(R,E)-4-methylbenzaldehyde O-(1,3-diphenylprop-2-yn-1-yl) oxime | 1388624-56-3

• 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: (R,E)-4-methylbenzaldehyde O-(1,3-diphenylprop-2-yn-1-yl) oxime
• CAS: 1388624-56-3
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: WQTBNVOXKUEKDF-MPPWSMNASA-N

反应信息

• 作为反应物：
  描述：

  (R,E)-4-methylbenzaldehyde O-(1,3-diphenylprop-2-yn-1-yl) oxime 在 [CuCl(cod)]2 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 (Z)-3-benzylidene-4-phenyl-2-(p-tolyl)-2,3-dihydroazete 1-oxide 、 (E)-3-benzylidene-4-phenyl-2-(p-tolyl)-2,3-dihydroazete 1-oxide 、 (E)-3-benzylidene-4-phenyl-2-(p-tolyl)-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
• 作为产物：
  描述：

  在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (R,E)-4-methylbenzaldehyde O-(1,3-diphenylprop-2-yn-1-yl) oxime
  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