高等学校化学学报 ›› 2006, Vol. 27 ›› Issue (1): 82-84.

• 研究简报 • 上一篇    下一篇

新型树状化合物1,3,5-三{3-[2,4,8,10-四氧杂\|9(3,5-二(2,6-二氧杂-4,4-二羟甲基环己基)苯基]螺[5.5]十一烷基}苯的制备

魏荣宝, 陈苏战,  梁娅, 刘秀明, 李洪波   

  1. 天津理工大学生物技术与化工学院, 天津 300191
  • 收稿日期:2004-12-20 出版日期:2006-01-10 发布日期:2006-01-10
  • 通讯作者: 魏荣宝(1945年出生), 男, 教授, 主要从事树状大分子化合物的研究. E-mail: wrb111@eyou.com
  • 基金资助:

    国家自然科学基金(批准号: 20472064)和天津市自然科学基金(批准号: 040884311)资助.

Synthesis of 1,3,5-Tri{3-[2,4,8,10-tetra\|oxa-9(3,5-di(2,6-dioxa-4,4-dihydroxymethylcyclohexyl)phenyl]spiro\[5.5]undecyl}benzene for Novel Dendrimer

 WEI Rong-Bao, CHEN Su-Zhan, LIANG Ya, LIU Xiu-Meng, LI Hong-Bo   

  1. College of Biotechnology & Chemical Engineering, Tianjin University of Technology, Tianjin 300191, China
  • Received:2004-12-20 Online:2006-01-10 Published:2006-01-10
  • Contact: WEI Rong-Bao,E-mail: wrb111@eyou.com

摘要:

本实验采用季戊四醇与苯三甲醛缩合, 制成树状化合物1,3,5-三{3-|[2,4,8,10-四氧杂-9(3,5-二(2,6-二氧杂-4,4-二羟甲基环己基)苯基)螺[5.5]十一烷基}苯. 该类树状分子具有手性螺环结构, 手性密度很高, 可开发成理想的高效手性催化剂[3~8], 具有诱人的应用前景.

关键词: 1,3,5-三甲苯; 1,3,5-苯三甲醛; 季戊四醇; 树状化合物

Abstract:

Dendrimers are the subject of intense attention recently because of their anticipated potentialities and the peculiar structural properties.  A novel synthetic route for the preparation of functionalized dendrons built on the 1,3,5-benzenetricarboxaldehyde core and endowed with a periphery of pentaerythritol groups has been developed.  1,3,5-Tri(2,6\|dioxa-4,4-dihydroxymethyl cyclohexyl) benzene(1) was synthesized by the condensation of 1,3,5\|benzenetricarboxaldehyde with pentaerythritol in the presence of hot CHCl3 and p-methyl benzene sulfonic acid  with 55% yield. By turning 1,3,5-benzenetricarboxaldehyde into its trioxime, it was protected to decrease the cross\|linked reaction with compound 1 both including many groups.    The reaction of compound 1 with 1,3,5-benzenetricarboxaldehyde trioxime and pentaerythritol afforded 1,3,5-tri{3-[2,4,8,10 -tetra-oxa-9(3,5-di(2,6-dioxa-4,4-dihydroxymethylcyclohexyl) phenyl\]spiro[5.5]undecyl}benzene (2) by using I2 as the catalyst, and the yield was 25.2%.  Product 2 and its intermediates were identified by IR, 1 H NMR, MS spectra and elemental analysis.

Key words: Mesitylene; 1,3,5-Benzenetricarboxaldehyde; Pentaerythritol; Dendrimer

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