(E)-acrylaldehyde O-[1-phenyl-3-(4-trifluoromethyl)phenylprop-2-yn-1-yl]oxime | 1228682-80-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-acrylaldehyde O-[1-phenyl-3-(4-trifluoromethyl)phenylprop-2-yn-1-yl]oxime
• 英文别名: (E)-N-[1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-ynoxy]prop-2-en-1-imine
• CAS: 1228682-80-1
• 化学式: C₁₉H₁₄F₃NO
• 分子量: 329.321
• InChiKey: YEYOKRPXJCHROX-OEAKJJBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-acrylaldehyde O-[1-phenyl-3-(4-trifluoromethyl)phenylprop-2-yn-1-yl]oxime 在 CuBr(PPh₃)₃ 、 三苯基膦 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 以52%的产率得到3-benzyl-2-[4-(trifluoromethyl)phenyl]pyridine N-oxide
  参考文献：
  名称：

  Copper-Catalyzed Tandem [2,3]-Rearrangement and 6π-3-Azatriene Electrocyclization in (E)-O-Propargylic α,β-Unsaturated Oximes

  摘要：

  Cu-catalyzed cyclizations of (E)-O-propargylic oximes of alpha,B-unsaturated aldehydes were successfully carried out to afford the corresponding pyridine oxides in good to high yields. As an example, (E)-acrylaldehyde O-1,3-diphenylprop-2-ynyl oxime (1b) was reacted for 5 h in the presence of CuBr(PPh(3))(3) (10 mol %) and PPh(3) (10 mol %) in DMSO at 120 degrees C to afford 3-benzyl-2-phenylpyridine-N-oxide (2b) in 84% yield. In this case, the reaction proceeded via Cu-catalyzed propargyl oxime-allenyl nitrone rearrangement followed by 6 pi-3-azatriene electrocyclization.

  DOI：

  10.1021/ja102436z
• 作为产物：
  描述：

  O-(1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-yl)hydroxylamine 、 丙烯醛 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (E)-acrylaldehyde O-[1-phenyl-3-(4-trifluoromethyl)phenylprop-2-yn-1-yl]oxime
  参考文献：
  名称：

  Copper-Catalyzed Tandem [2,3]-Rearrangement and 6π-3-Azatriene Electrocyclization in (E)-O-Propargylic α,β-Unsaturated Oximes

  摘要：

  Cu-catalyzed cyclizations of (E)-O-propargylic oximes of alpha,B-unsaturated aldehydes were successfully carried out to afford the corresponding pyridine oxides in good to high yields. As an example, (E)-acrylaldehyde O-1,3-diphenylprop-2-ynyl oxime (1b) was reacted for 5 h in the presence of CuBr(PPh(3))(3) (10 mol %) and PPh(3) (10 mol %) in DMSO at 120 degrees C to afford 3-benzyl-2-phenylpyridine-N-oxide (2b) in 84% yield. In this case, the reaction proceeded via Cu-catalyzed propargyl oxime-allenyl nitrone rearrangement followed by 6 pi-3-azatriene electrocyclization.

  DOI：

  10.1021/ja102436z

文献信息

• Copper-Catalyzed Tandem [2,3]-Rearrangement and 6π-3-Azatriene Electrocyclization in (<i>E</i>)<i>-O</i>-Propargylic α,β-Unsaturated Oximes
  作者：Itaru Nakamura、Dong Zhang、Masahiro Terada

  DOI：10.1021/ja102436z

  日期：2010.6.16

  Cu-catalyzed cyclizations of (E)-O-propargylic oximes of alpha,B-unsaturated aldehydes were successfully carried out to afford the corresponding pyridine oxides in good to high yields. As an example, (E)-acrylaldehyde O-1,3-diphenylprop-2-ynyl oxime (1b) was reacted for 5 h in the presence of CuBr(PPh(3))(3) (10 mol %) and PPh(3) (10 mol %) in DMSO at 120 degrees C to afford 3-benzyl-2-phenylpyridine-N-oxide (2b) in 84% yield. In this case, the reaction proceeded via Cu-catalyzed propargyl oxime-allenyl nitrone rearrangement followed by 6 pi-3-azatriene electrocyclization.