合成化学2024,Vol.32Issue(8) :711-716.DOI:10.15952/j.cnki.cjsc.1005-1511.23117

一种腐霉利衍生物的设计与合成

Design and Synthesis of A Putrescine Derivative

李庆 朱胜钦 刘娟 薛志勇
合成化学2024,Vol.32Issue(8) :711-716.DOI:10.15952/j.cnki.cjsc.1005-1511.23117

一种腐霉利衍生物的设计与合成

Design and Synthesis of A Putrescine Derivative

李庆 1朱胜钦 1刘娟 1薛志勇1
扫码查看

作者信息

  • 1. 武汉纺织大学化学与化工学院,湖北武汉 430073
  • 折叠

摘要

含羧基基团的腐霉利衍生物,其羧基能够与蛋白质分子发生酰化或重氮化反应,能够对农药残留快速进行分析检测,在食品安全领域具有潜在应用价值.以2-氯丙酸甲酯和甲基丙烯酸甲酯为原料,通过亲核取代、酯水解、脱水反应、烷基化、硝基还原、氨基酰基化、酸胺缩合和三氟乙酸水解8步反应合成了腐霉利半抗原衍生物,其结构经1H NMR,13C NMR和MS(ESI)表征,并对其关键的合成工艺进行优化.结果表明:2-氯丙酸甲酯和甲基丙烯酸甲酯的反应时间为96 h时,亲核取代反应的收率最高为70%.硝基还原过程中,以二氯亚锡水合物作还原剂,且二氯亚锡水合物与中间体8的物质的量之比为4.0∶1.0时,硝基还原反应收率最高为63%.当化合物5和化合物9的物质的量之比为1.5∶1.0,且反应温度为85 ℃时,氨基酰基化反应最高收率为50%.

Abstract

The carboxyl group of humus derivatives can acylation or diazotization with protein mole-cules,which can quickly analyze and detect pesticide residues,and has potential application value in the field of food safety.Using methyl 2-chloropropionate and methyl methacrylate as raw materials,the humus hapten derivatives were synthesized through an 8-step reaction of nucleophilic substitution,ester hydrolysis,dehydration,alkylation,nitro reduction,amino nucleophilic substitution,acid amine con-densation and trifluoroacetic acid hydrolysis.Their structures were characterized by 1H NMR,13C NMR and MS(ESI).The key synthesis process was optimized.The results showed that the reac-tion time of methyl 2-chloropropionate and methyl methacrylate was 96 h.The yield of the nucleophilic substitution reaction was up to 70%.In the nitro reduction process,when dichlorostannous hydrate was used as the reducing agent and the ratio of the amount of dichlorostannous hydrate to the amount of intermediate 8 was 4.0∶1.0,the nitro reduction reaction yield was the highest 63%.The maximum yield of aminoacylation was 50%when the ratio of compound 5 to compound 9 was 1.5∶1.0 and the reaction temperature was 85 ℃.

关键词

腐霉利/衍生物/烷基化/亲核取代/硝基还原/酸胺缩合

Key words

procymidone/ramification/alkylation/nucleophilic substitution/nitro reduction/acid a-mine condensation

引用本文复制引用

基金项目

国家自然科学基金资助项目(21602163)

湖北省自然科学基金资助项目(2016CFB261)

湖北省教育厅中青年人才项目(Q20161607)

生物质纤维与生态染整湖北省重点实验室开放课题项目(STRZ201907)

出版年

2024
合成化学
四川省化学化工学会 中国科学院成都有机化学研究所

合成化学

CSTPCD
影响因子:0.42
ISSN:1005-1511
段落导航相关论文