5-benzoyl-4,4-dimethyl-2-phenyl-4H-pyran-3-carbonitrile | 1253802-02-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-benzoyl-4,4-dimethyl-2-phenyl-4H-pyran-3-carbonitrile
• CAS: 1253802-02-6
• 化学式: C₂₁H₁₇NO₂
• 分子量: 315.371
• InChiKey: BJWZWIMCKHMPNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,2-dimethyl-1-cyano-1-benzoylethene 、 1-苯基-2-丙炔-1-酮 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以39%的产率得到5-benzoyl-4,4-dimethyl-2-phenyl-4H-pyran-3-carbonitrile
  参考文献：
  名称：

  Facile synthesis of highly functionalized six-membered heterocycles via PPh3-catalyzed [4+2] annulations of activated terminal alkynes and hetero-dienes: scope, mechanism, and application

  摘要：

  A novel [4+2] annulation between activated terminal alkynes and aza-dienes or oxo-dienes has been developed with the use of triphenylphosphine catalyst (20 mol %), which provides a facile method for synthesis of the corresponding highly functionalized dihydropyridines or dihydropyrans in good to excellent yields. The reaction mechanism has also been established, consisting formal hetero-Diels-Alder reaction catalyzed by PPh3 and [1,3]-proton transfer, which exhibits a large isotopic effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.043