(4E)-4-benzylidene-1-(4-methylphenyl)-3-phenylazetidin-2-one | 1388624-60-9

• 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: (4E)-4-benzylidene-1-(4-methylphenyl)-3-phenylazetidin-2-one
• 英文别名: (3E)-3-benzylidene-4-(4-methylphenyl)-1-oxido-2-phenyl-2H-azet-1-ium
• CAS: 1388624-60-9
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: JGMJAPGMIUFLHG-LTGZKZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-phenyl-3-(p-tolyl)prop-2-yn-1-ol 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 、 copper(I) bromide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 32.0h， 生成 (4E)-4-benzylidene-1-(4-methylphenyl)-3-phenylazetidin-2-one
  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

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.