有机化学 ›› 2014, Vol. 34 ›› Issue (9): 1875-1880.DOI: 10.6023/cjoc201405008 上一篇    下一篇

研究简报

三步缩合法合成2-苯基-1-羟基联三苯叉

王文丽a, 何清a,b, 丁茹a, 贺云a, 张尊听a   

  1. a 陕西师范大学化学化工学院, 教育部药用资源与天然药物化学重点实验室, 西北濒危药材资源开发国家工程实验室, 西安 710062;
    b 温州大学化学与材料工程学院, 温州 325027
  • 收稿日期:2014-03-06 修回日期:2014-03-27 出版日期:2014-09-25 发布日期:2014-06-03
  • 通讯作者: 张尊听 E-mail:zhangzt@snnu.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21372150)、陕西省自然科学基础研究计划(No. 2014JQ2073)和中央高校基本科研业务费专项资金(No. GK261001095)资助项 目.

Synthesis of 1-Hydroxy-2-phenyltriphenylene Derivatives by Three-Step Condensation

Wang Wenlia, He Qinga,b, Ding Rua, He Yuna, Zhang Zuntinga   

  1. a Key Laboratory of Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062;
    b College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027
  • Received:2014-03-06 Revised:2014-03-27 Online:2014-09-25 Published:2014-06-03
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21372150), the Natural Science Foundation of Shaanxi Province (No. 2014JQ2073) and the Fundamental Research Funds for the Central Universities (No. GK261001095).

以邻羟基苯乙酮为原料,与N,N-二甲基甲酰胺-二甲基缩醛(DMF-DMA)分子间缩合合成(E)-3-二甲氨基-1-(2'-羟基苯基)-1-丙烯酮中间体(2); 中间体2与1,3-二苯基丙酮在以DMF为溶剂,K2CO3存在下发生缩合反应生成4'-苯基-2,3'-羟基-1,1':2',1''-三联苯类化合物(3); 化合物3以乙腈-1% HCl (V:V=1:1)为溶剂,汞灯500 W照射分子内脱水关环合成2-苯基-1-羟基联三苯叉类化合物(4). 三步缩合法合成2-苯基-1-羟基联三苯叉具有操作简单、无需氧化剂与催化剂、原子利用率高等优点. 采用FT-IR,1H NMR,13C NMR和HRMS对化合物3和4进行了表征.

关键词: 4'-苯基-2,3'-羟基-1,1':2',1''-三联苯, 2-苯基-1-羟基联三苯叉, 光环化反应, 缩合反应

(E)-3-(Dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-ones (2) were synthesized by the condensation reaction of o-hydroxyacetophenones (1) and N,N-dimethylformamide-dimethyl acetal (DMF-DMA). Using DMF as solvent and K2CO3 as base, 4'-phenyl-(1,1':2',1''-terphenyl)-2,3'-diol (3) were synthesized via the condensation reaction of intermediate 2 and 1,3-diphenylacetones. 3 were dissolved in the solution of acetonitrile-1% HCl (V:V=1:1) and irradiated by 500 W mercury lamp, and 1-hydroxy-2-phenyltriphenylenes were obtained. This process to synthesize 4 has the advantages of simple operation, high efficiency of the atomic, without oxidant and catalyst. Compounds 3 and 4 were confirmed by the method of FT-IR, 1H NMR, 13C NMR, HRMS.

Key words: 4'-phenyl-(1,1':2',1''-terphenyl)-2,3'-diol, 1-hydroxy-2-phenyltriphenylene, photocyclization reaction, condensation reaction