ethyl (RS)-5-(2-oxo-4-phenylazetidin-1-yl)valerianate | 1013917-81-1

• 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: ethyl (RS)-5-(2-oxo-4-phenylazetidin-1-yl)valerianate
• CAS: 1013917-81-1
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: SGQBXRUYDQFVQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (RS)-5-(2-oxo-4-phenylazetidin-1-yl)valerianate 在 sodium hydroxide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.33h， 生成 N-{5-[(RS)-2-oxo-4-phenylazetidin-1-yl]valerianyl}-L-valyl-L-leucine methyl ester
  参考文献：
  名称：

  β-Lactam Derivatives as Enzyme Inhibitors: Peptidic Derivatives of (RS)-2-Oxo-4-phenylazetidine-1-alkanoic Acids

  摘要：

  4-Phenylazetidine-2-one was transformed into 4-phenylazetidine-1-alkanoic acids, which were reacted in the presence of diphenylphosphoroazidate with amino acid esters and dipeptide esters yielding beta-lactam peptides with different spacers between the lactam ring and the peptide moiety. All structures were established by elementary analyses, HPLC, optical rotation, and spectroscopic data and all new compounds were tested as inhibitors of PPE using standard procedures. Four compounds exhibited a weak activity compared with the standard inhibitor trifluoroacetyl-L-val-L-tyr-L-val.

  DOI：

  10.1007/s00706-007-0639-9
• 作为产物：
  描述：

  4-苯基-2-氮杂环丁酮 、 5-溴戊酸乙酯 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到ethyl (RS)-5-(2-oxo-4-phenylazetidin-1-yl)valerianate
  参考文献：
  名称：

  β-Lactam Derivatives as Enzyme Inhibitors: Peptidic Derivatives of (RS)-2-Oxo-4-phenylazetidine-1-alkanoic Acids

  摘要：

  4-Phenylazetidine-2-one was transformed into 4-phenylazetidine-1-alkanoic acids, which were reacted in the presence of diphenylphosphoroazidate with amino acid esters and dipeptide esters yielding beta-lactam peptides with different spacers between the lactam ring and the peptide moiety. All structures were established by elementary analyses, HPLC, optical rotation, and spectroscopic data and all new compounds were tested as inhibitors of PPE using standard procedures. Four compounds exhibited a weak activity compared with the standard inhibitor trifluoroacetyl-L-val-L-tyr-L-val.

  DOI：

  10.1007/s00706-007-0639-9