2-bromo-3-(4-hydroxybutyl)thiophene | 910108-11-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-bromo-3-(4-hydroxybutyl)thiophene
• 英文别名: 4-(2-Bromothiophen-3-yl)butan-1-ol
• CAS: 910108-11-1
• 化学式: C₈H₁₁BrOS
• 分子量: 235.145
• InChiKey: GIPMSMSKBKPAAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-3-(4-hydroxybutyl)thiophene 在 potassium fluoride 、 二(氰基苯)二氯化钯 、 silver nitrate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以70%的产率得到5,5'-dibromo-4,4'-bis(4-hydroxybutyl)-2,2'-bithiophene
  参考文献：
  名称：

  Palladium-Catalyzed C−H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined Oligothiophenes

  摘要：

  Synthesis of oligothiophenes of well-defined structures that possess 2-8 thiophene units is performed with a new synthetic strategy involving C-H homocoupling of bromothiophenes and cross-coupling with organostannanes. Tolerance of the carbon-bromine bond to the palladium-catalyzed C-H homocoupling results in oligothiophenes bearing C-Br bonds at the terminal thiophene rings, which allow further transformation by the catalysis of a transition-metal complex.

  DOI：

  10.1021/ja060749v
• 作为产物：
  描述：

  4-(3-thienyl)butanol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到2-bromo-3-(4-hydroxybutyl)thiophene
  参考文献：
  名称：

  Palladium-Catalyzed C−H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined Oligothiophenes

  摘要：

  Synthesis of oligothiophenes of well-defined structures that possess 2-8 thiophene units is performed with a new synthetic strategy involving C-H homocoupling of bromothiophenes and cross-coupling with organostannanes. Tolerance of the carbon-bromine bond to the palladium-catalyzed C-H homocoupling results in oligothiophenes bearing C-Br bonds at the terminal thiophene rings, which allow further transformation by the catalysis of a transition-metal complex.

  DOI：

  10.1021/ja060749v

文献信息

• Palladium-Catalyzed C−H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined Oligothiophenes
  作者：Masabumi Takahashi、Kentaro Masui、Hiroki Sekiguchi、Nobuhiko Kobayashi、Atsunori Mori、Masahiro Funahashi、Nobuyuki Tamaoki

  DOI：10.1021/ja060749v

  日期：2006.8.1

  Synthesis of oligothiophenes of well-defined structures that possess 2-8 thiophene units is performed with a new synthetic strategy involving C-H homocoupling of bromothiophenes and cross-coupling with organostannanes. Tolerance of the carbon-bromine bond to the palladium-catalyzed C-H homocoupling results in oligothiophenes bearing C-Br bonds at the terminal thiophene rings, which allow further transformation by the catalysis of a transition-metal complex.