有机化学 ›› 2013, Vol. 33 ›› Issue (05): 1057-1061.DOI: 10.6023/cjoc201211010 上一篇    下一篇

研究论文

5-三氟甲基胡椒醛的合成研究

王亚虎a,b, 韩民b, 张兰兰b, 周水平b, 段中余a   

  1. a 河北工业大学化工学院 天津 300130;
    b 天津天士力集团研究院现代中药研究所 天津 300410
  • 收稿日期:2012-11-07 修回日期:2012-12-21 出版日期:2013-05-25 发布日期:2013-01-07
  • 通讯作者: 段中余,zyduan@hebut.edu.cn E-mail:zyduan@hebut.edu.cn
  • 基金资助:

    天津市科技支撑计划重点(No. 12ZCZDSY01200)、河北省自然科学基金(No. B2010000039)、河北省教育厅高等学校科学研究(No. 2011121)和教育部归国留学基金(2012)资助项目.

Studies on the Synthesis of 5-Trifluoromethylpiperonal

Wang Yahua,b, Han Minb, Zhang Lanlanb, Zhou Shuipingb, Duan Zhongyua   

  1. a School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130;
    b Institute of Modern Tradtional Chinese Medicine, Institute of Tasly Academy, Tianjin Tasly Group Co. Ltd., Tianjin 300410
  • Received:2012-11-07 Revised:2012-12-21 Online:2013-05-25 Published:2013-01-07
  • Supported by:

    Project supported by Key Projects in the Tianjin Science & Technology Pillar Program (No. 12ZCZDSY01200), the Hebei Provincial Natural Science Foundation of China (No. B2010000039), the Hebei Education Department Research Project (No. 2011121) and the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry.

以香草醛为起始原料, 经碘代、脱甲基、亚甲基醚化、三氟甲基化反应以较高收率合成了5-三氟甲基胡椒醛, 产物结构经过了1H NMR, 13C NMR, 19F NMR和HRMS的确证. 重点研究了三氟甲基化反应, 考察了不同三氟甲基化试剂、溶剂、催化剂用量、反应温度以及反应时间对三氟甲基化反应收率的影响, 确定了最佳反应条件. 随后, 该方法成功运用于3, 4位不同取代的5-碘苯甲醛的三氟甲基化反应, 制得了三种5-三氟甲基胡椒醛的衍生物.

关键词: 5-三氟甲基胡椒醛, 三氟甲基化反应, 合成

5-Trifluoromethylpiperonal was obtained by iodination, demethylation, methylene etherification and trifluoromethyl reaction of vanillin in a satisfied yield. The chemical structure of the product was identified by 1H NMR, 13C NMR, 19F NMR and HRMS. The optimal reaction conditions were investigated, including trifluoromethylation reagents, solvents, catalyst amounts, reaction temperature and reaction time. Meanwhile, three hydroxy substituted derivatives of 3,4-dihydroxy- 5-iodo-benzaldehyde were acquired by trifluoromethylation reaction with this method.

Key words: 5-trifluoromethylpiperonal, trifluoromethylation reaction, synthesis