生物碱季胺盐化合物反应的研究

首都医科大学学报 ›› 2007, Vol. 28 ›› Issue (3): 367-369.

生物碱季胺盐化合物反应的研究

张建伟

首都医科大学化学生物学与药学院

收稿日期:2006-01-16 修回日期:1900-01-01 出版日期:2007-06-24 发布日期:2007-06-24

The Investigation about the Reaction of Naturally Occurring Alkaloid Quaternary Ammonium Salts

Zhang Jianwei

College of Pharmaceutical Sciences, Capital Medical University

Received:2006-01-16 Revised:1900-01-01 Online:2007-06-24 Published:2007-06-24

摘要/Abstract

摘要： 目的了解季胺盐与碱作用的化学反应方式。方法阿托品与溴乙腈反应制得季胺盐溴化N-腈甲基阿托品,得到的季胺盐在四氢呋喃中与过量氢化钠反应。为了使反应的研究简化,将阿托品水解为托品醇、再氧化为托品酮,托品酮季胺盐与氢化钠反应。结果溴化N-腈甲基阿托品与过量氢化钠反应得化合物3和化合物4。溴化N-腈甲基托品酮5与氢化钠反应得化合物7。结论阿托品化合物在氢化钠作用下是首先发生Hofm ann消除反应进而环合生成化合物7。

关键词: 生物碱, 托品酮, 季胺盐

Abstract: Objective To investigated the reaction situation of quaternary ammonium salts with base.Methods Atropine reacted with bromoacetonitrile to give N-cyanomethyl-atropine bromide which was treated with sodium borohydride.In order to simplify the study,hydrolysis of atropine afforded tropine.Oxidation of tropine with chromic oxide gave tropinone which can be quaternized to 5 in quantitative yield.Quaternary ammonium salts 5 was treated with NaH.Results N-cyanomethyl-atropine bromide was treated with sodium borohydride to give 3 and 4.Reaction of N-cyanomethyl-tropinone bromide with sodium borohydride leads to 7.Conclusion Atropine derivatives react with sodium borohydride to performed Hofmann elimination reaction and cyclize to produce 7.

Key words: naturally occurring alkaloid, tropinone, quaternary ammonium salts

中图分类号:

张建伟. 生物碱季胺盐化合物反应的研究[J]. 首都医科大学学报, 2007, 28(3): 367-369.

Zhang Jianwei. The Investigation about the Reaction of Naturally Occurring Alkaloid Quaternary Ammonium Salts[J]. Journal of Capital Medical University, 2007, 28(3): 367-369.

[1]	张建伟;樊媛洁. 氮杂环类化合物的反应研究[J]. 首都医科大学学报, 2011, 32(5): 658-660.
[2]	卢思奇;庞苏红;王凤芸;赵玉英;楼之岑. 苦参体外抗贾第虫药物作用的初步观察[J]. 首都医科大学学报, 1993, 14(2): 99-101.