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2012 , Vol. 32 >Issue 06: 1093 - 1100

DOI: https://doi.org/10.6023/cjoc1109211

研究论文

八元瓜环对1,ω-二(2-氨基吡啶)烷烃光致环加成反应的超分子催化性能的研究

  • 丛航 ,
  • 王杞生 ,
  • 张建新 ,
  • 陶朱 ,
  • 薛赛凤
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  • a 贵州大学应用化学研究所 贵阳 550002;
    b 贵州省天然产物重点实验室 贵阳 550003

收稿日期: 2011-09-21

  修回日期: 2012-01-11

  网络出版日期: 2012-02-22

基金资助

国家自然科学基金(No. 21162003)、贵州省科学技术基金(Nos. 黔科合J 字[2008]75, [2009]2073 及[2010]2126 号)资助项目.

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Supramolecular Catalysis of Cucurbit[8]uril on Photocycloaddition of 1,ω-Bi(2-aminopyridinium)alkylates

  • Cong Hang ,
  • Wang Qisheng ,
  • Zhang Jianxin ,
  • Tao Zhu ,
  • Xue Saifeng
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  • a Institute of Applied Chemistry, Guizhou University, Guiyang 550002;
    b Key Laboratory of Chemistry for Natural Products of Guizhou Province, Guiyang 550003

Received date: 2011-09-21

  Revised date: 2012-01-11

  Online published: 2012-02-22

Supported by

Project supported by the National Natural Science Foundation of China (No. 21162003), the Natural Science Foundation of Guizhou Province (Nos. [2008]75, [2009]2073, [2010]2126).

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摘要

合成了三种不同链长的1,ω-二(2-氨基吡啶)烷烃, 分别为二溴化1,4-二(2-氨基吡啶)丁烷(C4)、二溴化1,6-二(2-氨基吡啶)己烷(C6)、二溴化1,8-二(2-氨基吡啶)辛烷(C8). 考察了八元瓜环(Q[8])与上述三种1,ω-二取代烷烃的主客体相互作用, 运用1H NMR 及UV-vis 证明三种客体与Q[8]的作用模式均不相同. 在此基础上, 考察了八元瓜环对三种底物光致环加成反应的超分子催化性能. 结果表明, 由于三种底物与Q[8]的主客体作用模式不同, 八元瓜环对它们光二聚反应的超分子催化性能也各有差异.

关键词： 1,ω-二(2-氨基吡啶)烷烃; 瓜环; 光环加成反应; 主客体相互作用; 超分子催化

本文引用格式

丛航 , 王杞生 , 张建新 , 陶朱 , 薛赛凤 . 八元瓜环对1,ω-二(2-氨基吡啶)烷烃光致环加成反应的超分子催化性能的研究[J]. 有机化学, 2012 , 32(06) : 1093 -1100 . DOI: 10.6023/cjoc1109211

Abstract

Three kinds of 1,ω-bi(2-aminopyridinium)alkylates, which are the 1,4-bi(2-aminopyridinium)butane dibromide (C4), 1,6-bi(2-aminopyridinium)hexane dibromide (C6) and 1,8-bi(2-aminopyridinium)octane dibromide (C8), have been synthesized, respectively. The host-guest interactions of cucurbit[8]uril (Q[8]) with the above compounds have been investigated using 1H NMR and UV-vis spectra, and the results showed that there were different interaction models in the three host-guest systems. Subsequently, the photocycloaddition reactions of the substrates have been carried out in the presence of Q[8], and the dependence of the supramolecular catalytic active on the construction of substrate was observed.

Key words： 1,ω-bi(2-aminopyridinium)alkylates; cucurbituril; photocycloaddition; host-guest interaction; supramolecular catalysis

参考文献

[1] Freeman, W. A.; Mock, W. L.; Shih, N. Y. J. Am. Chem. Soc. 1981,103, 7367.  
[2] Day, A. I.; Arnold, A. P.; Blanck, R. J. Molecules 2003, 8(1), 74.  
[3] Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew.Chem., Int. Ed. 2005, 44(31), 4844.
[4] Yang, C.; Mori, T.; Origane, Y.; Ko, Y. H.; Selvapalam, N.; Kim,K.; Inoue, Y. J. Am. Chem. Soc. 2008, 130, 8574.  
[5] Cong, H.; Zhu, Q. J.; Xue, S. F.; Tao, Z.; Wei, G. Chin. Sci. Bull.2010, 55(32), 3633.  
[6] Montes-Navajas, P.; Corma, A.; Garcia, H. ChemPhysChem 2008,9, 713.  
[7] Halterman, R. L.; Moore, J. L.; Mannel, L. M. J. Org. Chem. 2008,73, 3266.  
[8] Saleh, N.; Koner, A. L.; Nau W. M. Angew. Chem., Int. Ed. 2008,47, 5398.  
[9] Cong, H.; Li, C.-R.; Xue, S.-F.; Tao, Z.; Zhu, Q.-J.; Wei, G. Org.Biomol. Chem. 2011, 9, 1041.  
[10] Zeng, J.-P.; Zhang, S.-M.; Zhang, Y.-Q.; Tao, Z.; Zhu, Q.-J.; Xue,S.-F.; Wei, G. Cryst. Growth Des. 2010, 10(10), 4509.  
[11] Ni, X.-L.; Lin, J.-X.; Zheng, Y.-Y.; Wu, W.-S.; Zhang, Y.-Q.; Xue,S.-F.; Zhu, Q.-J.; Tao, Z.; Day, A. I. Cryst. Growth Des. 2008, 8(9),3446.  
[12] Mock, W. L.; Shih, N. Y. J. Org. Chem. 1983, 48, 3618.  
[13] Cong, H.; Tao, Z.; Xue, S. F. Zhu, Q.-J. Curr. Org. Chem. 2011,15, 86.  
[14] Jon, S. Y.; Ko, Y. H.; Park, S. H.; Kim, H. J.; Kim, K. Chem.Commun. 2001, 1938.  
[15] Lei, L.; Luo, L.; Wu, X.-L.; Liao, G.-H.; Wu, L.-Z.; Tung C.-H.Tetrahedron Lett. 2008, 49, 1502.  
[16] Barooah, N.; Pemberton, B. C.; Johnson A. C.; Sivaguru, J. Photochem.Photobiol. Sci. 2008, 7, 1473.  
[17] Barooah, N.; Pemberton, B. C.; Sivaguru, J. Org. Lett. 2008,10(15), 3339.  
[18] Lei, L.; Luo, L.; Wu, X.-L.; Liao, G.-H.; Wu, L.-Z.; Tung C.-H.Tetrahedron Lett. 2008, 49, 1502.  
[19] Wang, R. B.; Yuan, L.; Macartney, D. H. J. Org. Chem. 2006, 71,1237.  
[20] Wang, Q. -S.; Cong, H.; Zhang, J.-X.; Tao, Z.; Xue. S.-F. Chin. J.Org. Chem. 2011, 31(7), 1049 (in Chinese).(王杞生, 丛航, 张建新, 陶朱, 薛赛凤, 有机化学, 2011, 31(7),1049.)  
[21] Wu, X.-L.; Luo, L.; Lei, L.; Liao, G.-H.; Wu, L.-Z.; Tung C.-H. J.Org. Chem. 2008, 73, 491.  
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