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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (01): 116-119. 上一篇    下一篇

研究简报

聚缩醛螺胞二醚的合成及结构表征

魏荣宝*，张杰，陈苏战，梁娅   

  1. (天津理工大学生化学院 天津 300191)
  • 收稿日期:2004-01-05 修回日期:2004-07-20 发布日期:2004-12-30
  • 通讯作者: 魏荣宝

Synthesis and Structure Characterization of Poly-acetal-spiro-vic-diether

WEI Rong-Bao*,ZHANG Jie,CHEN Su-Zhan,LIANG Ya   

  1. (Department of Biotechnology and Chemical Engineering, Tianjin University of Technology, Tianji 300191, China)
  • Received:2004-01-05 Revised:2004-07-20 Published:2004-12-30
  • Contact: WEI Rong-Bao

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在I2催化剂的作用下, 利用苯甲醛与季戊四醇反应, 制备了聚缩醛螺胞二醚的模型化合物3,9-二苯基-2,4,8,10-四氧杂螺[5.5]十一烷(1). 在此基础上, 利用1,3-苯二甲醛与不同摩尔比的季戊四醇合成了化合物1,3-二(2,6-二氧杂-4,4-二羟甲基环己基)苯(2)和2,4,8,10-四氧杂-3,9-二(3'-甲酰基苯基)螺[5.5]十一烷(3). 化合物2与化合物3反应, 制成标题化合物聚缩醛螺胞二醚4, 收率为95.4%. 用FTIR, 1H NMR对化合物1～4的结构进行了表征. 发现在含有手性轴化合物1, 3, 4的1H NMR谱中, 4个亚甲基中的8个氢原子裂分为4组双峰, 而不含有手性轴化合物中的4个亚甲基中的8个氢原子不裂分, 是个单峰. 这种不同不是由于化合物中刚性环所致, 而是由于有无手性轴造成的.

关键词: 3,9-二苯基-2,4,8,10-四氧杂螺[5.5]十一烷, 1,3-苯二甲醛, 聚缩醛螺胞二醚, 季戊四醇

In the presence of I2, the model compound 3,9-diphenyl-2,4,8,10-tetraoxa-spiro[5.5]undecane (1) was prepared by the reaction of benzaldehyde with pentaerythritol. The reaction of 1,3-benzodialdehyde with different equivalent of pentaerythritol afforded 1,3-di(2,6-dioxa-4,4-dihydroxymethyl-cyclohexyl)- benzene (2) and 2,4,8,10-tetraoxa-3,9-di(3'-formylphenyl)spiro[5.5]undecane (3), respectively. The title compound poly-acetal-spiro-vic-diether (4) was synthesized in 95.4% yield by the reaction of 2 with 3. The structures of compounds 1, 3 and 4 were characterized by FTIR and 1H NMR. In the 1H NMR spectra, the signals of eight hydrogen atoms of methylene groups in chiral axis-containing compounds 1, 3 and 4 were split into four groups of the doublets, but the corresponding signal of the hydrogen atoms was a single peak in compounds 5 and 6 un-containing chiral axis. This difference was not due to the presence of rigid cycle but the presence of chiral axis.

Key words: 1,3-benzodialdehyde, pentaerythritol, poly- acetal-spiro-vic-diether, 3,9-diphenyl-2,4,8,10-tetraoxa-spiro[5.5]undecane