4-(acetoxymethyl)-3-(p-methylphenyl)-2-methyl-5-phenylisoxazolidine | 164738-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-(acetoxymethyl)-3-(p-methylphenyl)-2-methyl-5-phenylisoxazolidine
• 英文别名: [2-Methyl-3-(4-methylphenyl)-5-phenyl-1,2-oxazolidin-4-yl]methyl acetate
• CAS: 164738-94-7
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: FJTADWUIZGJOSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 4-(acetoxymethyl)-3-(p-methylphenyl)-2-methyl-5-phenylisoxazolidine 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 以 苯 为溶剂， 150.0~170.0 ℃ 、6.59 MPa 条件下， 反应 24.0h， 以82%的产率得到5-(acetoxymethyl)-4-(p-methylphenyl)-3-methyl-6-phenyltetrahydro-1,3-oxazin-2-one
  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-methyl-4-tolylnitrone 、 乙酸桂酯 以 甲苯 为溶剂， 反应 24.0h， 以71%的产率得到4-(acetoxymethyl)-3-(p-methylphenyl)-2-methyl-5-phenylisoxazolidine
  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