2-bromo-1-(4-bromophenyl)-3,4,4-trichlorobut-3-en-1-one | 1065470-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-(4-bromophenyl)-3,4,4-trichlorobut-3-en-1-one
• 英文别名: 2-Bromo-1-(4-bromophenyl)-3,4,4-trichlorobut-3-en-1-one
• CAS: 1065470-02-1
• 化学式: C₁₀H₅Br₂Cl₃O
• 分子量: 407.316
• InChiKey: XKOXTQLLCHFJIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(4-bromophenyl)-3,4,4-trichlorobut-3-en-1-one 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 0.5h， 以92%的产率得到2-bromo-1-(4-bromophenyl)-3,4,4-trichlorobut-3-en-1-one
  参考文献：
  名称：

  Synthesis of 3,4-dibromo-3,4,4-trichloro-1-phenylbutan-1-one and 1-aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones from 3,4,4-trichlorobut-3-enoic acid

  摘要：

  Bromination of 3,4,4-trichlorobut-3-enoic acid in boiling carbon tetrachloride led to the formation of 2-bromo-3,4,4-trichlorobut-3-enoic acid as a result of replacement of hydrogen in the CH2 group. The reaction at 40 degrees C involved the double C=C bond to give 3,4-dibromo-3,4,4-trichlorobutanoic acid. The brominated acids were converted into the corresponding chlorides which were used to acylate benzene, toluene, and bromobenzene according to Friedel-Crafts. The acylation was not selective, and only the reaction of 3,4-dibromo-3,4,4-trichlorobutanoyl chloride with benzene gave 3,4-dibromo-3,4,4-trichloro-1-phenylbutan-1-one as the only product. 1-Aryl-2-bromo-3,4,4-trichlorobut-3-en-1-ones were synthesized by bromination of the corresponding 1-aryl-3,4,4-trichlorobut-3-en-1-ones which were prepared previously by Friedel-Crafts acylation of substituted benzenes with 3,4,4-trichlorobut-3-enoyl chloride.

  DOI：

  10.1134/s107042800711005x