6-(oxazol-4-yl)-2H-pyran-2-one | 1449232-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 6-(oxazol-4-yl)-2H-pyran-2-one
• 英文别名: 6-(1,3-Oxazol-4-yl)pyran-2-one
• CAS: 1449232-83-0
• 化学式: C₈H₅NO₃
• 分子量: 163.133
• InChiKey: MEAYCOWZSXLOAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 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：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(oxazol-4-yl)-2H-pyran-2-one 、 三氯化硼 、 (苯乙炔基)三氟硼酸钾 以 二氯甲烷 为溶剂， 反应 72.0h， 以55%的产率得到4-(2-(dichloroboryl)-[1,1'-biphenyl]-3-yl)oxazole
  参考文献：
  名称：

  A Mechanistic Study of the Lewis Base-Directed Cycloaddition of 2-Pyrones and Alkynylboranes

  摘要：

  Significant rate enhancements in the Diels-Alder reaction of alkynes and 2-pyrones bearing a Lewis basic group are observed when a combination of alkynyltrifluoroborates and BF3·OEt2 is used. This process generates functionalized aromatic compounds with complete regiocontrol. The observed rate enhancement was studied by density functional theory methods and appears to originate from coordination of the diene substrate to a mixture of alkynylborane intermediates, followed by a Lewis acid-mediated product equilibration step. Evidence for this mechanism is presented, as is the enhanced promotion of the cycloaddition via the use of alternative Lewis acid promoters.

  DOI：

  10.1021/ja501805r
• 作为产物：
  描述：

  2,3-丁二烯酸乙酯 、 4-噁唑甲醛 在 三环己基膦 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以61%的产率得到6-(oxazol-4-yl)-2H-pyran-2-one
  参考文献：
  名称：

  A Mechanistic Study of the Lewis Base-Directed Cycloaddition of 2-Pyrones and Alkynylboranes

  摘要：

  Significant rate enhancements in the Diels-Alder reaction of alkynes and 2-pyrones bearing a Lewis basic group are observed when a combination of alkynyltrifluoroborates and BF3·OEt2 is used. This process generates functionalized aromatic compounds with complete regiocontrol. The observed rate enhancement was studied by density functional theory methods and appears to originate from coordination of the diene substrate to a mixture of alkynylborane intermediates, followed by a Lewis acid-mediated product equilibration step. Evidence for this mechanism is presented, as is the enhanced promotion of the cycloaddition via the use of alternative Lewis acid promoters.

  DOI：

  10.1021/ja501805r