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化学进展 2015, Vol. 27 Issue (1): 70-78 DOI: 10.7536/PC140818 前一篇   后一篇

• 综述与评论 •

非均相环糊精在水相有机合成反应中的应用

沈海民*1, 武宏科1, 史鸿鑫1, 纪红兵2, 余武斌*1   

  1. 1. 浙江工业大学化学工程学院 杭州 310014;
    2. 中山大学化学与化学工程学院 广州 510275
  • 收稿日期:2014-08-01 修回日期:2014-10-01 出版日期:2015-01-15 发布日期:2014-11-24
  • 通讯作者: 沈海民, 余武斌 E-mail:haimshen@zjut.edu.cn;yuwb@zjut.edu.cn
  • 基金资助:

    国家自然科学基金项目(No. 21306176),浙江工业大学科研启动基金项目(No. G2817101103)和浙江省自然科学基金项目(No. LQ14B020002)资助

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Application of the Heterogeneous Cyclodextrins in Aqueous Phase Organic Synthesis

Shen Haimin*1, Wu Hongke1, Shi Hongxin1, Ji Hongbing2, Yu Wubin*1   

  1. 1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China;
    2. School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China
  • Received:2014-08-01 Revised:2014-10-01 Online:2015-01-15 Published:2014-11-24
  • Supported by:

    The work was supported by the National Natural Science Foundation of China (No. 21306176), the Scientific Research Launching Foundation of Zhejiang University of Technology (No. G2817101103), and the Zhejiang Provincial Natural Science Foundation (No. LQ14B020002).

本文详细综述了非均相环糊精在水相有机合成反应中的应用,包括非均相环糊精在水相氧化反应、还原反应、取代反应、加成反应和光催化反应中的应用。同时,全面阐述了在催化或促进水相有机合成反应中环糊精非均相化的策略,包括形成水不溶性交联聚合物和将环糊精固载在水不溶性载体上两种途径。目前非均相环糊精在水相有机合成反应中的应用还基本局限在简单的相转移催化剂领域,相关报道也较少,处于起步阶段;基于非均相环糊精构筑超分子仿酶是今后该领域的发展趋势和必然归属,应在发挥非均相优势的同时,保留环糊精单元在超分子仿酶构筑中的优良功用。

关键词： 环糊精, 非均相, 有机合成, 仿酶

The applications of the heterogeneous cyclodextrins in aqueous phase organic synthesis are reviewed in detail, including the applications in oxidation, reduction, substitution reaction, addition reaction and photocatalytic reaction. At the same time, the strategies to construct heterogeneous cyclodextrins in the catalysis or promotion of the aqueous phase organic synthesis are stated comprehensively, two strategies being the formation of water-insoluble cross-linking polymer and the grafting cyclodextrins to water-insoluble supporter. It is pointed out that the application of the heterogeneous cyclodextrins in aqueous phase organic synthesis is limited in the simple phase-transfer catalysis and there is fewer relevant literature, just in its infancy stage. The construction of artificial enzyme based on the heterogeneous cyclodextrins would be the development trend and inevitable affiliation in the construction of artificial enzyme based on cyclodextrins, possessing the advantage of the heterogeneous catalyst, meanwhile retaining the excellent function of the cyclodextrin unit in the construction of supramolecular artificial enzyme.

Contents
1 Introduction
2 Oxidation Reaction
3 Reduction Reaction
4 Substitution Reaction
5 Addition Reaction
6 Photocatalytic Reaction
7 Conclusion and outlook

Key words: cyclodextrin, heterogeneous, organic synthesis, artificial enzyme

中图分类号: 

