有机化学 ›› 2016, Vol. 36 ›› Issue (1): 202-206.DOI: 10.6023/cjoc201506023 上一篇    下一篇

研究简报

(+)-氧化樟脑的合成研究

张迪, 谢雄, 冯金生, 温鸿亮   

  1. 北京理工大学化工与环境学院 北京 100081
  • 收稿日期:2015-06-17 修回日期:2015-08-30 出版日期:2016-01-25 发布日期:2015-09-15
  • 通讯作者: 温鸿亮 E-mail:wen.hongliang816@gmail.com;analchemie@bit.edu.cn

Study on the Synthesis of (+)-Oxocamphor

Zhang Di, Xie Xiong, Feng Jinsheng, Wen Hongliang   

  1. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081
  • Received:2015-06-17 Revised:2015-08-30 Online:2016-01-25 Published:2015-09-15

(+)-氧化樟脑是(+)-樟脑在体内的代谢产物, 临床上主要用于治疗呼吸和循环衰竭. 目前(+)-氧化樟脑的合成方法存在反应时间长、反应条件剧烈、收率低、污染严重等问题. 本研究以天然(+)-樟脑为起始原料, 经过溴化、还原、酯化、水解和氧化反应合成了目标产物(+)-氧化樟脑. 各步中间体及目标产物经1H NMR、IR和GC-MS验证了结构, 并且运用单晶X射线衍射确定了关键中间体3,9-二溴樟脑的绝对构型. 这条路线反应条件温和, 操作简便, 避免了使用重金属作为氧化剂和还原剂, 是一条环境友好的合成路线.

关键词: (+)-氧化樟脑, 合成, 单晶

(+)-Oxocamphor is a metabolite of (+)-camphor in vivo, which is used to treat heart failure in clinic. However the present synthetic method has problems of long reaction time, serious pollution and low yield. In this paper we report an efficient synthesis of (+)-oxocamphor was reported via bromination, reduction, esterification, hydrolysis and oxidation using (+)-camphor as starting material. All the intermediates and (+)-oxocamphor were confirmed by 1H NMR, IR and GC-MS. The absolute configuration of 3,9-dibromocamphor was also ascertained by X-ray diffraction analysis. The overall yield of these 6-step procedures was about 10%.

Key words: (+)-oxocamphor, synthesis, single crystal