5-carboethoxy-6-methyl-4-(2-chlorophenyl)-3,4-dihydropyridin-2-one | 176383-21-4

• 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: 5-carboethoxy-6-methyl-4-(2-chlorophenyl)-3,4-dihydropyridin-2-one
• 英文别名: 5-ethoxycarbonyl-6-methyl-4-(2-chlorophenyl)-3,4-dihydropyridone；Ethyl 4-(2-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylate；ethyl 4-(2-chlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 176383-21-4
• 化学式: C₁₅H₁₆ClNO₃
• 分子量: 293.75
• InChiKey: XVLGEVREJURRPT-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C(Solv: ethanol (64-17-5))
• 沸点：
  457.2±45.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-carboethoxy-6-methyl-4-(2-chlorophenyl)-3,4-dihydropyridin-2-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以60%的产率得到4-(2-chlorophenyl)-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：

  乙酰乙酸乙酯 、 2-氯苯甲醛 在 Bi(NO₃)3*ZnCl₂*Al₂O₃ 乙酰胺 作用下， 以76%的产率得到5-carboethoxy-6-methyl-4-(2-chlorophenyl)-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

• 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。
• 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。
• 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。
• 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.