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2019 , Vol. 39 >Issue 10: 2892 - 2897

DOI: https://doi.org/10.6023/cjoc201903049

研究论文

5-(1-苯基-3-苯基丙基-2-炔基)-2,2-亚戊基-1,3-二噁烷-4,6-二酮衍生物的有效合成

  • 范乃立 ,
  • 许招会 ,
  • 向正兵 ,
  • 肖强 ,
  • 廖传文
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  • a 江西师范大学化学化工学院 南昌 330027
    b 江西省人民医院外科 南昌 330006

收稿日期: 2019-03-24

  修回日期: 2019-04-30

  网络出版日期: 2019-05-28

基金资助

江西省省研究生创新基金(YC2015-B023);江西省教育厅科技攻关(No. GJJ170170)

收起

Efficent Synthesis of 5-(1-Phenyl-3-phenylprop-2-ynyl)-2,2-pentylidene-1,3-dioxane-4,6-dione Derivatives

  • Naili Fan, ,
  • Zhaohui Xu, ,
  • Zhengbing Xiang, ,
  • Qiang Xiao, ,
  • Chuanwen Liao,
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  • a Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027
    b Department of General Surgery, Jiangxi Province People's Hospital, Nanchang 330006

Received date: 2019-03-24

  Revised date: 2019-04-30

  Online published: 2019-05-28

Supported by

Project supported by the Graduate Innovation Foundation of Jiangxi Province(YC2015-B023);the Science and Technology Research Project of Jiangxi Provincial Education Department(No. GJJ170170)

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摘要

在醋酸铜/铜催化体系作用下, 以醛、2,2-亚戊基-1,3-二噁烷-4,6-二酮和芳基乙炔为原料, 发生包含Knoevenagel缩合与共轭加成反应的多组分反应, 有效地合成了12种5-(1-苯基-3-苯基丙基-2-炔基)-2,2-亚戊基-1,3-二噁烷-4,6-二酮衍生物. 该工艺具有收率高(65%~88%)、反应温和、操作简单及过量铜粉还能回收利用等优点.

关键词： 多组分反应; 醋酸铜/铜; 2,2-亚戊基-1,3-二噁烷-4,6-二酮; 5-(1-苯基-3-苯基丙基-2-炔基)-2,2-亚戊基-1,3-二噁烷-4,6-二酮衍生物

本文引用格式

范乃立 , 许招会 , 向正兵 , 肖强 , 廖传文 . 5-(1-苯基-3-苯基丙基-2-炔基)-2,2-亚戊基-1,3-二噁烷-4,6-二酮衍生物的有效合成[J]. 有机化学, 2019 , 39(10) : 2892 -2897 . DOI: 10.6023/cjoc201903049

Abstract

A convenient and efficient approach for the synthesis of 5-(1-phenyl-3-phenylprop-2-ynyl)-2,2-pentylidene-1,3- dioxane-4,6-dione derivatives through a three-component reaction of aldehydes with 2,2-pentylidene-1,3-dioxane-4,6-dione and arylacetylene in the presence of Cu(OAc)2·H2O/Cu is described with 12 examples. The reaction tolerates a wide range of aldehydes furnishing the products with good to excellent isolated yields (65%~88%). Additionally, the synthetic protocol has the advantages of wild conditions, simple operation, and excessive copper reused.

Key words： multicomponent reaction; copper acetate/copper; 2,2-pentylidene-1;3-dioxane-4;6-dione; 5-(1-phenyl-3-phe- nylprop-2-ynyl)-2;2-pentylidene-1;3-dioxane-4,6-dione derivatives

