2-formyl-5-methoxyphenyl 2-chloroacetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-formyl-5-methoxyphenyl 2-chloroacetate
• 英文别名: (2-Formyl-5-methoxyphenyl) 2-chloroacetate；(2-formyl-5-methoxyphenyl) 2-chloroacetate
• 化学式: C₁₀H₉ClO₄
• 分子量: 228.632
• InChiKey: XUSLYZXOQXETSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-formyl-5-methoxyphenyl 2-chloroacetate 以 N,N-二甲基甲酰胺 为溶剂， 以34%的产率得到7-甲氧基香豆素
  参考文献：
  名称：

  在银阴极还原取代的 2-氯乙酸苯酯：香豆素的电合成

  摘要：

  To explore the electrosynthesis of coumarins, cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the reduction of the carbon-chlorine bond of five substituted phenyl 2-chloroacetates at silver cathodes in dimethylformamide (DMF) containing 0.10 M tetra-n-butylammonium tetrafluoroborate (TBABF(4)) as supporting electrolyte; the five substrates are 2-formylphenyl 2-chloroacetate (1a), 2-acetylphenyl 2-chloroacetate (2a), methyl 2-(2-chloroacetoxy)benzoate (3a), 2-formyl-5-methoxyphenyl 2-chloroacetate (4a), and 2-formyl-3,5-dimethoxyphenyl 2-chloroacetate (5a). We have examined (a) the effects of substituents on the benzene ring of the substrate as well as the nature of the aryl carbonyl moiety on the formation of the coumarin product and (b) the effect of solvent-namely, DMF, acetonitrile (CH3CN), benzonitrile (PhCN), and propylene carbonate (PC)-and substrate concentration on the yield of the coumarin. It was found that the most unsubstituted substrate (1a) afforded the highest yield (41%) of the desired coumarin in a DMF-TBABF(4) medium. A mechanistic scheme is proposed to account for the formation of the coumarin. Furthermore, the only other products seen in these reductions are 2-substituted phenols, which are precursors for synthesis of the various substrates. (C) 2014 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.0551412jes
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 氯乙酰氯 在 potassium hydroxide 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 2-formyl-5-methoxyphenyl 2-chloroacetate
  参考文献：
  名称：

  在银阴极还原取代的 2-氯乙酸苯酯：香豆素的电合成

  摘要：

  To explore the electrosynthesis of coumarins, cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the reduction of the carbon-chlorine bond of five substituted phenyl 2-chloroacetates at silver cathodes in dimethylformamide (DMF) containing 0.10 M tetra-n-butylammonium tetrafluoroborate (TBABF(4)) as supporting electrolyte; the five substrates are 2-formylphenyl 2-chloroacetate (1a), 2-acetylphenyl 2-chloroacetate (2a), methyl 2-(2-chloroacetoxy)benzoate (3a), 2-formyl-5-methoxyphenyl 2-chloroacetate (4a), and 2-formyl-3,5-dimethoxyphenyl 2-chloroacetate (5a). We have examined (a) the effects of substituents on the benzene ring of the substrate as well as the nature of the aryl carbonyl moiety on the formation of the coumarin product and (b) the effect of solvent-namely, DMF, acetonitrile (CH3CN), benzonitrile (PhCN), and propylene carbonate (PC)-and substrate concentration on the yield of the coumarin. It was found that the most unsubstituted substrate (1a) afforded the highest yield (41%) of the desired coumarin in a DMF-TBABF(4) medium. A mechanistic scheme is proposed to account for the formation of the coumarin. Furthermore, the only other products seen in these reductions are 2-substituted phenols, which are precursors for synthesis of the various substrates. (C) 2014 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.0551412jes

文献信息

• Desai, Vidya G.; Shet, Jyoti B.; Tilve, Santosh G., Journal of Chemical Research - Part S, 2003, # 10, p. 628 - 629
  作者：Desai, Vidya G.、Shet, Jyoti B.、Tilve, Santosh G.、Mali, Raghao S.

  DOI：——

  日期：——