| 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 |
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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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