带有不同端炔保护基团的新型苯乙炔树枝状化合物的合成  

Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

作　　者：许晨[1] 黄鹏程[1] 

机构地区：[1]北京航空航天大学材料科学与工程学院,北京100191

出　　处：《有机化学》2013年第3期551-557,共7页Chinese Journal of Organic Chemistry

摘　　要：以1,3,5-三溴苯为原料,通过Sonogashira反应,设计并合成了两种带有不同端炔保护基团的1,3,5-取代的苯乙炔树枝状化合物:1,3,5-三[3-(3-甲基-3-羟基-1-丁炔基)-5-(三异丙基硅乙炔基)苯基乙炔基]苯(B1)和1,3,5-三[3-(三甲基硅乙炔基)-5-(三异丙基硅乙炔基)苯基乙炔基]苯(B2),并对合成路线的选择进行了比较和讨论.用1H NMR,13C NMR,质谱,元素分析等表征手段确认了中间体及最终产物的结构.这两种苯乙炔树枝状化合物各自带有两类不同的周边端炔保护基团,可根据其脱保护条件的不同引入不同的周边功能基团.Using Sonogashira coupling reaction, two kinds of 1,3,5-substituted phenylacetylene dendrimers： 1,3,5-tris[3-（3- hydroxy-3-methyl-l-butynyl）-5-（triisopropylsilylethynyl）phenylethynyl]benzene （B1） and 1,3,5-tris[3-（trimethylsilylethynyl）- 5-（triisopropylsilylethynyl）phenylethynyl]benzene （B2） were synthetized and the synthetic routes were compared and dis- cussed. The structures of the target compounds and intermediates were confirmed by 1H NMR, 13C NMR, EI-MS, HRMS techniques and element analysis. In phenylacetylene dendrimers B1 and B2, the six terminal acetylene groups on their periph- ery were protected by two different kinds of groups, respectively. Based on the different deprotection conditions, two different kinds of functional groups could be introduced to BI and B2, respectively.

关 键 词：苯乙炔树枝状化合物 SONOGASHIRA反应 1 3 5-三[3-(3-甲基-3-羟基-1-丁炔基)-5-(三异丙基硅乙炔基)苯基乙炔基]苯 1 3 5-三[3-(三甲基硅乙炔基)-5-(三异丙基硅乙炔基)苯基乙炔基]苯 

分 类 号：O625.12[理学—有机化学]