1-(4-chlorophenyl)-3-methyl-2-(1-methylethyl)-4,5-dihydro-1H-imidazolium iodide | 1372812-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-chlorophenyl)-3-methyl-2-(1-methylethyl)-4,5-dihydro-1H-imidazolium iodide
• 英文别名: 1-(4-Chlorophenyl)-3-methyl-2-propan-2-yl-4,5-dihydroimidazol-3-ium;iodide
• CAS: 1372812-39-9
• 化学式: C₁₃H₁₈ClN₂*I
• 分子量: 364.657
• InChiKey: LBBUQYDDMRDTJD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.14
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(4-chlorophenyl)-N'-(2-methylpropionyl)ethylenediamine 在 trimethylsilyl polyphosphate 作用下， 以 二氯甲烷 为溶剂， 反应 0.47h， 生成 1-(4-chlorophenyl)-3-methyl-2-(1-methylethyl)-4,5-dihydro-1H-imidazolium iodide
  参考文献：
  名称：

  Synthesis and Synthetic Applications of 1-Aryl-2-alkyl-4,5-dihydro-1H-imidazoles

  摘要：

  An easy synthesis of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles 1 by cyclo-condensation of N-acyl-N'-arylethylenediamines 2 is described. Such precursors were synthesized by aminolysis of the corresponding N-(2-bromoethyl)amides 3. Cyclizations were performed using trimethylsilyl polyphosphate as a mild dehydrating agent, under microwave irradiation. Chemical properties of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles, typical of the amidine system, were studied. Reduction of dihydroimidazoles with sodium cyanoborohydride leads regiospecifically to N-alkyl-N'-arylethylenediamines 4, and nucleophilic attack to methyl iodide leads to the corresponding 1-aryl-2-alkyl-3-methyl-4,5-dihydro-1H-imidazolium salts 5.

  DOI：

  10.1080/00397911.2011.552155

文献信息

• Synthesis and Synthetic Applications of 1-Aryl-2-alkyl-4,5-dihydro-1<i>H</i>-imidazoles
  作者：Ana M. Reverdito、Isabel A. Perillo、Alejandra Salerno

  DOI：10.1080/00397911.2011.552155

  日期：2012.7.15

  An easy synthesis of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles 1 by cyclo-condensation of N-acyl-N'-arylethylenediamines 2 is described. Such precursors were synthesized by aminolysis of the corresponding N-(2-bromoethyl)amides 3. Cyclizations were performed using trimethylsilyl polyphosphate as a mild dehydrating agent, under microwave irradiation. Chemical properties of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles, typical of the amidine system, were studied. Reduction of dihydroimidazoles with sodium cyanoborohydride leads regiospecifically to N-alkyl-N'-arylethylenediamines 4, and nucleophilic attack to methyl iodide leads to the corresponding 1-aryl-2-alkyl-3-methyl-4,5-dihydro-1H-imidazolium salts 5.