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2019 , Vol. 39 >Issue 12: 3550 - 3559

DOI: https://doi.org/10.6023/cjoc201905009

研究简报

阳离子铝化合物催化合成2,8-二氧杂双环[3.3.1]壬烷

  • 杨敏荣 ,
  • 朱亚楠 ,
  • 徐凡
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  • 苏州大学材料与化学化工学部 苏州 215123

收稿日期: 2019-05-06

  修回日期: 2019-07-21

  网络出版日期: 2019-08-07

基金资助

国家自然科学基金（No.21272168）和江苏省高等学校自然科学研究（No.18KJA150007）资助项目.

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Cationic Aluminum Complex Catalyzed Synthesis of 2,8-Dioxabicyclo[3.3.1]nonanes

  • Yang Minrong ,
  • Zhu Ya'nan ,
  • Xu Fan
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  • College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received date: 2019-05-06

  Revised date: 2019-07-21

  Online published: 2019-08-07

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272168) and the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 18KJA150007).

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摘要

2，8-二氧杂双环[3.3.1]壬烷结构单元存在于多种天然生物活性物质中.阳离子铝化合物[AlCl（CH3CN）5]2+-[（AlCl4）2]2-·CH3CN可方便地由AlCl3在CH3CN中室温反应得到.其可有效催化2-羟基查尔酮和萘酚的傅克烷基化/缩酮化反应，生成二芳基稠合2，8-二氧杂双环[3.3.1]壬烷，产率中等到高.该方法所用催化剂价廉、易得，转化效率较高，为合成2，8-二氧杂双环[3.3.1]壬烷化合物提供了一种实用的新方法.

关键词： 阳离子铝化合物; 路易斯酸; 催化; 2,8-二氧杂双环[3.3.1]壬烷; 合成

本文引用格式

杨敏荣 , 朱亚楠 , 徐凡 . 阳离子铝化合物催化合成2,8-二氧杂双环[3.3.1]壬烷[J]. 有机化学, 2019 , 39(12) : 3550 -3559 . DOI: 10.6023/cjoc201905009

Abstract

2,8-Dioxabicyclo[3.3.1]nonane exists in many natural biologically active materials. Cationic aluminum complex[AlCl(CH3CN)5]2+[(AlCl4)2]2-·CH3CN can be easily prepared via the reaction of AlCl3 with CH3CN at room temperature. It served as efficient catalyst for the tandem Friedel-Crafts alkylation/ketalization reaction of 2-hydroxychalcones with naphthols to produce diaryl-fused 2,8-dioxabicyclo[3.3.1]nonanes in moderate to high yields. This method provides a practical process to afford this type of biologically important compounds in good yields using easily available and inexpensive catalyst.

Key words： cationic aluminum complex; Lewis acid; catalysis; 2,8-dioxabicyclo[3.3.1]nonane; synthesis

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