N-benzyl-5-(benzylamino)-3-oxohex-4-enamide | 84259-92-7

• 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: N-benzyl-5-(benzylamino)-3-oxohex-4-enamide
• CAS: 84259-92-7
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: QDAUMHJFJBQJEX-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C(Solv: ethanol (64-17-5))
• 沸点：
  575.4±50.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-5-(benzylamino)-3-oxohex-4-enamide 、 N,N-二甲基甲酰胺二甲基缩醛 以 甲苯 为溶剂， 反应 24.0h， 以58%的产率得到N,1-dibenzyl-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  A novel, two-step synthesis of 4-pyridone-3-carboxamides from 2-cyano-4-pyrones

  摘要：

  Reactions of 2-cyano-6-(trifluoromethyl)-4-pyrone, 2-cyano-4-pyrone, and 2-cyano-6-methyl-4-pyrone with aliphatic and aromatic amines in ethanol at -20 degrees C for 2-21 days gave 5-amino-3-oxopent-4-enamides in 28-78% yields, which were cyclized with DMF-DMA in toluene under ambient conditions to afford 4-pyridone-3-carboxamides in 31-70% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.132
• 作为产物：
  描述：

  在 吡啶 、 三氟乙酸酐 作用下， 以 乙醇 为溶剂， 生成 N-benzyl-5-(benzylamino)-3-oxohex-4-enamide
  参考文献：
  名称：

  A novel, two-step synthesis of 4-pyridone-3-carboxamides from 2-cyano-4-pyrones

  摘要：

  Reactions of 2-cyano-6-(trifluoromethyl)-4-pyrone, 2-cyano-4-pyrone, and 2-cyano-6-methyl-4-pyrone with aliphatic and aromatic amines in ethanol at -20 degrees C for 2-21 days gave 5-amino-3-oxopent-4-enamides in 28-78% yields, which were cyclized with DMF-DMA in toluene under ambient conditions to afford 4-pyridone-3-carboxamides in 31-70% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.132

文献信息

• Synthesis of 6-Substituted-4-Hydroxy-2-pyridinones via Intramolecular Ketene Trapping of Functionalized Enamine-Dioxinones
  作者：Bhavesh H. Patel、Andrew M. Mason、Anthony G. M. Barrett

  DOI：10.1021/ol202028t

  日期：2011.10.7

  The synthesis of various 6-substituted-4-hydroxy-2-pyridinones is reported. The functionalized keto-dioxinones were constructed via a diethylzinc mediated crossed Claisen condensation reaction and subsequent enamine formation, thermolysis, and cyclization–aromatization providing the pyridinone unit.

  报道了各种6-取代的-4-羟基-2-吡啶酮的合成。通过二乙基锌介导的交叉克莱森缩合反应和随后的烯胺形成，热解和环化芳香化反应构建了功能化的酮二恶酮，从而提供了吡啶酮单元。