2-hydroxy-3,5-dibromoacetophenone acetylhydrazone | 134627-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-3,5-dibromoacetophenone acetylhydrazone
• CAS: 134627-33-1
• 化学式: C₁₀H₁₀Br₂N₂O₂
• 分子量: 350.01
• InChiKey: TZQLIRBWRXUYTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3,5-dibromoacetophenone acetylhydrazone 在 lead(IV) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到2-acetyl-3,5-dibromoacetophenone
  参考文献：
  名称：

  Mechanism of the replacement of phenolic hydroxyl by carbonyl on lead tetraacetate treatment of o-hydroxyaryl ketone acylhydrazones

  摘要：

  A mechanistic study has been carried out on the reaction of acylhydrazones of omicron-hydroxyaryl ketones 6 with lead tetraacetate, which gives 1,2-diacylbenzenes 7 by a novel overall replacement of phenolic hydroxyl with an acyl group. Cross-over experiments demonstrate that the reaction is intramolecular. Oxygen-labeling evidence suggests that following formation of the 1,3,4-oxadiazoline 10, cyclization with loss of acetic acid leads to the tricyclic 1,3-dioxane 11. Elimination of nitrogen leads to an intermediate 12, which rearranges to the 1,2-diacylbenzene 7.

  DOI：

  10.1021/jo00017a013
• 作为产物：
  描述：

  3',5'-二溴-2'-羟基苯乙酮 、 乙酰肼 以 丙醇 为溶剂， 反应 20.0h， 以87%的产率得到2-hydroxy-3,5-dibromoacetophenone acetylhydrazone
  参考文献：
  名称：

  Mechanism of the replacement of phenolic hydroxyl by carbonyl on lead tetraacetate treatment of o-hydroxyaryl ketone acylhydrazones

  摘要：

  A mechanistic study has been carried out on the reaction of acylhydrazones of omicron-hydroxyaryl ketones 6 with lead tetraacetate, which gives 1,2-diacylbenzenes 7 by a novel overall replacement of phenolic hydroxyl with an acyl group. Cross-over experiments demonstrate that the reaction is intramolecular. Oxygen-labeling evidence suggests that following formation of the 1,3,4-oxadiazoline 10, cyclization with loss of acetic acid leads to the tricyclic 1,3-dioxane 11. Elimination of nitrogen leads to an intermediate 12, which rearranges to the 1,2-diacylbenzene 7.

  DOI：

  10.1021/jo00017a013