有机化学 ›› 2015, Vol. 35 ›› Issue (5): 1081-1089.DOI: 10.6023/cjoc201411006 上一篇    下一篇

研究论文

含联苯醚结构2(5H)-呋喃酮衍生物的合成

关丽涛a, 莫广珍b,a, 吴彦城b, 梁欣榆b, 罗俏芳b, 汪朝阳b   

  1. a 华南农业大学材料与能源学院 广州 510642;
    b 华南师范大学化学与环境学院 教育部环境理论化学重点实验室 广州 510006
  • 收稿日期:2014-11-05 修回日期:2014-12-09 出版日期:2015-05-25 发布日期:2014-01-05
  • 通讯作者: 关丽涛, 汪朝阳 E-mail:ltguan@scau.edu.cn;wangzy@scnu.edu.cn
  • 基金资助:

    国家自然科学基金(No.31200439)、广东省高等学校人才引进专项资金(No.粤财教[2011]431号)、广东省自然科学基金(No.2014A030313429)资助项目.

Synthesis of 2(5H)-Furanone Derivatives with Biphenyl Ether Unit

Guan Litaoa, Mo Guangzhenb,a, Wu Yanchengb, Liang Xinyub, Luo Qiaofangb, Wang Zhaoyangb   

  1. a College of Materials and Energy, South China Agricultural University, Guangzhou 510642;
    b School of Chemistry and Environment, South China Normal University; Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006
  • Received:2014-11-05 Revised:2014-12-09 Online:2015-05-25 Published:2014-01-05
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.31200439), the 3rd Talents Special Funds of Guangdong Higher Education (No.Guangdong-Finance-Education [2011]431) and the Natural Science Foundation of Guangdong Province (No.2014A030313429).

以硫酸为催化剂, 不同4'-烷氧基-4-羟基联苯与粘卤酸在甲苯溶剂中回流, 经脱水醚化反应合成了16个新型的5-(4'-烷氧基-4-联苯氧基)-3,4-二卤-2(5H)-呋喃酮化合物, 产率30%~58%(大部分47%以上). 中等产率可能与该酸催化的反应为SN2亲核取代反应有关. 新化合物的结构经FTIR, UV, 1H NMR, 13C NMR和元素分析确证. 这些具有不同生物活性基团化合物的设计与合成, 为新型2(5H)-呋喃酮衍生物的合成, 以及由不同羟基化合物合成芳香醚类化合物提供了参考.

关键词: 2(5H)-呋喃酮, 联苯结构, 合成, 芳香醚, 脱水醚化, SN2反应机理

Sixteen 5-(4'-alkoxybiphenyl-4-yloxy)-3,4-dihalo-2(5H)-furanones are synthesized via the direct dehydrative etherification reactions of 4'-alkoxybiphenyl-4-ol with mucochloric acid and mucobromic acid, respectively, using sulfuric acid as catalyst at reflux in toluene from 30% to 58% yields (mostly over 47%). The moderate yields may be due to that this acid-catalyzed etherification should be a SN2 nucleophilic substitution reaction. The structures of all newly synthesized compounds are elucidated and confirmed by FTIR, UV, 1H NMR, 13C NMR, and elemental analysis. The synthetic procedures afford not only an important strategy for the synthesis of 2(5H)-furanone derivatives having potential bioactivity, but also a simple method for the synthesis of aromatic ether from two different hydroxyl compounds.

Key words: 2(5H)-furanone, biphenyl structure, synthesis, aromatic ether, dehydrative etherification, SN2 reaction mechanism