开环葫芦脲在水中对芳烃和芳醛的增溶和对腙大环形成的促进作用

doi:10.6023/cjoc201910022

摘要/Abstract

利用核磁实验，研究了并入四个磺酸根或羧酸根的高水溶性开环葫芦脲对疏水性芳烃和芳醛的水相增溶作用.并入四个磺酸根的开环葫芦脲acCB-1能显著提高包括三联苯、4，4'-二甲基联苯和联苯-4，4'-二甲醛在内的芳烃和芳醛的水溶性，其中4，4'-二甲基联苯的溶解度可以提高到8.9 mmol/L，联苯-4，4'-二甲醛的溶解度可以提高到11.2 mmol/L.并入四个羧酸根的acCB-2可以把五氟甲苯和六氟苯在水中的溶解度提高到5.6和3.0 mmol/L.acCB-1还可以通过增溶芳香醛，促进其与酰肼反应形成腙.这一促进作用可以进一步应用于促进两个芳香二醛和一个芳香二酰肼在水中的反应，制备常规条件下不能形成的两个芳香腙大环.

关键词: 开环葫芦脲, 水相增溶, 包结, 芳烃, 芳醛, 腙, 大环化合物

The promotion of two sulfate or carboxylate-bearing acyclic cucurbiturils for the water-solubility of arenes and aromatic aldehydes is described. ¹H NMR experiments reveals that sulfate-bearing acyclic cucurbituril (acCB-1) signficantly improves the water-solubility of a number of arenes and aldehydes. For 4,4'-dimethylbiphenyl and biphenyl-4,4'-dicarbaldehyde, the solubility can be improved to 8.9 and 11.2 mmol/L, respectively. ¹⁹F NMR experiments demonstrate that carboxylate-bearing acyclic cucurbituril can increase the water-solubilities of pentafluorotoluene and hexafluorobenzene to 5.6 and 3.0 mmol/L, respectively. It is also found that the water-solubilization of acCB-1 for aromatic aldehydes can promote their reaction with acylhydrazines to form hydrozone derivatives. By making use of this promotion, two hydrazone-based macrocycles can be formed from the coupling reactions of two aromatic dialdehdes and one diacylhydrazine in water.

Key words: acyclic cucurbituril, water-solubilization, encapsulation, arene, aromatic aldehyde, hydrazine, macrocycle

引用此文

刘旭波, 林佳乐, 王辉, 张丹维, 黎占亭. 开环葫芦脲在水中对芳烃和芳醛的增溶和对腙大环形成的促进作用[J]. 有机化学, 2020, 40(3): 663-668.