参考文献

[1] (a) Bharate, S. B.; Nemmani, K. V. S.; Vishwakarma, R. A. Expert Opin. Ther. Pat. 2009, 19, 237.
[1] (b) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
[2] Knopfel, T. F.; Carreira, E. M. J. Am. Chem. Soc. 2003, 125, 6054.
[3] (a) Liu, S.; Fillion, E. . Org. Lett 2014, 16, 5748.
[3] (b) Jia, W.; Li, S.; Yu, M.; Chen, M.; Jiao, N. . Tetrahedron Lett 2009, 50, 5406.
[3] (c) Li, S.; Jia, W.; Jiao, N . Adv. Synth. Catal. 2009, 351, 569.
[4] Lee, E. J.; Gleason, F. K. Plant Sci. 1994, 103, 155.
[5] Edwards, K. R. PCT Int. Appl. 1982, 19.
[6] Huneck, S.; Schreiber, K. Phytochemistry 1972, 11, 2429.
[7] Fang, X.; Anderson, J. E.; Chang, C.; McLaughlin, J. L. Tetrahedron 1991, 47, 9751.
[8] (a) Puchot, C.; Samuel, O.; Dunach, E.; Zaho, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353.
[8] (b) Sinclair, J. A.; Molander, G. A.; Brown, H. C. J. Am. Chem. Soc. 1977, 99, 954.
[9] (a) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053.
[9] (b) Bruhn, M.; Brown, C. H.; Collins, P. W.; Palmer, J. R.; Dajani, E. Z.; Pappo, R. . Tetrahedron Lett 1976, 17, 235.
[10] (a) Hooz, J.; Layton, R. B. J. Am. Chem. Soc. 1971, 93, 7320.
[10] (b) Schwartz, J.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053.
[11] (a) Kim, S.; Lee, J. M. Tetrahedron Lett. 1990, 31, 7627.
[11] (b) Kim, S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783.
[12] (a) Knopfel, T. F.; Zarotti, P.; Ichikawa, T.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 9682.
[12] (b) Fujimori, S.; Knopfel, T. F.; Zarotti, P.; Ichikawa, T.; Carreira, E. M.; Boyall, D. Bull. Chem. Soc. Jpn. 2007, 80, 1635.
[12] (c) Fujimori, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 4964.
[12] (d) Zarotti, P.; Knopfel, T F.; Aschwanden, P.; Carreira, E. M . ACS Catal. 2012, 2, 1232.
[13] Mishra, S.; Liu, J.; Aponick, A. J. Am. Chem. Soc. 2017, 139: 3353.
[14] Fillion, E.; Zorzitto, A. K. J. Am. Chem. Soc. 2009, 131, 14608.
[15] Cui, S.; Walker, S. D.; Woo, J. C. S.; Borths, C. J.; Mukherjee, H.; Chen, M. J.; Faul, M. M . J. Am. Chem. Soc. 2010, 132, 436.
[16] Krabbe, S. W.; Do, D. T.; Johnson, J. S. Org. Lett. 2012, 14, 5932.
[17] Knopfel, T. F.; Boyall, D.; Carreira, E. M. Org. Lett. 2004, 6, 2281.
[18] (a) Xu, Z. H. Chin. J. Org. Chem. 2014, 34, 1687 (in Chinese).
[18] ( 许招会 , 有机化学 2014, 34, 1687.)
[18] (b) Yang, D. L.; Li, J. R.; Sun, K. N . Chin. J. Org. Chem. 2013, 33 2341 (in Chinese).
[18] ( 杨德利, 李加荣, 孙克宁, 路红燕, 刘明星, 史大昕 , 有机化学, 2013, 33 2341.)
[18] (c) Francesco, E.; Salvatore, G.; Ornelio, R . Tetrahedron Lett. 2011, 59 568.
[19] Lin, C. H.; Xu, Z. H.; Liao, W. L.; Qiu, Z. Y.; Xia, J. H. Chin. J. Org. Chem. 2015, 35, 212 (in Chinese).
[19] ( 林春花, 许招会, 廖维林, 邱曾烨, 夏剑辉, 有机化学, 2015, 35, 212.)
[20] (a) Xu, Z. H.; Zhang, H. F.; Xiong, Y. K.; Liu, D. Y.; Huang, Q. S. Heterocycles 2016, 92, 2252.
[20] (b) Xu, Z. H.; Zhang, H. F.; Lin, C. H.; Liu, D. Y . Heterocycles 2016, 92, 1031.
[20] (c) Zhou, P.; Xu, Z. H . J. Jiangxi Normal Univ. (Nat. Sci.) 2019, 43, 167 (in Chinese).
[20] ( 周鹏, 许招会 , 江西师范大学学报(自然科学版), 2019, 43, 167.)
[21] Xu, Z. H.; Chen, F. B.; Li, Y. Y.; Huang, Q. S.; Liao, C. W. Chin. J. Org. Chem. 2018, 38, 3101 (in Chinese).
[21] ( 许招会, 陈飞彪, 李瑜钰, 黄清水, 廖传文, 有机化学, 2018, 38, 3101.)
[22] Coates, G. E, Prakin, C. J. Inorg. Nucl. Chem. 1961, 22, 59.
[23] Manna, J.; John, K. D.; Hopkins, M. D. Adv. Organomet. Chem. 1995, 38, 79.
[24] Yan, N.; Xiong, B.; Liao, W. L.; Xu, Z. H. Chin. J. Org. Chem. 2010, 30, 1391 (in Chinese).
[24] ( 严楠, 熊斌, 廖维林, 许招会, 有机化学, 2010, 30, 1391.)
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