9,9-(′1,4-亚苯基)十四氢-二-吖啶-1,1,′8,8′-四酮缩双季戊四醇的合成  

Synthesis of 9,9′-(1,4-Phenylene) tetra-decahydro diacridine-1,1′,8,8′-tetra-one ketal dipentaerythritol

作　　者：梁娅[1] 刘秀明[1] 陈苏战[1] 魏荣宝[1] 

机构地区：[1]天津理工大学生物技术与化工学院,天津300191

出　　处：《应用化学》2007年第6期619-622,共4页Chinese Journal of Applied Chemistry

基　　金：国家自然科学基金(20472064);天津市自然科学基金(040004311);金属及分子基材料化学天津市重点实验室(南开大学)开放基金(0002)资助项目

摘　　要：利用1,3-环己二酮和1,4-苯二甲醛为原料,在微酸介质中通过羟醛缩合和脱水反应,合成了9,9′-(1,4-亚苯基)-2H,2′H,3H,3′H,4H,4′H,5H,5H,′6H,6′H,7H,7′H,9H,9′H-十四氢-二-吖啶-1,1,′8,8′-四酮(化合物Ⅰ)。提出了化合物Ⅰ生成的反应机理。将化合物Ⅰ与季戊四醇在I2催化下反应,生成了目标化合物9,9-(′1,4-亚苯基)-2H,2′H,3H,3′H,4H,4′H,5H,5H,′6H,6′H,7H,7′H,9H,9′H-十四氢-二-吖啶-1,1,′8,8′-四酮缩双季戊四醇(化合物Ⅱ),收率为40%。产物和中间体用IR1、H NMR、MS和元素分析进行了结构表征。在含有螺环单元的化合物Ⅱ1H NMR中,亚甲基中的8个氢由于受手性轴和苯环的影响而裂分成8重峰。This article deseribes the synthesis of 9,9＇-（1,4-phenylene）-2H,2＇H,3H,3＇H,4H,4＇H,5H, 5H＇ ,6H, 6＇H ,7H ,7 ＇H ,9H ,9＇H-tetradecahydro-dixanthene-1,1＇ ,8,8＇-tetra-one（ compound Ⅰ ） from 1,3-cyclohexedione and 1,4-benzenedicarbo-aldehyde through condensation and dehydration in acidic medium. The reaction mechanism was proposed. And then, the cyclization reaction between Ⅰ and pentaerythritol gave 9, 9＇-（1,4-phenylene）-2H,2H,2＇H, 2＇H, 3H, 3H, 3＇H, 3＇H,4H,4H,4＇H,4＇H, 5H, 5H, 5H＇, 5H＇, 6H, 6H, 6＇H,6＇H, 7 H, 7 H, 7＇ H, 7＇ H, 9H, 9＇ H-tetradecahydro dixanthene-1,1＇, 8,8＇-tetraone ketal di-pentaerythritol （ compound Ⅱ ） using 12 as a catalyst, and the yield was 40%. The structures of Ⅰ and Ⅱ were confirmed by IR, ^1H NMR, and MS. In ^1H NMR spectra, the peaks for the eight hydrogen atoms of the methylene groups in compound Ⅱ containing spiro-structure split into four doublets due to the presence of chiral axis and benzene ring. The reaction parameters and the formation of by-products were discussed.

关 键 词：对苯二甲醛 季戊四醇 螺环化合物 环己二酮 

分 类 号：O621.2[理学—有机化学]