methyl 4-(2-chlorophenyl)-1,4-dihydro-5-(1-imidazolylcarbonyl)-2,6-dimethyl-3-pyridinecarboxylate | 149143-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 4-(2-chlorophenyl)-1,4-dihydro-5-(1-imidazolylcarbonyl)-2,6-dimethyl-3-pyridinecarboxylate
• 英文别名: methyl 4-(2-chlorophenyl)-5-(imidazole-1-carbonyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate
• CAS: 149143-30-6
• 化学式: C₁₉H₁₈ClN₃O₃
• 分子量: 371.823
• InChiKey: UGHVJKOTCCCZRG-UHFFFAOYSA-N

物化性质

• 沸点：
  525.6±60.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-chlorophenyl)-1,4-dihydro-5-(1-imidazolylcarbonyl)-2,6-dimethyl-3-pyridinecarboxylate 在 正丁基锂 作用下， 以 水 、 乙腈 为溶剂， 反应 17.5h， 生成 methyl 4-(2-chlorophenyl)-1,4-dihydro-6-methyl-5-<(methylamino)carbonyl>-2-<(methylthio)methyl>-3-pyridinecarboxylate
  参考文献：
  名称：

  Metalation of Hantzsch esters and mixed amide esters: a general route to C-2 functionalized 1,4-dihydropyridines

  摘要：

  1,4-Dihydropyridine (Hantzsch) diesters 3a-e readily undergo metalation at the C-2 methyl (vinylogous ester) position on treatment with alkyllithium bases. The resulting anion intermediates can be treated with electrophilic reagents to afford 1,4-dihydropyridine products that have been chemically elaborated at the C-2 methyl position. The methodology permits a variety of electrophilic functionalities to be regiospecifically introduced at the C-2 methyl position of 1,4-dihydropyridines. Deuterium distribution studies with mixed dihydropyridine amide esters 20a and 20b having nonequivalent C-2 and C-6 methyl groups indicate specific metalation occurs at the C-2 methyl (vinylogous ester) position. Tri- and tetraanion formation is also possible at both vinylogous methyl and NH positions when the metalation reactions are performed with excess equivalents of n-BuLi or 8-BuLi bases.

  DOI：

  10.1021/jo00067a012
• 作为产物：
  描述：

  1,4-dihydro-2,6-dimethyl-4-(2'-chlorophenyl)-pyridine-3,5-dicarboxylic acid monomethyl ester 、 N,N'-羰基二咪唑 以 乙腈 为溶剂， 以59%的产率得到methyl 4-(2-chlorophenyl)-1,4-dihydro-5-(1-imidazolylcarbonyl)-2,6-dimethyl-3-pyridinecarboxylate
  参考文献：
  名称：

  Metalation of Hantzsch esters and mixed amide esters: a general route to C-2 functionalized 1,4-dihydropyridines

  摘要：

  1,4-Dihydropyridine (Hantzsch) diesters 3a-e readily undergo metalation at the C-2 methyl (vinylogous ester) position on treatment with alkyllithium bases. The resulting anion intermediates can be treated with electrophilic reagents to afford 1,4-dihydropyridine products that have been chemically elaborated at the C-2 methyl position. The methodology permits a variety of electrophilic functionalities to be regiospecifically introduced at the C-2 methyl position of 1,4-dihydropyridines. Deuterium distribution studies with mixed dihydropyridine amide esters 20a and 20b having nonequivalent C-2 and C-6 methyl groups indicate specific metalation occurs at the C-2 methyl (vinylogous ester) position. Tri- and tetraanion formation is also possible at both vinylogous methyl and NH positions when the metalation reactions are performed with excess equivalents of n-BuLi or 8-BuLi bases.

  DOI：

  10.1021/jo00067a012