N,2-dimethylpropan-1-imine oxide | 103558-96-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N,2-dimethylpropan-1-imine oxide
• CAS: 103558-96-9；103558-97-0；74530-99-7
• 化学式: C₅H₁₁NO
• 分子量: 101.148
• InChiKey: MLDHBTHLFCHRAA-GQCTYLIASA-N

物化性质

• 沸点：
  229.3±7.0 °C(Predicted)
• 密度：
  0.839±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  N,2-dimethylpropan-1-imine oxide 在 iridium(III) chloride 、 一氧化碳 、 4 Angstroem MS 作用下， 以 甲苯 、 苯 为溶剂， 25.0~170.0 ℃ 、6.59 MPa 条件下， 反应 36.0h， 生成 5-(ethoxycarbonyl)-6,6-dimethyl-4-isopropyltetrahydro-1,3-oxazine
  参考文献：
  名称：

  Selective Rhodium-Catalyzed Insertion of Carbon Monoxide into the Nitrogen-Oxygen Bond of Isoxazolidines. New Reduction, Migration, and Rearrangement Reactions Catalyzed by Iridium Complexes

  摘要：

  Reaction of isoxazolidines with carbon monoxide in benzene, catalyzed by the dimer of chloro(1,5-cyclooctadiene)rhodium, results in the formation of tetrahydro-1,3-oxazin-2-ones as the major or only product, often in fine yields. A novel conversion of 3-arylisoxazolidines to tetrahydro-1,3-oxazines occurs using an iridium catalyst (i.e. IrCl3 . 3H(2)O,Ir(CO)(3)Cl) and carbon monoxide. This remarkable reaction was shown to proceed by an intermolecular hydrogen transfer process. In some cases, an isomeric tetrahydro-1,3-oxazine, resulting from methyl migration from nitrogen to the carbon atom arising from carbon monoxide insertion, was isolated as a byproduct in the reaction. Isoxazolidines containing an alkyl group at the 3-position undergo a novel iridium-catalyzed rearrangement and ring expansion reaction. This transformation also occurred, albeit in lower yield, by treatment of 3-alkylisoxazolidines with hydrochloric acid in p-xylene.

  DOI：

  10.1021/jo00130a013
• 作为产物：
  描述：

  N-甲基羟胺盐酸盐 、 异丁醛 在 氢氧化钾 作用下， 以 苯 为溶剂， 生成 N,2-dimethylpropan-1-imine oxide
  参考文献：
  名称：

  Selective Rhodium-Catalyzed Insertion of Carbon Monoxide into the Nitrogen-Oxygen Bond of Isoxazolidines. New Reduction, Migration, and Rearrangement Reactions Catalyzed by Iridium Complexes

  摘要：

  Reaction of isoxazolidines with carbon monoxide in benzene, catalyzed by the dimer of chloro(1,5-cyclooctadiene)rhodium, results in the formation of tetrahydro-1,3-oxazin-2-ones as the major or only product, often in fine yields. A novel conversion of 3-arylisoxazolidines to tetrahydro-1,3-oxazines occurs using an iridium catalyst (i.e. IrCl3 . 3H(2)O,Ir(CO)(3)Cl) and carbon monoxide. This remarkable reaction was shown to proceed by an intermolecular hydrogen transfer process. In some cases, an isomeric tetrahydro-1,3-oxazine, resulting from methyl migration from nitrogen to the carbon atom arising from carbon monoxide insertion, was isolated as a byproduct in the reaction. Isoxazolidines containing an alkyl group at the 3-position undergo a novel iridium-catalyzed rearrangement and ring expansion reaction. This transformation also occurred, albeit in lower yield, by treatment of 3-alkylisoxazolidines with hydrochloric acid in p-xylene.

  DOI：

  10.1021/jo00130a013

文献信息

• Selective Rhodium-Catalyzed Insertion of Carbon Monoxide into the Nitrogen-Oxygen Bond of Isoxazolidines. New Reduction, Migration, and Rearrangement Reactions Catalyzed by Iridium Complexes
  作者：Kanjai Khumtaveeporn、Howard Alper

  DOI：10.1021/jo00130a013

  日期：1995.12

  Reaction of isoxazolidines with carbon monoxide in benzene, catalyzed by the dimer of chloro(1,5-cyclooctadiene)rhodium, results in the formation of tetrahydro-1,3-oxazin-2-ones as the major or only product, often in fine yields. A novel conversion of 3-arylisoxazolidines to tetrahydro-1,3-oxazines occurs using an iridium catalyst (i.e. IrCl3 . 3H(2)O,Ir(CO)(3)Cl) and carbon monoxide. This remarkable reaction was shown to proceed by an intermolecular hydrogen transfer process. In some cases, an isomeric tetrahydro-1,3-oxazine, resulting from methyl migration from nitrogen to the carbon atom arising from carbon monoxide insertion, was isolated as a byproduct in the reaction. Isoxazolidines containing an alkyl group at the 3-position undergo a novel iridium-catalyzed rearrangement and ring expansion reaction. This transformation also occurred, albeit in lower yield, by treatment of 3-alkylisoxazolidines with hydrochloric acid in p-xylene.