(Z)-4-(4-(trifluoromethyl)benzylidene)-3-phenylisoxazol-5(4H)-one | 1227841-39-5

• 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: (Z)-4-(4-(trifluoromethyl)benzylidene)-3-phenylisoxazol-5(4H)-one
• 英文别名: (4Z)-3-phenyl-4-[[4-(trifluoromethyl)phenyl]methylidene]-1,2-oxazol-5-one
• CAS: 1227841-39-5
• 化学式: C₁₇H₁₀F₃NO₂
• 分子量: 317.267
• InChiKey: CMJFCSCQNUAHIQ-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-4-(trifluoromethyl)benzaldehyde O-3-phenylpropioloyl oxime 在 [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 (E)-4-(4-(trifluoromethyl)benzylidene)-3-phenylisoxazol-5(4H)-one 、 (Z)-4-(4-(trifluoromethyl)benzylidene)-3-phenylisoxazol-5(4H)-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

• 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.