Synthesis and Characterization of the Trans-cyanopyrrolidone

Hu Bingcheng,  Lü Chunxu,   Liu Zuliang,  Ma Dengsheng
(School of Chemical Engineering, Nanjing University of Science & Technology,  Nanjing  210094)

Abstract  The mono-isomeric trans-2-cyano-2,3-dimethyl-3-methoxycarbomethyl-5-pyrrolidone, which is used to build the ring-A fragment of the tolyporphin model, was synthesized through the ring-opening reaction of the lactone ring in the bicyclolactam-lactone and the isolation method of the high performance liquid chromatography(HPLC). It was characterized by ¹H NMR, ¹³C NMR, IR, MS and elemental analysis. Then its space conformation was determined by the NOE technique.
Key words   Cyanopyrrolidone,  High performance liquid chromatography,  Tolyporphin model,  NOE technique

反式氰基吡咯烷酮的合成及表征

胡炳成  吕春绪  刘祖亮  马登生
(南京理工大学化工学院  南京  210094)

摘要  采用高效液相色谱(HPLC)分离手段，通过环并内酰胺-内酯的酯环开环反应合成了用来构筑托尼卟吩模型A环结构单元的单一异构体—–反式-2-氰基-2,3-二甲基-3-甲氧羰甲基-5-吡咯烷酮，通过¹H NMR、¹³C NMR、IR、MS和元素分析对其结构进行了确认，并以氢核磁共振的NOE技术测定了其空间构象。
关键词   氰基吡咯烷酮  高效液相色谱  托尼卟吩模型  NOE技术

胡炳成  男，34岁，副研究员，从事天然产物的合成及应用研究。  E-mail: hubingcheng@yahoo.com
2003-07-01收稿，2003-09-04接受

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