刘斌,徐小娜,仝红娟,朱周静.化学通报,2019,82(9):821-825.
N-取代-5-氧代吡咯烷-3-甲酸化合物的合成
Synthesis of N-Substituted-5-Oxopyrrolidine-3-Carboxylic Acids
投稿时间:2019-05-11  修订日期:2019-06-13
DOI:
中文关键词:  N-取代-5-氧代吡咯烷-3-甲酸  2-吡咯烷酮衍生物  Michael加成  合成  晶体结构
英文关键词:N-substituted-5-oxopyrrolidine-3-carboxylic acid  2-pyrrolidine derivatives  Michael addition reaction  synthesis  crystal structure
基金项目: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(18JK0954);陕西国际商贸学院校级课题(SMXY201805); 陕西国际商贸学院“中药药效物质研究”创新团队(SSY18TD01)建设项目资助。联系人简介:刘斌(1982-),男,博士,讲师,主要研究方向为药物分子设计合成。Emaillb125lb@163.com。 ,2*,徐小娜1,2,仝红娟1,2,朱周静1,2
作者单位E-mail
刘斌 陕西国际商贸学院医药学院
陕西省中药绿色制造技术协同创新中心
 
lb125lb@163.com 
徐小娜 陕西国际商贸学院医药学院  
仝红娟 陕西国际商贸学院医药学院  
朱周静 陕西国际商贸学院医药学院  
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中文摘要:
      报道一种N-取代-5-氧代吡咯烷-3-甲酸的合成方法。以衣康酸二甲酯为原料,分别和三种脂环胺发生Michael加成反应,制备得到三种N-取代-5-氧代吡咯烷-3-甲酸甲酯(2a~2c),再分别经过碱性水解得到三种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、ESI-MS确定。同时,以衣康酸甲酯与环丁胺的Michael加成反应为模型,确定该步的最佳反应工艺为:物料摩尔比n(环丁胺): n(衣康酸二甲酯)= 1.3 : 1,反应溶剂为甲苯,于110℃反应时间2 h。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。
英文摘要:
      Three kinds of methyl N-substituted-5-oxopyrrolidine-3-carboxylate derivatives (2a~2c) were synthesized by a Michael addition reaction of dimethyl itaconate and three types of alcyl amines respectively, then through hydrolysis reaction to afford N-substituted-5-oxopyrrolidine-3-carboxylic acids (1a~1c) respectively. The structure of the products and intermediates were confirmed by 1H NMR, 13C NMR and ESI-MS. The optimal reaction conditions were also investigated by using the Michael addition reaction of dimethyl itaconate and cyclobutanamine as model reaction. The optimal reaction conditions are as follows: The mole ratio of n (cyclobutanamine): n (dimethyl itaconate) = 1.3 : 1; The reaction was stirred in toluene at 110℃ for 2 hours. Compound 2b was obtained by the optimal reaction process in a yield of 91.2 %, and the structure of compound 2b was further confirmed by X-ray diffraction analysis.
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