高等学校化学学报

高等学校化学学报 ›› 2005, Vol. 26 ›› Issue (7): 1268.

• 研究论文 • 上一篇    下一篇

2,2'-二乙炔基-1,1'-联萘为模板构筑的新的环芳化合物的合成及其光学性质

安德烈, 杨少辉, 张志扬, 彭志鸿, 张英俊, 刘红玲   

  1. 湖南大学化学化工学院, 长沙410082
  • 收稿日期:2004-07-05 出版日期:2005-07-10 发布日期:2005-07-10
  • 通讯作者: 安德烈(1957年出生),男,教授,博士生导师,从事有机反应和功能有机化合物研究.E-mail:deliean@sina.com E-mail:deliean@sina.com
  • 基金资助:

    国家自然科学基金(批准号:20272012);教育部博士学科点专项基金(批准号:20020532004)资助

Synthesis of Novel Enantiomers Cyclophanes Using 2,2'-Diethynyl-1,1'-binaphthyls as a Structural Block and Their Optical Properties

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

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
  • Received:2004-07-05 Online:2005-07-10 Published:2005-07-10

PDF (PC)

被引次数

12

摘要： 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,分别以光学活性的(R)-和(S)-2,2'-二乙炔基-1,1'-联萘为模板,设计了2个有趣的拓扑环芳分子四联萘笼状对映异构体(R,R,R,R)-2和(S,S,S,S)-2.其合成路线涉及保护基的控制导入、苯连接桥的链接、保护基的脱去以及偶合成环反应4个步骤.用MS,IR,UV-Vis,1HNMR,13CNMR和元素分析等技术对其进行了表征,并比较了其光学性质.研究结果表明,采用这种模板合成方法能够有效地获得具有单一手性的目标化合物.镜像特征的圆二色(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: 光学活性, 联萘衍生物, 结构模板, 环芳化合物, 对映异构体

Abstract: We employed (R)- and (S)-2,2'-diethynyl-1,1'-binaphthyl with a highly stable chirality as the structural blocks and investigated the synthesis of two topologically interesting tetrabinaphthyl cage compounds (R,R,R,R)-2 and (S,S,S,S)-2 via the multi steps reactions including the introduction of protecting group, linking of benzene-bridge, removal of protecting group as well as intermolecular cross-coupling. As expected, the results from MS, IR, UV-Vis, 1H, 13CNMR, elemental analysis and optical properties indicate that this method is very effective for obtaining compound 2 in enantiomer form. The enantiomer relation of the two isomers was reflected unambiguously by their circular dichroism(CD) spectra with exact mirror images and specific rotations [α]D data.

Key words: Optical activity, Binaphthyl derivatives, Structural block, Cyclophane compound, Enantiomer

中图分类号: 

TrendMD: