5-bromo-3',4'-dibutyl-5''-methyl-2,2':5',2''-terthiophene | 950526-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-bromo-3',4'-dibutyl-5''-methyl-2,2':5',2''-terthiophene
• CAS: 950526-28-0
• 化学式: C₂₁H₂₅BrS₃
• 分子量: 453.532
• InChiKey: COHUZBLRMHZWAG-UHFFFAOYSA-N

物化性质

• 沸点：
  481.5±45.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.96
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-bromo-3',4'-dibutyl-5''-methyl-2,2':5',2''-terthiophene 在 正丁基锂 、 iron(III)-acetylacetonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 40.5h， 以48%的产率得到3',4',3'''',4''''-tetrabutyl-5,5'''''-dimethyl-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene
  参考文献：
  名称：

  Reverse Selectivity in m-CPBA Oxidation of Oligothiophenes to Sulfones

  摘要：

  Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.

  DOI：

  10.1021/ol071369x
• 作为产物：
  描述：

  3',4'-dibutyl-5-methyl-2,2':5',2''-terthiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 溶剂黄146 、 丙酮 为溶剂， 以84%的产率得到5-bromo-3',4'-dibutyl-5''-methyl-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Reverse Selectivity in m-CPBA Oxidation of Oligothiophenes to Sulfones

  摘要：

  Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.

  DOI：

  10.1021/ol071369x