Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 614-624.DOI: 10.6023/cjoc201909029 Previous Articles Next Articles
黄国保a, 陈志林a, 韦贤生a, 陈钰a, 李秀英a, 仲辉b, 谭明雄a
收稿日期:
2019-09-18
修回日期:
2019-10-31
发布日期:
2020-04-02
通讯作者:
仲辉, 谭明雄
E-mail:lxya8401@163.com;tanmx00@163.com
基金资助:
Huang Guobaoa, Chen Zhilina, Wei Xianshenga, Chen Yua, Li Xiuyinga, Zhong Huib, Tan Mingxionga
Received:
2019-09-18
Revised:
2019-10-31
Published:
2020-04-02
Supported by:
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Huang Guobao, Chen Zhilin, Wei Xiansheng, Chen Yu, Li Xiuying, Zhong Hui, Tan Mingxiong. Recent Progress on the Construction and Function of Macrocyclic Compounds Containing Hydrogen Bond Donors[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 614-624.
[1] (a) Liu, Y.; You, C. C.; Zhang, H. Y. Supramolecular Chemistry—Molecular Recognition and Self-Assembly of Synthetic Receptors, Nankai University Press, Tianjin, 2003 (in Chinese). (刘育, 尤长城, 张衡益, 超分子化学——合成受体的分子识别与组装, 天津, 南开大学出版社, 2003.) (b) Luo, Q. H. Macrocyclic Chemistry—Host-Guest Compound and Supramolecular, Science Press, Beijing, 2009 (in Chinese). (罗勤慧, 大环化学——主-客体化合物和超分子, 科学出版社, 北京, 2009.) [2] Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017. [3] Huang, G.-B.; Jiang, W. Prog. Chem. 2015, 27, 744(in Chinese). (黄国保, 蒋伟, 化学进展, 2015, 27, 744.) [4] (a) Zheng, B.; Wang, F.; Dong, S.-Y.; Huang, F.-H. Chem. Soc. Rev. 2012, 5, 1621. (b) Cheng, H.-B.; Zhang, H.-Y.; Liu, Y. J. Am. Chem. Soc. 2013, 135, 10190. [5] (a) Liu, Y.; Chen, Y. Acc. Chem. Res. 2006, 10, 681. (b) Chen, Y.; Liu, Y. Chem. Soc. Rev. 2010, 39, 495. [6] (a) Guo, D.-S.; Wang, K.; Liu, Y. J. Inclusion Phenom. Macrocyclic Chem. 2008, 1-2, 1. (b) Guo, D.-S.; Liu, Y. Chem. Soc. Rev. 2012, 41, 5907. [7] (a) Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F. Acc. Chem. Res. 2012, 45, 1294. (b) Cragg, P. J.; Sharma, K. Chem. Soc. Rev. 2012, 41, 597. (c) Ogoshi, T.; Yamagishi, T.-A. Eur. J. Org. Chem. 2013, 15, 2961. (d) Zhang, H.; Zhao, Y. Chem.-Eur. J. 2013, 19, 16862. (e) Wang, M.-X. Chem. Commun. 2008, 4541. (f) Guo, Q.-H.; Fu, Z.-D.; Zhao, L.; Wang, M.-X. Angew. Chem., Int. Ed. 2014, 53, 13548. (g) Wang, M.-X. Acc. Chem. Res. 2012, 45, 182. (h) Chen, H.; Fan, J.; Hu, X.; Ma, J.; Wang, S.; Li, J.; Yu, Y.; Jia, X.; Li, C. Chem. Sci. 2015, 6, 197. (i) Tian, X. H.; Chen, C. F. Org. Lett. 2010, 12, 524. (j) Xue, M.; Chen, C. F. Org. Lett. 2009, 11, 5294. (k) Wang, J. H.; Feng, H. T.; Zheng, Y. S. Chem. Commun. 2014, 50, 11407. (l) Chun, Y.; Singh, N. J.; Hwang, I. C.; Lee, J. W.; Yu, S.-U.; Kim, K.-S. Nat. Commun. 2013, 4, 1797. (m) Lee, S.; Chen, C.-H.; Flood, A.