N-Boc-乙烯基甘氨酸甲酯及其异构化物的简便合成  

Convenient synthesis of methyl N-Boc-vinylglycinate and its isomer

作　　者：奉强 杨洋 刘新羽 许宏宇 张小玲 FENG Qiang;YANG Yang;LIU Xin-yu;XU Hong-yu;ZHANG Xiao-ling(Chemical Basis and Innovation Sichuan Experimental Teaching Demonstration Center,College of Chemistry and Life Sciences,Chengdu Normal University,Chengdu 611130,China.)

机构地区：[1]成都师范学院化学与生命科学学院,化学基础与创新四川省实验教学示范中心,四川成都611130

出　　处：《化学研究与应用》2024年第7期1669-1675,共7页Chemical Research and Application

基　　金：四川省科技计划资助项目(2023NSFSC0101)资助;大学生创新创业项目(202214389043)资助。

摘　　要：乙烯基甘氨酸是一种天然存在结构最简单的非蛋白β,γ-不饱和氨基酸,是合成众多具有生物活性物质的手性砌块,其自身及其衍生物亦显示出广泛的抗菌活性。以蛋氨酸为原料,经酯化反应、N-Boc保护反应、高碘酸钠氧化生成亚砜反应和以三甲苯作溶剂回流消除反应,合成得到N-Boc乙烯基甘氨酸甲酯。优化实验条件,反应以55~70%产率得到目标化合物。产物结构经^(1)H NMR、^(13)C NMR和MS确证。实验通过添加碱可选择得到碳碳双键移位异构体,同时提出了异构体生成的可能机理。此合成路线具有路线短、成本低、产率高、适合工业化放大生产特点。Vinylglycine is a naturally occurring non-proteinβ,y-unsaturated amino acid with the simplest structure,which is a chiral building block for the synthesis of many biologically active substances,showing a wide range of antimicrobial activities along with its derivatives.N-Boc vinylglycine methyl ester was obtained by esterification reaction,N-Boc protection reaction,sodium periodate oxi-dation reaction and refluxing elimination reaction,using methionine as raw material.Under the optimized reaction conditions,the tar-get compound was obtained with a yield of 55~70%,and its structure was confirmed by^(1)H NMR、^(13)C NMR and MS.The carbon-carbon double bond shifted isomer was obtained selectively through presenting base,and the reaction mechanism of isomer genera-tion was also hypothesized.This synthetic route was characterized by the short route,low cost,high yield and was suitable for indus-trial scale-up production.

关 键 词：N-Boc乙烯基甘氨酸甲酯 蛋氨酸 区域选择性 绿色合成 

分 类 号：O621.3[理学—有机化学]