(5'-Bromo-1,1-dioxo-1H-1λ⁶-[2,2']bithiophenyl-5-yl)-tert-butyl-dimethyl-silane | 211737-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (5'-Bromo-1,1-dioxo-1H-1λ⁶-[2,2']bithiophenyl-5-yl)-tert-butyl-dimethyl-silane
• 英文别名: [5-(5-Bromothiophen-2-yl)-1,1-dioxothiophen-2-yl]-tert-butyl-dimethylsilane
• CAS: 211737-31-4
• 化学式: C₁₄H₁₉BrO₂S₂Si
• 分子量: 391.425
• InChiKey: BVEDSUJGBDBWJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-Butyl-dimethyl-[2,2';5',2'']terthiophen-5-yl-silane 、 (5'-Bromo-1,1-dioxo-1H-1λ⁶-[2,2']bithiophenyl-5-yl)-tert-butyl-dimethyl-silane 在 tetrakis(triphenylarsine)palladium(0) 正丁基锂 、 三丁基氯化锡 作用下， 生成 5,5''''-Bis-(tert-butyl-dimethyl-silanyl)-[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene 1,1-dioxide
  参考文献：
  名称：

  Oligothiophene S,S-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes

  摘要：

  Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)(4) generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G* ab initio calculations on 2,2'-bithiophene and the corresponding mono- and bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the pi,pi* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.

  DOI：

  10.1021/jo980507g
• 作为产物：
  描述：

  2-(叔丁基二甲基硅烷基)噻吩 在 tetrakis(triphenylarsine)palladium(0) N-溴代丁二酰亚胺(NBS) 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 61.0h， 生成 (5'-Bromo-1,1-dioxo-1H-1λ⁶-[2,2']bithiophenyl-5-yl)-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Oligothiophene S,S-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes

  摘要：

  Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)(4) generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G* ab initio calculations on 2,2'-bithiophene and the corresponding mono- and bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the pi,pi* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.

  DOI：

  10.1021/jo980507g

文献信息

• Oligothiophene <i>S</i>,<i>S</i>-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes
  作者：G. Barbarella、L. Favaretto、G. Sotgiu、M. Zambianchi、L. Antolini、O. Pudova、A. Bongini

  DOI：10.1021/jo980507g

  日期：1998.8.1

  Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)(4) generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G* ab initio calculations on 2,2'-bithiophene and the corresponding mono- and bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the pi,pi* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.