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[1] Takahashi K. Chem. Rev., 1998, 98: 2013.
[2] 纪红兵(Ji H B), 黄丽泉(Huang L Q), 石东坡(Shi D P), 周贤太(Zhou X T). 有机化学(Chinese Journal of Organic Chemistry), 2008, 28(12): 2072.
[3] Zhao W, Zhong Q. J. Inclusion Phenom. Macrocyclic Chem., 2012, 72: 1.
[4] Breslow R, Dong S D. Chem. Rev., 1998, 98: 1997.
[5] Marinescu L, Bols M. Curr. Org. Chem., 2010, 14: 1380.
[6] Woggon W D. Curr. Org. Chem., 2010, 14: 1362.
[7] 沈海民(Shen H M), 纪红兵(Ji H B). 有机化学(Chinese Journal of Organic Chemistry), 2011, 31(6): 791.
[8] 沈海民(Shen H M), 纪红兵(Ji H B). 有机化学(Chinese Journal of Organic Chemistry), 2012, 32(6): 975.
[9] 王海波(Wang H B), 赵猛(Zhao M), 计亮年(Ji L N), 毛宗万(Mao Z W). 化学进展(Progress in Chemistry), 2013, 25(4): 577.
[10] French R R, Holzer P, Leuenberger M G, Woggon W D. Angew. Chem. Int. Ed., 2000, 39: 1267.
[11] French R R, Holzer P, Leuenberger M, Nold M C, Woggon W D. J. Inorg. Biochem., 2002, 88: 295.
[12] Breslow R, Zhang X, Huang Y. J. Am. Chem. Soc., 1997, 119: 4535.
[13] Yang J, Breslow R. Angew. Chem. Int. Ed., 2000, 39: 2692.
[14] Yang J, Gabriele B, Belvedere S, Huang Y, Breslow R. J. Org. Chem., 2002, 67: 5057.
[15] Dong Z Y, Liu J Q, Mao S Z, Huang X, Yang B, Ren X J, Luo G M, Shen J C. J. Am. Chem. Soc., 2004, 126: 16395.
[16] Dong Z Y, Liang K, Wang C Y, Huang X, Mao S, Li X Z, Xu J Q, Liu J Q, Luo G M, Shen J C. J. Mol. Catal. A-Chem., 2007, 277: 193.
[17] Jiao A Q, Yang N, Wang J P, Toure A, Xu X M, Jin Z Y. J. Inclusion Phenom. Macrocyclic Chem., 2012, 74: 335.
[18] Yin Y Z, Jiao S F, Lang C, Liu J Q. Rsc Adv., 2014, 4: 25040.
[19] Yin Y Z, Jiao S F, Lang C, Liu J Q. Soft Matter, 2014, 10: 3374.
[20] Wang Y Q, Han B H. Chinese J. Chem., 2013, 31: 569.
[21] 沈海民(Shen H M), 武宏科(Wu H K), 纪红兵(Ji H B), 史鸿鑫(Shi H X). 有机化学(Chinese Journal of Organic Chemistry), 2014, 34(4): 630.
[22] 沈海民(Shen H M), 纪红兵(Ji H B), 武宏科(Wu H K), 史鸿鑫(Shi H X). 有机化学(Chinese Journal of Organic Chemistry), 2014, 34(8): 1549.
[23] 沈海民(Shen H M), 纪红兵(Ji H B). 有机化学(Chinese Journal of Organic Chemistry), 2012, 32(9): 1684.
[24] Shen H M, Ji H B. Tetrahedron Lett., 2012, 53: 3541.
[25] Shen H M, Ji H B. Carbohyd. Res., 2012, 354: 49.
[26] Shen H M, Ji H B. Tetrahedron, 2013, 69: 8360.
[27] Marinescu L G, Doyagueez E G, Petrillo M, Fernandez-Mayoralas A, Bols M. Eur. J. Org. Chem., 2010: 157.
[28] Bjerre J, Bols M. J. Inclusion Phenom. Macrocyclic Chem., 2011, 69: 417.
[29] Fenger T H, Bols M. J. Inclusion Phenom. Macrocyclic Chem., 2011, 69: 397.
[30] Zhou Y, Lindback E, Pedersen C M, Bols M. Tetrahedron Lett., 2014, 55: 2304.
[31] Yang Z J, Jiang H G, Zhou X T, Fang Y X, Ji H B. Supramol. Chem., 2012, 24: 379.
[32] Yang Z J, Zeng H, Zhou X T, Ji H B. Tetrahedron, 2012, 68: 5912.
[33] Jiang H G, Yang Z J, Zhou X T, Fang Y X, Ji H B. Chinese J. Chem. Eng., 2012, 20: 784.
[34] Yang Z J, Ji H B. Acs Sustainable Chem. Eng., 2013, 1: 1172.
[35] Yang Z J, Zeng H, Zhou X T, Ji H B. Supramol. Chem., 2013, 25: 233.
[36] Kang Y, Zhou L L, Li X, Yuan J Y. J. Mater. Chem., 2011, 21: 3704.
[37] Zhu J, Wang P C, Lu M. J. Brazil. Chem. Soc., 2013, 24: 171.
[38] Chalasani R, Vasudevan S. Acs Nano, 2013, 7: 4093.
