(E)-benzaldehyde O-(1-(13)C,2-(13)C-1,3-diphenylprop-2-yn-1-yl)oxime | 1311378-61-6

• 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)-benzaldehyde O-(1-(13)C,2-(13)C-1,3-diphenylprop-2-yn-1-yl)oxime
• 英文别名: benzaldehyde O-(1,3-diphenylprop-2-yn-1-yl)oxime
• CAS: 1311378-61-6
• 化学式: C₂₂H₁₇NO
• 分子量: 313.361
• InChiKey: FFJIZBOFENXSED-ONCYQLLLSA-N

反应信息

• 作为反应物：
  描述：

  (E)-benzaldehyde O-(1-(13)C,2-(13)C-1,3-diphenylprop-2-yn-1-yl)oxime 在 copper(I) bromide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到(E)-2-(13)C,3-(13C)-3-benzylidene-2,4-diphenyl-2,3-dihydroazete 1-oxide
  参考文献：
  名称：

  Regioselective Transformation of O-Propargylic Arylaldoximes to Four-Membered Cyclic Nitrones by Copper-Catalyzed Skeletal Rearrangement

  摘要：

  （E）-O-亲核-丙烯基 arylation 酰胺在铜催化剂的作用下进行定向选择性转化，生成相应的四元环 nitroso 中间体。该反应通过 N- allenyl nitroso 间体的 [2,3]-重排和 4π 电环化过程完成，涉及碳氧键的断裂。在较好的收率下得到了四元环的硝基氧化物。

  DOI：

  10.1021/ol2012583

文献信息

• Copper-Catalyzed Skeletal Rearrangement of O-Propargylic Aryloximes into Four-Membered Cyclic Nitrones - Chirality Transfer and Mechanistic Insight
  作者：Itaru Nakamura、Yu Kudo、Toshiharu Araki、Dong Zhang、Eunsang Kwon、Masahiro Terada

  DOI：10.1055/s-0031-1290819

  日期：2012.5

  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.