-H. Nat. Chem. 2013, 5, 704. [8] Shimizu, L. S.; Smith, M. D.; Hughes, A. D.; Shimizu, K. D. Chem. Commun. 2001, 1592. [9] (a) Shimizu, L. S.; Hughes, A. D.; Smith, M. D.; Davis, M. J.; Zhang, P.; Loye zur, H.; Shimizu, K. D. J. Am. Chem. Soc. 2003, 125, 14972. (b) Yang, J.; Dewal, M. B.; Shimizu, L. S. J. Am. Chem. Soc. 2006, 128, 8122. (c) Yang, J.; Dewal, M. B.; Profeta, S.; Smith, M. D.; Li, Y.; Shimizu, L. S. J. Am. Chem. Soc. 2008, 130, 612. (d) Dewal, M. B.; Xu, Y.; Yang, J.; Mohammed, F.; Smith, M. D.; Shimizu, L. S. Chem. Commun. 2008, 3909. (e) Yang, J.; Dewal, M. B.; Sobransingh, D.; Smith, M. D.; Xu, Y.; Shimizu, L. S. J. Org. Chem. 2009, 74, 102. (f) Xu, Y.; Smith, M. D.; Krause, J.; Shimizu, L. S. J. Org. Chem. 2009, 74, 4874. (f) Roy, K.; Wang, C.; Smith, M.-D.; Pellechia, P.; Shimizu, L. S. J. Org. Chem. 2010, 75, 5453. [10] (a) Meshcheryakov, D.; Arnaud-Neu, F.; Böhmer, V.; Bolte, M.; Cavaleri, J.; Hubscher-Bruder, V.; Thondorf, I.; Weener, S. Org. Biomol. Chem. 2008, 6, 3244. (b) Meshcheryakov, D.; Böhmer, V.; Bolte, M.; Hubscher-Bruder, V.; Arnaud-Neu, F. Chem. Eur. J. 2009, 15, 4811. [11] Dawn, S.; Dewal, M. B.; Sobransingh, D.; Paderes, M. C.; Wibowo, A.; Smith, M.; Krause, J.; Pellechia, P.; Shimizu, L. S. J. Am. Chem. Soc. 2011, 133, 7025. [12] Roy, K.; Wang, C.; Smith, M. D.; Dewal, M. B.; Wibowo, A. C.; Brown, J. C.; Ma, S.; Shimizu, L. S. Chem. Commun. 2011, 47, 277. [13] Geer, M. F.; Smith, M. D.; Shimizu, L. S. CrystEngComm 2011, 13, 3665. [14] Roy, K.; Wibowo, A.; Pellechia, P.; Ma, S.; Geer, M.; Shimizu, L. S. Chem. Mater. 2012, 24, 4773 [15] Geer, M. F.; Walla, M.; Solntsev, K.; Strassert, C.; Shimizu, L. S. J. Org. Chem. 2013, 78, 5568. [16] Xiao, T.; Li, S.; Zhang, X.; Lin, C.; Wang, L. Y. Chin. J. Chem. 2013, 31, 627. [17] Zhang, D. S.; Chen, J. P.; Zeng, Y.; Yu, T. J.; Li, Y. Chin. J. Org. Chem. 2013, 33, 110(in Chinese). (张读山, 陈金平, 曾毅, 于天君, 李嫕, 有机化学, 2013, 33, 110.) [18] Kretschemer, C.; Dittmann, G.; Beck, J. Beilstein J. Org. Chem. 2014, 10, 1834. [19] Huang, G. B.; He, Z.; Cai, C.; Pan, F.; Yang, D.; Rissanen, K.; Jiang, W. Chem. Commun. 2015, 51, 15490. [20] Huang, G. B.; Valkonen, A.; Rissanen, K.; Jiang, W. Chem. Commun. 2016, 52, 9078. [21] Huang, G. B.; Liu, V.; Valkonen, A.; Yao, H.; Rissanen, K.; Jiang, W. Chin. Chem. Lett. 2018, 29, 91. [22] (a) Kondo, S.; Sonoda, H.; Katsu, T.; Unno, M. Sens. Actuators, B 2011, 160, 684. (b) Satake, A.; Ishizawa, Y.; Katagiri, H.; Kondo, S. J. Org. Chem. 2016, 81, 9848. [23] Osawa, K.; Tagaya, H.; Kondo, S. J. Org. Chem. 2019, 84, 6623. [24] Tromans, R.; Carter, T.; Chabanne, T.; Crump, M.; Li, H.; Matlock, J.; Orchard, M.; Davis, A. P. Nat. Chem. 2019, 11, 