4-(methylamino)-1,2,4-triazole | 21614-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(methylamino)-1,2,4-triazole
• 英文别名: 4-methylamino-4H-1,2,4-triazole；4-Methylamino-4H-1,2,4-triazol；1-Methylamino-1,3,4-triazol；methyl-[1,2,4]triazol-4-yl-amine；N-methyl-1,2,4-triazol-4-amine
• CAS: 21614-53-9
• 化学式: C₃H₆N₄
• 分子量: 98.1074
• InChiKey: ZYQVFAIBEOYOFM-UHFFFAOYSA-N

物化性质

• 沸点：
  199.4±23.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-碘-3-硝基苯 、 4-(methylamino)-1,2,4-triazole 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以36%的产率得到4-nitro-2-iodo-N-methylaniline
  参考文献：
  名称：

  Alkylaminonitrobenzenes by vicarious nucleophilic amination with 4-(alkylamino)-1,2,4-triazoles

  摘要：

  DOI：

  10.1021/jo00252a018
• 作为产物：
  描述：

  tosylate de 4-amino-1-methyl-4H-1,2,4-triazolium 在 sodium hydroxide 作用下， 以60%的产率得到4-(methylamino)-1,2,4-triazole
  参考文献：
  名称：

  Synthèse, étude théorique et évaluation biologique de dérivés du 4-amino-4H-1,2,4-triazole analogues des antibiotiques β-lactamiques

  摘要：

  The synthesis of three classes of potential antibiotic compounds derived from 4-amino-4H- 1,2,4-triazole and related to beta-lactam antibiotics is described. Their originality belongs to the replacement of the beta-lactam carbonyl moiety by another electrophilic centre of the same sp2 geometry. As a result, their interaction with the bacterial target enzyme might lead to the formation of a covalent complex different from the classical acylenzyme. A theoretical study of their structural analogy and their reactivity compared to those of a model beta-lactam justifies their interest in the present context. However, the actual biological results indicate a lack of antibacterial activity.

  DOI：

  10.1016/0223-5234(92)90003-j

文献信息

• KATRITZKY, ALAN R.;LAURENZO, KATHLEEN S., J. ORG. CHEM., 53,(1988) N 17, 3978-3982
  作者：KATRITZKY, ALAN R.、LAURENZO, KATHLEEN S.

  DOI：——

  日期：——
• Alkylaminonitrobenzenes by vicarious nucleophilic amination with 4-(alkylamino)-1,2,4-triazoles
  作者：Alan R. Katritzky、Kathleen S. Laurenzo

  DOI：10.1021/jo00252a018

  日期：1988.8
• Synthèse, étude théorique et évaluation biologique de dérivés du 4-amino-4H-1,2,4-triazole analogues des antibiotiques β-lactamiques
  作者：B Pirotte、G Dive、J Delarge、B Masereel、L Dupont、L Thunus、M Schynts、J Coyette、JM Frère

  DOI：10.1016/0223-5234(92)90003-j

  日期：1992.4

  The synthesis of three classes of potential antibiotic compounds derived from 4-amino-4H- 1,2,4-triazole and related to beta-lactam antibiotics is described. Their originality belongs to the replacement of the beta-lactam carbonyl moiety by another electrophilic centre of the same sp2 geometry. As a result, their interaction with the bacterial target enzyme might lead to the formation of a covalent complex different from the classical acylenzyme. A theoretical study of their structural analogy and their reactivity compared to those of a model beta-lactam justifies their interest in the present context. However, the actual biological results indicate a lack of antibacterial activity.