N-((S)-1-Benzyl-3-nitro-2-oxo-propyl)-acetamide | 139168-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((S)-1-Benzyl-3-nitro-2-oxo-propyl)-acetamide
• 英文别名: N-[(2S)-4-nitro-3-oxo-1-phenylbutan-2-yl]acetamide
• CAS: 139168-60-8
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: MJQCCWAKRGVHKK-NSHDSACASA-N

物化性质

• 沸点：
  479.8±45.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-乙酰-L-苯丙氨酸 、 nitromethane sodium salt 在 N,N'-羰基二咪唑 作用下， 生成 N-((S)-1-Benzyl-3-nitro-2-oxo-propyl)-acetamide
  参考文献：
  名称：

  Silica gel-catalyzed Knoevenagel condensation of peptidyl cyanomethyl ketones with aromatic aldehydes and ketones. A novel Michael acceptor functionality for C-modified peptides: the benzylidene and alkylidene cyanomethyl ketone function

  摘要：

  Simple preparation of cyanomethyl ketone derivatives 5a-5b of N-acetylphenylalanine and N-acetylleucylphenylalanine is accomplished by condensation of the corresponding activated carboxylic acids 3a-3b and the carbanion of tert-butyl cyanoacetate to give enols 4a-4b, which are then hydrolyzed and decarboxylated. These cyanomethyl ketone compounds 5a-5b are allowed to react with aromatic aldehydes and ketones in the presence of silica gel to give the Knoevenagel condensation adducts 7-18. Malononitrile, benzoylacetonitrile, and nitroacetonitrile are also reactive. These transformations can be brought about without significant epimerization.

  DOI：

  10.1021/jo00032a042

文献信息

• Silica gel-catalyzed Knoevenagel condensation of peptidyl cyanomethyl ketones with aromatic aldehydes and ketones. A novel Michael acceptor functionality for C-modified peptides: the benzylidene and alkylidene cyanomethyl ketone function
  作者：Denis Brillon、Gilles Sauve

  DOI：10.1021/jo00032a042

  日期：1992.3

  Simple preparation of cyanomethyl ketone derivatives 5a-5b of N-acetylphenylalanine and N-acetylleucylphenylalanine is accomplished by condensation of the corresponding activated carboxylic acids 3a-3b and the carbanion of tert-butyl cyanoacetate to give enols 4a-4b, which are then hydrolyzed and decarboxylated. These cyanomethyl ketone compounds 5a-5b are allowed to react with aromatic aldehydes and ketones in the presence of silica gel to give the Knoevenagel condensation adducts 7-18. Malononitrile, benzoylacetonitrile, and nitroacetonitrile are also reactive. These transformations can be brought about without significant epimerization.