52. [25] (a) Shorthill, B. J.; Avetta, C. T.; Glass, T. E. J. Am. Chem. Soc. 2004, 126, 12732. (b) Sharma, S. K.; Upreti, S.; Gupta, R. Eur. J. Inorg. Chem. 2007, 3247. (c) Gasparrini, F.; Pierini, M.; Villani, C.; Filippi, A.; Speranza, M. J. Am. Chem. Soc. 2008, 130, 522. (d) Shang, X. F.; Lin, H.; Cai, Z. S.; Lin, H. K. J. Heterocycl. Chem. 2008, 45, 1329. (d) Ghorai, A.; Gayen, A.; Kulsi, G.; Padmanaban, E.; Laskar, A.; Achari, B.; Mukhopadhyay, C.; Chattopadhyay, P. Org. Lett. 2011, 13, 5512. [26] (a) Fuller, A. M.; Leigh, D. A.; Lusby, P. J.; Oswald, I. D. H.; Parsons, S.; Walker, D. B. Angew. Chem. 2004, 116, 4004. (b) Leigh, D. A.; Venturini, A.; Wilson, A. J.; Wong, J. K. Y.; Zerbetto, F. Chem.-Eur. J. 2004, 10, 4960. (c) Fuller, A. M.; Leigh, D. A.; Lusby, P. J.; Oswald, I. D. H.; Parsons, S.; Walker, D. B. J. Am. Chem. Soc. 2005, 137, 12612. (d) Crowley, J. D.; Leigh, D. A.; Lusby, P. J.; McBurney, R. T.; Perret-Aebi, L. E.; Petzold, C.; Slawin, A. M. Z.; Symes, M. D. J. Am. Chem. Soc. 2007, 129, 15085. (e) Barrell, M. J.; Leigh, D. A.; Lusby, P. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. 2008, 47, 8036. (f) Altieri, A.; Aucagne, V.; Carrillo, R.; Clarkson, G.; D,Souza, D. M.; Dunnet, J.; Leigh, D. A.; Mullen, K. M. Chem. Sci. 2011, 2, 1922. [27] (a) Klein, E.; Ferrand, Y.; Auty, E. K.; Davis, A. P. Chem. Commun. 2007, 2390. (b) Ferrand, Y.; Crump, M. P.; Davis, A. P. Science 2007, 318, 619. (c) Klein, E.; Ferrand, Y.; Barwell, N. P.; Davis, A. P. Angew. Chem., Int. Ed. 2008, 48, 2693. (d) Challinor, L.; Klein, E.; Davis, A. P. Synlett 2008, 14, 2137. [28] Qin, B.; Chen, X. Y.; Fang, X.; Shu, Y. Y.; Yip, Y. K.; Yan, Y.; Pan, S. Y.; Ong, W. Q.; Ren, C. L.; Su, H. B.; Zeng, H. Q. Org. Lett. 2008, 10, 5127. [29] Qin, B.; Ren, C.; Ye, R.; Sun, C.; Chalid, K.; Chen, X.; Li, Z.; Xue, F.; Su, H.; Chass, G.; Zeng, H. Q. J. Am. Chem. Soc. 2010, 132, 9564. [30] (a) Helsel, A. J.; Brown, A. L.; Yamato, K.; Feng, W.; Yuan, L. H.; Clements, A.; Harding, S. V.; Szabo, G.; Shao, Z. F.; Gong, B. J. Am. Chem. Soc. 2008, 130, 15784. (b) Wang, X.; Liu, R.; Sathyamoorthy, B.; Yamato, K.; Liang, G.; Shen, L.; Ma, S.; Sukumaran, D.; Szyperski, T.; Fang, W.; He, L.; Chen, X.; Gong, B. J. Am. Chem. Soc. 2015, 137, 5879. [31] Yang, Y.; Feng, W.; Hu, J.; Zou, S.; Gao, R.; Yamato, K.; Kline, M.; Cai, Z.; Gao, Y.; Wang, Y.; Li, Y.; Yang, Y.; Yuan, L.; Zeng, X.; Gong, B. J. Am. Chem. Soc. 2011, 133, 18590. [32] (a) Ferrand, Y.; Klein, E.; Barwell, N. P.; Crump, M. P.; J. Vicent, J. C.; Boons, G.