(1E,4E)-4-(2-methyl-2-phenylhydrazono)-1-(p-tolyl)pent-1-en-3-one | 1357080-24-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,4E)-4-(2-methyl-2-phenylhydrazono)-1-(p-tolyl)pent-1-en-3-one
• CAS: 1357080-24-0
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: KQLJQHNSMOOBEG-ZWWNTAHPSA-N

反应信息

• 作为反应物：
  描述：

  (1E,4E)-4-(2-methyl-2-phenylhydrazono)-1-(p-tolyl)pent-1-en-3-one 在 三氟甲磺酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 2,3-dimethyl-5-(p-tolyl)pyrrol-1-methylphenylamine
  参考文献：
  名称：

  Synthesis of Pyrroles through a 4π-Electrocyclic Ring-Closure Reaction of 1-Azapentadienyl Cations

  摘要：

  1-Azapenta-1,4-diene-3-ols 4a-m are easily accessible from 1-azapenta-1,4-dien-3-ones 3a-i and organo-lithium compounds. Treatment of the compounds 4a-m with strong acid (triflic acid) generates 1-azapentadienyl cations in situ upon protonation at the hydroxyl oxygen atom and subsequent water elimination. The intermediate cations undergo facile 4 pi-electrocyclization under ambient condition to give diversely substituted pyrroles 6a-m in moderate to good yield. The product pyrrole 6k could be characterized by X-ray diffraction. Quantum chemical calculations were performed to elucidate the mechanism of this reaction with respect to starting compounds, transition states, and products. They support the proposed mechanism of a 4 pi-conrotatory Mobius-type electrocyclic ring-closure reaction.

  DOI：

  10.1021/jo202477h
• 作为产物：
  描述：

  3-(2-methyl-2-phenylhydrazono)butan-2-one 、 对甲基苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以44%的产率得到(1E,4E)-4-(2-methyl-2-phenylhydrazono)-1-(p-tolyl)pent-1-en-3-one
  参考文献：
  名称：

  Synthesis of Pyrroles through a 4π-Electrocyclic Ring-Closure Reaction of 1-Azapentadienyl Cations

  摘要：

  1-Azapenta-1,4-diene-3-ols 4a-m are easily accessible from 1-azapenta-1,4-dien-3-ones 3a-i and organo-lithium compounds. Treatment of the compounds 4a-m with strong acid (triflic acid) generates 1-azapentadienyl cations in situ upon protonation at the hydroxyl oxygen atom and subsequent water elimination. The intermediate cations undergo facile 4 pi-electrocyclization under ambient condition to give diversely substituted pyrroles 6a-m in moderate to good yield. The product pyrrole 6k could be characterized by X-ray diffraction. Quantum chemical calculations were performed to elucidate the mechanism of this reaction with respect to starting compounds, transition states, and products. They support the proposed mechanism of a 4 pi-conrotatory Mobius-type electrocyclic ring-closure reaction.

  DOI：

  10.1021/jo202477h