带有不同端炔保护基团的新型苯乙炔树枝状化合物的合成

doi:10.6023/cjoc201211031

有机化学 ›› 2013, Vol. 33 ›› Issue (03): 551-557.DOI: 10.6023/cjoc201211031 上一篇下一篇

研究论文

带有不同端炔保护基团的新型苯乙炔树枝状化合物的合成

许晨, 黄鹏程

北京航空航天大学材料科学与工程学院北京 100191

收稿日期:2012-11-15 修回日期:2012-12-14 发布日期:2012-12-18
通讯作者: 黄鹏程 E-mail:huangpc@buaa.edu.cn

Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

Xu Chen, Huang Pengcheng

College of Material Science and Technology, Beihang University, Beijing 100191

Received:2012-11-15 Revised:2012-12-14 Published:2012-12-18

文章分享

1. 带有不同端炔保护基团的新型苯乙炔树枝状化合物的合成.PDF(879KB)

摘要/Abstract

以1,3,5-三溴苯为原料, 通过Sonogashira反应, 设计并合成了两种带有不同端炔保护基团的1,3,5-取代的苯乙炔树枝状化合物: 1,3,5-三[3-(3-甲基-3-羟基-1-丁炔基)-5-(三异丙基硅乙炔基)苯基乙炔基]苯(B₁)和1,3,5-三[3-(三甲基硅乙炔基)-5-(三异丙基硅乙炔基)苯基乙炔基]苯(B₂), 并对合成路线的选择进行了比较和讨论. 用¹H NMR, ¹³C NMR, 质谱, 元素分析等表征手段确认了中间体及最终产物的结构. 这两种苯乙炔树枝状化合物各自带有两类不同的周边端炔保护基团, 可根据其脱保护条件的不同引入不同的周边功能基团.

关键词: 苯乙炔树枝状化合物, Sonogashira反应, 1,3,5-三[3-(3-甲基-3-羟基-1-丁炔基)-5-(三异丙基硅乙炔基)苯基乙炔基]苯, 1,3,5-三[3-(三甲基硅乙炔基)-5-(三异丙基硅乙炔基)苯基乙炔基]苯

Using Sonogashira coupling reaction, two kinds of 1,3,5-substituted phenylacetylene dendrimers: 1,3,5-tris[3-(3- hydroxy-3-methyl-1-butynyl)-5-(triisopropylsilylethynyl)phenylethynyl]benzene (B₁) and 1,3,5-tris[3-(trimethylsilylethynyl)- 5-(triisopropylsilylethynyl)phenylethynyl]benzene (B₂) were synthetized and the synthetic routes were compared and discussed. The structures of the target compounds and intermediates were confirmed by ¹H NMR, ¹³C NMR, EI-MS, HRMS techniques and element analysis. In phenylacetylene dendrimers B₁ and B₂, the six terminal acetylene groups on their periphery were protected by two different kinds of groups, respectively. Based on the different deprotection conditions, two different kinds of functional groups could be introduced to B₁ and B₂, respectively.

Key words: phenylacetylene dendrimer, Sonogashira reaction, 1,3,5-tris[3-(3-hydroxy-3-methyl-1-butynyl)-5-(triisopropyl- silylethynyl)phenylethynyl]benzene, 1,3,5-tris[3-(trimethylsilylethynyl)-5-(triisopropylsilylethynyl)phenylethynyl]benzene

引用此文

许晨, 黄鹏程. 带有不同端炔保护基团的新型苯乙炔树枝状化合物的合成[J]. 有机化学, 2013, 33(03): 551-557.

Xu Chen, Huang Pengcheng. Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes[J]. Chin. J. Org. Chem., 2013, 33(03): 551-557.

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

分享此文

参考文献

[1] Yang, L.-L.; Dong, Y.-M.; Hu, X.-L.; Liu, A.-H. Acta Chim. Sinica 2012, 70, 21 (in Chinese).
(杨柳林, 董炎明, 胡晓兰, 刘安华, 化学学报, 2012, 70, 21.)

[2] Ma, C.; Li, L.; Sun, J.-S.; Zhao, F.; Li, Y.-L. Chin. J. Org. Chem. 2011, 31, 1977 (in Chinese).
(马茶, 李龙, 孙金声, 赵丰, 李易隆, 有机化学, 2011, 31, 1977.)

[3] Li, L.; Ma, C.; Sun, J.-S.; Zhao, F.; Pang, Z.-L.; Li, Y.-L. Chin. J. Org. Chem. 2012, 32, 304 (in Chinese).
(李龙, 马茶, 孙金声, 赵丰, 庞正炼, 李易隆, 有机化学, 2012, 32, 304.)

[4] Harigaya, K. Phys. Chem. Chem. Phys. 1999, 1, 1687.

[5] Devadoss, C.; Bharathi, P.; Moore, J. S. J. Am. Chem. Soc. 1996, 118(40), 9635.

