SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 01: 189 - 192

DOI: https://doi.org/10.6023/cjoc1105292

研究简报

一锅法合成含两种桥联链的杯[4]双冠醚和双杯[4]冠醚

  • 叶进启 ,
  • 杨发福 ,
  • 张筱逸 ,
  • 焦自玉 ,
  • 郭红玉
展开
  • a 福建师范大学化学与材料学院 福州 350007;
    b 福建师范大学福建省高分子材料重点实验室 福州 350007

收稿日期: 2011-05-29

  修回日期: 2011-08-18

  网络出版日期: 2011-09-05

基金资助

国家自然科学基金(No. 20402002)、福建省自然科学基金(No. 2011J01031)、福建省高校杰出青年科研人才培育计划(No. JA10056)、福建省教育厅重点(No. JA11044)资助项目.

收起

One-Pot Syntheses of Calix[4]-bis-crowns and Biscalix[4]crown with Two Kinds of Bridging Chains

  • YE Jin-Qi ,
  • YANG Fa-Fu ,
  • ZHANG Xiao-Yi ,
  • JIAO Zi-Yu ,
  • GUO Hong-Yu
Expand
  • a College of Chemistry and Materials, Fujian Normal University, Fuzhou 350007;
    b Fujian Key Laboratory of Polymer Materials, Fujian Normal University, Fuzhou 350007

Received date: 2011-05-29

  Revised date: 2011-08-18

  Online published: 2011-09-05

Supported by

Project supported by the National Natural Science Foundation of China (No. 20402002), the Natural Science Foundation of Fujian Province (No. 2011J01031), the Program for Excellent Young Researchers in University of Fujian Province (No. JA10056), and the Project of Fujian Provincial Department of Education (No. JA11044).

Fold

摘要

报道了“一锅法”合成含两种桥联链的新型杯[4]双冠醚和双杯[4]冠醚. 杯[4]芳烃先与N,N'-乙撑基-二(2-氯乙酰胺)发生“1+1”缩合反应, 然后直接加入三甘醇双对甲苯磺酸酯继续进行“2+2”缩合反应, 合成了含两种桥联链的新型双杯[4]冠醚4. 按照相似程序, 杯[4]芳烃先后与N,N'-乙撑基-二(2-氯乙酰胺)、溴乙酸乙酯和二乙烯三胺反应, 得到含两种桥联链的新型杯[4]双冠醚5. 化合物5 进一步与异硫氰酸苯酯反应合成带硫脲支链的杯[4]双冠醚6. 所有新化合物的结构与构象经元素分析、质谱、核磁共振谱等表征证实.

关键词： 杯[4]冠醚; 双杯[4]芳烃; 合成; 一锅法

本文引用格式

叶进启 , 杨发福 , 张筱逸 , 焦自玉 , 郭红玉 . 一锅法合成含两种桥联链的杯[4]双冠醚和双杯[4]冠醚[J]. 有机化学, 2012 , 32(01) : 189 -192 . DOI: 10.6023/cjoc1105292

Abstract

The one-pot synthesis of novel calix[4]-bis-crowns and biscalix[4]crown with two kinds of bridging chains was described. Calix[4]arene was firstly reacted with N,N'-ethylenebis(2-chloroacetamide) in “1+1” condensation, and then triethylene glycol ditosylate was added directly to give a new biscalix[4]crown 4 with two kinds of bridging chains in “2+2” condensation. According to similar procedure, by successively reacting calix[4]arene with N,N'-ethylenebis(2-chloroacetamide), ethyl bromoacetate and diethylenetriamine, a new calix[4]-bis-crowns 5 with two kinds of bridging chains was prepared. Further reacting compound 5 with phenyl isothiocyanate afforded calix[4]-bis-crowns 6 with thiourea branched chain. The structures and conformation of new compounds were characterized by elemental analyses, ESI-MS, 1H NMR, etc.

Key words： calix[4]crown; biscalix[4]arene; synthesis; one-pot

参考文献

[1] Liu, Y.; You, C. C.; Zhang, H. Y. Supramolecular Chemistry, Nankai University Publication, Tianjin, 2001, pp. 351～356 (in Chinese). (刘育, 尤长城, 张衡益, 超分子化学, 天津南开大学出版社, 2001, pp. 351～356.)

[2] Asfari, Z.; Böhmer, V.; Harrowfield, J.; Vicens, J. Calixarenes, Kluwer Academic Publishers, Netherlands, 2001, pp. 130～154.

[3] Bondy, C. R.; Loeb, S. J. Coord. Chem. Rev. 2003, 240, 77.

[4] Chen, Y. Y.; Yang, F. F.; Lu, X. R. Tetrahedron Lett. 2000, 41, 1571.

[5] Zheng, Q. Y.; Chen, C. F.; Huang, Z. T. Chin. J. Chem. 2000, 18, 104.

[6] Casnati, A.; Ca, N. D.; Sansone, F.; Ugozzoli, F.; Ungaro, R. Tetrahedron 2004, 60, 7869.

[7] Oueslati, I.; Thuéry, P.; Shkurenko, O.; Suwinska, K.; Harrowfield, J.; Abidi, R.; Vicens, J. Tetrahedron 2007, 63, 62.

[8] Tang, F. S.; Yang, F. F.; Huang, Z. S.; Hong, B. Q.; Guo, H. Y. Chin. J. Org. Chem. 2009, 29(8), 1278 (in Chinese). (唐富胜, 杨发福, 黄智胜, 洪碧琼, 郭红玉, 林建荣, 有机化学, 2009, 29(8), 1278.)

[9] Yang, F. F.; Zheng, X. H.; Guo, H. Y.; Liu, C. H.; Guo, Y. J. Inclusion Phenom. Macrocyclic Chem. 2008, 62, 371.

[10] Oueslati, I. Tetrahedron, 2007, 63, 10840.

[11] Guan, B.; Gong, S. L.; Wu, X. J.; Li, Z. H.; Chen, Y. Y. J. Inclusion Phenom. Macrocyclic Chem. 2006, 54, 81.

[12] Chawla, H. M.; Singh, S. P.; Upreti, S. Tetrahedron 2007, 63, 5636.

[13] Asfari, Z.; Nicoille, X.; Vicens, J. J. Inclusion Phenom. Macrocyclic Chem. 1999, 33, 251.

[14] Asfari, Z.; Thuery, P.; Nierlich, M.; Vicens, J. Tetrahedron Lett. 1999, 40, 499.

[15] Chawla, H. M.; Singh, S. P.; Upreti, S. Tetrahedron 2006, 62, 9758.

[16] Bitter, I.; Grün, A.; Balazs, B.; Töth, G.; Horvath, G.; Töke, L. Synth. Commun. 1999, 29, 3905.

[17] Bok, J. H.; Kim, H. J.; Lee, J. W.; Kim, S. K.; Choi, J. K.; Vicens, J.; Kim, J. S. Tetrahedron Lett. 2006, 47, 1237.

[18] Kim, H. J.; Kim, S. H.; Kim, J. H.; Anh, L. N.; Lee, J. H.; Lee, C. H.; Kim, J. S. Tetrahedron Lett. 2009, 50, 2782.
Options
文章导航

/

〈 〉