(Z)-butylidene(phenyl)azane oxide | 24423-92-5

• 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: (Z)-butylidene(phenyl)azane oxide
• 英文别名: N-phenylbutan-1-imine oxide
• CAS: 24423-92-5
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: GPNGHYDPRFCIHF-LUAWRHEFSA-N

物化性质

• 熔点：
  75.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  281.0±23.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  烯丙基三甲基硅烷 、 (Z)-butylidene(phenyl)azane oxide 以83%的产率得到
  参考文献：
  名称：

  HOSOMI, AKIRA;SHOJI, HIROAKI;SAKURAI, HIDEKI, CHEM. LETT., 1985, N 7, 1049-1052

  摘要：

  DOI：
• 作为产物：
  描述：

  正丁醛 、 苯基羟胺 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (Z)-butylidene(phenyl)azane oxide
  参考文献：
  名称：

  Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives

  摘要：

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.

  DOI：

  10.1021/jo00121a018

文献信息

• Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives
  作者：Masahiro Miura、Masahiro Enna、Kazumi Okuro、Masakatsu Nomura

  DOI：10.1021/jo00121a018

  日期：1995.8

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.
• HOSOMI, AKIRA;SHOJI, HIROAKI;SAKURAI, HIDEKI, CHEM. LETT., 1985, N 7, 1049-1052
  作者：HOSOMI, AKIRA、SHOJI, HIROAKI、SAKURAI, HIDEKI

  DOI：——

  日期：——