4-diphenylmethylene-3-phenylisoxazol-5-one | 36298-66-5

• 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: 4-diphenylmethylene-3-phenylisoxazol-5-one
• 英文别名: 4-(diphenylmethylene)-3-phenylisoxazol-5(4H)-one；4-benzhydrylidene-3-phenyl-4H-isoxazol-5-one；4-Benzhydrylidene-3-phenyl-1,2-oxazol-5-one
• CAS: 36298-66-5
• 化学式: C₂₂H₁₅NO₂
• 分子量: 325.367
• InChiKey: KMAMFIXHRRLMLT-UHFFFAOYSA-N

物化性质

• 沸点：
  465.6±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-diphenylmethylene-3-phenylisoxazol-5-one 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醚 为溶剂， 生成 4-(4-methoxy-trityl)-3-phenyl-2H-isoxazol-5-one
  参考文献：
  名称：

  Harhash,A.H. et al., Indian Journal of Chemistry, 1973, vol. 11, p. 1 - 3

  摘要：

  DOI：
• 作为产物：
  描述：

  benzophenone O-3-propioloyl oxime 在 [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) 作用下， 以 乙腈 为溶剂， 以87%的产率得到4-diphenylmethylene-3-phenylisoxazol-5-one
  参考文献：
  名称：

  Gold-Catalyzed Cyclization and Subsequent Arylidene Group Transfer of O-Propioloyl Oximes

  摘要：

  Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 degrees C in the presence of Au(PPh(3))NTf(2) (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.

  DOI：

  10.1021/ol100581m

文献信息

• Unprecedented Rearrangement Reaction of Nitrile Oxides and a Sterically Congested 4-Ylidene-5-isoxazolone
  作者：Francesco Foti、Giovanni Grassi、Francesco Risitano、Giuseppe Bruno、Francesco Nicolo

  DOI：10.3987/com-00-9106

  日期：——

  The reaction between nitrile oxides and 4-diphenylmethylene-3phenylisoxazol-5-one (5) proceeds in an unprecedented fashion to yield 4-diphenylmethylene-2,3,3-trisubstituted derivatives (10). Their structure was determined by an X-Ray diffraction study.
• Gold-Catalyzed Cyclization and Subsequent Arylidene Group Transfer of <i>O</i>-Propioloyl Oximes
  作者：Itaru Nakamura、Masashi Okamoto、Masahiro Terada

  DOI：10.1021/ol100581m

  日期：2010.6.4

  Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 degrees C in the presence of Au(PPh(3))NTf(2) (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.
• Harhash,A.H. et al., Indian Journal of Chemistry, 1973, vol. 11, p. 1 - 3
  作者：Harhash,A.H. et al.

  DOI：——

  日期：——