(2E,3E)-5-(1-(benzyloxy)-4,5-dimethyl-2-phenylpyrrol-3-yl)-3-methyl-5-phenylpent-3-en-2-one O-benzyl oxime | 1357080-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (2E,3E)-5-(1-(benzyloxy)-4,5-dimethyl-2-phenylpyrrol-3-yl)-3-methyl-5-phenylpent-3-en-2-one O-benzyl oxime
• 英文别名: (E,E)-5-(4,5-dimethyl-2-phenyl-1-phenylmethoxypyrrol-3-yl)-3-methyl-5-phenyl-N-phenylmethoxypent-3-en-2-imine
• CAS: 1357080-58-0
• 化学式: C₃₈H₃₈N₂O₂
• 分子量: 554.732
• InChiKey: AKKODFDIKPUDNS-VCJOMYQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(benzyloxyimino)-1-phenylpent-1-en-3-one 在 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2E,3E)-5-(1-(benzyloxy)-4,5-dimethyl-2-phenylpyrrol-3-yl)-3-methyl-5-phenylpent-3-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

文献信息

• Synthesis of Pyrroles through a 4π-Electrocyclic Ring-Closure Reaction of 1-Azapentadienyl Cations
  作者：Rishikesh Narayan、Roland Fröhlich、Ernst-Ulrich Würthwein

  DOI：10.1021/jo202477h

  日期：2012.2.17

  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.