(-)-3-hydroxy-1-isopropyl-4,4-dimethyl-3-phenylazetidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (-)-3-hydroxy-1-isopropyl-4,4-dimethyl-3-phenylazetidin-2-one
• 英文别名: (3S)-3-hydroxy-4,4-dimethyl-3-phenyl-1-propan-2-ylazetidin-2-one
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: JPSJFSPZJNFLNV-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-diisopropyl-2-oxo-2-phenylacetamide 反应 40.0h， 生成 (-)-3-hydroxy-1-isopropyl-4,4-dimethyl-3-phenylazetidin-2-one
  参考文献：
  名称：

  通过手性结晶态的非手性氧代酰胺的光环化形成手性β-内酰胺

  摘要：

  将大量制备的非手性氧代酰胺N，N - N-二异丙基苯基乙醛酰胺的手性晶体进行固态辐照，以得到旋光性β-内酰胺3-羟基-1-异丙基-4,4-二甲基-3-苯基氮杂环丁烷-2-酮具有较高的光学和化学收率。

  DOI：

  10.1039/c39870001413

文献信息

• Toda, Fumio; Miyamoto, Hisakazu, Journal of the Chemical Society. Perkin transactions I, 1993, # 10, p. 1129 - 1132
  作者：Toda, Fumio、Miyamoto, Hisakazu

  DOI：——

  日期：——
• TODA, FUMIO;YAGI, MINORU;SODA, SHIN-ICHI, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 18, 1413-1414
  作者：TODA, FUMIO、YAGI, MINORU、SODA, SHIN-ICHI

  DOI：——

  日期：——
• Stereochemistry of Asymmetric β-Lactam Formation Involving Achiral Glyoxylamide Derivatives
  作者：D. Hashizume、H. Kogo、A. Sekine、Y. Ohashi、H. Miyamoto、F. Toda

  DOI：10.1107/s0108270194012412

  日期：1995.5.15

  The crystals of three glyoxylamide compounds, N,N-diisopropyl(o-methylphenyl)glyoxylamide, C15H21NO2, N,N-diisopropyl(p-methylphenyl)glyoxylamide, C15H21NO2 and N, N-diisopropyl(m,p-dimethylphenyl) glyoxylamide, C16H23NO2, have been analyzed by X-ray structure analysis. In each compound, the two carbonyl groups have a twisted conformation. This results in a short contact between the C atom of one of the carbonyl groups and the C atom of an isopropyl group. On exposure to visible light, a bond may form between these two C atoms and a beta-lactam with a four-membered ring is produced. These results are consistent with those observed in the related glyoxylamide containing no methyl substituents.
• Formation of a chiral β-lactam by photocyclisation of an achiral oxo amide in its chiral crystalline state
  作者：Fumio Toda、Minoru Yagi、Shin-ichi Sōda

  DOI：10.1039/c39870001413

  日期：——

  Chiral crystals of the achiral oxo amide N,N-di-isopropylphenylglyoxylamide, prepared in large quantities, were irradiated in the solid state to give the optically active β-lactam 3-hydroxy-1-isopropyl-4,4-dimethyl-3-phenylazetidin-2-one in high optical and chemical yields.

  将大量制备的非手性氧代酰胺N，N - N-二异丙基苯基乙醛酰胺的手性晶体进行固态辐照，以得到旋光性β-内酰胺3-羟基-1-异丙基-4,4-二甲基-3-苯基氮杂环丁烷-2-酮具有较高的光学和化学收率。