(3E)-1-oxido-2,4-diphenyl-3-[[4-(trifluoromethyl)phenyl]methylidene]-2H-azet-1-ium | 1388624-72-3

• 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: (3E)-1-oxido-2,4-diphenyl-3-[[4-(trifluoromethyl)phenyl]methylidene]-2H-azet-1-ium
• CAS: 1388624-72-3
• 化学式: C₂₃H₁₆F₃NO
• 分子量: 379.381
• InChiKey: FLCJPHNQVDDRDW-HMMYKYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-4-(trifluoromethyl)benzaldehyde O-1,3-diphenylprop-2-ynyl oxime 以 乙腈 为溶剂， 反应 110.0h， 生成 (3E)-1-oxido-2,4-diphenyl-3-[[4-(trifluoromethyl)phenyl]methylidene]-2H-azet-1-ium 、 (Z)-3-benzylidene-4-phenyl-2-[4-(trifluoromethyl)phenyl]-2,3-dihydroazete 1-oxide 、 (E)-3-benzylidene-4-phenyl-2-[4-(trifluoromethyl)phenyl]-2,3-dihydroazete 1-oxide
  参考文献：
  名称：

  Copper-Catalyzed Skeletal Rearrangement of O-Propargylic Aryloximes into Four-Membered Cyclic Nitrones - Chirality Transfer and Mechanistic Insight

  摘要：

  Copper-catalyzed skeletal rearrangement of O-propargylic aryloximes (E)-1 were carried out to afford the corresponding four-membered cyclic nitrones 2 in good to excellent yields. The optimal reactions conditions of the highly regioselective reactions involved the use of [CuCl(cod)](2) in acetonitrile at 70 degrees C. In the case of (Z)-1, however, the reaction proceeded in the absence of the copper catalysts to afford the identical compound 2 in good yields. Furthermore, the reactions were also carried out using chiral substrates (R)-1 in the presence of Cu catalysts to afford (R)-2 with good levels of chirality transfer.

  DOI：

  10.1055/s-0031-1290819