English
新闻公告
More
化学进展 2008, Vol. 20 Issue (12): 1933-1944 前一篇   后一篇

• 综述与评论 •

基于杯[4]芳烃的手性识别*

卿光焱1 刘顺英2 何永炳1**

  

  1. (1. 武汉大学化学与分子科学学院 武汉 430072;
    2. 华东师范大学新药创制先进技术研究院 上海 200062)

  • 收稿日期:2008-01-21 修回日期:2008-03-14 出版日期:2008-12-24 发布日期:2008-12-25
  • 通讯作者: 何永炳

Chiral Recognition Based on Calix[4]arene

Qing Guangyan1 Liu Shunying2 He Yongbing1**

  

  1. (1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China; 2. Advanced Research Center of NBIC Integrated Drug Discovery and Development, East China Normal University, Shanghai, 200062, China)
  • Received:2008-01-21 Revised:2008-03-14 Online:2008-12-24 Published:2008-12-25
  • Contact: He Yongbing
手性杯芳烃是一类重要的主体化合物,在手性识别、对映体分离和不对称催化等方面有着广泛的用途。[4]芳烃引其稳定的构象和易于修饰的特点,成为研究最为广泛的杯芳烃分子,其中大量的文献报道了能够用于对映体识别和检测的手性[4]芳烃。在手性识别的研究中,荧光、紫外和核磁是3中最常见的研究方法,本文根据这3种方法进行分类,综述了近年来以杯[4]芳烃为分子骨架的手性受体的合成及其在手性识别中的应用。最后对手性[4]芳烃的发展前景作了展望。

Chiral calixarenes are a class of important host compounds and have wide applications in chiral recognition, enantiomer separation and asymmetrical catalysis. calix[4]arena is investigated most widely due to its stable conformation and easy derivatization. Among them lots of works reported the chiral calix[4]arenas can be used in enantiometric recognition and dectection. Fluorescence, UV-vis and NMR are the most common methods in the research of chiral recognition. Acording to these methods, the latest research progress in the synthesis of chiral receptors based on calix[4]arenas and theri applications in the chiral recognition are summerized. The prospect of chiral calix[4]arena is also discussed.

中图分类号: 

()

