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化学学报
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化学学报 ›› 2005, Vol. 63 ›› Issue (9): 861-865. 上一篇    下一篇

研究论文

以手征性联萘为模板合成一种新的螺旋环芳分子

安德烈*，张志扬，杨少辉，张英俊，彭志鸿，刘红玲   

  1. (湖南大学化学化工学院 长沙 410082)
  • 投稿日期:2004-11-05 修回日期:2005-01-05 发布日期:2010-12-10
  • 通讯作者: 安德烈

Synthesis of a Novel Helical Cyclophane Using Chiral Binaphthyl as Structural Templates

AN De-Lie*, ZHANG Zhi-Yang, YANG Shao-Hui, ZHANG Ying-Jun, PENG Zhi-Hong, LIU Hong-Ling   

  1. (College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
  • Received:2004-11-05 Revised:2005-01-05 Published:2010-12-10
  • Contact: AN De-Lie

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1137

被引次数

31 | 3

基于2,2'-二取代的联萘衍生物在手性构型上高度稳定的特点, 分别从光学活性的(R)-和(S)-2,2'-二乙炔基-1,1'-联萘结构模板出发, 通过Sonogashira 偶连反应导入苄基砜, 然后用二异丙基氨基锂(LDA)处理制得的联萘二砜成功地合成了一种新的螺旋环芳分子——对映异构体(R,P)-3和(S,M)-3. MS, IR, 1H和13C NMR以及元素分析表征了这些化合物．镜象特征的圆二色(CD)谱和比旋光度[α]D的测定结果清楚地反映了它们的对映异构关系．

关键词: 手征联萘衍生物, 结构模板, 联萘二砜, 螺旋环芳, 对映异构体

The chiral binaphthyls is one of the most important precursors for constructing optical molecules. In this paper, (R)- and (S)-2,2'-diethynyl-1,1'-binaphthyl with highly stable chiral configurations were employed as structural templates, and a new type of helical cyclophane compounds (R,P)-3 and (S,M)-3 were synthesized in enantiopure form by the introduction of benzyl sulfone through Sonogashira coupling reaction, followed by the treatment of disulfone with lithium diisopropylamide (LDA). MS, IR, 1H and 13C NMR as well as elemental analysis characterized compound 3. The enantiomeric relation of two isomers was reflected unambiguously by their circular dichroism spectra with exact mirror images and specific rotations [α]D data.

Key words: chiral binaphthyl, structural template, binaphthyl disulfone, helical cyclophane, enantiomer