(+/-)-3-acetoxy-1-(4-methoxyphenyl)-2-oxo-1-azaspiro[3.5]nonane | 1313597-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (+/-)-3-acetoxy-1-(4-methoxyphenyl)-2-oxo-1-azaspiro[3.5]nonane
• 英文别名: [1-(4-Methoxyphenyl)-2-oxo-1-azaspiro[3.5]nonan-3-yl] acetate
• CAS: 1313597-25-9
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: ZUEWJMWNCOUDOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-3-acetoxy-1-(4-methoxyphenyl)-2-oxo-1-azaspiro[3.5]nonane 在 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到(+/-)-3-hydroxy-1-(4-methoxyphenyl)-2-oxo-1-azaspiro[3.5]-nonane
  参考文献：
  名称：

  Entrapment and Kinetic Resolution of Stabilized Axial and Equatorial Conformers of Spiro-β-lactams

  摘要：

  The facile synthesis of the stabilized axial and equatorial conformers of spiro-beta-lactams was achieved via entrapment of cyclohexanone imines (Schiff bases) with acetoxyacetyl chloride in a [2 + 2] -cycloaddition reaction followed by their kinetic resolution. The immobilization of the racemic substrates on an inert solid support significantly reduced the reaction time and improved the enantioselectivity of conformers during kinetic resolution. The mechanism of the formation of the spiro-beta-lactams was explored using B3LYP/6-31+G* level quantum chemical calculations.

  DOI：

  10.1021/jo200363x
• 作为产物：
  描述：

  N-(4-methoxyphenyl)cyclohexanimine 、 乙酰氧基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以5.2 g的产率得到(+/-)-3-acetoxy-1-(4-methoxyphenyl)-2-oxo-1-azaspiro[3.5]nonane
  参考文献：
  名称：

  Entrapment and Kinetic Resolution of Stabilized Axial and Equatorial Conformers of Spiro-β-lactams

  摘要：

  The facile synthesis of the stabilized axial and equatorial conformers of spiro-beta-lactams was achieved via entrapment of cyclohexanone imines (Schiff bases) with acetoxyacetyl chloride in a [2 + 2] -cycloaddition reaction followed by their kinetic resolution. The immobilization of the racemic substrates on an inert solid support significantly reduced the reaction time and improved the enantioselectivity of conformers during kinetic resolution. The mechanism of the formation of the spiro-beta-lactams was explored using B3LYP/6-31+G* level quantum chemical calculations.

  DOI：

  10.1021/jo200363x