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S-和R-五味子丙素非对映异构体的圆二色谱研究
引用本文:李岩峰,董黎红,王威,王强,王书洋,赵鹏,常俊标.S-和R-五味子丙素非对映异构体的圆二色谱研究[J].光谱学与光谱分析,2009,29(10):2748-2750.
作者姓名:李岩峰  董黎红  王威  王强  王书洋  赵鹏  常俊标
作者单位:1. 天津大学药物科学与技术学院,天津 300072
2. 郑州大学化学系,河南 郑州 450001
3. 河南省精细化工重点实验室,河南 郑州 450001
基金项目:国家自然科学基金,国家杰出青年科学基金 
摘    要:园二色谱(CD)是测定有机化合物绝对构型的常用方法。文章用圆二色谱仪对合成的4个联苯类化合物进行了表征(2个非桥键联苯化合物和2个桥键联苯化合物),得到两对几乎完全对称的圆二色谱谱图。根据其圆二色谱Cotton效应确定了4个化合物的联苯键的绝对构型。化合物3分别在256 nm出现负的Cotton效应,且在220 nm出现正的Cotton效应,表明这个化合物是S-构型;而化合物3’出现了相反的Cotton效应,表明这个化合物是S-构型。由化学相关法可以得知化合物2是R-构型, 化合物2’是R-构型。通过这些数据得出结论, 以S-噁唑啉为手性合成子的Ullmann反应得到的是S-构型联苯类化合物, 而以S-噁唑啉为手性合成子的Ullmann反应得到的是R-构型型联苯类化合物。

关 键 词:五味子丙素  非对映异构体  圆二色光谱  Cotton效应  
收稿时间:2008/8/6

Study on the Circular Dichroism of(S)-and(R)-Wuweizisu C
LI Yan-feng,DONG Li-hong,WANG Wei,WANG Qiang,WANG Shu-yang,ZHAO Peng,CHANG Jun-biao.Study on the Circular Dichroism of(S)-and(R)-Wuweizisu C[J].Spectroscopy and Spectral Analysis,2009,29(10):2748-2750.
Authors:LI Yan-feng  DONG Li-hong  WANG Wei  WANG Qiang  WANG Shu-yang  ZHAO Peng  CHANG Jun-biao
Institution:1. College of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China2. Department of Chemistry, Zhengzhou University, Zhengzhou 450001, China3. Henan Key Laboratory of Fine Chemicals, Zhengzhou 450001, China
Abstract:The circular dichroism (CD) is an excellent method for determining the absolute stereochemistry of organic compounds. The CD spectra of four biphenyl compounds were determined by using CD spectrometer, and two pairs of symmetrical CD spectra were obtained. The absolute configuration of biphenyl bond was confirmed by the Cotton effect according to the CD rule. The CD spectrum of compound 3 shows a negative Cotton effect at 256 nm, and a positive Cotton effect at 220 nm, which predicts an S-configuration of biphenyl according to an experimental CD rule. Conversely, the CD spectrum of compound 3' displays a positive Cotton effect at 256 nm, and a negative Cotton effect at 219 nm, which predicts an R-configuration of biphenyl. And the regularity of oxazoline-mediated Ullmann reaction was obtained, too.
Keywords:Wuweizisu C  Diastereomer  Circular dichroism spectrum  Cotton effect
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