3-(2,4,5-trimethoxyphenyl)-2-cyclopenten-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2,4,5-trimethoxyphenyl)-2-cyclopenten-1-one
• 英文别名: 3-(2,4,5-Trimethoxyphenyl)cyclopent-2-en-1-one；3-(2,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: CZMPRXCCVSDBCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-环戊烯酮 、 2,4,5-三甲氧基苯甲酸 在 palladium(II) trifluoroacetate air 、 silver carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以81%的产率得到3-(2,4,5-trimethoxyphenyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  Heck-Type Arylation of 2-Cycloalken-1-ones with Arylpalladium Intermediates Formed by Decarboxylative Palladation and by Aryl Iodide Insertion

  摘要：

  A palladium-catalyzed decarboxylative arylation reaction was shown to produce Heck-type coupling products using a number of different arene carboxylic acid and 2-cycloalken-1-one substrates. The more conventional Heck coupling of an aryl iodide and a 2-cycloalken-1-one reactant was also briefly explored for comparison, where it was found that phosphine-free (Jeffery) conditions afforded the highest yield of product.

  DOI：

  10.1021/ol0363467

文献信息

• Heck-Type Arylation of 2-Cycloalken-1-ones with Arylpalladium Intermediates Formed by Decarboxylative Palladation and by Aryl Iodide Insertion
  作者：Daisuke Tanaka、Andrew G. Myers

  DOI：10.1021/ol0363467

  日期：2004.2.1

  A palladium-catalyzed decarboxylative arylation reaction was shown to produce Heck-type coupling products using a number of different arene carboxylic acid and 2-cycloalken-1-one substrates. The more conventional Heck coupling of an aryl iodide and a 2-cycloalken-1-one reactant was also briefly explored for comparison, where it was found that phosphine-free (Jeffery) conditions afforded the highest yield of product.