(1E,2Z)-cinnamaldehyde O-(1,3-diphenylprop-2-yn-1-yl)oxime | 1228682-55-0

• 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: (1E,2Z)-cinnamaldehyde O-(1,3-diphenylprop-2-yn-1-yl)oxime
• 英文别名: (1Z,2E)-cinnamaldehyde O-(1,3-diphenylprop-2-yn-1-yl) oxime；(Z,E)-N-(1,3-diphenylprop-2-ynoxy)-3-phenylprop-2-en-1-imine
• CAS: 1228682-55-0
• 化学式: C₂₄H₁₉NO
• 分子量: 337.421
• InChiKey: ZMLIIPHVVXAYKR-GFDOFWDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1E,2Z)-cinnamaldehyde O-(1,3-diphenylprop-2-yn-1-yl)oxime 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以58%的产率得到3-benzyl-2,6-diphenylpyridine N-oxide
  参考文献：
  名称：

  Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides

  摘要：

  (Z)-Propargylic oxime ethers derived from alpha,beta-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4 pi electrocyclization, and ring expansion. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.107
• 作为产物：
  描述：

  2-(1,3-diphenylprop-2-ynyloxy)isoindoline-1,3-dione 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1E,2Z)-cinnamaldehyde O-(1,3-diphenylprop-2-yn-1-yl)oxime 、 (1E)-cinnamaldehyde O-(1,3-diphenylprop-2-yn-1-yl) oxime
  参考文献：
  名称：

  Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides

  摘要：

  (Z)-Propargylic oxime ethers derived from alpha,beta-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4 pi electrocyclization, and ring expansion. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.107

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.
• Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides
  作者：Itaru Nakamura、Dong Zhang、Masahiro Terada

  DOI：10.1016/j.tetlet.2011.09.107

  日期：2011.11

  (Z)-Propargylic oxime ethers derived from alpha,beta-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4 pi electrocyclization, and ring expansion. (C) 2011 Elsevier Ltd. All rights reserved.