4-(t-butoxy)-2-bromocyclopent-2-enone | 485401-53-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(t-butoxy)-2-bromocyclopent-2-enone
• 英文别名: 2-Bromo-4-[(2-methylpropan-2-yl)oxy]cyclopent-2-en-1-one；2-bromo-4-[(2-methylpropan-2-yl)oxy]cyclopent-2-en-1-one
• CAS: 485401-53-4
• 化学式: C₉H₁₃BrO₂
• 分子量: 233.105
• InChiKey: FXCHOTQPZBGHOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(t-butoxy)-2-bromocyclopent-2-enone 在 TEA 作用下， 以 乙醚 为溶剂， 反应 1.75h， 生成 1-(t-butoxy)-5-p-methoxyphenyl-1,4-pentadiene-3-one
  参考文献：
  名称：

  The Retro-Nazarov Reaction

  摘要：

  Treatment of 2-bromo-4-t-butoxy-2-cyclopentenone with an amine base in refluxing trifluoroethanol afforded a ring-opened product in moderate yield. The mechanism of the reaction has been formulated as a retro-Nazarov reaction in which an oxyallylic cation undergoes ring-opening to a dienone. Several other examples of the reaction have been established through a protocol involving the conjugate addition of an organocuprate to 2-bromo-4-t-butoxy-2-cyclopentenone followed by treatment of the adducts with base in refluxing trifluoroethanol.

  DOI：

  10.1021/ja028729q
• 作为产物：
  描述：

  4-(叔丁氧基)-2-环戊烯酮 在 溴 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 2.17h， 以97%的产率得到4-(t-butoxy)-2-bromocyclopent-2-enone
  参考文献：
  名称：

  The Retro-Nazarov Reaction

  摘要：

  Treatment of 2-bromo-4-t-butoxy-2-cyclopentenone with an amine base in refluxing trifluoroethanol afforded a ring-opened product in moderate yield. The mechanism of the reaction has been formulated as a retro-Nazarov reaction in which an oxyallylic cation undergoes ring-opening to a dienone. Several other examples of the reaction have been established through a protocol involving the conjugate addition of an organocuprate to 2-bromo-4-t-butoxy-2-cyclopentenone followed by treatment of the adducts with base in refluxing trifluoroethanol.

  DOI：

  10.1021/ja028729q

文献信息

• The Retro-Nazarov Reaction
  作者：Michael Harmata、Dong Reyoul Lee

  DOI：10.1021/ja028729q

  日期：2002.12.1

  Treatment of 2-bromo-4-t-butoxy-2-cyclopentenone with an amine base in refluxing trifluoroethanol afforded a ring-opened product in moderate yield. The mechanism of the reaction has been formulated as a retro-Nazarov reaction in which an oxyallylic cation undergoes ring-opening to a dienone. Several other examples of the reaction have been established through a protocol involving the conjugate addition of an organocuprate to 2-bromo-4-t-butoxy-2-cyclopentenone followed by treatment of the adducts with base in refluxing trifluoroethanol.