[1 ] Stibor I , Zlatuíková P. Top Curr. Chem. , 2005 , 255 : 31 —63
[2 ] Lehn J M. Supramolecular Chemistry. Concepts and Perspectives. VCH: Weinheim , 1995
[3 ] Naemura K, Tobe Y, Kaneda T. Coord. Chem. Rev. , 1996 ,148 : 199 —219
[4 ] Murakami Y, Kikuchi J , Hayashida O , et al . Chem. Rev. ,1996 , 96 : 721 —758
[5 ] 刘育(Liu Y) , 尤长城(You C C) , 张衡益(Zhang H Y) . 超分子化学( Supermolecular Chemistry) . 天津: 南开大学出版社(Tianjin : Nankai University Press) , 2000. 306 —384
[6 ] Ripmeester J A , Enright G D , Moudrakovski I L , et al . Chem.Commun. , 2006 , 4986 —4996
[7 ] Zhang C L , Gong S L , Chen Y Y. Chin. J . Org. Chem. , 2007 ,27 : 795 —805
[8 ] Lhoták P. Top Curr. Chem. , 2005 , 255 : 65 —95
[9 ] Pu L. Chem. Rev. , 2004 , 104 : 1687 —1716
[10] Martínez-Máìez R , Sancenón F. Chem. Rev. , 2003 , 103 :4419 —4476
[11] Lee F. Tetrahedron , 2000 , 56 : 6151 —6170
[12] Ragusa A , Rossi S , Kilburn J D , et al . Chem. Eur. J . , 2005 ,11 : 5674 —5688
[13] Grady T, Harris S J , Diamond D , et al . Anal . Chem. , 1996 ,68 : 3775 —3782
[14] Lynam C , Jennings K, Diamond D , et al . Anal . Chem. , 2002 ,74 : 59 —66
[15] Lynam C , Diamond D. J . Mater. Chem. , 2005 , 15 : 307 —314
[16] Liu S Y, He Y B , Qing G Y, et al . Tetrahedron : Asymmetry ,2005 , 16 : 1527 —1534
[17] Qing G Y, He YB , Wang F , et al . Eur. J . Org. Chem. , 2007 ,11 : 1768 —1778
[18] Qing G Y, He YB , Chen Z H , et al . Tetrahedron : Asymmetry ,2006 , 17 : 3144 —3151
[19] Qing G Y, Wang F , He Y B , et al . Supramol . Chem. , 2008 ,2008 , 20 : 635 —641
[20] Luo J , Zheng Q Y, Huang Z T, et al . Tetrahedron , 2005 , 61 :8517 —8528
[21] Qing G Y, Qin H J , He Y B , et al . Supramol . Chem. , 2008 ,20 : 265 —271
[22] Qing G Y, Chen Z H , He YB , et al . Chin. J . Chem. , 2008 ,26 : 721 —728
[23] Kubo Y, Maeda S , Kubo M, et al . Nature , 1996 , 382 : 522 —524
[24] Kubinyi M, Pál K, Baranyai P , et al . Chirality , 2004 , 16 :174 —179
[25] Qing G Y, He YB , Zhao Y, et al . Eur. J . Org. Chem. , 2006 ,1574 —1580
[26] Durmaz M, Alpaydin S , Yilmaz M, et al . Tetrahedron :Asymmetry , 2006 , 17 : 2322 —2327
[27] Durmaz M, Alpaydin S , Yilmaz M, et al . Tetrahedron :Asymmetry , 2007 , 18 : 900 —905
[28] Karakucuk A , Durmaz M, Yilmaz M, et al . Tetrahedron :Asymmetry , 2006 , 17 : 1963 —1968
[29] Kocabas E , Sirit A , Yilmaz M, et al . Chirality , 2008 , 20 : 26 —34
[30] Pinkhassik E , Stibor I , Ungaro R , et al . J . Org. Chem. , 1997 ,62 : 8654 —8659
[31] Arena G, Contino A , Ungaro R , Sciotto D , et al . Tetrahedron Lett . , 1999 , 40 : 1597 —1600
[32] Sansone F , Barboso S , Ungaro R , et al . Tetrahedron Lett . ,1999 , 40 : 4741 —4744
[33] Sdira S B , Felix C P , Lamartine R J , et al . J . Org. Chem. ,2003 , 68 : 6632 —6638
[34] Sdira S B , Felix C P , Lamartine R J , et al . Tetrahedron Lett . ,2005 , 46 : 5659 —5663
[35] Ito K, Noike M, Kida A , et al . J . Org. Chem. , 2002 , 67 :7519 —7522
[36] He Y B , Li J F , Wu C T, et al . Wuhan Univ. J . Natural Sciences , 2001 , 6 : 729 —732
[37] He YB , Xiao YJ , Wu C T, et al . Tetrahedron Lett . , 2002 , 43 :6249 —6253
[38] Zheng Y S , Zhang C. Org. Lett . , 2004 , 6 : 1189 —1192
[39] Yakovenko A V , Boyko V I , Kalchenko V O , et al . J . Org.Chem. , 2007 , 72 : 3223 —3231
[40] Narumi F , Hattori T, Matsumura N , et al . Tetrahedron , 2004 ,60 : 7827 —7833
[41] Shirakawa S , Moriyama A , Shimizu S. Org. Lett . , 2007 , 9 :3117 —3119
[42] Castellano R K, Kim B H , Rebek J Jr. J . Am. Chem. Soc. ,1997 , 119 : 12671 —12672
[43] Castellano R K, Nuckolls C , Rebek J Jr. J . Am. Chem. Soc. ,1999 , 121 : 11156 —11163
[44] Brewster R E , Shuker S B. J . Am. Chem. Soc. , 2002 , 124 :7902 —7903
[45] Budka J , Tkadlecová M, Lhoták P , et al . Tetrahedron , 2000 ,56 : 1883 —1887
[46] Guo W, Wang J , Cheng J P , et al . Tetrahedron Lett . , 2002 ,43 : 5665 —5667
[47] Liu F , Lu G Y, He WJ , et al . Thin Solid Films , 2004 , 468 :244 —249
[48] Krawinkler K H , Maier N M, Ungaro R , et al . Chirality , 2003 ,15 : S17 —S29
[49] Krawinkler K H , Maier N M, Sajovic E , et al . J .Chromatography A , 2004 , 1053 : 119 —131
[50] Cherenok S , Vovk A , Kalchenko V , et al . Org. Lett . , 2006 , 8 :549 —552
[51] Lambert A , Regnouf-de-Vains J B , Ruiz-Lopez M F , et al . J .Phys. Org. Chem. , 2006 , 19 : 157 —166
[52] Zheng Y S , Ji A , Chen X J , et al . Chem. Commun. , 2007 ,3398 —3400
[53] JoséV L G, Concepción Domingo G R , Sanchez-Cortes S , et al .Langmuir , 2006 , 22 : 10924 —10926
[54] Cygan M T, Collins G E , Dunbar T D , et al . Anal . Chem. ,1999 , 71 : 142 —148

[1] 罗钧, 郑炎松. 手性杯芳烃及其超分子手性[J]. 化学进展, 2018, 30(5): 601-615.
[2] 龚德君, 高冠斌, 张明曦, 孙涛垒. 手性金团簇的制备、性质及应用[J]. 化学进展, 2016, 28(2/3): 296-307.
[3] 靳清贤, 李晶, 李孝刚, 张莉, 方少明, 刘鸣华. 超分子凝胶的手性功能应用:手性分子识别与不对称催化[J]. 化学进展, 2014, 26(06): 919-930.
[4] 武金丹, 巨勇. 基于天然产物骨架的分子离子识别体系[J]. 化学进展, 2013, 25(11): 1888-1897.
[5] 安众福 陈润锋 史慧芳 马琮 石乃恩 黄维. 联萘酚衍生物的光电功能及其应用*[J]. 化学进展, 2010, 22(10): 1973-1982.
[6] 黄辉,郑立飞,邹小伟,成义祥. 基于1,1'-联-2萘酚衍生物的手性荧光传感器*[J]. 化学进展, 2008, 20(04): 508-517.
[7] 翁文,韩景立,陈友遵,黄晓佳. 手性传感器研究进展*[J]. 化学进展, 2007, 19(11): 1820-1825.
[8] 翁文,姚碧霞,陈秀琴,陈友遵,林文士,曾庆乐. 液相色谱手性拆分机理的热力学方法研究*[J]. 化学进展, 2006, 18(0708): 1056-1064.
[9] 罗钧,郑企雨,陈传峰,黄志镗. 固有手性杯芳烃的研究*[J]. 化学进展, 2006, 18(0708): 897-906.
[10] 何新亚,林炳承,丁永生. 亲和毛细管电泳研究生物分子的手性识别*[J]. 化学进展, 2002, 14(05): 332-.
阅读次数
全文


摘要

基于杯[4]芳烃的手性识别*