3-benzyl-2-phenylpyridine N-oxide | 1228682-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-benzyl-2-phenylpyridine N-oxide
• 英文别名: 3-Benzyl-1-oxido-2-phenylpyridin-1-ium；3-benzyl-1-oxido-2-phenylpyridin-1-ium
• CAS: 1228682-94-7
• 化学式: C₁₈H₁₅NO
• 分子量: 261.323
• InChiKey: GFOFUDGNZHZJHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-acrylaldehyde O-(1,3-diphenylprop-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 5.0h， 以84%的产率得到3-benzyl-2-phenylpyridine 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

文献信息

• 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.
• 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.