以3,5-二溴-1-{3-(十二烷氧基)-2-[(十二烷氧基)甲基]丙氧基}苯和2-甲基-3-丁炔-2-醇为原料,经选择性Sonogashira偶联反应,Sonogashira偶联反应和去硅保护基反应制得中间体——3-乙炔基-5-(3-甲基-3-羟基)-丁炔基-1-(3-十二烷氧基)-2-{[(十二烷氧基)甲基]丙氧基}苯(6);6经改良的Glaser偶联反应(Cu I为催化剂,Et3N为溶剂)合成了一个新型的丁二炔衍生物(1)。6与2,2'-[(2,5-二碘-1,4-亚苯基)双(氧基)]双(四氢-2H-吡喃)经Sonogashira偶联,脱THP保护基和改良的Glaser偶联反应合成了一个新型的丁二炔衍生物(2)。中间体,1和2的结构经^1H NMR,^13C NMR和MALDI-TOF-MS表征。
A novel diacetylene derivative( 1) was synthesized by improved Glaser-coupling reaction( Cu I as catalyst and Et3 N as solvent) of 3-ethynyl-5-( 3-methyl-3-hydroxyl)-butynyl-1-( 3-dodecyloxy)-2-{ [( dodecyloxy) methyl]propoxy} benzene( 6),which was obtained by selective Sonogashira reaction,Sonogashira-coupling reaction and deprotection from 3,5-dibromo-1-{ 3-( dodecyloxy)-2-[( dodecyloxyyl) methyl]propoxy} benzene and 2-methyl-3-butyn-2-ol. A novel diacetylene derivative( 2) was synthesized by Sonogashira reaction,THP deprotection reaction and improved Glaser-coupling reaction from 6 and 2,2'-[( 2,5-diiodo-1,4-phenylene) bis( oxy) ]bis( tetrahydro-2H-pyran). Structures of intermediate,1 and 2 were characterized by ^1 H NMR,^13 C NMR and MALDI-TOF-MS.