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  

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

作　　者：安德烈[1] 杨少辉[1] 张志扬[1] 彭志鸿[1] 张英俊[1] 刘红玲[1] 

机构地区：[1]湖南大学化学化工学院,长沙410082

出　　处：《高等学校化学学报》2005年第7期1268-1272,M005,共6页Chemical Journal of Chinese Universities

基　　金：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

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M S,IR,UV-V is,1H NM R,13C NM R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.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, -{-}^-{13-}C NMR, 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 -_D data.

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 

分 类 号：O624[理学—有机化学]