2-(2-ethyl-4-methyl-1H-imidazol-1-yl)phenylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-ethyl-4-methyl-1H-imidazol-1-yl)phenylamine
• 英文别名: 2-(2-Ethyl-4-methylimidazol-1-yl)aniline；2-(2-ethyl-4-methylimidazol-1-yl)aniline
• 化学式: C₁₂H₁₅N₃
• 分子量: 201.271
• InChiKey: QJTRITOVXCRFIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-ethyl-4-methyl-1H-imidazol-1-yl)phenylamine 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 反应 6.5h， 生成 4-chloro-1-ethyl-3-methylimidazo<1,5-a>quinoxaline
  参考文献：
  名称：

  Novel compounds possessing potent cAMP and cGMP phosphodiesterase inhibitory activity. Synthesis and cardiovascular effects of a series of imidazo[1,2-a]quinoxalinones and imidazo[1,5-a]quinoxalinones and their aza analogs

  摘要：

  A series of novel imidazoquinoxalinones and their aza analogues were prepared by the cyclization of o-amino(H-1-imidazol-1-yl)aryls and heteroaryls with carbonyldiimidazole. The compounds were screened for inhibition of Type I and Type IV phosphodiesterases (PDE's) and evaluated for their vasorelaxant and positive inotropic activities in vitro. In general, compounds having potent PDE inhibitory activity also possessed good inotropic and vasodilator activity, although linear correlations between these activities could not be established.

  DOI：

  10.1021/jm00113a002
• 作为产物：
  描述：

  2-乙基-4-甲基咪唑 在 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 生成 2-(2-ethyl-4-methyl-1H-imidazol-1-yl)phenylamine
  参考文献：
  名称：

  Selective synthesis of 4,5-dihydroimidazo- and imidazo[1,5-a]quinoxalines via modified Pictet–Spengler reaction

  摘要：

  An efficient tandem approach for the selective synthesis of 4,5-dihydroimidazo[1,5-a]quinoxalines 6a-g and imidazo[1,5-a]quinoxalines 7a-h by the reaction of 2-imidazolyl anilines 4a-c with aryl aldehydes 5a-k under mild reaction conditions is described. Introduction of electron releasing alkyl groups in substrates 4a-b was found to be instrumental for the success of the reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.052

文献信息

• Selective synthesis of 4,5-dihydroimidazo- and imidazo[1,5-a]quinoxalines via modified Pictet–Spengler reaction
  作者：Akhilesh Kumar Verma、Rajeev Ranjan Jha、V. Kasi Sankar、Raj Pal Singh

  DOI：10.1016/j.tetlet.2013.08.052

  日期：2013.11

  An efficient tandem approach for the selective synthesis of 4,5-dihydroimidazo[1,5-a]quinoxalines 6a-g and imidazo[1,5-a]quinoxalines 7a-h by the reaction of 2-imidazolyl anilines 4a-c with aryl aldehydes 5a-k under mild reaction conditions is described. Introduction of electron releasing alkyl groups in substrates 4a-b was found to be instrumental for the success of the reaction. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel compounds possessing potent cAMP and cGMP phosphodiesterase inhibitory activity. Synthesis and cardiovascular effects of a series of imidazo[1,2-a]quinoxalinones and imidazo[1,5-a]quinoxalinones and their aza analogs
  作者：David D. Davey、P. W. Erhardt、E. H. Cantor、S. S. Greenberg、W. R. Ingebretsen、J. Wiggins

  DOI：10.1021/jm00113a002

  日期：1991.9

  A series of novel imidazoquinoxalinones and their aza analogues were prepared by the cyclization of o-amino(H-1-imidazol-1-yl)aryls and heteroaryls with carbonyldiimidazole. The compounds were screened for inhibition of Type I and Type IV phosphodiesterases (PDE's) and evaluated for their vasorelaxant and positive inotropic activities in vitro. In general, compounds having potent PDE inhibitory activity also possessed good inotropic and vasodilator activity, although linear correlations between these activities could not be established.