2-bromo-5-(tert-butyldimethylsilyl)thiophene | 207844-32-4

• 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: 2-bromo-5-(tert-butyldimethylsilyl)thiophene
• 英文别名: 5-(t-butyldimethylsilyl)-2-bromothiophene；Silane, (5-bromo-2-thienyl)(1,1-dimethylethyl)dimethyl-；(5-bromothiophen-2-yl)-tert-butyl-dimethylsilane
• CAS: 207844-32-4
• 化学式: C₁₀H₁₇BrSSi
• 分子量: 277.3
• InChiKey: KLEOAOPEERKQTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-5-(tert-butyldimethylsilyl)thiophene 在 正丁基锂 、 ZnCl₂-N,N,N’,N’-tetramethylethylenediamine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.58h， 生成 5-(tert-butyldimethylsilyl)-2-thienylzinc chloride
  参考文献：
  名称：

  S-Pechmann dye: a thiolactone-containing organic dye with a pronounced electron-accepting character and its solid-state photophysical properties

  摘要：

  我们合成了一种 Pechmann 染料的硫类似物。除了长波长吸收和荧光之外，它还在循环伏安法中显示出多种氧化还原过程和低还原电位。硫的尺寸效应是其增强电子接受特性的原因。

  DOI：

  10.1039/c3cc41007b
• 作为产物：
  描述：

  2-(叔丁基二甲基硅烷基)噻吩 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-bromo-5-(tert-butyldimethylsilyl)thiophene 、 3-bromo-2-t-butyldimethylsilyl-thiophene
  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

• A cyclic octithiophene containing β,β′-linkages
  作者：Kengo Asai、Aiko Fukazawa、Shigehiro Yamaguchi

  DOI：10.1039/c5cc00570a

  日期：——

  A cyclic octithiophene containing β,β′-linkages showed red-shifted fluorescence compared to α-quaterthiophene and a spin delocalization in the radical cation state.

  一种含有β,β′-连接的环状八硫代噻吩与α-四硫代噻吩相比，显示出红移荧光，并且在自由基阳离子状态下表现出自旋离域性。
• 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.
• S-Pechmann dye: a thiolactone-containing organic dye with a pronounced electron-accepting character and its solid-state photophysical properties
  作者：Aiko Fukazawa、Makoto Adachi、Ken Nakakura、Shohei Saito、Shigehiro Yamaguchi

  DOI：10.1039/c3cc41007b

  日期：——

  A sulfur analogue of a Pechmann dye has been synthesized. In addition to long-wavelength absorption and fluorescence, it showed multiple redox processes with low reduction potentials in cyclic voltammetry. The size effect of sulfur is responsible for its enhanced electron-accepting character.

  我们合成了一种 Pechmann 染料的硫类似物。除了长波长吸收和荧光之外，它还在循环伏安法中显示出多种氧化还原过程和低还原电位。硫的尺寸效应是其增强电子接受特性的原因。