2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester | 130734-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester
• 英文别名: methyl 2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carboxylate；methyl 1,2,3,4-tetrahydo-6-methyl-2-oxo-4-phenylpyridine-5-carboxylate；4-phenyl-5-methoxycarbonyl-6-methyl-3,4-dihydropyridin-2(1H)-one；2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester；methyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-1H-pyridine-5-carboxylate
• CAS: 130734-36-0
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: HDIJQUVQZCXAKF-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198 °C
• 沸点：
  438.0±45.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 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：

  2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester 在 sodium perchlorate 作用下， 以100%的产率得到methyl 2-methyl-6-oxo-4-phenyl-1,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  5-羧基-6-甲基-3,4-二氢-2(1H)-吡啶酮衍生物的合成及其电化学氧化成2-吡啶酮

  摘要：

  摘要 合成了一系列不同取代的5-羧基-6-甲基-3,4-二氢-2(1H)-吡啶酮衍生物，并通过循环伏安法测定了它们的氧化电位。得到的 2-吡啶酮结构和在尝试合成 4-(2-羟基苯基) 取代的 3,4-二氢-2(1H)-吡啶酮的过程中形成的三环杂环通过单晶 X 射线晶体学证实。

  DOI：

  10.1016/j.cplett.2016.02.045
• 作为产物：
  描述：

  methyl (E)-3-[[(E)-3-phenylprop-2-enoyl]amino]but-2-enoate 在 三乙胺 作用下， 生成 2-methyl-6-oxo-4-phenyl-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Mahalanabis, Kumar K.; Mukherjee, Attreyee, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 2, p. 291 - 302

  摘要：

  DOI：

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。
• N-Heterocyclic Carbene Catalyzed Reactions of α-Bromo-α,β-unsaturated Aldehydes/α,β-Dibromoaldehydes with 1,3-Dinucleophilic Reagents
  作者：Changsheng Yao、Donglin Wang、Jun Lu、Tuanjie Li、Weihui Jiao、Chenxia Yu

  DOI：10.1002/chem.201103358

  日期：2012.2.13

  Carbenes ring true: N‐Heterocyclic carbene (NHC) catalyzed reactions of α‐bromo‐α,β‐unsaturated aldehydes/α,β‐dibromoaldehydes with 1,3‐dinucleophilic reagents, such as 1,3‐dicarbonyl compounds, β‐enamino ketones, and β‐enamino esters through umpolung processes gave functionalized 3,4‐dihydropyranones and 3,4‐dihydropyridinones (see scheme). The availability of the starting materials, lack of external

  Carbenes正确：N-杂环卡宾（NHC）催化α-溴代α，β-不饱和醛/α，β-二溴代醛与1,3-二亲核试剂（例如1,3-二羰基化合物，β-烯氨基）的反应通过umpolung工艺获得的酮和β-烯胺酯可得到功能化的3,4-二氢吡喃酮和3,4-二氢吡啶酮（参见方案）。原材料的可用性，缺乏外部氧化剂以及产品的实用性使该策略具有吸引力。
• Acid-catalyzed, regioselective [3 + 3] annulation of enaminones and α-substituted cinnamic acids: access to 3,4-dihydropyridones and 2-piperidinones
  作者：Sivanna Chithanna、Animesh Roy、Ding-Yah Yang

  DOI：10.1039/d1ob01115d

  日期：——

  acid-catalyzed Michael addition of enaminones to electron-deficient α-substituted cinnamic acids followed by lactamization, whereas the latter was synthesized by the same methodology except that cinnamic acids were replaced with coumarin 3-carboxylic acids. A unique regioselective reactivity of the enaminones toward different cinnamic acid derivatives is described.

  报道了一种合成结构多样的 3,4-二氢吡啶酮和 2-哌啶酮的有效策略。前者是通过将烯胺酮与缺电子α-取代的肉桂酸进行酸催化迈克尔加成，然后进行内酰胺化来制备的，而后者是通过相同的方法合成的，只是肉桂酸被香豆素 3-羧酸取代。描述了烯胺酮对不同肉桂酸衍生物的独特区域选择性反应性。
• 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。