Liu Xu-Bo, Lin Jia-Le, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting. Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 663-668.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Birch, H.; Redman, A. D.; Letinski, D. J.; Lyon, D. Y.；Mayer, P. Anal. Chim. Acta 2019, 1086, 16.
(b) Li, H.; Jia, X.; Li, Y.; Shi, X.; Hao, J. J. Phys. Chem. B 2006, 110, 68.
(c) Chen, Y.; Huang, F.; Li, Z.-T.; Liu, Y. Sci. China Chem. 2018, 61, 979.
(d) Yang, Z.; Peng, Y.; Qiu, L. Chin. Chem. Lett. 2018, 29, 1839.
(e) Wang, K.; Guo, D.-S.; Liu, Y. Chem.-Eur. J. 2012, 18, 8758.
(f) Wang, K.; Guo, D.-S.; Liu, Y. Chem.-Eur. J. 2010, 16, 8006.
[2] (a) Liu, R.; Zhang, Y.; Wu, W.; Liang, W.; Huang, Q.; Yu, X.; Xu, W.; Zhou, D.; Selvapalam, N.; Yang, C. Chin. Chem. Lett. 2019, 30, 577.
(b) Zhang, L.; Zhang, Y.-M.; Liu, G.; Liu, Y. Chin. Chem. Lett. 2019, 30, 120.
(c) Zhang, Y.-M.; Xu, Q.-Y.; Liu, Y. Sci. China Chem. 2019, 62, 549.
(d) Xu, C.; Xu, L.; Ma, X. Chin. Chem. Lett. 2018, 29, 970.
(e) Zhao, Q.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2018, 29, 84.
(f) Song, S.; Li, M.; Gong, X.; Han, H.; Zhou, Y.; Wang, L.; Shuang, S.; Dong, C. Chem. Res. Chin. Univ. 2018, 34, 203.
(g) Zhang, Y.; Chen, Y.; Li, J.; Liang, L.; Liu, Y. Acta Chim. Sinica 2018, 76, 622(in Chinese). (张依, 陈湧, 李晶晶, 梁璐, 刘育, 化学学报, 2018, 76, 622.)
(h) Wang, R.; Wei, Z.; Guo, J.; Feng, Y.; Xu, E.; Duan, H.; Lin, Y.; Yang, Q.; Du, J.; Li, Y. Chem. Res. Chin. Univ. 2018, 34, 180.
(i) Chen, X.-M.; Chen, Y.; Liu, Y. Chin. J. Chem. 2018, 36, 526.
(j) Liu, A.; Xiong, C.; Ma, X.; Ma, W.; Sun, R. Chin. J. Chem. 2019, 37, 793.
(k) Song, C.; Xiao, Y.; Li, K.; Zhang, X.; Lu, Y. Chin. Chem. Lett. 2019, 30, 1249.
(l) Fang, X.; Yan, D. Sci. China Chem. 2018, 61, 397.
[3] (a) Loftsson, T.; Brewster, M. E. J. Pharm. Sci. 1996, 85, 1017.
(b) Uekaji, Y.; Terao, K. J. Inclusion Phenom. Macrocyclic Chem.. 2019, 93, 3.
(c) Shao, W.; Liu, X.; Wang, T.; Hu, X. Chin. J. Org. Chem. 2018, 38, 1107(in Chinese). (邵为, 刘昕, 王婷婷, 胡晓玉, 有机化学, 2018, 38, 1107.)
(d) Li, J.; Pan, D.; Yi, J.; Hao, L.; Kang, Q.; Liu, X.; Lu, L.; Lu, J. Carbohydr. Polym. 2019, 223, 115115.
(e) Liu, G.; Yuan, Q.; Hollett, G.; Zhao, W.; Kang, Y.; Wu, J. Polym. Chem. 2018, 9, 3436.
(f) Bian, X.; Zhao, B.; Pang, B.; Zheng, Z.; Liu, S.; Liu, Z.; Song, F. Chin. J. Chem. 2019, 37, 581.
(g) Yang, Z.; Peng, Y.; Qiu, L. Chin. Chem. Lett. 2018, 29, 1839.
(h) Liang, L.; Chen, Y.; Chen, X.-M.; Zhang, Y.; Liu, Y. Chin. Chem. Lett. 2018, 29, 989.
(i) Wang, X.; Yang, Y.; Fan, L.; Yang, F.; Wu, D. Sci. China Chem. 2018, 61, 311.
