N-benzylidene-2,4-diphenyl-1H-imidazol-5-amine | 106410-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzylidene-2,4-diphenyl-1H-imidazol-5-amine
• 英文别名: N-(2,5-diphenyl-1H-imidazol-4-yl)-1-phenylmethanimine
• CAS: 106410-36-0
• 化学式: C₂₂H₁₇N₃
• 分子量: 323.397
• InChiKey: IYIRKZHUFFOQFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzylidene-2,4-diphenyl-1H-imidazol-5-amine 在 盐酸 、 水 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以87%的产率得到2,4-diphenyl-1H-imidazol-5-ammonium chloride
  参考文献：
  名称：

  MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

  摘要：

  A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first-in-class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.035
• 作为产物：
  描述：

  4-nitroso-diphenylimidazole 在 盐酸 、 水 、 tin(ll) chloride 作用下， 生成 N-benzylidene-2,4-diphenyl-1H-imidazol-5-amine
  参考文献：
  名称：

  Cusmano; Ruccia, Gazzetta Chimica Italiana, 1955, vol. 85, p. 1329,1335

  摘要：

  DOI：

文献信息

• Acyclic amidines in the Strecker-like Groebke-Blackburn-Bienayme’ (GBB) reaction
  作者：Jacqueline Smith、Mayowa Osunsanya、Ikechi Nwadike、Brenda Tankeu

  DOI：10.1016/j.tetlet.2022.153876

  日期：2022.6

  multi-component method to form imidazoles using cyclic amidines. In order to expand the scope of this reaction, we have explored the GBBR with acyclic amidines. We found that the acyclic amidine, benzamidine performed similarly to cyclic amidines with the electronics of the aldehyde having a significant influence on reaction yield. Other acyclic amidines including guanidine were less successful however the

  Groebke-Blackburn-Bienayme' 反应 (GBBR) 是一种成熟的多组分方法，可使用环状脒形成咪唑。为了扩大该反应的范围，我们探索了带有无环脒的GBBR。我们发现无环脒、苯甲脒的表现与环状脒相似，醛的电子对反应产率有显着影响。包括胍在内的其他无环脒不太成功，但是胍衍生物乙酰胍显示出前景。这些发现表明，无环脒有可能用于开发可进一步官能化的新咪唑。
• MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines
  作者：Christan E. Bell、Arthur Y. Shaw、Fabio De Moliner、Christopher Hulme

  DOI：10.1016/j.tet.2013.11.035

  日期：2014.1

  A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first-in-class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles. (C) 2013 Elsevier Ltd. All rights reserved.
• Cusmano; Ruccia, Gazzetta Chimica Italiana, 1955, vol. 85, p. 1329,1335
  作者：Cusmano、Ruccia

  DOI：——

  日期：——