tetrabromobutatriene | 79426-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetrabromobutatriene
• CAS: 79426-22-5
• 化学式: C₄Br₄
• 分子量: 367.66
• InChiKey: DACODXZYLLFXCN-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  251.0±40.0 °C(Predicted)
• 密度：
  2.667±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  苯硼酸 、 tetrabromobutatriene 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以11%的产率得到1,1,4-tribromo-2-phenylbut-1-en-3-yne
  参考文献：
  名称：

  Tetrabromobutatriene:  Completing the Perhalocumulene Series

  摘要：

  Tetrabromobutatriene, C4Br4, can be prepared directly from dibromobutadiyne by reaction with Br-2 at -25 degreesC in concentrated hexanes solution. The cumulene precipitates out of the reaction mixture as a yellow powder. Under palladium-catalyzed coupling conditions, C4Br4 can undergo allylic rearrangement, giving a mixture of products, including some with butenyne backbones. However, in furan solution, C4Br4 reacts cleanly at its central double bond to give the furan Diels-Alder adduct. Under Suzuki conditions, this adduct reacts at the furan double bond rather than at bromide.

  DOI：

  10.1021/ol049734x
• 作为产物：
  描述：

  dibromobutadiyne 在 溴 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以36%的产率得到tetrabromobutatriene
  参考文献：
  名称：

  Tetrabromobutatriene:  Completing the Perhalocumulene Series

  摘要：

  Tetrabromobutatriene, C4Br4, can be prepared directly from dibromobutadiyne by reaction with Br-2 at -25 degreesC in concentrated hexanes solution. The cumulene precipitates out of the reaction mixture as a yellow powder. Under palladium-catalyzed coupling conditions, C4Br4 can undergo allylic rearrangement, giving a mixture of products, including some with butenyne backbones. However, in furan solution, C4Br4 reacts cleanly at its central double bond to give the furan Diels-Alder adduct. Under Suzuki conditions, this adduct reacts at the furan double bond rather than at bromide.

  DOI：

  10.1021/ol049734x