高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (11): 2119-2121.

• 研究快报 • 上一篇    下一篇

光催化下(-)-马鞭烯酮的重排

宋志光1, 李叶芝1,2, 黄化民1   

  1. 1. 吉林大学化学学院, 长春130023;
    2. 吉林大学超分子结构与材料教育部重点实验室, 长春130023
  • 收稿日期:2004-06-02 出版日期:2004-11-24 发布日期:2004-11-24
  • 基金资助:

    国家自然科学基金(批准号:20172019)资助

Rearrangement Reaction of (-)-Verbenone by Photocatalysis

SONG Zhi-Guang1, LI Ye-Zhi1,2, HUANG Hua-Min1   

  1. 1. College of Chemistry, Jilin University, Changchun 130023, China;
    2. Key Laboratory for Supramolecular Structure and Materials of Ministry of Education, Jilin University, Changchun 130023, China
  • Received:2004-06-02 Online:2004-11-24 Published:2004-11-24

关键词: (-)-&alpha, -蒎烯, (-)-马鞭烯酮, (-)-异菊花烯酮

Abstract: We reported a facile synthesis of (-)-isochrysanthenone(2) from (-)-α-pinene in a high yield. When(-)-α-pinene reacted with O2 in the presence of Co[4-Me(C5H4N)2]Br2 used as a catalyst, the crude product of (-)-verbenone(1) was formed, and the crude product 1 was directly irradiated with ultraviolet light and converted into the (-)-isochrysanthenone(2). The structure of compound 2 was converted to a cyclic ester(4) by Baeyer-Villiger oxidation, the compound 4 was hydrolyzed to form a crystal 2,2,4-trimethyl-5-oxy-3-cyclohexenyl carboxylic acid 5. Compound 5 was confirmed by IR, 1H NMR and X-ray crystal analysis. In summary, we found that under the condition of photochemical rearrangement of (-)-verbenone and (+)-verbenone, different compounds were obtained, they are not enantiomers.

Key words: Pinene, (-)-Verbenone, (-)-Isochrysanthenone

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