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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (5): 545-551. 上一篇    下一篇

研究论文

p,p′-芳炔桥连的四联萘拓扑环芳分子的设计与合成

白灵卫1，张志扬1，陈强1，严宏1，彭志鸿*,1，杨崧*,2，安德烈*,1   

  1. (1湖南大学化学化工学院 化学生物传感与计量学国家重点实验室 长沙 410082)
    (2湖南中医药大学药学院 长沙 410007)
  • 投稿日期:2007-06-26 修回日期:2007-11-15 发布日期:2008-03-14
  • 通讯作者: 安德烈

Design and Synthesis of Novel Topologically Interesting Cyclophanes with p,p′-Arylene Ethynylene Connection Modes

BAI Ling-Wei1 ,ZHANG Zhi-Yang1 CHEN Qiang1, YAN Hong1, PENG Zhi-Hong*,1, YANG Song*,2 ,AN De-Lie*,1   

  1. (1 State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
    (2 School of Pharmaceutical Sciences, Hunan University of Traditional Chinese Medicine, Changsha 410007)
  • Received:2007-06-26 Revised:2007-11-15 Published:2008-03-14
  • Contact: AN De-Lie

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基于联萘衍生物手性构型高度稳定的特点, 以光学活性的(R)-2,2'-二乙炔基-1,1'-联萘为模板, 设计了3个有趣的拓扑环芳分子——含有4个手性联萘单元的(R,R,R,R)-2a～2c, 并探讨了它们的合成. 合成路线涉及三甲基硅(Me3Si-)保护基的控制导入, 对位取代的芳基连接桥的链接, 保护基的脱去以及分子间偶合成环4个步骤. 用比旋光度([α]D), MS, IR, UV-Vis, 1H和13C NMR以及元素分析表征了这些化合物.

关键词: 光学活性, 联萘衍生物, 结构模板, 环芳化合物

(R)-2,2'-Diethynyl-1,1'-binaphthyl with a highly stable chiral configuration was employed as a structural template, and three novel topologically interesting tetrabinaphthyl cyclophanes (R,R,R,R)-2a～2c were synthesized in an enantiopure form via four-step reactions including the introduction of protecting group (Me3Si-), linking of para-substituted benzene-bridge, removal of protecting group and intermolecular cross-coupling. The specific rotations ([α]D), MS, IR, UV-Vis, 1H and 13C NMR as well as elemental analysis characterized all intermediates and the target compound 2.

Key words: chirality, binaphthyl, structural template, cyclophane