1-methyl-4,5-diphenyl-1H-imidazole-2-carbonitrile | 67921-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-4,5-diphenyl-1H-imidazole-2-carbonitrile
• 英文别名: 1-methyl-4,5-diphenyl-1H-imidazole-2-carbonitrile；2-Cyano-4,5-diphenyl-1-methylimidazol；1-Methyl-4,5-diphenylimidazole-2-carbonitrile
• CAS: 67921-78-2
• 化学式: C₁₇H₁₃N₃
• 分子量: 259.31
• InChiKey: YNIAPWUUMOXGCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  436.1±48.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 1-methyl-4,5-diphenyl-1H-imidazole 3-oxide 在 MS 4 Angstroem 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到1-methyl-4,5-diphenyl-1H-imidazole-2-carbonitrile
  参考文献：
  名称：

  Synthesis of Imidazole Derivatives Using 2-Unsubstituted 1H-Imidazole 3-Oxides

  摘要：

  The reaction of 1,4,5-trisubstituted 1H-imidazole 3-oxides 1 with Ac2O in CH2Cl2 at 0-5 degrees leads to the corresponding 1,3-dihydro-2H-imidazol-2-ones 4 in good yields. In refluxing Ac2O, the N-oxides 1 are transformed to N-acetylated 1,3-dihydro-2H-imidazol-2-ones 5. The proposed mechanisms for these reactions are analogous to those for N-oxides of 6-membered heterocycles (Scheme 2). A smooth synthesis of 1H-imidazole-2-carbonitriles 2 starting with 1 is achieved by treatment with trimethylsilanecarbonitrile (Me2SiCN) in CH2Cl2 at 0-5 degrees (Scheme 3).

  DOI：

  10.1002/(sici)1522-2675(20000412)83:4<728::aid-hlca728>3.0.co;2-b

文献信息

• Synthesis of Imidazole Derivatives Using 2-Unsubstituted 1H-Imidazole 3-Oxides
  作者：Grzegorz Mlostoń、Małgorzata Celeda、G. K. Surya Prakash、George A. Olah、Heinz Heimgartner

  DOI：10.1002/(sici)1522-2675(20000412)83:4<728::aid-hlca728>3.0.co;2-b

  日期：2000.4.12

  The reaction of 1,4,5-trisubstituted 1H-imidazole 3-oxides 1 with Ac2O in CH2Cl2 at 0-5 degrees leads to the corresponding 1,3-dihydro-2H-imidazol-2-ones 4 in good yields. In refluxing Ac2O, the N-oxides 1 are transformed to N-acetylated 1,3-dihydro-2H-imidazol-2-ones 5. The proposed mechanisms for these reactions are analogous to those for N-oxides of 6-membered heterocycles (Scheme 2). A smooth synthesis of 1H-imidazole-2-carbonitriles 2 starting with 1 is achieved by treatment with trimethylsilanecarbonitrile (Me2SiCN) in CH2Cl2 at 0-5 degrees (Scheme 3).