Acta Chimica Sinica ›› 2008, Vol. 66 ›› Issue (5): 545-551. Previous Articles     Next Articles

Original Articles

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)
  • 收稿日期:2007-06-26 修回日期:2007-11-15 出版日期:2008-03-14 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 Online:2008-03-14 Published:2008-03-14
  • Contact: AN De-Lie

(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)-2a2c 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