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有机化学 ›› 2007, Vol. 27 ›› Issue (9): 1155-1158. 上一篇    下一篇

研究简报

新型树形化合物1,3,5-三-[7-(7-甲基-2,2-二-(2,2-二羟甲基-3-羟基丙氧基羰基)-6,8-二氧杂螺[3.5]-壬基)]苯的合成

梁娅，李洪波，魏荣宝*，陈苏战，刘秀明，孙光远   

  1. (天津理工大学生物技术与化学工程学院 天津 300191)
  • 收稿日期:2006-03-06 修回日期:2007-01-23 发布日期:2007-08-30
  • 通讯作者: 魏荣宝

Synthesis of New Arborescent Compound 1,3,5-Tri-[7-(7-methyl-2,2-di-(2,2-dihydroxymethyl-3-hydroxy-propoxycarbonyl)-6,8-dioxaspiro[3.5]nonyl)]benzene

LIANG Ya,LI Hong-Bo,WEI Rong-Bao*,CHEN Su-Zhan
LIU Xiu-Ming,SUN Guang-Yuan   

  1. (College of Biotechnology & Chemical Engineering, Tianjin University of Technology, Tianjin 300191)
  • Received:2006-03-06 Revised:2007-01-23 Published:2007-08-30
  • Contact: WEI Rong-Bao

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被引次数

27

以丙酮和甲酸乙酯为原料, 在醇钠的作用下合成了1,3,5-三乙酰基苯(1). 1与二溴新戊二醇在酸的作用下发生缩酮化反应, 制成1,3,5-三-(1-甲基-2,6-二氧杂-4,4-二溴甲基环己基)苯(2). 2与5,5-二甲基-4,6-二氧杂-1,3-环己二酮在乙醇钠的作用下合成了1,3,5-三-[7-(7-甲基-2,2-二-乙氧羰基-6,8-二氧杂螺[3.5]-壬基)]苯(3). 将3在氯仿中与季戊四醇进行酯交换反应得到产物1,3,5-三-[7-(7-甲基-2,2-二-(2,2-二羟甲基-3-羟基丙氧基羰基)-6,8-二氧杂螺[3.5]-壬基)]苯(4). 收率为47.7%. 标题化合物及中间产物使用IR, 1H NMR和MS或元素分析进行了表征.

关键词: 1,3,5-三乙酰基苯, 二溴新戊二醇, 树形化合物, 5,5-二甲基-4,6-二氧杂-1,3-环己二酮

Ketalazation of the triacetylbenzene (1) with 2,2-dibromomethyl-1,3-propanediol by using 4-methyl-benzenesulfonic acid as catalyst, yielded 1,3,5-tri-(1-methyl-2,6-dioxaspiro-4,4-dibromomethyl- cyclohexyl)benzene (2), which reacted with 5,5-dimethyl-4,6-dioxa-1,3-cyclohexanedione in C2H5ONa giving 1,3,5-tri-[7-(7-methyl-2,2-di-ethoxycarbonyl-6,8-dioxaspiro[3.5]-nonyl)]benzene (3). Treatment of 3 with 2,2-dihydroxymethyl-1,3-propanediol in CHCl3 afforded 1,3,5-tri-[7-(7-methyl-2,2-di- (2,2-dihydroxyl- methyl-3-hydroxy-propoxycarbonyl)-6,8-dioxaspiro[3.5]-nonyl)]benzene (4) in 47.7% yield. The compound 4 and its intermediates were identified by IR, 1H NMR, MS spectra and elemental analysis.

Key words: 1,3,5-triacetyl benzene, 2,2-dibromomethyl-1,3-propanediol, dendrimer, 5,5-dimethyl-4,6-di-oxa-1,3-cyclohexanedione