Methyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate | 177763-74-5

• 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: Methyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate
• 英文别名: 4-(4-methoxycarbonylphenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-one；Methyl 4-[4-(methoxycarbonyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate；methyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 177763-74-5
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: IGHUKMISNZCQDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate 在 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 6-methoxycarbonyl-5-(4-methoxycarbonylphenyl)-7-methyl-5,8-dihydro-2H-pyrido[3,2-e][1,3]thiazin-2-iminium chloride
  参考文献：
  名称：

  A straightforward synthesis and structure of unprecedented iminium salts of dihydropyrido[3,2-e][1,3]thiazines

  摘要：

  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.

  DOI：

  10.1016/j.tet.2005.11.054
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 乙酰乙酸甲酯 、 对甲酰基苯甲酸甲酯 在 乙酸铵 作用下， 反应 0.25h， 以89%的产率得到Methyl 4-(4-methoxycarbonylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyridine-5-carboxylate
  参考文献：
  名称：

  微波辐射下无溶剂合成4-芳基取代的5-烷氧基羰基-6-甲基-3,4-二氢吡啶酮

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(03)00625-7

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。
• 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。
• 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.
• 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.