手性咪唑啉酮离子液体的合成

有机化学 ›› 2011, Vol. 31 ›› Issue (9): 1433-1439. 上一篇下一篇

研究论文

手性咪唑啉酮离子液体的合成

张焕，李海岗，吴海虹*

(华东师范大学化学系上海市绿色化学与化工工程绿色化重点实验上海 200062)

收稿日期:2010-09-26 修回日期:2011-03-20 发布日期:2011-04-20
通讯作者: 吴海虹 E-mail:hhwu@chem.ecnu.edu.cn

Synthesis of Chiral Imidazolinone-Based Ionic Liquids

ZHANG Huan, LI Hai-Gang, WU Hai-Hong

(Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062)

Received:2010-09-26 Revised:2011-03-20 Published:2011-04-20

文章分享

摘要/Abstract

手性离子液体在不对称合成中作为手性诱导物具有广泛的应用前景. 手性咪唑啉酮类催化剂是有机胺催化剂中重要的一种类型, 是不对称有机催化领域研究的热点之一. 从绿色化、经济化的角度出发, 以天然手性源物质L-酪氨酸为起始原料, 经过酯化、胺解、关环、[3＋2]环加成等多步反应合成了7种未见文献报道的手性咪唑啉酮类离子液体, 并通过¹H NMR, ¹³C NMR, ESI-MS, , DSC, TGA等方法对其结构及性质进行了表征.

关键词: L-酪氨酸, 手性咪唑啉酮, Click反应, 手性离子液体

The chiral ionic liquids have broad applications as inducers for asymmetric reactions. Chiral imidazo1idinones are important sorts of aminocatalysts, which have been attracted much attention in re-search of enantioselective organocatalysis field. From the view of greening and economization, 7 new chiral imidazo1idinone ionic liquids with different anions are synthesized from L-tyrosine, which is a kind of natural chiral materials, through esterfication, amination, cyclization, [3＋2] cycloaddition, etc. The structures and properities were characterized by ¹H NMR, ¹³C NMR, ESI-MS, IR, , DSC and TGA methods.

Key words: L-tyrosine, chiral imidazolidinone, click reaction, chiral ionic liquid

中图分类号:

O621.3

引用此文

张焕, 李海岗, 吴海虹. 手性咪唑啉酮离子液体的合成[J]. 有机化学, 2011, 31(9): 1433-1439.

ZHANG Huan, LI Hai-Gang, WU Hai-Hong. Synthesis of Chiral Imidazolinone-Based Ionic Liquids[J]. Chin. J. Org. Chem., 2011, 31(9): 1433-1439.

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

分享此文

参考文献

References

1. (a) Lee , S.-G, Park, J. H.; Kang J.; Lee, J. K. Chem. Commun. 2001, 1698

(b) Yadav, J. S.; Reddy, B. V. S.; Baishya, G. J. Org. Chem. 2003, 68, 7098

2. Liu, W.-S.; Tao, G.-H.; He, L.; Kou, Y.; Chin. J. Org. Chem. 2006, 26, 1031(in chinese)

(刘伟山; 陶国宏; 何玲; 寇元有机化学，2006，26，1031)

3. (a) Wasserscheid, P.; B?smanna, A.; Bolmb C. Chem. Commun. 2002, 200

(b) Luo, S.-Z.; Mi, X.-L. ; Zhang, L.; Liu, S.; Xu, H.; Cheng, J.-P. Tetrahedron 2007, 63, 1923.

(c) Cao, X.; Yue, C.-G.; Chin. J. Org. Chem. 2010, 30, 816 (in chinese)

(曹霞; 乐长高有机化学，2010，30，816)

4. Howarth, J.; HanIon, K.; Fayne, D.; McCormac, P. Tetrahed. Lett . 1997, 38, 3097

5. Wu, N.; Wu, H.-H.; Jiang, Y.-W.; Chin. J. Org. Chem. 2008, 28, 104 (in chinese)

(吴楠; 吴海虹; 蒋咏文有机化学，2008，28，104)

6. Siyutkin, D. E.; Kucherenko, A. S.; Struchkova, M. I.; Zlotin, S. G. Tetrahedron Lett. 2008, 49, 1212.

7. Li, F. -R.; Song, Q.; Zhao, L.; Yuan, L.-M.; Chem. J. Chin. Universities, 2009, 30, 258 (in chinese)

(李芙蓉; 宋卿; 赵丽; 袁黎明高等学校化学学报, 2009, 30, 258)

8. (a) Loh, T. P.; Feng, L. C.; Yang, H. Y.; Yang, J. Y. Tetrahedron Lett. 2002 43, 8741

(b) Luo, S.-P.; Wang, L.-P.; Yue, H.-D.; Yue, C.-G.; Yang, W.-L.; Xu, D.-Q.; Xu. Z.-Y.; Acta Chimica Sinica, 2006, 64, 1483 (in chinese)

(罗书平; 王丽萍; 岳华栋; 乐长高; 杨文龙; 许丹倩; 徐振元化学学报, 2006, 64, 1483)

9. Austin, J. F. ; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.

10. Yao, C.-F.; Sun, C.-X.; Yan, S.-Y.; Wu, H.-H.; Progress in Chem. 2008, 20(6), 887 (in chinese).

(姚成福; 孙彩霞; 闫少宇; 吴海虹化学进展, 2008, 20, 887)

11. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.

12. Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000 , 122,

9874

13. (a) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.

(b) Fonseca, M. T. H.; List, B. Angew. Chem. Int. Ed. 2004 , 43, 3958.

14. (a) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108.

(b) Beeson, T. D.; MacMillan, D. W. C. J. Am. Chem. Soc., 2005, 127, 8826.

15. Paras, N. A.; MaeMillan, D. W. C. J. Am. Chem. Soc., 2001,123,4370

16. Yao, L.; Smith, B. T.; Aube, J. J. Org. Chem. 2004, 69, 1720.

17. Nonaka, H.; Tsukiji, S.; Ojida, A.; Hamachi, I.; J. Am. Chem. Soc. 2007, 129, 15777.

18. Ciampi, S.; Bocking, T.; Kilian, K. A.; James, M.; Harper, J. B.; Gooding, J. J. Langmuir 2007, 23, 9320.

[1]	潘国军, 肖娜, 沈棣, 陈明朗, 李屹, 芦逵, 杨杨, 孟欣, 郁彭. 新型槲皮素缀合物的合成与降糖活性研究[J]. 有机化学, 2017, 37(1): 133-140.
[2]	沈宝星, 钱鹰. 新型萘酰亚胺-氟硼二吡咯荧光分子的合成、荧光共振能量转移及细胞成像[J]. 有机化学, 2016, 36(4): 774-781.
[3]	霍景沛, 韦新平, 莫广珍, 彭湃, 钟铭丽, 陈任宏, 汪朝阳. 双-1,2,3-三唑化合物的合成与应用研究进展[J]. 有机化学, 2014, 34(1): 92-106.

手性咪唑啉酮离子液体的合成

Synthesis of Chiral Imidazolinone-Based Ionic Liquids

PDF

可视化

被引次数

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 3

编辑推荐

相关统计

本文评价