5-carboethoxy-6-methyl-4-(4-methoxyphenyl)-3,4-dihydropyridin-2-one | 398995-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-carboethoxy-6-methyl-4-(4-methoxyphenyl)-3,4-dihydropyridin-2-one
• 英文别名: ethyl 4-(4-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate；ethyl 4-(4-methoxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 398995-48-7
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: OUYXCOLQGYRMTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-carboethoxy-6-methyl-4-(4-methoxyphenyl)-3,4-dihydropyridin-2-one 在 titanium(IV) dioxide 作用下， 以 氯仿 为溶剂， 反应 1.4h， 生成 ethyl 4-(4-methoxyphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-5-carboxylate
  参考文献：
  名称：

  电子转移诱导的TiO 2锐钛矿型纳米粒子对2-氧代1,2,3,4-四氢吡啶的氧化：空间和电子取代效应

  摘要：

  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。

  DOI：

  10.1007/s13738-018-1407-y
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-甲氧基苯甲醛 在 Bi(NO₃)3*ZnCl₂*Al₂O₃ 乙酰胺 作用下， 以85%的产率得到5-carboethoxy-6-methyl-4-(4-methoxyphenyl)-3,4-dihydropyridin-2-one
  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

• 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。
• 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。
• 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。
• 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.