5-acetyl-6-methyl-4-(3-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile

• 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-acetyl-6-methyl-4-(3-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile
• 英文别名: 5-acetyl-6-methyl-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-3-carbonitrile
• 化学式: C₁₅H₁₃N₃O₄
• mdl: MFCD01218415
• 分子量: 299.286
• InChiKey: VCNQQNJFPTUNOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-acetyl-6-methyl-4-(3-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile 在 硝酸 作用下， 反应 0.08h， 以42%的产率得到5-Acetyl-6-methyl-4-(3-nitro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
  参考文献：
  名称：

  2-吡啶酮衍生物的合成及强心活性

  摘要：

  近年来，在吡啶-2(IH)-酮中发现了新的强心物质（氨力农、米力农），用于治疗心功能不全。目前正在对在 5-杂基-、5-杂基烷基取代和含杂基的 4,5 和 5,6-退火吡啶-2-(iH)-one 系列中具有正性肌力作用的材料进行深入研究。然而，这些化合物的合成是复杂的。5-羰基取代的吡啶-2-(iH)-酮 [4, 5, 7-10] 也吸引了药理学兴趣，这些化合物是合成的起始化合物。

  DOI：

  10.1007/bf00772852
• 作为产物：
  描述：

  5-acetyl-2-amino-6-methyl-4-(3-nitrophenyl)-4H-pyran-3-carbonitrile 在 水 、 对甲苯磺酸 作用下， 反应 2.5h， 以88%的产率得到5-acetyl-6-methyl-4-(3-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile
  参考文献：
  名称：

  Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media

  摘要：

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.086

文献信息

• Imidazole-catalyzed Three-component Cascade Reaction for the Facile Synthesis of Highly Substituted 3,4-Dihydropyridin-2-one Derivatives
  作者：Zhiqiang Liu、Lu Tan、Qi Wu、Xianfu Lin

  DOI：10.1002/cjoc.201200500

  日期：2012.10

  one‐pot protocol for the synthesis of valuable 3,4‐dihydropyridin‐2‐ones from the condensation of aldehyde with cyanoacetamide and 1,3‐dicarbonyl compounds in the presence of imidazole was developed. A series of aldehydes and 1,3‐dicarbonyl compounds were employed to examine the scope of substrates for this protocol. This reaction proceeded through the formation of one ring and four new bonds (two CC, one

  开发了一种新颖的一锅法，用于在咪唑存在下由醛与氰基乙酰胺和1,3-二羰基化合物的缩合反应合成有价值的3,4-二氢吡啶-2-酮。一系列醛和1,3-二羰基化合物被用于检查该方案的底物范围。该反应通过一个环和四个新的键（两个C的形成进行 C，一种C 经由序列N，一个CC）涉及Knoevenagel缩合，Michael加成和分子内环化具有中度至良好的产率。所有新化合物均通过IR，1 H NMR，13 C NMR和HRMS表征。
• Synthesis of 3,4-dihydropyridin-2-one derivatives in convergent mode applying bio catalyst vitamin B1 and polymer supported catalyst PEG–SO3H from two different sets of building blocks
  作者：Koyel Pradhan、Pranabes Bhattacharyya、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.08.030

  日期：2012.10

  Two highly efficient, green protocols have been developed for the synthesis of 3,4-dihydropyridin-2-one derivatives from different starting materials exploring two reaction specific catalysts, vitamin B1 (VB1), and PEG–SO3H. VB1 catalyzed simple and convenient protocol has been developed for the synthesis of 3,4-dihydropyridin-2-one derivatives by the installation of aldehyde, cyanoacetamide, and 1

  两个高效，绿色协议已经开发了用于3,4-二氢吡啶-2-酮从不同的原料衍生物的探索两个反应特定的催化剂，维生素B合成1（VB 1）和PEG-SO 3 H. VB 1通过安装醛，氰基乙酰胺和1,3-二羰基化合物，已开发出催化简单方便的方案，用于合成3,4-二氢吡啶-2-酮衍生物。此外，通过形成4 H-吡喃核和PEG-SO 3 H催化的一锅法，将醛，丙二腈和1,3-二羰基化合物简单地结合起来，也合成了3,4-二氢吡啶-2-酮衍生物。重排。
• Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media
  作者：Pranabes Bhattacharyya、Koyel Pradhan、Sanjay Paul、Asish R. Das

  DOI：10.1016/j.tetlet.2012.06.086

  日期：2012.8

  A green and highly efficient protocol has been developed for the synthesis of 4H-pyran scaffolds installing a one-pot three-component coupling reaction of an aldehyde, malononitrile, and a 1,3-diketo compound using nano structured ZnO as the catalyst in aqueous alcoholic medium. A greener method to synthesize 3,4-dihydropyridin-2-one has also been developed by rearranging 4H-pyran derivatives in aqueous medium applying p-TSOH as the right catalyst source. A wide spectrum of functional groups was tolerated in both the developed synthetic protocols with good to excellent yield of the targeted molecules. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and cardiotonic activity of 2-pyridone derivatives
  作者：A. A. Krauze、V. N. Garalene、G. Ya. Dubur

  DOI：10.1007/bf00772852

  日期：1993.1

  recent years new cardiotonic materials (amrinone, milrinone) have been found among the pyridin-2(IH)-ones for the treatment of cardiac insufficiency. An intensive search is presently being carried out for materials with a positive inotropic effect in the 5-heteryl-, 5-heterylalkyl substituted, and heteryl-containing 4,5and 5,6-annelated pyridin-2-(iH)-one series. However, the synthesis of these compounds

  近年来，在吡啶-2(IH)-酮中发现了新的强心物质（氨力农、米力农），用于治疗心功能不全。目前正在对在 5-杂基-、5-杂基烷基取代和含杂基的 4,5 和 5,6-退火吡啶-2-(iH)-one 系列中具有正性肌力作用的材料进行深入研究。然而，这些化合物的合成是复杂的。5-羰基取代的吡啶-2-(iH)-酮 [4, 5, 7-10] 也吸引了药理学兴趣，这些化合物是合成的起始化合物。