1-[4-Bromo-3-(4-bromo-2-octanoyl-5-trimethylsilylthiophen-3-yl)-5-trimethylsilylthiophen-2-yl]octan-1-one | 1186018-10-9

• 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: 1-[4-Bromo-3-(4-bromo-2-octanoyl-5-trimethylsilylthiophen-3-yl)-5-trimethylsilylthiophen-2-yl]octan-1-one
• CAS: 1186018-10-9
• 化学式: C₃₀H₄₈Br₂O₂S₂Si₂
• 分子量: 720.821
• InChiKey: UGTQNLKVKVHHDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.18
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-Bromo-3-(4-bromo-2-octanoyl-5-trimethylsilylthiophen-3-yl)-5-trimethylsilylthiophen-2-yl]octan-1-one 在 titanium(III) chloride 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 反应 21.0h， 以71%的产率得到(1,8-Dibromo-4,5-diheptyl-2-trimethylsilylthieno[3,2-e][1]benzothiol-7-yl)-trimethylsilane
  参考文献：
  名称：

  Functionalized Thiophene-Based [7]Helicene: Chirooptical Properties versus Electron Delocalization

  摘要：

  The functionalized, enantiomerically pure [7]helicene 1 derived from bis(benzodithiophene) functionalized with four heptyl groups is prepared from 1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene building block 2. Such [7]helicene structure, functionalized with bromines at the terminal positions of the helicene inner rim and multiple solubilizing alkyl groups, is an attractive building block for long [n]helicenes and oligo[7]helicenes. Chirooptical properties and the degree of electron delocalization are determined and compared to those of analogous carbon-sulfur [7]helicene and [7]helicenes derived from benzodithiophene to provide a correlation between chirooptical properties and the degree of electron delocalization. [7]Helicene 1 possesses a moderately increased electron delocalization, but its chirooptical properties are similar to those for analogous [7]helicenes with relatively lower electron delocalization, indicating that chirooptical properties are not significantly affected by electron delocalization for this series of [7]helicenes. Molecular structures of racemic [7]helicene 1 and its benzodithiophene building block 2 are confirmed by single-crystal X-ray analysis. Crystals of 2 are chiral and adopt the shape of long, flexible, flat needles that can be readily bent.

  DOI：

  10.1021/jo901769c
• 作为产物：
  描述：

  N-甲氧基-N-甲基辛酰胺 、 4,4'-dibromo-5,5'-di(trimethylsilyl)-3,3'-dithienyl 在 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 4.5h， 以53%的产率得到1-[4-Bromo-3-(4-bromo-2-octanoyl-5-trimethylsilylthiophen-3-yl)-5-trimethylsilylthiophen-2-yl]octan-1-one
  参考文献：
  名称：

  Functionalized Thiophene-Based [7]Helicene: Chirooptical Properties versus Electron Delocalization

  摘要：

  The functionalized, enantiomerically pure [7]helicene 1 derived from bis(benzodithiophene) functionalized with four heptyl groups is prepared from 1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene building block 2. Such [7]helicene structure, functionalized with bromines at the terminal positions of the helicene inner rim and multiple solubilizing alkyl groups, is an attractive building block for long [n]helicenes and oligo[7]helicenes. Chirooptical properties and the degree of electron delocalization are determined and compared to those of analogous carbon-sulfur [7]helicene and [7]helicenes derived from benzodithiophene to provide a correlation between chirooptical properties and the degree of electron delocalization. [7]Helicene 1 possesses a moderately increased electron delocalization, but its chirooptical properties are similar to those for analogous [7]helicenes with relatively lower electron delocalization, indicating that chirooptical properties are not significantly affected by electron delocalization for this series of [7]helicenes. Molecular structures of racemic [7]helicene 1 and its benzodithiophene building block 2 are confirmed by single-crystal X-ray analysis. Crystals of 2 are chiral and adopt the shape of long, flexible, flat needles that can be readily bent.

  DOI：

  10.1021/jo901769c