diethyl 4-(2-chloro-5-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 21881-53-8

• 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: diethyl 4-(2-chloro-5-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: 2,6-dimethyl-3,5-dicarboethoxy-4-(2-chloro-5-nitrophenyl)-1,4-dihydropyridine；dibenzyl 4-(2′-chloro-5′-nitrophenyl) hantzsch ester；3,5-Diethyl 4-(2-chloro-5-nitrophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• CAS: 21881-53-8
• 化学式: C₁₉H₂₁ClN₂O₆
• 分子量: 408.839
• InChiKey: KDZKXCNAMNJRNO-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C
• 沸点：
  507.7±50.0 °C(predicted)
• 密度：
  1.288±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-氯-5-硝基苯甲醛 在 ammonium acetate 作用下， 反应 17.0h， 以65%的产率得到diethyl 4-(2-chloro-5-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  σ键引发从芳基重氮盐生成芳基的过程。

  摘要：

  σ键亲核试剂和分子氧将芳基重氮盐转化为芳基。实验和计算研究表明，汉茨酯将氢化物转移到芳基重氮化合物上，并且氧引发了重氮中间体的自由基断裂，从而产生了芳基。在各种形成键的反应中已经说明了这种加成-断裂过程通过极性自由基交换机理产生芳基的操作简便性。

  DOI：

  10.1039/d0ob00205d

文献信息

• PEG-Mediated Catalyst-Free Synthesis of Hantzsch 1,4-Dihydropyridines and Polyhydroquinoline Derivatives
  作者：V. Siddaiah、G. Mahaboob Basha、G. Padma Rao、U. Viplava Prasad、R. Suryachendra Rao

  DOI：10.1080/00397911.2010.528289

  日期：2012.3.1

  Abstract Hantzsch 1,4-dihydropyridines and polyhydroquinoline derivatives were synthesized in good yields by PEG-mediated, catalyst–free synthesis under solvent-free conditions. The products were directly recrystallized from hot methanol. The reaction gave excellent yields with low- as well as high-molecular-weight polyethylene glycols. GRAPHICAL ABSTRACT

  摘要 Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物在无溶剂条件下通过PEG介导的无催化剂合成以良好的收率合成。产物直接从热甲醇中重结晶。该反应对低分子量和高分子量聚乙二醇产生了极好的收率。图形概要
• Facile and Green Synthesis of 1,4-Dihydropyridine Derivatives in <i>n</i>-Butyl Pyridinium Tetrafluoroborate
  作者：Xiao Yun Wu

  DOI：10.1080/00397911.2010.525773

  日期：2012.2.1

  l,4-Dihydropyridine derivatives were synthesized from the one-pot condensation of aldehydes, acetoacetates, and ammonium acetate in room-temperature ionic liquid n-butyl pyridinium tetrafluoroborate ([BPy][BF4]). Compared with classical Hantzsch reaction conditions, this new method has the advantage of excellent yields, short reaction time, and easy workup. The recovered ionic liquid could be recycled for at least five runs without losing its activity.