6-甲基-4-(3-硝基苯基)-2-氧代-1,2,3,4-四氢吡啶-5-羧酸甲酯 | 130734-38-2

• 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: 6-甲基-4-(3-硝基苯基)-2-氧代-1,2,3,4-四氢吡啶-5-羧酸甲酯
• 英文名称: 6-methyl-5-methoxycarbonyl-4-(3-nitrophenyl)-3,4-dihydropyridone
• 英文别名: methyl 1,4,5,6-tetrahydro-2-methyl-4-(3-nitrophenyl)-6-oxopyridine-3-carboxylate；Methyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate；4-(3-nitrophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-one；4-(3-nitrophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridone；Methyl 2-methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate；methyl 6-methyl-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 130734-38-2
• 化学式: C₁₄H₁₄N₂O₅
• 分子量: 290.276
• InChiKey: RZCSIXRGZZQPRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-甲基-4-(3-硝基苯基)-2-氧代-1,2,3,4-四氢吡啶-5-羧酸甲酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以52%的产率得到4-(3-nitrophenyl)-5-oxo-1,2,3,4,5,7-hexahydrofuro<3,4-b>-2(1H)-pyridone
  参考文献：
  名称：

  来自4-芳基取代的5-烷氧基羰基-6-甲基-3,4-二氢吡啶酮的新型六氢呋喃[3,4- b ] -2（1 H）-吡啶酮

  摘要：

  标题化合物6是由相应的4-芳基取代的5-烷氧基羰基-6-甲基-3，4-二氢吡啶酮4以良好的产率一步制备的。量子化学计算揭示了具有扭曲的二氢吡啶酮环和两个有利构象的非平面分子。13C nmr数据和理论计算支持对烯烃部分的强推挽效应。

  DOI：

  10.1002/jhet.5570330118
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 间硝基苯甲醛 、 乙酰乙酸甲酯 在 ammonium acetate 、 溶剂黄146 作用下， 反应 10.0h， 以63%的产率得到6-甲基-4-(3-硝基苯基)-2-氧代-1,2,3,4-四氢吡啶-5-羧酸甲酯
  参考文献：
  名称：

  来自4-芳基取代的5-烷氧基羰基-6-甲基-3,4-二氢吡啶酮的新型六氢呋喃[3,4- b ] -2（1 H）-吡啶酮

  摘要：

  标题化合物6是由相应的4-芳基取代的5-烷氧基羰基-6-甲基-3，4-二氢吡啶酮4以良好的产率一步制备的。量子化学计算揭示了具有扭曲的二氢吡啶酮环和两个有利构象的非平面分子。13C nmr数据和理论计算支持对烯烃部分的强推挽效应。

  DOI：

  10.1002/jhet.5570330118

文献信息

• Eco-Friendly Methodology to Prepare N-Heterocycles Related to Dihydropyridines: Microwave-Assisted Synthesis of Alkyl 4-Arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate and 4-Arylsubstituted-4,7-dihydrofuro[3,4-b]pyridine-2,5(1H,3H)-dione
  作者：Hortensia Rodríguez、Osnieski Martin、Margarita Suarez、Nazario Martín、Fernando Albericio

  DOI：10.3390/molecules16119620

  日期：——

  Here we describe the efficient synthesis of alkyl 4-arylsubstituted-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylates and 4-arylsubstituted-4,7-dihydro-furo[3,4-b]pyridine-2,5(1H,3H)-diones via microwave-accelerated reaction of alkyl 4-arylsubstituted-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylates with the appropriate reagents. This eco-friendly approach to these valuable dihydropyridine derivatives does not involve the harsh or highly contaminating conditions common in classical heating and offers a reduction or even elimination of solvent use and recovery, simplification of the work-up procedures, facility of scale up, and low energy consumption, in addition to moderate to higher yields.

  本文描述了通过微波加速反应，高效合成烷基4-芳基取代-6-氯-5-甲酰基-2-甲基-1,4-二氢吡啶-3-羧酸酯和4-芳基取代-4,7-二氢-呋喃[3,4-b]吡啶-2,5(1H,3H)-二酮的方法。该环保合成途径不涉及传统加热中的苛刻或高度污染条件，减少了溶剂使用和回收，简化了后处理步骤，易于规模放大，能耗低，并且产率适中至较高。
• Efficient sonochemical synthesis of alkyl 4-aryl-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carboxylate derivatives
  作者：Enrique Ruiz、Hortensia Rodríguez、Julieta Coro、Vladimir Niebla、Alfredo Rodríguez、Roberto Martínez-Alvarez、Hector Novoa de Armas、Margarita Suárez、Nazario Martín

