中华医学超声杂志

应用化学 ›› 2010, Vol. 27 ›› Issue (10): 1238-1240.DOI: 10.3724/SP.J.1095.2010.90863

• 研究简报 • 上一篇    

茶螺烷酮合成的新工艺

刘长辉,文瑞明*,雷雪松,张哲   

  1. (湖南城市学院化学与环境工程系 益阳 413000)
  • 收稿日期:2009-12-22 修回日期:2010-03-24 出版日期:2010-10-10 发布日期:2010-10-10
  • 通讯作者: 文瑞明,男,教授; E-mail:wenruiming@sohu.com; 研究方向：有机合成
  • 基金资助:
    湖南省科技计划资助项目（2009GK3175）

A New Synthetic Approach to Theaspirone

LIU Chang-Hui, WEN Rui-Ming*, LEI Xue-Song, ZHANG Zhe   

  1. (Department of Chemistry and Environmental Engineering,Hunan City University,Yiyang 413000)
  • Received:2009-12-22 Revised:2010-03-24 Published:2010-10-10 Online:2010-10-10

PDF

1837

摘要：

以α-紫罗兰酮为原料，经间氯过氧苯甲酸环氧化、甲醇钠开环、超声波辐射Pd/C催化甲酸铵选择性碳碳双键加H、硼氢化钠还原、脱水环化及乙酰丙酮亚钴催化烯丙位氧气氧化等6步反应，以总收率52.6％合成了食用香料2,6,10,10-四甲基-1-氧杂-螺[4.5]-6-癸烯-8-酮(茶螺烷酮)。 用IR、1H NMR、MS谱及元素分析等测试技术表征了产物的结构和组成。

关键词: 茶螺烷酮, 超声波辐射, α-紫罗兰酮, 选择性氧化还原, 烯丙位氧化

Abstract:

An edible perfume theaspirone, 1-oxa-8-oxo-2,6,10,10-tetramethyl-spiro-[4,5]-6-decene, was synthesized from α-ionone with 52.6% overall yield via six steps including epoxiation by metachloroperbenzoic acid, ring-opening in the presence of sodium methoxide, selective reduction of carbon-carbon double bond catalyzed by Pd/C with ammoniumformate under ultrasonic irridiation, then reduction with sodium borohydride, intramolecular cyclodehydration and allylic oxidation catalyzed by acetylacetone cobalt(Ⅱ) with oxygen gas. The structures and compositions of the product and some intermediates were characterized by IR, 1H NMR, MS and elemental analysis.

Key words: theaspirone, ultrasonic irradiation, α-ionone, selective reduction, allylic oxidation

中图分类号: 

网站版权 © 应用化学     本网站备案：吉ICP备12000082号