(3R,4S)-1-Benzyl-4-ethyl-3-hydroxy-4-methyl-azetidin-2-one | 180839-91-2

• 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: (3R,4S)-1-Benzyl-4-ethyl-3-hydroxy-4-methyl-azetidin-2-one
• 英文别名: (3R,4S)-1-benzyl-4-ethyl-3-hydroxy-4-methylazetidin-2-one
• CAS: 180839-91-2
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: QFFWTIZHQYGHPE-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-Benzyl-4-ethyl-3-hydroxy-4-methyl-azetidin-2-one 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 碳酸氢钠 、 potassium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以95%的产率得到(S)-3-Benzyl-4-ethyl-4-methyl-oxazolidine-2,5-dione
  参考文献：
  名称：

  Concise synthesis of α-alkyl α-amino acids and their incorporation into peptides viaβ-lactam-derived α-amino acid N-carboxy anhydrides

  摘要：

  alpha-Hydroxy beta-lactams in which C-4 exists as a quaternary carbon are transformed in a single one-pot operation into alpha,alpha-dialkyl alpha-amino acid N-carboxy anhydrides providing a new approach to conformationally restricted peptide segments from non alpha-amino acid precursors.

  DOI：

  10.1039/cc9960001269
• 作为产物：
  描述：

  (3R,4S)-1-Benzyl-3-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-azetidin-2-one 在 palladium on activated charcoal sodium periodate 、 高氯酸 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 17.0h， 生成 (3R,4S)-1-Benzyl-4-ethyl-3-hydroxy-4-methyl-azetidin-2-one
  参考文献：
  名称：

  Concise synthesis of α-alkyl α-amino acids and their incorporation into peptides viaβ-lactam-derived α-amino acid N-carboxy anhydrides

  摘要：

  alpha-Hydroxy beta-lactams in which C-4 exists as a quaternary carbon are transformed in a single one-pot operation into alpha,alpha-dialkyl alpha-amino acid N-carboxy anhydrides providing a new approach to conformationally restricted peptide segments from non alpha-amino acid precursors.

  DOI：

  10.1039/cc9960001269

文献信息

• Concise synthesis of α-alkyl α-amino acids and their incorporation into peptides viaβ-lactam-derived α-amino acid N-carboxy anhydrides
  作者：Claudio Palomo、J. M. Aizpurua、Iñaki Ganboa、Beatriz Odriozola、Raquel Urchegui、Helmar Görls

  DOI：10.1039/cc9960001269

  日期：——

  alpha-Hydroxy beta-lactams in which C-4 exists as a quaternary carbon are transformed in a single one-pot operation into alpha,alpha-dialkyl alpha-amino acid N-carboxy anhydrides providing a new approach to conformationally restricted peptide segments from non alpha-amino acid precursors.