6-(2-oxo-2H-pyran-6-yl)benzonitrile

• 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: 6-(2-oxo-2H-pyran-6-yl)benzonitrile
• 英文别名: 4-(6-Oxopyran-2-yl)benzonitrile
• 化学式: C₁₂H₇NO₂
• 分子量: 197.193
• InChiKey: ALJQLQCDVFMDBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-丁二烯酸乙酯 、 4-氰基苯甲醛 在 三环戊基膦 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以79%的产率得到6-(2-oxo-2H-pyran-6-yl)benzonitrile
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of 6-Substituted 2-Pyrones:  Manifestation of E/Z-Isomerism in the Zwitterionic Intermediate

  摘要：

  We report a one-step phosphine-catalyzed annulation between aldehydes and ethyl allenoate to form 6-substituted 2-pyrones. The mechanistic rationale for this reaction requires explicit discussion of the EIZ-isomerism of the zwitterionic intermediate formed by the addition of a phosphine to the allenoate. Sterically demanding trialkylphosphines facilitate the shift of equilibrium toward the E-isomeric zwitterion and lead to the formation of 6-substituted 2-pyrones. Various aromatic as well as aliphatic aldehydes undergo the transformation in moderate to excellent yield.

  DOI：

  10.1021/ol050946j

文献信息

• Phosphine-Catalyzed Synthesis of 6-Substituted 2-Pyrones:  Manifestation of <i>E</i>/<i>Z</i>-Isomerism in the Zwitterionic Intermediate
  作者：Xue-Feng Zhu、Arnaud-Pierre Schaffner、Ronald C. Li、Ohyun Kwon

  DOI：10.1021/ol050946j

  日期：2005.7.1

  We report a one-step phosphine-catalyzed annulation between aldehydes and ethyl allenoate to form 6-substituted 2-pyrones. The mechanistic rationale for this reaction requires explicit discussion of the EIZ-isomerism of the zwitterionic intermediate formed by the addition of a phosphine to the allenoate. Sterically demanding trialkylphosphines facilitate the shift of equilibrium toward the E-isomeric zwitterion and lead to the formation of 6-substituted 2-pyrones. Various aromatic as well as aliphatic aldehydes undergo the transformation in moderate to excellent yield.