2-isopropyl-1,4,5-triphenyl-1H-imidazole | 915104-92-6

• 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-isopropyl-1,4,5-triphenyl-1H-imidazole
• 英文别名: 2-Isopropyl-1,4,5-triphenyl-1H-imidazole；1,4,5-triphenyl-2-propan-2-ylimidazole
• CAS: 915104-92-6
• 化学式: C₂₄H₂₂N₂
• 分子量: 338.452
• InChiKey: CZRVJQRJWRZRHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  异丁醛 、 苯胺 、 二苯基乙炔 在 ammonium acetate 、 氧气 、 三甲基乙酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 以78%的产率得到2-isopropyl-1,4,5-triphenyl-1H-imidazole
  参考文献：
  名称：

  Metal-Free, Acid-Promoted Synthesis of Imidazole Derivatives via a Multicomponent Reaction

  摘要：

  An expedient and metal-free synthetic route has been developed for the construction of tri- and tetrasubstituted imidazole derivatives via acid promoted multicomponent reaction methodology. The reaction proceeded smoothly with a range of functionalities to produce the imidazole scaffolds in good to excellent yields.

  DOI：

  10.1021/ol402892z

文献信息

• Efficient Synthesis of 5-Substituted 2,3-Diphenyl and 5-Substituted 1-Aryl-2,3-diphenyl Imidazoles Using Polyethylene Glycol
  作者：Biswanath Das、Chithaluri Sudhakar、Yallamalla Srinivas

  DOI：10.1080/00397910903318633

  日期：2010.8.16

  Treatment of benzoin with an aldehyde and NH4OAc in polyethylene glycol (PEG-400) under reflux afforded a 5-substituted 2,3-diphenyl imidazole while the same reaction along with an additional aniline produced 5-substituted 1-aryl 2,3-diphenyl imidazole. No any catalyst or solvent was required to carry out this conversion, and the imidazoles were formed in excellent yields.

  在回流条件下，在聚乙二醇 (PEG-400) 中用醛和 NH4OAc 处理安息香得到 5-取代的 2,3-二苯基咪唑，而相同的反应与额外的苯胺一起生成 5-取代的 1-芳基 2,3-二苯基咪唑。进行这种转化不需要任何催化剂或溶剂，并且以极好的收率形成咪唑。
• Synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in water using p-dodecylbenzenesulfonic acid as catalyst
  作者：Biswanath Das、Jajula Kashanna、Rathod Aravind Kumar、Paramesh Jangili

  DOI：10.1007/s00706-012-0770-0

  日期：2013.2

  2,4,5-Trisubstituted imidazoles have been synthesized by treatment of benzil with aldehydes and ammonium acetate in water under reflux in the presence of p-dodecylbenzenesulfonic acid as catalyst. The same reaction using an additional amine affords 1,2,4,5-tetrasubstituted imidazoles. The products are formed in high yields within 4 h under eco-friendly conditions.
• Metal-Free, Acid-Promoted Synthesis of Imidazole Derivatives via a Multicomponent Reaction
  作者：Chung-Yu Chen、Wan-Ping Hu、Pi-Cheng Yan、Gopal Chandru Senadi、Jeh-Jeng Wang

  DOI：10.1021/ol402892z

  日期：2013.12.20

  An expedient and metal-free synthetic route has been developed for the construction of tri- and tetrasubstituted imidazole derivatives via acid promoted multicomponent reaction methodology. The reaction proceeded smoothly with a range of functionalities to produce the imidazole scaffolds in good to excellent yields.