(S)-(-)-3-hydroxy-7(e)-ethyl-1-(4-methoxyphenyl)-2-oxo-1-azaspiro[3.5]nonane

• 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: (S)-(-)-3-hydroxy-7(e)-ethyl-1-(4-methoxyphenyl)-2-oxo-1-azaspiro[3.5]nonane
• 英文别名: (3S)-7-ethyl-3-hydroxy-1-(4-methoxyphenyl)-1-azaspiro[3.5]nonan-2-one
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: PSIGPVJVFGJASU-YAJUMTOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙基环己酮 在 Arthrobacter sp. lipase (ABL, MTCC 5125) 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.5h， 生成 (S)-(-)-3-hydroxy-7(e)-ethyl-1-(4-methoxyphenyl)-2-oxo-1-azaspiro[3.5]nonane 、 (R)-(+)-3-acetoxy-7(e)-ethyl-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

文献信息

• Entrapment and Kinetic Resolution of Stabilized Axial and Equatorial Conformers of Spiro-β-lactams
  作者：Naveen Anand、Bhahwal A. Shah、Munish Kapoor、Rajinder Parshad、Rattan L. Sharma、Maninder S. Hundal、Ajay P. S. Pannu、Prasad V. Bharatam、Subhash C. Taneja

  DOI：10.1021/jo200363x

  日期：2011.8.5

  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.