Studies on the Synthesis of 5-Trifluoromethylpiperonal

doi:10.6023/cjoc201211010

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 1057-1061.DOI: 10.6023/cjoc201211010 Previous Articles Next Articles

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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

收稿日期:2012-11-07 修回日期:2012-12-21 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 Yahu^a,b, Han Min^b, Zhang Lanlan^b, Zhou Shuiping^b, 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

Received:2012-11-07 Revised:2012-12-21 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.

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

Cite this article

Wang Yahu, Han Min, Zhang Lanlan, Zhou Shuiping, Duan Zhongyu. Studies on the Synthesis of 5-Trifluoromethylpiperonal[J]. Chin. J. Org. Chem., 2013, 33(05): 1057-1061.

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[1] Luo, M.; Ma H.-Z.; Su. Q.-D.; Li, Q.-R. Chin J. Struct. Chem. 2002, 21, 538.
[2] Yang, D.-Q.; Lv, F.; Li, W.-H.; Jiang, Q.-J.; Guo, W. Chin. J. Org. Chem. 2004, 24, 1465 (in Chinese).
(杨定乔, 吕芬, 李文辉, 蒋启军, 郭维, 有机化学, 2004, 24, 1465).
[3] Müller, K.; Faeh, C.; Diederich, F. Science. 2007, 317, 1881.
[4] Jiang, H.-Z.; Song, L.-P.; Luo, H.-H.; Yi, H.; Zhu, S.-Z.; Hao, J. J. Shanghai Univ. (Nat. Sci. Ed.) 2011, 17, 458 (in Chinese).
(蒋海珍, 宋力平, 罗会华, 易海, 朱仕正, 郝健, 上海大学学报(自然科学版), 2011, 17, 458.)
[5] Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
[6] Shinde, A. T.; Zangade, S. B.; Chavan, S. B. A. Synth. Commun. 2010, 40, 3506.
[7] Chen, X.; Qiao, X.; Cui, M.-F.; Zhang, J.-P.; Tang, J.-H. New Chem. Mater. 2005, 33, 63 (in Chinese).
(陈献, 乔旭, 崔咪芬, 张进平, 汤吉海, 化工新型材料, 2005, 33, 63.)
[8] Lei, H.; Zhu, H.-J.; Han, B.-Y.; Xu, S.-L. Fine Chem. 2004, 21, 639 (in Chinese).
(雷宏, 朱红军, 韩邦友, 徐守林, 精细化工中间体, 2004, 21, 639.)
[9] Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese).
(卿凤翎, 有机化学, 2012, 32, 815.)
[10] Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
[11] Chang, Y.; Cai, C. Tetrahedron Lett. 2005, 46, 3161.
[12] Markovich, K. M.; Tantishaiyakul, V.; Hamada, A.; Miller D. D.; Romstedt, K. J.; Shams G.; Shin Y.; Fraundorfer, P. F.; Doyle K.; Feller, D. R. J. Med. Chem. 1992, 35, 466.
[13] Chen, Q-Y,; Duan, J-X.;. Tetrahedron Lett. 1993, 34, 4241.
[14] Achelle, S.; Ple, N.; Turck, A.; Bouillon, J. P.; Portella, C. J. Heterocycl. Chem. 2006, 43, 1243.
[15] Bentley, J. M.; Adams D. R.; Bebbington, D.; Benwell, K. R.; Bickerdike, M. J.; Davidson, J. E. P.; Dawson, C. E.; Dourish, C. T.; Duncton, M. A. J.; Gaur, S.; George, A. R.; Giles, P. R.; Hamlyn, R. J.; Kennett, G. A.; Knight, A. R.; Malcolm, C. S.; Mansell, H. L.; Misra, A.; Monck, N. J. T.; Pratt, R. M.; Quirk, K.; Roffey, J. R. A.; Vickers, S. P.; Cliffe, I. A. Bioorg. Med. Chem. Lett. 2004, 14, 2367.
[16] Chen, Q.-Y. J. Fluorine Chem. 1995, 72, 241.
[17] Wu, T. R.; Shen, L.; Chong, J. M. Org. Lett. 2004, 6, 2701.
[18] Bueno, A. B.; Flynn, C. J.; Gilmore, J.; Marcos, A.; Montero, C.; Porterc, W.; Williamsb. A. C. Tetrahedron Lett. 2005, 46, 7769.
[19] Chen, Q.-Y.; Wu, S.-W. J. Chem. Soc., Chem. Commun. 1989, 705.
[20] Liu, C.; Chen, Q.-Y. Eur. J. Org. Chem. 2005, 3680.
[21] Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V. D.; Roy, S. Tetrahedron 2011, 67, 2161.
[22] Corbett, R. E.; Mcdowall, M. A. J. Chem. Soc., 1958, 3740.
[23] Anhoury, M. L.; Crooy, P.; Neys, R. D.; Eliaers, J. J. Chem. Soc., Perkin Trans. 1 1974, 1015.
[24] Nammalwar, B.; Bunce, R. A.; Berlin, K. D.; Bourne, C. R.; Bourne, P. C.; Barrow, E. W.; Barrow, W. W. Org. Prep. Proced. Int. 2012, 44, 146.
[25] Backstrom, R.; Honkanen, E.; Pippuri, A.; Kairisalo, P.; Pystynen, J.; Heinola, K.; Nissinen, E.; Linden, I. B.; Mannisto, P. T.; Kaakkla, S.; Pohto, P. J. Med. Chem. 1989, 32, 841.

5-三氟甲基胡椒醛的合成研究

Studies on the Synthesis of 5-Trifluoromethylpiperonal

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