4-methyl-1-[methyl(phenyl)amino]-5-phenyl-1H-imidazole

• 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-methyl-1-[methyl(phenyl)amino]-5-phenyl-1H-imidazole
• 英文别名: N,4-dimethyl-N,5-diphenylimidazol-1-amine
• 化学式: C₁₇H₁₇N₃
• 分子量: 263.342
• InChiKey: AZERZTFKUNJJGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-1-[methyl(phenyl)amino]-5-phenyl-1H-imidazole 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 1.5h， 生成 2-(4-chlorobenzoyl)-1,5-dimethyl-4-phenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis of 2-Keto-imidazoles Utilizing N-Arylamino-Substituted N-Heterocyclic Carbenes

  摘要：

  A new method for the synthesis of 2-aroyl-, 2-heteroaroyl-, and 2-cinnamoyl-substituted imidazoles in very good yields has been developed. The reaction employs novel nitrogen heterocyclic carbenes (NHCs), namely, N-arylamino-substituted NHCs, formed in situ from the corresponding imidazolium salts, and subsequent reaction with aromatic, heteroaromatic, and cinnamic aldehydes without utilizing transition metals or expensive specialized catalysts.

  DOI：

  10.1021/jo102244x
• 作为产物：
  描述：

  3-溴苯丙酮 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 2.17h， 生成 4-methyl-1-[methyl(phenyl)amino]-5-phenyl-1H-imidazole
  参考文献：
  名称：

  1-Arylamino-1H-imidazoles by "Oxidative Reduction" --- Conversion of 1-Arylamino-2,3-dihydro-1H-imidazole-2-thiones

  摘要：

  DOI：

  10.3987/com-98-8116

文献信息

• <i>N</i>-Aminoimidazole Derivatives Inhibiting Retroviral Replication via a Yet Unidentified Mode of Action
  作者：Irene M. Lagoja、Christophe Pannecouque、Arthur Van Aerschot、Myriam Witvrouw、Zeger Debyser、Jan Balzarini、Piet Herdewijn、Erik De Clercq

  DOI：10.1021/jm0211117

  日期：2003.4.1

  The synthesis of a series of N-aminoimidazoles (NAIMs) with an uncommon spectrum of antiretroviral activity is described. From a group of 60 closely related molecules, we were able to subdivide the molecules in different groups based on their anti-HIV and anti-SIV activity in vitro (i) molecules acting on a new, immediate postintegration step, (ii) molecules acting on both postintegration and HIV-1 reverse transcriptase (RT) as NNRTI, and (iii) molecules that mainly act at the HIV-1 RT according to an NNRTI-type mode of action.
• 1-Arylamino-1H-imidazoles by "Oxidative Reduction" --- Conversion of 1-Arylamino-2,3-dihydro-1H-imidazole-2-thiones
  作者：Joachim G. Schantl、Irene M. Lagoja

  DOI：10.3987/com-98-8116

  日期：——
• Synthesis of 2-Keto-imidazoles Utilizing <i>N</i>-Arylamino-Substituted N-Heterocyclic Carbenes
  作者：Tryfon Zarganes-Tzitzikas、Constantinos G. Neochoritis、Julia Stephanidou-Stephanatou、Constantinos A. Tsoleridis

  DOI：10.1021/jo102244x

  日期：2011.3.4

  A new method for the synthesis of 2-aroyl-, 2-heteroaroyl-, and 2-cinnamoyl-substituted imidazoles in very good yields has been developed. The reaction employs novel nitrogen heterocyclic carbenes (NHCs), namely, N-arylamino-substituted NHCs, formed in situ from the corresponding imidazolium salts, and subsequent reaction with aromatic, heteroaromatic, and cinnamic aldehydes without utilizing transition metals or expensive specialized catalysts.