天然产物研究与开发 ›› 2017, Vol. 29 ›› Issue (9): 1573-1579.doi: 10.16333/j.1001-6880.2017.9.021

• 开发研究 • 上一篇    下一篇

碱催化合成4-甲基-2′-羟基-4′-甲氧基查尔酮及其晶体结构

刘存芳*,王俊宏,邵先钊,吴睿   

  1. 陕西理工大学 陕西省催化基础与应用重点实验室,汉中 723000
  • 出版日期:2017-09-27 发布日期:2017-09-27
  • 基金资助:

    陕西省科技厅社会发展科技攻关项目(2015SF270);陕西省教育厅服务地方专项项目(15JF013)

Alkali-catalyzed Synthesis of 4-Methyl-2′-hydroxyl-4′-methoxychalcone and Its Crystal Structure

LIU Cun-fang*, WANG Jun-hong, SHAO Xian-zhao, WU Rui   

  1. Shaanxi Key Laboratory for Catalysis, Shaanxi University of Technology, Hanzhong 723000, China
  • Online:2017-09-27 Published:2017-09-27

摘要: 探讨超声波辅助下用碱催化合成查尔酮的方法。常温超声波辅助下用碱催化使丹皮酚和4-甲基苯甲醛发生克莱森-斯密特反应,生成一种含有1,3-二苯基丙烯酮结构的丹皮酚衍生物:4-甲基-2′-羟基-4′-甲氧基查尔酮,产率高达71.57%,经过现代光谱学技术紫外、红外、质谱并结合核磁的氢谱、碳谱以及135°DEPT 谱表征其结构。用X射线衍射技术分析该丹皮酚衍生物的单晶结构并确定其分子的构型和构象,4-甲基-2′-羟基-4′-甲氧基查尔酮属于单斜晶系中的P2(1)/n空点群,晶胞参数:a=1.1288(10) nm、b=0.6916(6) nm、c=2.0509(4) nm、α=90.0(8)°、β =109.8(8)°、γ=90(8) °,晶胞体积V 为1.4056 (5) nm3,密度Dc为1.272 mg/cm3。在超声波辅助下用碱催化可使丹皮酚和4-甲基苯甲醛通过克莱森-斯密特反应来合成含有1,3-二苯基丙烯酮结构的丹皮酚衍生物。

关键词: 丹皮酚, 合成, 克莱森-斯密特反应, 查尔酮, 晶体结构

Abstract: The synthesis method of chalcone was investigated under the assistance of ultrasonic irradiation with alkali as the catalyst.A novel paeonol derivative named 4-methyl-2′-hydroxyl-4′-methoxychalcone was synthesized in alkaline medium under the assistance of ultrasonic irradiation,the reaction of paeonol and 4-methylbenzaldehyde was by Claisen-Schmidt condensation reaction at room temperature,its yield reached 71.57%,its structure existing 1,3-diphenyl acrylic ketone was characterized by UV,IR,MS,1H NMR, 13C NMR and 135° DEPT.The crystal structure of 4-methyl-2′-hydroxyl-4′-methoxychalcone was also characterized by Xray structure analysis,its crystal belonged to space group P2(1)/n in triclinic crystallographic system,and its cell parameters: a=1.1288(10) nm, b=0.6916(6)nm, c=2.0509(4) nm, α=90.0(8)°, β =109.8(8)°, γ=90(8) °,V=1.4056 (5) nm3, Dc=1.272 mg/cm3.The novel paeonol derivative existing 1,3-diphenyl acrylic ketone in the molecular structure was synthesized through the reaction of paeonol and 4-methylbenzaldehyde under the assistance of ultrasonic irradiation with alkali as the catalyst.

Key words: paeonol, synthesis, Claisen-Schmidt condensation reaction, chalcone, crystal structure

中图分类号: 

O625.42