1-(benzyloxy)-5-(2-bromophenyl)-3-isopropyl-2-methylpyrrole | 1357080-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(benzyloxy)-5-(2-bromophenyl)-3-isopropyl-2-methylpyrrole
• 英文别名: 5-(2-Bromophenyl)-2-methyl-1-phenylmethoxy-3-propan-2-ylpyrrole
• CAS: 1357080-50-2
• 化学式: C₂₁H₂₂BrNO
• 分子量: 384.316
• InChiKey: VOXXQJGIKXXXBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2E,4E)-5-(2-bromophenyl)-3-hydroxy-3-isopropylpent-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30%的产率得到1-(benzyloxy)-5-(2-bromophenyl)-3-isopropyl-2-methylpyrrole
  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.