[4] (a) Ma, Y.; Xue, M.; Zhang, Z.; Chi, X.; Huang, F. Tetrahedron 2013, 69, 4532.
(b) Li, Z.; Hou, N.; Shao, W.; Xiao, S.; Lin, C.; Wang, L. Chin. J. Org. Chem. 2018, 38, 2002(in Chinese). (李臻益, 候娜娜, 邵为, 肖守军, 林晨, 王乐勇, 有机化学, 2018, 38, 2002.)
(c) Shu, X.; Xu, K.; Hou, D.; Li, C. Isr. J. Chem. 2018, 58, 1194.
(d) Li, Z.; Yang, J.; Huang, F. Chin. J. Chem. 2018, 36, 59.
(e) Yang, X.; Mao, W.; Liu, Y.; Li, L.; Ma, D. Chin. J. Chem. 2019, 37, 575.
[5] (a) Mock, W. L. Top. Curr. Chem. 1995, 175, 1.
(b) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844.
(c) Yang, X.; Liu, F.; Zhao, Z.; Liang, F.; Zhang, H.; Liu, S. Chin. Chem. Lett. 2018, 29, 1560.
(d) Jiao, Y.; Zhang, X. Acta Chim. Sinica 2018, 76, 659(in Chinese). (焦阳, 张希, 化学学报, 2018, 76, 659.)
(e) Wang, H.; Kan, J.; Bian, B.; Chen, Q.; Tao, Z.; Xiao, X. Chin. J. Org. Chem. 2018, 38, 3094(in Chinese). (王海燕, 阚京兰, 边炳, 陈青, 陶朱, 肖昕, 有机化学, 2018, 38, 3094.)
(f) Yu, S.-B.; Qi, Q.; Yang, B.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Small 2018, 14, 1801037.
(g) Li, X.-F.; Yu, S.-B.; Yang, B.; Tian, J.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Sci. China Chem. 2018, 61, 830.
(h) Zhang, B.; Dong, Y.; Li, J.; Yu, Y.; Li, C.; Cao, L. Chin. J. Chem. 2019, 37, 269.
(i) Bai, D.; Zhou, Y.; Lu, J.; Liu, Q.; Chen, Q.; Tao, Z.; Xiao, X. Chin. J. Org. Chem. 2018, 38, 1477(in Chinese). (白东, 周杨, 卢季红, 刘青云, 陈青, 陶朱, 肖昕, 有机化学, 2018, 38, 1477.)
(j) Xu, H.; Wang, Q. Chin. Chem. Lett. 2019, 30, 337.
(k) Wu, W.; Song, S.; Cui, X.; Sun, T.; Zhang, J.-X.; Ni, X.-L. Chin. Chem. Lett. 2018, 29, 95.
(l) Wu, Y.-P.; Yan, M.; Gao, Z.-Z; Hou, J.-L.; Wang, H.; Zhang, D.-W.; Zhang, J.; Li, Z.-T. Chin. Chem. Lett. 2019, 30, 1383.
(m) Yan, M.; Liu, X.-B.; Gao, Z.-Z.; Wu, Y.-P.; Hou, J.-L.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Org. Chem. Front. 2019, 6, 1698.
(n) Wu, Y.-P.; Wang, Z.-K.; Wang, H.; Zhang, D.-W.; Zhao, X.; Li, Z.-T. Acta Chim. Sinica 2019, 77, 735(in Chinese). (吴义鹏, 王泽坤, 王辉, 张丹维, 赵新, 黎占亭, 化学学报, 2019, 77, 735.)
(o) Li, T.-T.; Wen, L.-L.; Ji, H.-L.; Liu, F.-Y.; Sun, S.-G. Chin. Chem. Lett. 2017, 28, 463.
[6] (a) Huang, J.; Xu, Z.; Lian, X.; Zhang, X.; Tao, Z.; Zhou, Q.; Zhang, Q.; Wei, G. Chem. J. Chin. Univ. 2018, 39, 2425(in Chinese). (黄净净, 许志玲, 练小卫, 张晓东, 陶朱, 周清娣, 张前军, 卫钢, 高等学校化学学报, 2018, 39, 2425.)
(b) Lian, X.; Huang, J.; Tao, Z.; Zhou, Q.; Zhang, Q.; Wei, G. Chem. J. Chin. Univ. 2018, 39, 226(in Chinese). (练小卫, 黄净净, 陶朱, 周清娣, 张前军, 卫钢, 高等学校化学学报, 2018, 39, 226.)
(c) Li, S.; Chan, J. Y.-W.; Li, Y.; Bardelang, D.; Zheng, J.; Yew, W. W.; Chan, D. P.-C.; Lee, S. M. Y.; Wang, R. Org. Biomol. Chem. 2016, 14, 7563.
