噻吩基)苯氧基]-2-3-环氧丙烷的两步合成法  

Two Steps Synthesis of(2S)-1-[(2-thienyl)phenoxy]-2-3-propylene oxide

作　　者：张峰 张雷刚 林兴龙 黄正伟 解鸣涛 张叶青 ZHANG Feng;ZHANG Leigang;LIN Xinglong;HUANG Zhengwei;XIE Mingtao;ZHANG Yeqing(Zhejiang YongTai Technology Co.,Ltd.,Linhai 317016,China)

机构地区：[1]浙江永太科技股份有限公司,浙江临海317016

出　　处：《生物化工》2024年第5期71-75,共5页Biological Chemical Engineering

摘　　要：目的:以廉价、易得的(R)-环氧氯丙烷为起始原料构筑手性中心,合成(2S)-1-[(2-噻吩基)苯氧基]-2-3-环氧丙烷。方法:(R)-环氧氯丙烷与2-(噻吩-2-基)苯酚在弱碱性条件下反应生成中间体,再在强碱性条件下环合生成(2S)-1-[(2-噻吩基)苯氧基]-2-3-环氧丙烷。结果:经过两步比较温和的反应,生成双聚合杂质和手性异构体纯度约0.30%的粗品,经过重结晶得到高纯度目标化合物(双聚合杂质纯度0.02%,手性异构体纯度0.10%,单一杂质纯度<0.1%)。结论:(R)-环氧氯丙烷为起始原料构筑手性中心,产物容易分离、提纯,为(2S)-1-[(2-噻吩基)苯氧基]-2-3-环氧丙烷的工业化合成路径提供了有益参考。Objective:To synthesize(2S)-1-[(2-thiophenyl)phenoxy]-2-3-propane oxide from cheap and readily available(R)-epichlorohydrin.Methods:(R)-epichlorohydrin reacts with 2-(thiophene-2-yl)phenol to form intermediate under weak base condition,and then cycles to form(2S)-1-[(2-thiophenyl)phenoxy]-2-3-propane oxide under strong base condition.Results:after two steps of relatively mild reaction,a crude product with a bipolymeric impurity and chiral isomer content of about 0.30%is generated,and a high-purity target compound(bipolymeric impurity content of 0.02%,chiral isomer content of 0.10%,and single impurity content of<0.1%)is obtained by recrystallization.Conclusion:(R)-epichlorohydrin is used as the starting material to construct chiral center,and the product can be separated and purified easily,which provides a useful reference for the industrial synthesis of(2S)-1-[(2-thiophenyl)phenoxy]-2-3-propane oxide.

关 键 词：2-(噻吩-2-基)苯酚 (R)-环氧氯丙烷 (2S)-1-[(2-噻吩基)苯氧基]-2-3-环氧丙烷 两步合成 

分 类 号：O621.3[理学—有机化学]