有机化学 ›› 2011, Vol. 31 ›› Issue (04): 486-489. 上一篇    下一篇

研究论文

含氨基的金刚烷桥头二取代化合物合成研究

谢炳玉1,郭建维*,1,刘卅2,彭进平1   

  1. (1广东工业大学轻工化工学院 广州 510006)
    (2华南理工大学材料科学与工程学院 广州 510640)
  • 收稿日期:2010-08-29 修回日期:2010-10-06 发布日期:2010-11-23
  • 通讯作者: 谢炳玉 E-mail:xiebingyu.515@163.com
  • 基金资助:

    金刚烷及其应用技术研究开发

Synthesis of Briddgehead Bis-substituted Amino-adamantane Compounds

Xie Bingyu1 Guo Jianwei*,1 Liu Sa2 Peng Jinping1   

  1. (1 Faculty of Chemical Engineering & Light Industry, Guangdong University of Technology, Guangzhou 510006)
    (2 College of Material Science & Engineering, Southchina University of Technology, Guangzhou 510640)
  • Received:2010-08-29 Revised:2010-10-06 Published:2010-11-23

采用金刚烷甲酸为原料, 经溴代、叠氮化、库尔提斯重排、水解等四步反应合成了3-氨基-1-金刚烷醇(糖尿病药物中间体), 总收率为34%|以金刚烷甲酸为原料, 在无需卤素取代下, 通过里特反应、水解反应合成了3-氨基-1-金刚烷甲酸盐酸盐(抗肿瘤药物中间体), 总收率为73%. 采用元素分析、红外光谱、质谱、核磁共振谱等手段对两种产物的进行了结构鉴定, 分别提出了可能的反应机理.

关键词: 3-氨基-1-金刚烷醇, 3-氨基-1-金刚烷甲酸盐酸盐, 合成

3-Amino-1-adamantanol, a key intermediate of anti-diabetic drug, was successfully synthesized via bromization, azido, Curtius rearrangement and hydrolysis processes by using adamantane carboxylic acid as the starting raw material. The overall yield of 3-amino-1-adamantanol was 34%. 3-Amino- 1-adamantane carboxylic acid hydrochloride, an anti-neoplastic agent,was synthesized from adamantane carboxylic acid by Ritter, hydrolysis reaction in total yield of 73%. The structures of products were identified by elemental analysis, IR, MS, 1H NMR, etc. In addition, the possible reaction mechanisms were respectively proposed.

Key words: 3-amino-1-adamantanol, 3-amino-1-adamantane carboxylic acid hydrochloride, synthesis

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