  DOI：10.1016/j.ultsonch.2011.07.003

  日期：2012.3

  facile, efficient and environment-friendly protocol for the synthesis of 6-chloro-5-formyl-1,4-dihydropyridine derivatives has been developed by the convenient ultrasound-mediated reaction of 2(1H)pyridone derivatives with the Vilsmeier-Haack reagent. This method provides several advantages over current reaction methodologies including a simpler work-up procedure, shorter reaction times and higher yields

  通过2（1H）吡啶酮衍生物与Vilsmeier-Haack试剂的便捷超声介导反应，已开发出一种简便，高效且环境友好的合成6-氯-5-甲酰基-1,4-二氢吡啶衍生物的方案。 。与当前的反应方法相比，该方法具有多个优点，包括更简单的后处理步骤，更短的反应时间和更高的产率。
• Synthesis of 5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives and their electrochemical oxidation to 2-pyridones
  作者：Rufus Smits、Baiba Turovska、Sergey Belyakov、Aiva Plotniece、Gunars Duburs

  DOI：10.1016/j.cplett.2016.02.045

  日期：2016.4

  series of variously substituted 5-carboxy-6-methyl-3,4-dihydro-2(1H)-pyridone derivatives were synthesized and their oxidation potentials determined by cyclic voltammetry. The resulting 2-pyridone structure and a tricyclic heterocycle which was formed during an attempted synthesis of 4-(2-hydroxyphenyl) substituted 3,4-dihydro-2(1H)-pyridone were confirmed by single crystal X-ray crystallography.

  摘要 合成了一系列不同取代的5-羧基-6-甲基-3,4-二氢-2(1H)-吡啶酮衍生物，并通过循环伏安法测定了它们的氧化电位。得到的 2-吡啶酮结构和在尝试合成 4-(2-羟基苯基) 取代的 3,4-二氢-2(1H)-吡啶酮的过程中形成的三环杂环通过单晶 X 射线晶体学证实。
• Solvent-free synthesis of 4-aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones under microwave irradiation
  作者：Hortensia Rodrı́guez、Margarita Suarez、Rolando Pérez、Alain Petit、André Loupy

  DOI：10.1016/s0040-4039(03)00625-7

  日期：2003.4

  4-Aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones have been prepared in one-pot condensation from Meldrum's acid, methyl acetoacetate and the appropriate benzaldehyde in the presence of ammonium acetate using microwave irradiation without solvent. This rapid method produced pure products in high yields (81–91%) due essentially to a specific non-thermal microwave effect (17–28%) by conventional

  在没有溶剂的情况下，在微波辐射下，在乙酸铵的存在下，由Meldrum的酸，乙酰乙酸甲酯和适当的苯甲醛通过一锅缩合反应制得了4-芳基取代的5-烷氧基羰基-6-甲基-3,4-二氢吡啶酮。这种快速方法主要由于在相同条件下进行常规加热而产生的特定非热微波效应（17-28％），从而可以高产率（81-91％）生产纯净产品。
• Oxygen-bridged tetrahydropyridines, hexahydropyridines, and dihydropyridones via a Hantzsch-like synthesis with 4-(2-hydroxyphenyl)but-3-en-2-one
  作者：Jan Světlík、Igor Goljer、František Tureček

  DOI：10.1039/p19900001315

  日期：——

  Substituted oxygen-bridged tetrahydro-2-pyridones and tetrahydropyridines (4) and (7) were synthesized by condensation of 4-(2-hydroxyphenyl)but-3-en-2-one (1) with Meldrum's acid (2) and 3-aminocrotononitrile, respectively, in the presence of ammonium acetate. Analogous cyclo-condensations of (1) with methyl 3-amino-2,4-dicyanobut-2-enoate (8) and methyl 3-amino-2-cyanopentene-2-dioate (10) led to

  通过将4-（2-羟苯基）but-3-en-2-one（1）与Meldrum's酸（2）和3缩合合成取代的氧桥联的四氢-2-吡啶酮和四氢吡啶（4）和（7）。-氨基丁腈分别在乙酸铵的存在下。类似的（环缩合1）与3-氨基-2,4- dicyanobut -2-烯酸乙酯（8）和甲基3-氨基-2- cyanopentene -2-二酸盐（10导致氧桥hexahydropyridines）（9）和（11）分别在哌啶环中具有不同的立体化学。讨论了这些氧桥联杂环的立体定向途径中的二分法。还报道了4-芳基取代的二氢-2-吡啶酮的制备。