摘要
本文以衣康酸二甲酯为原料,分别和3种脂环胺发生Michael加成反应,得到3种N-取代-5-氧代吡咯烷-3-甲酸甲酯(2a^2c),再经碱性条件下水解得到3种N-取代-5-氧代吡咯烷-3-甲酸(1a^1c)。目标化合物及中间体结构通过1H NMR、13C NMR和ESI-MS确证。同时,以衣康酸二甲酯与环丁胺的Michael加成反应为模型,确定该步的优化反应工艺为:物料摩尔比n(环丁胺)∶n(衣康酸二甲酯)=1.3∶1,甲苯作溶剂,110℃反应2h。在该反应条件下,化合物2b收率为91.2%,其结构进一步通过X-射线单晶衍射确证。
Three kinds of methyl N-substituted-5-oxopyrrolidine-3-carboxylate(2 a^2 c)were synthesized by a Michael addition reaction of dimethyl itaconate and three types of alcyl amines respectively,and they were further hydrolyzed under basic conditions to afford three N-substituted-5-oxopyrrolidine-3-carboxylic acids(1 a^1 c).The structure of the products and intermediates were confirmed by 1H NMR,13 C NMR and ESI-MS.Taking the Michael addition reaction of dimethyl itaconate and cyclobutylamine as a model,the optimized reaction process of this step was finally determined as follows:n(cyclobutanamine)∶n(dimethyl itaconate)=1.3∶1,reacting in toluene at 110℃for 2 h.Compound 2 b was obtained in a yield of 91.2%,and its structure was further confirmed by X-ray single crystal diffraction.
作者
刘斌
徐小娜
仝红娟
朱周静
Liu Bin;Xu Xiaona;Tong Hongjuan;Zhu Zhoujing(School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Xi’an712046;Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province,Xi’an712046)
出处
《化学通报》
CAS
CSCD
北大核心
2019年第9期821-825,共5页
Chemistry
基金
陕西省自然科学基础研究计划(面上)项目(2018JM7046)
陕西省教育厅2018年度专项科研计划项目(18JK0954)
陕西国际商贸学院校级课题(SMXY201805)和陕西国际商贸学院“中药药效物质研究”创新团队建设项目(SSY18TD01)资助