-J.; Ingale, S.; Davis, A. P. Angew. Chem., Int. Ed. 2009, 49, 1775. (b) Davis, A. P. Org. Biomol. Chem. 2009, 7, 3629. (c) Barwell, N. P.; Crump, M. P.; Davis, A. P. Angew. Chem., Int. Ed. 2009, 48, 7363. [33] Barwell, N. P.; Davis, A. P. J. Org. Chem. 2011, 76, 6548. [34] (a) Sookcharoenpinyo, B.; Klein, E.; Ferrand, Y.; Walker, B.; Brotherhood, P.; Ke, C.; Crump, M. P.; Davis, A. P. Angew. Chem., Int. Ed. 2012, 51, 4586. (b) Ke, C.; Destecroix, H.; Crump, M. P.; Davis, A. P. Nat. Chem. 2012, 4, 718. (c) Howgego, J.; Butts, C.; Crump, M. P.; Davis, A. P. Chem. Commun. 2013, 49, 3110. (d) Destecroix, H.; Renney, C.; Mooibroek, T.; Carter, T.; Stewart, P.; Crump, M. P.; Davis, A. P. Angew. Chem. Int. Ed. 2015, 54, 2057. (e) Rios, P.; Carter, T.; Mooibroek, T.; Crump, M. P.; Lisbjerg, M.; Pittelkow, M.; Supekar, N.; Boons, G.; Davis, A. P. Angew. Chem., Int. Ed. 2016, 55, 3387. (f) Carter, T.; Mooibroek, T.; Stewart, P.; Crump, M. P.; Galan, M.; Davis, A. P. Angew. Chem., Int. Ed. 2016, 55, 9311. (g) Mandal, P.; Kauffmann, B.; Destecroix, H.; Ferrand, Y.; Davis, A. P.; Huc, I. Chem. Commun. 2016, 52, 9355. (h) Rios, P.; Mooibroek, T.; Carter, T.; Willams, C.; Wilson, M.; Crump, M. P.; Davis, A. P. Chem. Sci. 2017, 8, 4056. [35] Chen, M. J.; Han, S. J.; Jiang, L. S.; Zhou, S. G.; Jiang, F.; Xu, Z. K.; Liang, J. D.; Zhang, S. H. Chem. Commun. 2010, 46, 3932. [36] Yang, D. K.; Zeng, Z. J.; Chen, M. J.; Pan, S. W.; Yang, Y.; Li, M.; Lei, C. Y.; Jiang. L. S. Acta Chim. Sinica 2012, 74, 1385(in Chinese). (杨登科, 曾志坚, 陈木娟, 潘绍武, 杨宇, 李媚, 雷春燕. 蒋腊生化学学报, 2012, 74, 1385.) [37] Wang, D.; You, L.; Wang, J.; Wang, H.; Zhang, D.; Li, Z. T. Tetrahedron Lett. 2013, 54, 6967. [38] Chen, Y.; Wang, L.; Zhang, L.; Zhu, J.; Wang, H.; Zhang, D.; Li, Z. T. Tetrahedron 2014, 70, 5483. [39] Huang, G.; Wang, S.; Ke, H.; Yang, L.; Jiang, W. J. Am. Chem. Soc. 2016, 138, 14550 [40] Martí-Centelles, V.; Burguete, M. I.; Luis, S. J. Org. Chem. 2016, 81, 2143. [41] Mao, L.; Pan, W.; Fu, Y.; Chen, L.; Xu, M.; Ren, Y.; Feng, W.; Yuan, L. Org. Lett. 2017, 19, 18. [42] Wang, F. F.; Ou, M.; Deng, Y. X.; Ran, X.; Zhang, Q. L.; Zhu, B. X. Chin. J. Org. Chem. 2014, 34, 334(in Chinese). (王芳芳, 欧敏, 邓雅欣, 冉旭, 张奇龙, 朱必学, 有机化学, 2014, 34, 334.) [43] Wei, X. K.; Gu, J. C.; Liu, X. L.; Huang, C.; Zhu, B. X. Chin. J. Org. Chem. 2018, 38, 3386(in Chinese). (魏小康, 谷静池, 刘兴丽, 黄超, 朱必学, 有机化学, 2018, 38, 3386.) [44] (a) Johnston, A. G.; Leigh, D. A.; Pritchard, R. J.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1209. (b) Leigh, D. A.; Venturini, A.; Wilson, A. J.; Wong, J. K. Y.; Zerbetto, F. Chem.-Eur. J. 2004, 10, 4960. [45] María, D.; Claramunt, R.; Torralba, M.; Torres, M.; Elguero, J. Tetrahedron Lett. 2019, 60, 1206. |
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