以手征性联萘为模板合成一种新的螺旋环芳分子  

Synthesis of a Novel Helical Cyclophane Using Chiral Binaphthyl as Structural Templates

作　　者：安德烈[1] 张志扬[1] 杨少辉[1] 张英俊[1] 彭志鸿[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：《化学学报》2005年第9期861-865,i004,共6页Acta Chimica Sinica

基　　金：国家自然科学基金(No.20272012);教育部博士学科点专项基金(No.20020532004)

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,分别从光学活性的(R)-和(S)-2,2'-二乙炔基-1,1'-联萘结构模板出发,通过Sonogashira偶连反应导入苄基砜,然后用二异丙基氨基锂(LDA)处理制得的联萘二砜成功地合成了一种新的螺旋环芳分子——对映异构体(R,P)-3和(S,M)-3.MS,IR,1H和13CNMR以及元素分析表征了这些化合物.镜象特征的圆二色(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.The chiral binaphthyls is one of the most important precursors for constructing optical molecules. In this paper, (R)- and (S)-2,2'-diethynyl-1,1'-binaphthyl with highly stable chiral configurations were employed as structural templates, and a new type of helical cyclophane compounds (R,P)-3 and (SM-3 were synthesized in enantiopure form by the introduction of benzyl sulfone through Sonogashira coupling reaction, followed by the treatment of disulfone with lithium diisopropylamide (LDA). MS, IR, H-1 and C-13 NMR as well as elemental analysis characterized compound 3. The enantiomeric relation of two isomers was reflected unambiguously by their circular dichroism spectra with exact mirror images and specific rotations [alpha](D) data.

关 键 词：模板合成 分子 螺旋 手征性 联萘衍生物 对映异构体 光学活性 二异丙基 ^13C 测定结果 比旋光度 分析表征 二取代 乙炔基 ^1H 圆二色 化合物 NMR 构型 手性 IR 锂 

分 类 号：O621.25[理学—有机化学]