(d) Chu, J. J.; Apps, M. G.; Wheate, N. J. Supramol. Chem. 2014, 26, 648.
(e) Ma, W.-J.; Chen, J.-M.; Jiang, L.; Yao, J.; Lu, T.-B. Mol. Pharm. 2013, 10, 4698.
(f) Huang, Y.; Xue, S.-F.; Tao, Z.; Zhu, Q.-J.; Zhang, H.; Lin, J.-X.; Yu, D.-H. J. Inclusion Phenom. Macrocyclic Chem. 2008, 61, 171.
(g) Zhao, Y.; Buck, D. P.; Morris, D. L.; Pourgholami, M. H.; Day, A. I.; Collins, J. G. Org. Biomol. Chem. 2008, 6, 4509.
(h) Yang, B.; Zhang, X.-D.; Li, J.; Tian, J.; Wu, Y.-P.; Yu, F.-X.; Wang, R.; Wang, H.; Zhang, D.-W.; Liu, Y.; Zhou, L.; Li, Z.-T. CCS Chem. 2019, 1, 156.
(i) Zhang, Z.; Kan, J.; Feng, H.; Liu, Q.; Tao, Z.; Xiao, X. Chin. J. Org. Chem. 2018, 38, 1972(in Chinese). (张智睿, 阚京兰, 冯华明, 刘青云, 陶朱, 肖昕, 有机化学, 2018, 38, 1972.)
(j) Zhang, T.; Liu, Y.; Hu, B.; Zhang, C.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2019, 30, 949.
(k) Yi, J.; Song, S.; Zhang, S.; Zhang, S.; Tian, M.; Ni, X. Chem. J. Chin. Univ. 2018, 39, 911(in Chinese). (易君明, 宋森, 张胜, 张少威, 田蒙奎, 倪新龙, 高等学校化学学报, 2018, 39, 911.)
(l) Bai, D.; Wang, X.; Gao, Z.; Qiu, S.; Tao, Z.; Zhang, J.; Xiao, X. Chin. J. Org. Chem. 2017, 37, 2022(in Chinese). (白东, 王鑫, 高中政, 邱胜超, 陶朱, 张建新, 肖昕, 有机化学, 2017, 37, 2022.)
(m) Yin, Z.-J.; Wu, Z.-Q.; Lin, F.; Qi, Q.-Y.; Xu, X.-N.; Zhao, X. Chin. Chem. Lett. 2017, 28, 1167.
(n) Gao, Z.; Yang, L.; Bai, D.; Chen, L.; Tao, Z.; Xiao, X. Chem. J. Chin. Univ. 2017, 38, 212(in Chinese). (高中政, 杨立国, 白东, 陈丽霞, 陶朱, 肖昕, 高等学校化学学报, 2017, 38, 212.)
[7] Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621.
[8] (a) Ma, D.; Zavalij, P. Y.; Isaacs, L. J. Org. Chem. 2010, 75, 4786.
(b) Ma, D.; Glassenberg, R.; Ghosh, S.; Zavalij, P. Y.; Isaacs, L. Supramol. Chem. 2012, 24, 325.
(c) Zhang, M.; Sigwalt, D.; Isaacs, L. Chem. Commun. 2015, 51, 14620.
[9] (a) Ma, D.; Hettiarachchi, G.; Nguyen, D.; Zhang, B.; Wittenberg, J. B.; Zavalij, P. Y.; Briken, V.; Isaacs, L. Nat. Chem. 2012, 4, 503.
(b) Zhang, B.; Zavalij, P. Y.; Isaacs, L. Org. Biomol. Chem. 2014, 12, 2413.
[10] (a) Mao, D.; Liang, Y.; Liu, Y.; Zhou, X.; Ma, J.; Jiang, B.; Liu, J.; Ma, D. Angew. Chem., Int. Ed. 2017, 56, 12614.
(b) Mao, W.; Mao, D.; Yang, F.; Ma, D. Chem.-Eur. J. 2019, 25, 2272.
[11] Choi, H.; Ahn, J.; Kim, S.; Kim, H.; Jung, J. H. Chem. Commun. 2016, 52, 7600.
[12] Kotha, S.; Shah, V. R. Synthesis 2007, 3653.
[13] Zha, D.; You, L. ACS Appl. Mater. Interfaces 2016, 8, 2399.
[14] Zhang, D.; Li, Z. Chin. J. Org. Chem. 2012, 32, 2009(in Chinese). (张丹维, 黎占亭, 有机化学, 2012, 32, 2009.)
[15] Wei, X.; Gu, J.; Liu, X.; Huang, C.; Zhu, B. 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.)