2-methyli-1H-imidazo[4,5-d]phenazine | 14317-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-methyli-1H-imidazo[4,5-d]phenazine
• 英文别名: 2-methyl-1H-imidazo[4,5-b]phenazine；2-methylimidazo-[4,5-d]-phenazine；2-methyl-1H-imidazo[4,5-b]phenazine；2-Methylimidazo<4,5-b>phenazin
• CAS: 14317-16-9
• 化学式: C₁₄H₁₀N₄
• 分子量: 234.26
• InChiKey: ZPQQNNBHJZZHES-UHFFFAOYSA-N

物化性质

• 熔点：
  335 °C(Solv: ethanol (64-17-5))
• 沸点：
  566.8±15.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,3-二氨基吩嗪 、 乙酸酐 反应 0.5h， 以78%的产率得到2-methyli-1H-imidazo[4,5-d]phenazine
  参考文献：
  名称：

  On the Synthesis of Pyrazino[2,3-b]phenazine and 1H-Imidazo[4,5-b]phenazine Derivatives

  摘要：

  Several pyrazino[2,3-D]phenazine derivatives were prepared by the reaction of 2,3-diaminophenazine with different 1,2-diketones. Nucleophilic substitution of 2,3-dibromomethyl-pyrazino[2,3-b]phenazine with propanol, morpholine, and potassium thiocyanate gave 2,3-bis(propoxymethyl)-pyrazino[2,3-b]phenazine 2,3-bis-(4-morpholinylmethyl)-pyrazino[2,3-b]phenazine, and 2,3-bis-(cyanosulfanylmethyl)-pyrazino[2,3-b]phenazine. 2-Aryl-1H-imidazo[4,5-b]phenazine derivatives were synthesized by a one-pot reaction of 1,3-diaminophenazine with different aromatic aldehydes or acids. Reaction of 2,3-diaminophenazine with acetic anhydride and formic acid afforded 1H-imidazo[4,5-b]phenazine and 2-methyl-1H-imidazo[4,5-b]phenazine. Chemical and spectroscopic evidences for the product structures of the new compounds are presented.

  DOI：

  10.1007/pl00010183

文献信息

• On the Synthesis of Pyrazino[2,3-b]phenazine and 1H-Imidazo[4,5-b]phenazine Derivatives
  作者：Atef M. Amer、Adel A. El-Bahnasawi、Mohamed R. H. Mahran、Mostafa Lapib

  DOI：10.1007/pl00010183

  日期：1999.10

  Several pyrazino[2,3-D]phenazine derivatives were prepared by the reaction of 2,3-diaminophenazine with different 1,2-diketones. Nucleophilic substitution of 2,3-dibromomethyl-pyrazino[2,3-b]phenazine with propanol, morpholine, and potassium thiocyanate gave 2,3-bis(propoxymethyl)-pyrazino[2,3-b]phenazine 2,3-bis-(4-morpholinylmethyl)-pyrazino[2,3-b]phenazine, and 2,3-bis-(cyanosulfanylmethyl)-pyrazino[2,3-b]phenazine. 2-Aryl-1H-imidazo[4,5-b]phenazine derivatives were synthesized by a one-pot reaction of 1,3-diaminophenazine with different aromatic aldehydes or acids. Reaction of 2,3-diaminophenazine with acetic anhydride and formic acid afforded 1H-imidazo[4,5-b]phenazine and 2-methyl-1H-imidazo[4,5-b]phenazine. Chemical and spectroscopic evidences for the product structures of the new compounds are presented.