[6] Kopelman, R.; Shortreed, M.; Shi, Z.-Y.; Tan, W.; Xu, Z.; Moore, J. S.; Bar-Haim, A.; Klafter, J. Phys. Rev. Lett. 1997, 78, 1239.

[7] Nakano, M.; Fujita, H.; Takahata, M.; Yamaguchi, K. J. Am. Chem. Soc. 2002, 124, 9648.

[8] Wang, P.-W.; Liu, Y.-J.; Devadoss, C.; Bharathi, P.; Moore, J. S. Adv. Mater. 1996, 8, 237.

[9] Wu, Z.; Xiong, Y.; Zou, J.; Wang, L.; Liu, J.; Chen, Q.; Yang, W.; Peng, J.; Cao, Y. Adv. Mater. 2008, 20, 2359.

[10] Astruc, D.; Boisselier, E.; Ornelas, C. Chem. Rev. 2010, 110, 1857.

[11] Ayabe, M.; Ikeda, A.; Kubo, Y.; Takeuchi, M.; Shinkai, S. Angew. Chem., Int. Ed. 2002, 41, 2790.

[12] Xu, Z.-F.; Moore, J. S. Polym. Prep. 1993, 1, 128.

[13] Adhikari, R. M.; Duan, L.; Hou, L.-D. Chem. Mater. 2009, 21, 4638.

[14] Rana, D.; Gangopadhyay, G. Chem. Phys. Lett. 2001, 334, 314.

[15] Li, J.; Huang, P.-C. Res. Chem. Intermed. 2012, 38, 403.

[16] Pesak, D. Ph.D. Dissertation, University of Illinois, Illinois, 1995.

[17] Chen, Q.-Y.; Ma, Y.-W.; Wang, C.-Y.; Shen, Y.-J. Chin. J. Org. Chem. 2012, 32, 1526 (in Chinese).
(陈秋燕, 麻玉雯, 王成云, 沈永嘉, 有机化学, 2012, 32, 1526.)

[18] Littke, A. F.; Fu, G.-C. Angew. Chem., Int. Ed. 2002, 41, 4176.

[19] Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.

[20] Ji, Z.; Li, S.; Li, Y. Inorg. Chem. 2010, 49, 1337.

[21] Melissaris, A. P.; Litt, M. H. J. Org. Chem. 1994, 59, 5818.

[22] Li, J.; Huang, P.-C. Beilstein J. Org. Chem. 2011, 7, 426.

[23] Lim, Y.-K.; Jiang, X.; Bollinger, J. C.; Lee, D. J. Mater. Chem. 2007, 17, 1969.

[24] Baxter, P. N. W. Chem. Eur. J. 2003, 9, 5011.

[25] Xu, Z.; Moore, J. S. Angew. Chem., Int. Ed. 1993, 32, 246.

[26] Rodriguez, J. G.; Esquivias, J.; Lafuente, A.; Diaz, C. J. Org. Chem. 2003, 68, 8120.

[27] Bo, Z.-S.; Schluter, A. D. J. Org. Chem. 2002, 67, 5327.
[28] Yoosaf, K.; Llanes-Pallas, A.; Marangoni, T.; Belbakra, A.; Marega, R.; Botek, E.; Champagne, B.; Bonifazi, D.; Armaroli, N. Chem. Eur. J. 2011, 17, 3262.

带有不同端炔保护基团的新型苯乙炔树枝状化合物的合成

Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 9

编辑推荐

相关统计

本文评价

[1]	温燕梅, 谢建英, 冯润光, 黄绪明. 1,7-二芳基-1,6-庚二炔化合物的合成[J]. 有机化学, 2015, 35(3): 735-738.
[2]	陈秋燕, 麻玉雯, 王成云, 沈永嘉. 1,3,5-三[(4'-乙炔基苯基)乙炔基]苯的合成[J]. 有机化学, 2012, 32(08): 1526-1532.
[3]	毛超旭, 汪朝阳, 谭越河, 薛福玲. 金属催化的2(5H)-呋喃酮反应研究进展[J]. 有机化学, 2011, 31(9): 1377-1387.
[4]	王鹏, 赵静静, 王忠卫, 曹德龙, 徐建忠. 一例新型桥联吡啶化合物的合成和结构研究[J]. 有机化学, 2011, 31(05): 757-761.
[5]	张国平, 李品华. 超声辐射下醋酸钯催化Sonogashira偶联反应[J]. 有机化学, 2010, 30(01): 117-119.
[6]	靳玄烨^a ; 肖强^,b; 巨勇,a. 钯催化合成嘧啶核苷衍生物的研究进展[J]. 有机化学, 2009, 29(01): 44-54.
[7]	周磊,江焕峰^c. (E)-烯二炔化合物的高选择性合成[J]. 有机化学, 2006, 26(12): 1682-1695.
[8]	段新方,张站斌. 铯盐促进的有机反应[J]. 有机化学, 2006, 26(04): 573-578.
[9]	王晔峰,邓维,刘磊,郭庆祥. Sonogashira反应研究的最新进展[J]. 有机化学, 2005, 25(01): 8-24.