[39] Zhang X, Wu F, Deng N S. Catal. Commun., 2010, 11: 422.
[40] Kiasat A R, Sayyahi S. Catal. Commun., 2010, 11: 484.
[41] Mori K, Yoshioka N, Kondo Y, Takeuchi T, Yamashita H. Green Chem., 2009, 11: 1337.
[42] Schlatter A, Kundu M K, Woggon W D. Angew. Chem. Int. Ed., 2004, 43: 6731.
[43] Schlatter A, Woggon W D. Adv. Synth. Catal., 2008, 350: 995.
[44] Jiao A Q, Yang N, Wang J P, Xu X M, Jin Z Y. J. Inclusion Phenom. Macrocyclic Chem., 2013, 75: 155.
[45] Kiasat A R, Nazari S. Catal. Commun., 2012, 18:102.
[46] Kiasat A R, Nazari S. Catal. Sci. Technol., 2012, 2: 1056.
[47] Kiasat A R, Nazari S. J. Mol. Catal. A-Chem., 2012, 365: 80.
[48] Kiasat A R, Nazari S. J. Inclusion Phenom. Macrocyclic Chem., 2013, 76: 363.
[49] Kiasat A R, Zarinderakht N, Sayyahi S. Chinese J.Chem., 2012, 30: 699.
[50] Kumar V P, Narender M, Sridhar R, Nageswar Y V A, Rao K R. Chem. Commun., 2007, 37: 4331.
[51] Ji H B, Huang L Q, Shen H M, Zhou X T. Chem. Eng. J., 2011, 167: 349.
[52] Ramesh K, Murthy S N, Karnakar K, Nageswar Y V D. Tetrahedron Lett., 2011, 52: 4734.
[53] Nageswar Y V D, Ramesh K, Murthy S N. Tetrahedron Lett., 2011, 52: 2362.
[54] Kiasat A R, Nazari S, Davarpanah J. J. Serb. Chem. Soc., 2014, 79: 401.
[55] Tahir M N, Qamar R U, Adnan A, Cho E, Jung S. Tetrahedron Lett., 2013, 54: 3268.
[56] Doyaguez E G, Rodriguez-Hernandez J, Corrales G, Fernandez-Mayoralas A, Gallardo A. Macromolecules, 2012, 45: 7676.
[57] Khalafi-Nezhad A, Panahi, F. ACS Sustainable Chem. Eng., 2014, 2: 1177.
[58] Kaboudin B, Mostafalu R, Yokomatsu T. Green Chem., 2013, 15: 2266.
[59] Inoue Y, Wada T, Sugahara N, Yamamoto K, Kimura K, Tong L H, Gao X M, Hou Z J, Liu Y. J. Org. Chem., 2000, 65: 8041.
[60] Gao Y Y, Inoue M, Wada T, Inoue Y. J. Inclusion Phenom. Macrocyclic Chem., 2004, 50: 111.
[61] Fukuhara G, Mori T, Wada T, Inoue Y. Chem. Commun., 2005, 4199.
[62] Fukuhara G, Mori T, Wada T, Inoue Y. J. Org. Chem., 2006, 71: 8233.
[63] Lu R H, Yang C, Cao Y J, Wang Z Z, Wada T, Jiao W, Mori T, Inoue Y. Chem. Commun., 2008, 374.
[64] Lu R H, Yang C, Cao Y J, Tong L H, Jiao W, Wada T, Wang Z Z, Mori T, Inoue Y. J. Org. Chem., 2008, 73: 7695.
[65] Yang C, Mori T, Wada T, Inoue Y. New J. Chem., 2007, 31: 697.
[66] Liang W T, Yang C, Nishijima M, Fukuhara G, Mori T, Mele A, Castiglione F, Caldera F, Trotta F, Inoue Y. Beilstein J. Org. Chem., 2012, 8:1305.
[67] Luo L, Liao G H, Wu X L, Lei L, Tung C H, Wu L Z. J. Org. Chem., 2009, 74: 3506.
[68] Ikeda H, Nihei T, Ueno A. J. Org. Chem., 2005, 70: 1237.
[69] Yang C, Fukuhara G, Nakamura A, Origane Y, Fujita K, Yuan D Q, Mori T, Wada T, Inoue Y. J. Photoch. Photobio. A, 2005, 173: 375.
[70] Yang C, Nakamura A, Fukuhara G, Origane Y, Mori T, Wada T, Inoue Y. J. Org. Chem., 2006, 71: 3126.
[71] Nakamura A, Inoue Y. J. Am. Chem. Soc., 2005, 127: 5338.
[72] Ke C F, Yang C, Mori T, Wada T, Liu Y, Inoue Y. Angew. Chem. Int. Edit., 2009, 48: 6675.
[73] Yao J B, Yan Z Q, Ji J C, Wu W H, Yang C, Nishijima M, Fukuhara G, Mori T, Inoue Y. J. Am. Chem. Soc., 2014, 136: 6916.
[74] Qiu H B, Yang C, Inoue Y, Che S N. Org. Lett., 2009, 11: 1793.
[75] Breslow R. Accounts Chem. Res., 1995, 28: 146.
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