Browse > Article
http://dx.doi.org/10.5012/jkcs.2011.55.2.251

A Highly Stereoselective Synthesis and Crystal Structure of (E)-4'-Amino-3,4,5- trimethoxystilbene  

Li, Xia-Bing (Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, and School of Chemistry and Materials Science, Shaanxi Normal University)
Zhang, Xi-Quan (Jiangsu Chia Tai Tianqing Pharmaceutical Co., Ltd.)
Gu, Hong-Mei (Jiangsu Chia Tai Tianqing Pharmaceutical Co., Ltd.)
Li, Bao-Lin (Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, and School of Chemistry and Materials Science, Shaanxi Normal University)
Publication Information
Journal of the Korean Chemical Society / v.55, no.2, 2011 , pp. 251-255 More about this Journal
Abstract
A new and highly stereoselective synthesis of (E)-4'-amino-3,4,5-trimethoxystilbene was achieved by using 3,4,5-trimethoxybenzaldehyde and p-nitrotoluene as starting materials through condensation under solvent-free condition and followed by the reducing of nitro group with the system of $NH_2NH_2/FeCl_3$/C in ethanol. The crystal structure of (E)-4'-amino-3,4,5-trimethoxystilbene was also determined by X-ray diffraction analysis.
Keywords
(E)-4'-amino-3,4,5-trimethoxystilbene; (E)-3,4,5-trimethoxy-4'-nitrostilbene; Stereoselectivity; Crystal structure; Hydrogen bond;
Citations & Related Records

Times Cited By SCOPUS : 0
연도 인용수 순위
  • Reference
1 Timko, J. M.; Moore, S. S.; Walba, D. M.; Hiberty, P.C.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 4207.   DOI
2 Wang, M. L.; Chang, K. R. Ind. Eng. Chem. Res. 1990, 29(1), 40.   DOI
3 Cao, Y. Q.; Dai, Z.; Zhang, R.; Chen, B. H. Synth. Commun. 2004, 34, 2965.   DOI
4 Bernstein, J.; Mirsky, K. Acta Cryst. A 1978, 34, 161.   DOI
5 Silverstein, R. M.; Baeeler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds; Wiley & Sons: New York, 1981, pp 264-265.
6 Zhang, J.; Chen, S. F.; Klausmeyer, K. K.; Kane, R. R. Acta Cryst. C 2003, 59, 381.
7 Gordon, G. C.; Charles, R. E.; Robert, A.G.; Hilary, A. J. Tetrahedron Lett. 2006, 47, 2245.   DOI
8 Chen, X. M.; Cai, J. W. Single-Crystal Structure Analysis Principles and Practices, Science Press: Beijing, 2004, p 101.
9 Ogawa, K.; Sano, T.; Yoshimura, S.; Takeuchi, Y.; Toriumi, K. J. Am. Chem. Soc. 1992, 114, 1041.   DOI
10 Harada, J.; Ogawa, K. J. Am. Chem. Soc. 2001, 123, 10884.   DOI
11 Soomro, S. A.; Schulz, A.; Meier, H. Tetrahedron 2006, 62, 8089.   DOI
12 Pinney, K. G.; Mejia M. P.; Villalobos, V. M.; Rosenquist, B. E.Pettit, G. R. Verdier-Pinard, P.; Hamel, E. Bioorg. Med. Chem. 2000, 8, 2417.   DOI
13 Bai, R.; Petit, G. R.; Hamel, E. Biochem. Pharmacol. 1990, 39, 1941.   DOI
14 Pettit, G. R.; Singh, S. B.; Cragg, G. M. J. Org. Chem. 1985, 50, 3404.   DOI
15 Pettit, G. R.; Singh, S. B.; Schmidt, J. M.; Nivin, M. L.; Hamel, E.; Lin, C. M. J. Nat. Prod. 1988, 51, 517.   DOI
16 Chang, J. Y.; Yang, M. F.; Chang, C. Y.; Chen, C. M.; Kuo, C. C.; Liou, J. P. J. Med. Chem. 2006, 49, 6412.   DOI
17 Zhang, X. Q.; Gu, H. M.; Xu, H. J.; Fu, H.; Li, B. L.; Guo, J.; Lai, Y. T.; Wang, W. China Patent 100861805, 2006.
18 Du, J.; Zhang, X. Q.; Guo, J.; Gu, H. M; Xu, H. J.; Li, B. L. Huaxue Yanjiu Yu Yingyong 2009, 21(1), 120.
19 Sheldrick, G. M. SHELXS-97. Program for the Solution of Crystal Structures. University of Gottingen, Germany, 1997.
20 Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures, University of Gottingen, Germany, 1997.
21 Cushman, M.; Nagarathnam, D.; Gopal, D.; Chakraborti, A. K.; Lin, C. M.; Hamel, E. J. Med. Chem. 1991, 34, 2579.   DOI
22 Zou, S.; Zhang, X. J.; Lin, H. Z. China Patent 101118854, 2003.
23 Li, B. L.; Zhang, Z. G.; Wang, W.; Li, J.; Wang, C. W. Z. Naturforsch. B 2008, 63b, 77.
24 Brem, G.; Lowpy, A.; Sansonlet, J. Isr. J. Chem. 1985, 26, 291.   DOI