2-cyano-3-methyl-5-(1-pyrrolidinyl)-2,4-hexadienamide | 255846-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-cyano-3-methyl-5-(1-pyrrolidinyl)-2,4-hexadienamide
• 英文别名: (2E,4E)-2-cyano-3-methyl-5-pyrrolidin-1-ylhexa-2,4-dienamide
• CAS: 255846-05-0
• 化学式: C₁₂H₁₇N₃O
• 分子量: 219.286
• InChiKey: JTXGAQJDABXYNA-PPZOTWNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-3-methyl-5-(1-pyrrolidinyl)-2,4-hexadienamide 以 四氢呋喃 为溶剂， 生成 3-氰基-4,6-二甲基-2-羟基吡啶
  参考文献：
  名称：

  Regioselective Synthesis of 2(1H)-Pyridinones from β-Aminoenones and Malononitrile. Reaction Mechanism

  摘要：

  The identification of some intermediates of the reactions between beta-aminoenones and malononitrile to give 2(1H)-pyridinones has allowed us to obtain valuable information concerning its mechanism. These reactions begin with a conjugated addition of the nitrile to the enone followed by elimination. The compounds thus obtained cyclize to nonisolable 2H-pyran-2-imine. This afforded 2(1H)-pyridinones by ring opening to unsaturated aminoamides followed by cyclization (Dimroth-type rearrangement).

  DOI：

  10.1021/jo991121o
• 作为产物：
  描述：

  4-tetrahydro-1H-pyrrol-1-ylpent-3-en-2-one 、 丙二腈 以 乙醇 为溶剂， 生成 2-cyano-3-methyl-5-(1-pyrrolidinyl)-2,4-hexadienamide 、 2-cyano-3-methyl-5-(1-pyrrolidinyl)-2,4-hexadienamide
  参考文献：
  名称：

  Regioselective Synthesis of 2(1H)-Pyridinones from β-Aminoenones and Malononitrile. Reaction Mechanism

  摘要：

  The identification of some intermediates of the reactions between beta-aminoenones and malononitrile to give 2(1H)-pyridinones has allowed us to obtain valuable information concerning its mechanism. These reactions begin with a conjugated addition of the nitrile to the enone followed by elimination. The compounds thus obtained cyclize to nonisolable 2H-pyran-2-imine. This afforded 2(1H)-pyridinones by ring opening to unsaturated aminoamides followed by cyclization (Dimroth-type rearrangement).

  DOI：

  10.1021/jo991121o