研究简报

新型天麻素中间体类似物的高效合成

  • 许招会 ,
  • 李瑜钰 ,
  • 刘德永 ,
  • 肖强
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  • a 江西师范大学化学化工学院 南昌 330027;
    b 江西省人民医院骨科 南昌 330006

收稿日期: 2018-04-02

  修回日期: 2018-05-15

  网络出版日期: 2018-07-05

基金资助

Project supported by the National Natural Science Foundation of China (No. 81760297), the Graduate Innovation Fundation of Jiangxi Province (No. YC2015-B023) and the Science and Technology Research Project of Jiangxi Provincial Education Department (No. GJJ170170).

Highly Efficent Synthesis of Novel Gastrodine Intermediate Analogues

  • Xu Zhaohui ,
  • Li Yuyu ,
  • Liu Deyong ,
  • Xiao Qiang
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  • a Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027;
    b Department of Orthpaedics, Jiangxi Province People's Hospital, Nanchang 330006

Received date: 2018-04-02

  Revised date: 2018-05-15

  Online published: 2018-07-05

Supported by

Project supported by the National Natural Science Foundation of China (No. 81760297), the Graduate Innovation Fundation of Jiangxi Province (No. YC2015-B023) and the Science and Technology Research Project of Jiangxi Provincial Education Department (No. GJJ170170).

摘要

在葡萄糖酸的催化作用下,以4-甲酰基苯基-2,3,4,6-O-四乙酰基-β-D-葡萄糖苷和1,3-二噁烷-4,6-二酮为原料,发生Knoevenagel缩合反应合成了10种新型天麻素中间体类似物.该反应具有收率高(78%~92%)、反应温和、操作简单及环境友好等优点.此外,葡萄糖酸还可重复使用.

本文引用格式

许招会 , 李瑜钰 , 刘德永 , 肖强 . 新型天麻素中间体类似物的高效合成[J]. 有机化学, 2018 , 38(11) : 3118 -3122 . DOI: 10.6023/cjoc201804005

Abstract

Ten gastrodine intermediate analogues were synthesized by the Knoevenagel reaction of 4-formylphenyl(2,3,4,6-tetra-O-acetyl)-β-D-glucoside and 1,3-dioxane-4,6-dione with gluconic acid as a catalyst. In this reaction there are many advantages with good to excellent yields (78%~92%), mild conditions, simple operations and environmental friendliness. Additionally, gluconic acid could be recycled and reused many times without lossing its efficiency.

参考文献

[1] Wang, M. W.; Hao, X.; Chen, K. Philos. Trans. R. Soc., B 2007, 362, 1093.
[2] Zhou, J. Acta Chim. Sin. 1980, 38, 7.
[3] Liu, J.; Mori, A. Neuropharmacology 1992, 31, 1287.
[4] Park, S.; Kim, D. S.; Kang, S. Appl. Environ. Microbiol. 1994, 60, 3903.
[5] Ahn, E. K.; Jeon, H. J.; Lim, E. J.; Jung, H. J. J. Ethnopharmacol. 2007, 110, 476.
[6] Sha, J. Z.; Mao, H. K. Chin. Pharm. Bull. 1987, 22, 27(in Chinese). (沙静姝, 毛洪奎, 药学通报, 1987, 22, 27.)
[7] Wu, C. R.; Hsieh, M. T.; Huang, S. C.; Chang, W. H.; Chen, C. F. Planta Med. 1996, 62, 317.
[8] Wen, H.; Lin, C. L.; Ling, Q.; Ge, H.; Ma, L.; Cao, R. H.; Wan, Y. Q.; Peng, W. L.; Wang, Z. H.; Song, H. C. Eur. J. Med. Chem. 2008, 43, 166.
[9] Zhu, Q. L.; Tang, Q.; Li, Y.; Yin, S. F. Chin. J. Org. Chem. 2006, 26, 1264(in Chinese). (祝钱莉, 唐强, 李颖, 尹述凡, 有机化学, 2006, 26, 1264.)
[10] Hu, C.; Yang, H. J.; Yin, S. F. Chin. J. Org. Chem. 2009, 29, 89(in Chinese). (胡翠, 杨鸿均, 李颖, 尹述凡, 有机化学, 2009, 29, 89.)
[11] Zheng, L.; Yin, X. J.; Yang, C. L.; Li, Y.; Yin, S. F. Chem. J. Nat. Compd. 2011, 47, 170.
[12] Chen, B. C. Heterocyles 1991, 32, 529.
[13] (a) Bian, Y. J.; Qin, Y; Xiao, L. W.; Li, J. T. Chin. J. Org. Chem. 2006, 26, 1165(in Chinese). (边延江, 秦英, 肖立伟, 李记太, 有机化学, 2006, 26, 1165.)
(b) Huang, W. Y.; Qian, Z. H. Acta Chim. Sinica 1987, 45, 1175(in Chinese). (黄维垣, 钱昭辉, 化学学报, 1987, 45, 1175.)
[14] Fillion, E.; Dumas, A. M.; Hogg, S. A. J. Org. Chem. 2006, 71, 9899.
[15] Lin, C. H.; Yuan, J. J.; Liu, D. Y.; Zhang, H. F.; Xu, Z. H. Chin. J. Org. Chem. 2017, 37, 1560(in Chinese). (林春花, 袁建军, 刘德永, 张后富, 许招会, 有机化学, 2017, 37, 1560.)
[16] Tahmassebi, W. D.; Wilson, L. J. A.; Kieser, J. M. Synth. Commun. 2009, 39, 2605.
[17] Pesyan, N. N.; Gharib, A.; Behroozi, M.; Shokr, A. Arabian J. Chem. 2013, 5, 1.
[18] Rao, P. S.; Venkataratnam, R. V. Indian J. Chem. B. 1993, 32B, 484.
[19] Tahmassebi, D.; Wilson, L. J. A.; Kieser, J. M. Synth. Commun. 2009, 40, 260.
[20] Zhou, Z. H.; Yang, J.; Li, M. H.; Gu, Y. L. Green Chem. 2011, 13, 2204.
[21] Li, B. H.; Li, P. H.; Fang, X. N.; Li, C. X.; Sun, J. L.; Mo, L. P. Tetrahedron 2013, 69, 1057.
[22] Yan, N.; Xia, J. H.; Xiong, Y. K.; Xiong, B.; Lin, C. H.; Liao, W. L. Chin. J. Org. Chem. 2014, 34, 2487(in Chinese). (严楠, 夏剑辉, 熊云奎, 熊斌, 林春花, 廖维林, 有机化学, 2014, 34, 2487.)
[23] Xu, Z. H.; Zhou, P.; Tu, Y. H.; Liu, D. Y.; Liao, W. L.; Liao, C. W. Heterocycles 2017, 94, 1115.
[24] Lars, K.; Joachim, T. J. Carbohydr. Chem. 2003, 22, 9.

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