hydroxy(5-oxocyclopent-1-enyl)phenylacetic acid methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: hydroxy(5-oxocyclopent-1-enyl)phenylacetic acid methyl ester
• 英文别名: Methyl 2-hydroxy-2-(5-oxocyclopenten-1-yl)-2-phenylacetate；methyl 2-hydroxy-2-(5-oxocyclopenten-1-yl)-2-phenylacetate
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: UZEVONROUMIBKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酰甲酸甲酯 、 2-环戊烯酮 在 二苯基甲氧基膦 作用下， 反应 72.0h， 以68%的产率得到hydroxy(5-oxocyclopent-1-enyl)phenylacetic acid methyl ester
  参考文献：
  名称：

  Organocatalysts of tertiary-phosphines and amines catalyzed reactions of α-keto esters with cyclopent-2-enone

  摘要：

  The reaction of g.-keto esters with cyclopent-2-enone catalyzed by tertiary-phosphines provides the corresponding Baylis-Hillman adducts. Among the catalysts, diphenylmethylphosphine was found to be the most effective promoter allowing the reaction to proceed smoothly at room temperature and to give the corresponding adducts in higher yields in the presence of p-nitrophenol. Whereas, the similar reaction of a-keto esters with cyclopent-2-enone catalyzed by tertiary-amine of DBU furnishes the corresponding aldol adducts with syn-configuration exclusively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.067

文献信息

• Organocatalysts of tertiary-phosphines and amines catalyzed reactions of α-keto esters with cyclopent-2-enone
  作者：Min Shi、Wen Zhang

  DOI：10.1016/j.tet.2005.09.067

  日期：2005.12

  The reaction of g.-keto esters with cyclopent-2-enone catalyzed by tertiary-phosphines provides the corresponding Baylis-Hillman adducts. Among the catalysts, diphenylmethylphosphine was found to be the most effective promoter allowing the reaction to proceed smoothly at room temperature and to give the corresponding adducts in higher yields in the presence of p-nitrophenol. Whereas, the similar reaction of a-keto esters with cyclopent-2-enone catalyzed by tertiary-amine of DBU furnishes the corresponding aldol adducts with syn-configuration exclusively. (c) 2005 Elsevier Ltd. All rights reserved.