一种新颖的构建(E)-3-芳氧基丙烯酸酯衍生物的方法
收稿日期: 2014-05-01
修回日期: 2014-05-07
网络出版日期: 2014-06-11
基金资助
广东省自然科学基金（No. S2012040007868）和广东省优秀青年基金（No. 2013LYM_0059）资助项目.
A Novel Construction Method for (E)-3-Aryloxyacrylate Derivatives
Received date: 2014-05-01
Revised date: 2014-05-07
Online published: 2014-06-11
Supported by
Project supported by the Natural Science Foundation of Guangdong Province (No. S2012040007868) and the Excellent Young Scientist Fund of Guangdong Province Education Department (No.2013LYM_0059).
以炔酸酯和酚类化合物为原料，N，N-二甲基甲酰胺（DMF）为溶剂，CuO/CH3ONa为促进体系，经过分子间的加成和自由基反应，成功地构建出了（E）-3-芳氧基丙烯酸酯衍生物. 采用IR，1H NMR，13C NMR和元素分析对目标产物进行了表征. 研究表明该方法具有原料便宜易得、后处理操作简单和产品纯度高等优点.
关键词： 炔酸酯; 酚类化合物; 分子间加成; (E)-3-芳氧基丙烯酸酯衍生物
陈翠 , 谭丽泉 , 邱会华 . 一种新颖的构建(E)-3-芳氧基丙烯酸酯衍生物的方法[J]. 有机化学, 2014 , 34(10) : 2152 -2155 . DOI: 10.6023/cjoc201405001
This paper reports a novel intermolecular addition and free radical homolytic reaction for the synthesis of (E)-3-aryloxyacrylate derivatives from alkynoates and phenols using N,N-dimethylformamide (DMF) as the solvent and CuO/CH3ONa as the system of promotion. The structures of product were confirmed by IR, 1H NMR, 13C NMR and elemental analysis. The results showed that this synthetic route had the advantages of easy-obtained raw materials, simple work-up and high purity product.
Key words： alkynoates; phenols; intermolecular addition; (E)-3-aryloxyacrylates
[1] McInturff, E. L. Mowat, J.; Waldeck, A. R.; Krische, M. J. J. Am. Chem. Soc. 2013, 135, 17230.
[2] Han, X. Y.; Wang, Y. Q.; Zhong, F. R.; Lu, Y. X. J. Am. Chem. Soc. 2011, 133, 1726.
[3] Anastasaki, A.; Nikolaou, V.; Zhang, Q.; Burns, J.; Samanta, S. R.; Waldron, C.; Haddleton, A. J.; McHale, R.; Fox, D.; Percec, V.; Wilson, P.; Haddleton, D. M. J. Am. Chem. Soc. 2014, 136, 1141.
[4] Percec, V.; Guliashvili, T.; Ladislaw, J. S.; Wistrand, A.; Stjerndahl, A.; Sienkowska, M. J.; Monteiro, M. J.; Sahoo, S. J. Am. Chem. Soc. 2006, 128, 14156.
[5] Walker, E. H.; Apblett, A. W.; Walker, R.; Zachary, A. Chem. Mater. 2004, 16, 5336.
[6] Xu, Y. H.; Lu, J.; Loh, T. P. J. Am. Chem. Soc. 2009, 131, 1372.
[7] Shirai, M.; Mitsukura, K.; Okamura, H. Chem. Mater. 2008, 20, 1971.
[8] Tan, P.; Li, N. B.; Xu, X. H. Chin. J. Org. Chem. 2012, 32, 2162.
[9] Fan, M. J.; Li, G. Q.; Li, L. H.; Yang, S. D.; Liang, Y. M. Synthesis 2006, 2286.
[10] Han, Y.; Sun, J.; Sun, Y.; Gao, H.; Yan, C. G. Chin. J. Org. Chem. 2012, 32, 1577.
[11] Øpstad, C. L.; MelØ, T. B.; Sliwka, H. R.; Partali, V. Tertrahedron 2009, 65, 7616.
[12] Chen, Y. Y.; Zhang, X. J.; Yuan, H. M.; Wei, W. T.; Yan, M. Chem. Commun. 2013, 49, 10974.
[13] Wei, W. T.; Dong, X. J.; Nie, S. Z.; Chen, Y. Y.; Zhang, X. Z.; Yan, M. Org. Lett. 2013, 15, 6018.
[14] Li, C. L.; Zhang, Y. C.; Li, P. H.; Wang, L. J. Org. Chem. 2011, 76, 4692.
[15] Kinart, W. J.; Kinart, A. Appl. Organomet. Chem. 2007, 21, 373.
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