2-acetyl-3,5-dibromoacetophenone | 134627-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-3,5-dibromoacetophenone
• 英文别名: 1-(2-Acetyl-3,5-dibromophenyl)ethanone
• CAS: 134627-34-2
• 化学式: C₁₀H₈Br₂O₂
• 分子量: 319.98
• InChiKey: BJGCTQPBQFHGDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-acetyl-3,5-dibromoacetophenone 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以43%的产率得到1-(3,5-Dibromo-2-{1-[(E)-hydroxyimino]-ethyl}-phenyl)-ethanone oxime
  参考文献：
  名称：

  Electron impact mass spectra of some dioximes ofo-diacyl benzenes

  摘要：

  AbstractThe electron impact mass spectra of the new synthesized dioximes of o‐diacyl benzenes (2) are reported. In addition to the molecular ion, characteristic peaks appear at values corresponding to the [M − OH] +, [M − NOH]+ and [M − NHOH]+ ions. No initial dehydration of the molecular ion has been observed.

  DOI：

  10.1002/oms.1210261015
• 作为产物：
  描述：

  3',5'-二溴-2'-羟基苯乙酮 在 lead(IV) acetate 作用下， 以 四氢呋喃 、 丙醇 为溶剂， 反应 22.0h， 生成 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

文献信息

• Mechanism of the replacement of phenolic hydroxyl by carbonyl on lead tetraacetate treatment of o-hydroxyaryl ketone acylhydrazones
  作者：Alan R. Katritzky、Philip A. Harris、Antigoni Kotali

  DOI：10.1021/jo00017a013

  日期：1991.8

  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.
• Electron impact mass spectra of some dioximes ofo-diacyl benzenes
  作者：Antigoni Kotali

  DOI：10.1002/oms.1210261015

  日期：1991.10

  AbstractThe electron impact mass spectra of the new synthesized dioximes of o‐diacyl benzenes (2) are reported. In addition to the molecular ion, characteristic peaks appear at values corresponding to the [M − OH] +, [M − NOH]+ and [M − NHOH]+ ions. No initial dehydration of the molecular ion has been observed.