有机化学
有機化學
유궤화학
CHINESE JOURNAL OF ORGANIC CHEMISTRY
2009年
12期
2017-2020
,共4页
赵可清%杨高帆%余文浩%汪必琴%胡平
趙可清%楊高帆%餘文浩%汪必琴%鬍平
조가청%양고범%여문호%왕필금%호평
盘状液晶%苯并菲%2-羟基-3-甲氧基-6,7,10,11-四烷氧基苯并菲%2-羟基-3,6,7,10,11-五烷氧基苯并菲%选择性脱甲基
盤狀液晶%苯併菲%2-羥基-3-甲氧基-6,7,10,11-四烷氧基苯併菲%2-羥基-3,6,7,10,11-五烷氧基苯併菲%選擇性脫甲基
반상액정%분병비%2-간기-3-갑양기-6,7,10,11-사완양기분병비%2-간기-3,6,7,10,11-오완양기분병비%선택성탈갑기
discotic liquid crystal%triphenylene%2-hydroxy-3-methoxy-6,7,10,11-tetra-(alkoxy)tripheny-lene%2-hydroxy-3,6,7,10,11-penta(alkoxy)triphenylene%selective demethylation
羟基苯并菲[TP(OH)(OR)_5]是一类重要的盘状液晶中间体.根据苯并菲衍生物间极性差异,设计了一条简便的合成与分离羟基苯并菲的方法:在70%硫酸中用FeCl_3氧化邻苯二醚与2-甲氧基苯酚三聚成环,分离获得2,3,6,7,10,11-六烷氧基苯并菲[TP(OR)_6]和2-羟基-3-甲氧基-6,7,10,11-四烷氧基苯并菲[TP(OH)(OMe)(OR)_4].后者再经醚化,Ph_2PLi脱甲基得2-羟基-3,6,7,10,11-五烷氧基苯并菲[TP(OH)(OR)_5].三步反应总收率14%～19%.
羥基苯併菲[TP(OH)(OR)_5]是一類重要的盤狀液晶中間體.根據苯併菲衍生物間極性差異,設計瞭一條簡便的閤成與分離羥基苯併菲的方法:在70%硫痠中用FeCl_3氧化鄰苯二醚與2-甲氧基苯酚三聚成環,分離穫得2,3,6,7,10,11-六烷氧基苯併菲[TP(OR)_6]和2-羥基-3-甲氧基-6,7,10,11-四烷氧基苯併菲[TP(OH)(OMe)(OR)_4].後者再經醚化,Ph_2PLi脫甲基得2-羥基-3,6,7,10,11-五烷氧基苯併菲[TP(OH)(OR)_5].三步反應總收率14%～19%.
간기분병비[TP(OH)(OR)_5]시일류중요적반상액정중간체.근거분병비연생물간겁성차이,설계료일조간편적합성여분리간기분병비적방법:재70%류산중용FeCl_3양화린분이미여2-갑양기분분삼취성배,분리획득2,3,6,7,10,11-륙완양기분병비[TP(OR)_6]화2-간기-3-갑양기-6,7,10,11-사완양기분병비[TP(OH)(OMe)(OR)_4].후자재경미화,Ph_2PLi탈갑기득2-간기-3,6,7,10,11-오완양기분병비[TP(OH)(OR)_5].삼보반응총수솔14%～19%.
Monohydroxytriphenylene [TP(OH)(OR)_5] is an important intermediate for functionalized or polymeric discotic liquid crystals. Based on the polarity difference among triphenylene derivatives, a new simple method was designed to synthesize monohydroxytriphenylene [TP(OHXOR)_5]: oxidative trimerization of 1,2-dialkoxybenzene and 2-methoxyphenol by FeCl_3 in 70% sulfuric acid resulted in 2,3,6,7,10,11-hexa(alkoxy)triphenylene [TP(OR)_6] and 2-hydroxy-3-methoxy-6,7,10,11-tetra(alkoxy)triphenylene [TP(OH)-(OMe)(OR)_4], then alkylation with RBr and demethylation with Ph_2PLi afforded the title compounds. The total yield of the three steps was in the range of 14%～19%.
