4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-one | 176383-18-9

• 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: 4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-one
• 英文别名: methyl 4-(2-chlorophenyl)-6-methyl-3,4-dihydropyridone-5-carboxylate；Methyl 4-(2-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate；methyl 4-(2-chlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 176383-18-9
• 化学式: C₁₄H₁₄ClNO₃
• 分子量: 279.723
• InChiKey: DQQKMWMDDQIQDK-UHFFFAOYSA-N

物化性质

• 熔点：
  198-199 °C
• 沸点：
  447.5±45.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-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56%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：

  甲醇 、 5-(2-氯苄亚基)-2,2-二甲基-1,3-二恶烷-4,6-二酮 、 1,3-dioxin-4-one 生成 4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  4-芳基取代的5-羧基-6-甲基-3,4-二氢吡啶酮的固相合成

  摘要：

  通过固相合成，使用Wang树脂从固定的β-酮酸酯中进行了固相合成，并进一步进行了Hantzsch型杂环化反应，从而有效地制备了3,4-二氢-2-吡啶酮。

  DOI：

  10.1016/s0040-4039(01)02172-4

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。
• 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。
• 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.
• Synthesis of methyl 4-aryl-6-methyl-4,7-dihydro-1H-pyrazolo-[3,4-b]pyridine-5-carboxylates from methyl 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates
  作者：Yamila Verdecia、Margarita Suárez、Alhmed Morales、Elena Rodríguez、Estael Ochoa、Leandro González、Nazario Martín、Margarita Quinteiro、Carlos Seoane、José L. Soto

  DOI：10.1039/p19960000947

  日期：——

  Novel methyl 4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5 3a-e have been prepared in a two step procedure from the readily available 2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylates 1a-e by treatment with the Vilsmeier-Haack reagent. Further treatment of the novel o-chloroformyl substituted methyl 1,4-dihydropyridine-5-carboxylates 2a-e with hydrazine affords the corresponding methyl pyrazolo[3,4-b]pyridine-5-carboxylates in good yields. Semiempirical calculations reveal a favoured geometry with a boat conformation in the dihydropyridine system and a planar pyrazole ring.