N-(3-aminophenyl)-3-diazopyruvamide | 160776-89-6

• 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-(3-aminophenyl)-3-diazopyruvamide
• 英文别名: N-(3-aminophenyl)-3-diazo-2-oxopropanamide
• CAS: 160776-89-6
• 化学式: C₉H₈N₄O₂
• 分子量: 204.188
• InChiKey: NQRWVOQJVYJQIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-aminophenyl)-3-diazopyruvamide 在 N-甲基吗啉 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 反应 12.25h， 生成 N-{3-[(2-Bromo-acetyl)-(2-hydroxy-benzyl)-amino]-phenyl}-malonamic acid methyl ester
  参考文献：
  名称：

  Development of a New Family of Thiol Specific Photoactivatable Crosslinking Agents

  摘要：

  A new family of thiol specific photoactivatable cross-linking agents has been developed by the combination of the bromoacetyl function and the diazopyruvamide group. Various bromoacetyl-diazopyruvoyl (bromoacetyl-DAP) derivatives have been synthesized and their reaction chemistry with thiols investigated and photochemistry explored. The trimodular bioprobe 17 design evolved from application of this chemistry. The trifunctionality of 17 is characterized by the presence of (1) a bromoacetyl function that modifies thiol groups through alkylation, (2) a diazopyruvoyl function which upon photolysis undergoes Wolff rearrangement generating a reactive ketene that can acylate nucleophiles, and (3) a phenolic function that acts as a characterization handle through radioiodination labeling via standard techniques. These bifunctional and trifunctional photoprobes typified by N-bromoacetyl-N'-(3-diazopyruvoyl)-m-phenylenediamine (7a) have been used to successfully cross-link a 14 aa peptide(Q) from the alpha(2)-adrenergic receptor to purified G protein.

  DOI：

  10.1021/jo00126a055
• 作为产物：
  描述：

  间苯二胺 、 (Z)-1-偶氮基-3-(4-硝基苯氧基)-3-氧代丙-1-烯-2-醇 以 乙酸乙酯 为溶剂， 反应 12.0h， 以83%的产率得到N-(3-aminophenyl)-3-diazopyruvamide
  参考文献：
  名称：

  Development of a New Family of Thiol Specific Photoactivatable Crosslinking Agents

  摘要：

  A new family of thiol specific photoactivatable cross-linking agents has been developed by the combination of the bromoacetyl function and the diazopyruvamide group. Various bromoacetyl-diazopyruvoyl (bromoacetyl-DAP) derivatives have been synthesized and their reaction chemistry with thiols investigated and photochemistry explored. The trimodular bioprobe 17 design evolved from application of this chemistry. The trifunctionality of 17 is characterized by the presence of (1) a bromoacetyl function that modifies thiol groups through alkylation, (2) a diazopyruvoyl function which upon photolysis undergoes Wolff rearrangement generating a reactive ketene that can acylate nucleophiles, and (3) a phenolic function that acts as a characterization handle through radioiodination labeling via standard techniques. These bifunctional and trifunctional photoprobes typified by N-bromoacetyl-N'-(3-diazopyruvoyl)-m-phenylenediamine (7a) have been used to successfully cross-link a 14 aa peptide(Q) from the alpha(2)-adrenergic receptor to purified G protein.

  DOI：

  10.1021/jo00126a055