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2013 , Vol. 33 >Issue 03: 517 - 522

DOI: https://doi.org/10.6023/cjoc201211005

研究论文

苯磺酸铜催化“一锅法”合成1-氨甲酸酯基烷基-2-萘酚

  • 王敏 ,
  • 宋吉磊 ,
  • 万鑫 ,
  • 杨忠勇
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  • 渤海大学化学化工与食品安全学院 锦州 121013

收稿日期: 2012-11-06

  修回日期: 2012-12-05

  网络出版日期: 2012-12-20

基金资助

辽宁省科技厅博士科研启动基金(No. 20091001)资助项目.

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Copper Benzenesulfonate-Promoted One-Pot Synthesis of 1-Carbamatoalkyl-2-naphthols

  • Wang Min ,
  • Song Jilei ,
  • Wan Xin ,
  • Yang Zhongyong
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  • College of Chemistry, Chemical Engineering and Food Safety, Bohai University, Jinzhou 121013

Received date: 2012-11-06

  Revised date: 2012-12-05

  Online published: 2012-12-20

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摘要

以2-萘酚、醛和氨基甲酸酯为原料, 苯磺酸铜为催化剂, 在加热、无溶剂条件下, 通过三组分“一锅法”合成了1-氨甲酸酯基烷基-2-萘酚衍生物. 考察了催化剂用量、反应温度和溶剂对产品收率的影响. 结果表明, 仅2 mol%苯磺酸铜就可以催化该反应的进行. 反应结束后, 催化剂重复使用4次, 催化活性无明显下降. 通过1H NMR, 13C NMR, IR,质谱和元素分析对产品结构进行表征. 提出了可能的催化作用机理.

关键词： 氨甲酸酯基烷基萘酚; 金属苯磺酸盐; 多组分反应; 无溶剂; 路易斯酸

本文引用格式

王敏 , 宋吉磊 , 万鑫 , 杨忠勇 . 苯磺酸铜催化“一锅法”合成1-氨甲酸酯基烷基-2-萘酚[J]. 有机化学, 2013 , 33(03) : 517 -522 . DOI: 10.6023/cjoc201211005

Abstract

1-Carbamatoalkyl-2-naphthol derivatives were obtained from one-pot three-component condensation of 2-naphthol, aldehydes, and carbamates catalyzed by copper benzenesulfonate under thermal solvent-free conditions. The effects of amount of catalyst, reaction temperature and solvent on the products yields were investigated. Experimental results showed that only 2 mol% copper benzenesulfoante was enough to induce the conversion. After reaction, catalyst could be recycled four times without distinct loss of catalytic activity. The structures of all products were characterized by 1H NMR, 13C NMR, IR, MS techniques and elemental analysis. A mechanism to rationalize the reaction was proposed.

Key words： carbamatoalkyl naphthols; metal benzenesulfonate; multicomponent reactions; solvent-free condition; Lewis acids

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