ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate | 176383-20-3

• 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: ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate
• 英文别名: 5-ethoxycarbonyl-6-methyl-4-(3-nitrophenyl)-3,4-dihydropyridone；Ethyl 2-methyl-4-(3-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate；ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 176383-20-3
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: QCUWAWAFSOAOLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate 在 dipotassium peroxodisulfate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以83%的产率得到ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2-dihydropyridine-5-carboxylate
  参考文献：
  名称：

  立体和电子取代对5-碳乙氧基-2-氧-1,2,3,4-四氢吡啶的热氧化的影响

  摘要：

  在乙腈水溶液中，过氧化二硫酸钾将各种4-芳基取代的5-羰基乙氧基-2-氧-1,2,3,4-四氢吡啶氧化为相应的4-芳基-5-羰基乙氧基-2-氧-1,2-二氢吡啶在热条件下。获得的产物具有良好至优异的产率。基于所提出的机理，在速率确定步骤中发生了通过原位形成的羟基从杂环的C 4原子中除去氢的过程，该过程受取代芳基的空间和电子效应的影响与该原子相连的基团，以及与氧化反应有关的自由基中间体的稳定性。实验结果得到了计算研究的支持。

  DOI：

  10.1007/s13738-016-0966-z
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 乙酰乙酸乙酯 、 间硝基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 10.0h， 生成 ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate
  参考文献：
  名称：

  立体和电子取代对5-碳乙氧基-2-氧-1,2,3,4-四氢吡啶的热氧化的影响

  摘要：

  在乙腈水溶液中，过氧化二硫酸钾将各种4-芳基取代的5-羰基乙氧基-2-氧-1,2,3,4-四氢吡啶氧化为相应的4-芳基-5-羰基乙氧基-2-氧-1,2-二氢吡啶在热条件下。获得的产物具有良好至优异的产率。基于所提出的机理，在速率确定步骤中发生了通过原位形成的羟基从杂环的C 4原子中除去氢的过程，该过程受取代芳基的空间和电子效应的影响与该原子相连的基团，以及与氧化反应有关的自由基中间体的稳定性。实验结果得到了计算研究的支持。

  DOI：

  10.1007/s13738-016-0966-z

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。
• Novel hexahydrofuro[3,4-<i>b</i>]-2(1<i>H</i>)-pyridones from 4-aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones
  作者：Alhmed Morales、Estael Ochoa、Margarita Suárez、Yamila Verdecia、Leandro González、Nazario Martín、Margarita Quinteiro、Carlos Seoane、José L. Soto

  DOI：10.1002/jhet.5570330118

  日期：1996.1

  The title compounds 6 have been prepared in a one-step procedure from the corresponding 4-aryl substituted 5-alkoxycarbonyl-6-methyl-3,4-dihydropyridones 4 in good yields. Quantum chemical calculations reveal a non-planar molecule with a distorted dihydropyridone ring and two favoured conformations. The 13C nmr data and theoretical calculations support a strong push-pull effect on the olefinic moiety

  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。
• High-throughput preparation of alkyl 4-aryl substituted-2-methyl-6-thioxo-1,4,5,6-tetrahydropyridine-3-carboxylates under microwave irradiation
  作者：Hortensia Rodríguez、Julieta Coro、Anabel Lam、Esperanza Salfrán、Javier Rodríguez-Salarichs、Margarita Suárez、Fernando Albericio、Nazario Martin

  DOI：10.3998/ark.5550190.0012.909

  日期：——

  An efficient high-throughput synthesis of 4-aryl substituted 1,4,5,6-tetrahydro-2-methyl-6thioxopyridine-3-carboxylates 5a-p was developed by using Lawesson’s reagent, a very effective thionating reagent for carbonyl compounds, under conventional conditions and microwave irradiation. In order to gain a better understanding of the structure of the heterocycles obtained, theoretical calculations at the

  4-芳基取代的 1,4,5,6-四氢-2-甲基-6thioxopyridine-3-carboxylates 5a-p 的高效高通量合成是通过使用 Lawesson 试剂开发的，劳森试剂是一种非常有效的羰基化合物硫代试剂，在常规条件和微波辐射。为了更好地理解所得杂环的结构，进行了从头算水平的理论计算。
• A straightforward synthesis and structure of unprecedented iminium salts of dihydropyrido[3,2-e][1,3]thiazines
  作者：Margarita Suárez、Hector Novoa、Yamila Verdecia、Estael Ochoa、Amaury Alvarez、Rolando Pérez、Roberto Martínez-Alvarez、Dolores Molero、Carlos Seoane、Norbert M. Blaton、Oswald M. Peeters、Nazario Martín

  DOI：10.1016/j.tet.2005.11.054

  日期：2006.2

  Unprecedented 2-iminium chloride salts of 5,8-dihydro-2H-pyrido[3,2-e][1,3]thiazines derivatives (8) were easily synthesized in one step from the corresponding o-chloroformyl-1,4-dihydropyridime (2) and thiourea. The Structural Study has been carried out by X-ray crystallography and theoretical calculations at the B3LYP/6-31G* levels and reveal that the new salts exhibit appropriate structural features to behave as calcium channel modulators. (c) 2005 Elsevier Ltd. All rights reserved.