1,4,5,6-四氢-2-甲基-4-(3-硝基苯基)-6-氧代-3-吡啶羧酸 | 423120-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,4,5,6-四氢-2-甲基-4-(3-硝基苯基)-6-氧代-3-吡啶羧酸
• 英文名称: 2-Methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid
• 英文别名: 6-methyl-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylic acid
• CAS: 423120-04-1
• 化学式: C₁₃H₁₂N₂O₅
• 分子量: 276.249
• InChiKey: PRDVRYDVJJPJMM-UHFFFAOYSA-N

物化性质

• 沸点：
  541.5±50.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4,5,6-四氢-2-甲基-4-(3-硝基苯基)-6-氧代-3-吡啶羧酸 在 Candida antarctica lipase B 、 水 、 caesium carbonate 作用下， 以 甲醇 、 乙醚 、 甲基叔丁基醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 methyl (4R)-6-methyl-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives

  摘要：

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.012
• 作为产物：
  描述：

  (±)-5-[(2-cyanoethyl)oxycarbonyl]-6-methyl-4-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyridone 在 水 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 以60%的产率得到1,4,5,6-四氢-2-甲基-4-(3-硝基苯基)-6-氧代-3-吡啶羧酸
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active 4-aryl-5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives

  摘要：

  A series of racemic 4-ary1-5-(tert-butoxycarbonyl)-6-methyl-3,4-dihydro-2(1H)-pyridones have been prepared by means of a modified Hantzsch reaction using commercially available starting materials. An easy removal of the tert-butyl group of these pyridones and subsequent reaction with cesium carbonate and chloromethyl 2-methylpropanoate provided us suitable substrates (+/-)-5 to be used in lipase-catalyzed hydrolysis reactions. Lipase B from Candida antarctica (CAL-B) was the most adequate lipase in the hydrolysis of (+/-)-5. Despite the low enantioselectivity values obtained (E <= 12), several optically active pyridone derivatives were finally isolated with high enantiomeric excesses (ee >= 91%) and moderate yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.012

文献信息

• Solid-phase synthesis of 4-aryl substituted 5-carboxy-6-methyl-3,4-dihydropyridones
  作者：Hortensia Rodrı́guez、Osvaldo Reyes、Margarita Suarez、Hilda E. Garay、Rolando Pérez、Luis Javier Cruz、Yamila Verdecia、Nazario Martı́n、Carlos Seoane

  DOI：10.1016/s0040-4039(01)02172-4

  日期：2002.1

  Substituted 3,4-dihydro-2-pyridones have been efficiently prepared by solid-phase synthesis using Wang resin from the immobilised β-ketoester and further Hantzsch-type heterocyclisation.

  通过固相合成，使用Wang树脂从固定的β-酮酸酯中进行了固相合成，并进一步进行了Hantzsch型杂环化反应，从而有效地制备了3,4-二氢-2-吡啶酮。