(R,E)-4-(rrifluoromethyl)benzaldehyde O-[1-phenylhex-2-yn-1-yl]oxime | 1388624-52-9

• 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: (R,E)-4-(rrifluoromethyl)benzaldehyde O-[1-phenylhex-2-yn-1-yl]oxime
• CAS: 1388624-52-9
• 化学式: C₂₀H₁₈F₃NO
• 分子量: 345.364
• InChiKey: VMEDYEOCRKNKQZ-WWJLXRQJSA-N

反应信息

• 作为反应物：
  描述：

  (R,E)-4-(rrifluoromethyl)benzaldehyde O-[1-phenylhex-2-yn-1-yl]oxime 在 [CuCl(cod)]2 作用下， 以 乙腈 为溶剂， 反应 36.0h， 生成 (Z)-3-benzylidene-4-propyl-2-(4-(trifluoromethyl)phenyl)-2,3-dihydroazete 1-oxide 、 (E)-3-benzylidene-4-propyl-2-[4-(trifluoromethyl)phenyl]-2,3-dihydroazete 1-oxide 、 (E)-3-benzylidene-4-propyl-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
• 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-(rrifluoromethyl)benzaldehyde O-[1-phenylhex-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