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

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

(¹State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
(²School 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

Abstract

(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

Cite this article

BAI Ling-Wei ,ZHANG Zhi-Yang CHEN Qiang, YAN Hong, PENG Zhi-Hong*^,1, YANG Song*^,2 ,AN De-Lie*^,1. Design and Synthesis of Novel Topologically Interesting Cyclophanes with p,p′-Arylene Ethynylene Connection Modes[J]. Acta Chimica Sinica, 2008, 66(5): 545-551.

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p,p′-芳炔桥连的四联萘拓扑环芳分子的设计与合成

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

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