ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate | 313967-69-0

• 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-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate
• 英文别名: 5-carboethoxy-4-(4-nitrophenyl)-6-methyl-3,4-dihydropyridin-2-one；Ethyl 2-methyl-4-(4-nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate；ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 313967-69-0
• 化学式: C₁₅H₁₆N₂O₅
• 分子量: 304.302
• InChiKey: HCASZXKWEGJYAD-UHFFFAOYSA-N

物化性质

• 熔点：
  134-136°C
• 沸点：
  523.2±50.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

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-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate 在 劳森试剂 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 0.17h， 以93%的产率得到ethyl 2-methyl-4-(4-nitrophenyl)-6-thioxo-1,4,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  微波辐射下烷基4-芳基取代-2-甲基-6-硫代-1,4,5,6-四氢吡啶-3-羧酸酯的高通量制备

  摘要：

  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。

  DOI：

  10.3998/ark.5550190.0012.909
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 对硝基苯甲醛 在 Bi(NO₃)3*ZnCl₂*Al₂O₃ 缩二脲 作用下， 以66%的产率得到ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate
  参考文献：
  名称：

  Simple and efficient one‐pot synthesis of 3,4‐dihydro‐2‐pyridones via solid‐supported Bi(III)nitrate catalyzed double michael addition‐azaannulation

  摘要：

  Abstractmagnified image4‐Aryl‐5‐carboethoxy‐6‐methyl‐2,3‐dihydro‐2‐pyridones were obtained, in high yield, by heating ternary mixtures of appropriate aldehydes, ethylacetoacetate and compounds possessing NH2‐C=X functionality, in presence of immobilized Bi(III)nitrate and co‐catalyst Zn(II)chloride, under solventless conditions. The reaction proceeds smoothly at 140±5°C and seems to involve double Michael addition‐azaannulation.

  DOI：

  10.1002/jhet.5570450209

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。
• Electron-transfer induced oxidation of 2-oxo-1,2,3,4-tetrahydropyridines using TiO2 anatase-nanoparticles: steric and electronic substitution effects
  作者：Hamid Reza Memarian、Mahdieh Kalantari

  DOI：10.1007/s13738-018-1407-y

  日期：2018.9

  The steric and electronic effects of 4-substitution in various 4-aryl substituted 5-carboethoxy-2-oxo-1,2,3,4-tetrahydropyridines were investigated by exposing them to the UV-light in the presence or absence of the TiO2 anatase-nanoparticles. The results clearly indicate the effective presence of the photo-catalyst and also the electron-donating effect of 4-aryl substitution on drastic decreasing of

  通过在存在或不存在TiO的情况下将其暴露于紫外光下，研究了4-取代在各种4-芳基取代的5-碳乙氧基-2-氧-1,2,3,4-四氢吡啶中的空间和电子效应2种锐钛矿型纳米粒子。结果清楚地表明光催化剂的有效存在，以及4-芳基取代的电子给体作用对辐照时间的急剧减少。DFT计算研究和循环伏安法测量结果支持了有关4取代基电子性质的实验结果。
• Steric and electronic substitution effects on the thermal oxidation of 5-carboethoxy-2-oxo-1,2,3,4-tetrahydropyridines
  作者：Hamid Reza Memarian、Mahdieh Kalantari

  DOI：10.1007/s13738-016-0966-z

  日期：2017.1

  by the hydroxyl radical formed in situ is occurred in the rate determining step, which is influenced by the steric and electronic effects of the substituted aryl group attached to this atom and also the stability of the radical intermediate involved in the oxidation reaction. The experimental results were supported by the computational studies.

  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。
• Simple and efficient one‐pot synthesis of 3,4‐dihydro‐2‐pyridones via solid‐supported Bi(III)nitrate catalyzed double michael addition‐azaannulation
  作者：Jagjeet Singh、Summon Koul、Rattan L. Sharma、Tej K. Razdan、Ajay P. S. Pannu

  DOI：10.1002/jhet.5570450209

  日期：2008.3

  Abstractmagnified image4‐Aryl‐5‐carboethoxy‐6‐methyl‐2,3‐dihydro‐2‐pyridones were obtained, in high yield, by heating ternary mixtures of appropriate aldehydes, ethylacetoacetate and compounds possessing NH2‐C=X functionality, in presence of immobilized Bi(III)nitrate and co‐catalyst Zn(II)chloride, under solventless conditions. The reaction proceeds smoothly at 140±5°C and seems to involve double Michael addition‐azaannulation.