5-三氟甲基胡椒醛的合成研究有机化学.pdfVIP

DOI: 10.6023/cjoc201211010 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 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 (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) 摘要 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 Studies on the Synthesis of 5-Trifluoromethylpiperonal Wang, Yahua,b Han, Minb Zhang, Lanlanb Zhou, Shuipingb Duan, Zhongyu*,a 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) Abstract 5-Trifluoromethylpiperonal was obtained by iodination, demethylation, methylene etherification and trifluoro- methyl 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, cata- lyst 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