(E)-3-benzylidene-4-(4-methoxyphenyl)-2-(naphthalene-2-yl)-2,3-dihydroazete 1-oxide | 1311378-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-3-benzylidene-4-(4-methoxyphenyl)-2-(naphthalene-2-yl)-2,3-dihydroazete 1-oxide
• 英文别名: (3E)-3-benzylidene-4-(4-methoxyphenyl)-2-naphthalen-2-yl-1-oxido-2H-azet-1-ium
• CAS: 1311378-57-0
• 化学式: C₂₇H₂₁NO₂
• 分子量: 391.469
• InChiKey: SJEPPGBVPPPVDK-UQQQWYQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-甲氧基苯基)-3-苯基-1-丙炔-3-醇 在 [CuCl(cod)]2 、 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 21.0h， 生成 (E)-3-benzylidene-4-(4-methoxyphenyl)-2-(naphthalene-2-yl)-2,3-dihydroazete 1-oxide 、 (Z)-3-benzylidene-4-(4-methoxyphenyl)-2-(naphthalene-2-yl)-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

文献信息

• Regioselective Transformation of <i>O</i>-Propargylic Arylaldoximes to Four-Membered Cyclic Nitrones by Copper-Catalyzed Skeletal Rearrangement
  作者：Itaru Nakamura、Toshiharu Araki、Dong Zhang、Yu Kudo、Eunsang Kwon、Masahiro Terada

  DOI：10.1021/ol2012583

  日期：2011.7.15

  (E)-O-Propargylic arylaldoximes were regioselectively converted, In the presence of copper catalysts, into their corresponding four-membered cyclic nitrones In good to excellent yields. The reactions proceeded via a tandem [2,3]-rearrangement and 4 pi-electrocyclization of the N-allenylnitrone intermediate and involved cleavage of the carbon-oxygen bond.

  （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。
• 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.