(2E,4E)-5-(4-chlorophenyl)-3-hydroxy-3-(p-tolyl)pent-4-en-2-one O-benzyl oxime | 1357080-38-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E,4E)-5-(4-chlorophenyl)-3-hydroxy-3-(p-tolyl)pent-4-en-2-one O-benzyl oxime
• CAS: 1357080-38-6
• 化学式: C₂₅H₂₄ClNO₂
• 分子量: 405.924
• InChiKey: ABCSAKLNSDRKDZ-ZINJUWMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(4-chlorophenyl)-3-hydroxy-3-(p-tolyl)pent-4-en-2-one O-benzyl oxime 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到1-(benzyloxy)-5-(4-chlorophenyl)-2-methyl-3-(p-tolyl)pyrrole
  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：

  4-氯苯甲醛 在 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2E,4E)-5-(4-chlorophenyl)-3-hydroxy-3-(p-tolyl)pent-4-en-2-one O-benzyl oxime
  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