5-acetyl-6-methyl-4-(4-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile | 1350309-92-0

• 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-(4-nitro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyridine-3-carbonitrile
• 英文别名: 5-acetyl-6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyridine-3-carbonitrile
• CAS: 1350309-92-0
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: UPNKPFHVMSHIKK-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

• 作为产物：
  描述：

  5-acetyl-2-amino-6-methyl-4-(4-nitrophenyl)-4H-pyran-3-carbonitrile 在 水 、 对甲苯磺酸 作用下， 反应 2.5h， 以87%的产率得到5-acetyl-6-methyl-4-(4-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。
• Chem-grafted Zn-SSA as an Efficient Heterogeneous Catalyst to Synthesize 2-Pyridinones
  作者：Li Jun Zhang、Xiang Zhang、Zhen Sheng You、Heng Li、Tian Feng、Wei Li Wang

  DOI：10.1007/s10562-016-1806-6

  日期：2016.10

  Chemo-selectivity is always a hard problem in preparing 2-pyridinones. Silica sulfuric acid (SSA) modified with zinc chloride (Zn-SSA) was found to be a high efficient heterogeneous catalyst to solve this problem. Under Zn-SSA and solvent-free conditions, the one-pot cyclocondensation of 1,3-dicarbonyl compounds, malononitrile and arylaldehydes to afford 2-pyridinones was conveniently implemented. The heterogeneous reaction was much efficient and promising in pharmaceutical study and industrial production.Improving chemo-selectivity is always a hard problem in preparing 2-pyridinones. Silica sulfuric acid (SSA) modified with zinc chloride (Zn-SSA) was found to be efficient heterogeneous catalyst to solve this problem. Under Zn-SSA and solvent-free conditions, the one-pot cyclocondensation of 1,3-dicarbonyl compounds, malononitrile and arylaldehydes to afford 2-pyridinones was conveniently implemented. The heterogeneous reaction was much efficient and promising in pharmaceutical study and industrial production.[GRAPHICS].