7,7-dimethyl-2,5-dioxo-4-phenyl-1,2,3,4,5,6,7,8-octahydro-quinoline-3-carbonitrile | 300844-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7,7-dimethyl-2,5-dioxo-4-phenyl-1,2,3,4,5,6,7,8-octahydro-quinoline-3-carbonitrile
• 英文别名: 7,7-dimethyl-2,5-dioxo-4-phenyl-3,4,6,8-tetrahydro-1H-quinoline-3-carbonitrile
• CAS: 300844-19-3
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: NGUXDLYFLLKSTH-UHFFFAOYSA-N

物化性质

• 沸点：
  561.5±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 在 水 、 对甲苯磺酸 作用下， 反应 6.0h， 以82%的产率得到7,7-dimethyl-2,5-dioxo-4-phenyl-1,2,3,4,5,6,7,8-octahydro-quinoline-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

• 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.