1,3-bis(tert-butyldimethylsilyl)isothianaphthene | 136132-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,3-bis(tert-butyldimethylsilyl)isothianaphthene
• 英文别名: (2-Benzothiene-1,3-diyl)bis[tert-butyl(dimethyl)silane]；tert-butyl-[3-[tert-butyl(dimethyl)silyl]-2-benzothiophen-1-yl]-dimethylsilane
• CAS: 136132-57-5
• 化学式: C₂₀H₃₄SSi₂
• 分子量: 362.727
• InChiKey: HRXHGLLOGOFODT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• 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：

  1,3-bis(tert-butyldimethylsilyl)isothianaphthene 、 邻苯二甲酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以73%的产率得到{2-[3-(tert-Butyl-dimethyl-silanyl)-benzo[c]thiophene-1-carbonyl]-phenyl}-[3-(tert-butyl-dimethyl-silanyl)-benzo[c]thiophen-1-yl]-methanone
  参考文献：
  名称：

  A new route to 1,3-disubstituted benzo[c]thiophenes

  摘要：

  A facile synthesis of 1,3-dichlorobenzo[c]thiophene 3 is described. Lithium-chlorine exchange of 3, followed by reaction with various electrophiles, provides a route to 1-acyl-3-chlorobenzo[c]thiophenes, as well as to the very stable 1,3-bis(tert-butyldimethylsilyl)benzo[c]thiophene (9). Compound 9 undergoes silyl replacement reactions with acylating agents, as well as an unusual oxidative desilylation by I2 or TiCl4, to give the capped disilylated dimer, trimer, and tetramer (16, 17, and 18) of benzo[c]thiophene.

  DOI：

  10.1021/jo00021a012
• 作为产物：
  描述：

  1,3-二氢-2-苯并噻吩-1,3-二酮 在 正丁基锂 、 五氯化磷 、 sodium iodide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 1,3-bis(tert-butyldimethylsilyl)isothianaphthene
  参考文献：
  名称：

  A new route to 1,3-disubstituted benzo[c]thiophenes

  摘要：

  A facile synthesis of 1,3-dichlorobenzo[c]thiophene 3 is described. Lithium-chlorine exchange of 3, followed by reaction with various electrophiles, provides a route to 1-acyl-3-chlorobenzo[c]thiophenes, as well as to the very stable 1,3-bis(tert-butyldimethylsilyl)benzo[c]thiophene (9). Compound 9 undergoes silyl replacement reactions with acylating agents, as well as an unusual oxidative desilylation by I2 or TiCl4, to give the capped disilylated dimer, trimer, and tetramer (16, 17, and 18) of benzo[c]thiophene.

  DOI：

  10.1021/jo00021a012

文献信息

• Optical Absorption Spectra of Aromatic Isothianaphthene Oligomers: Theory and Experiment
  作者：C. Quattrocchi、R. Lazzaroni、J. L. Bredas、R. Kiebooms、D. Vanderzande、J. Gelan、L. Van Meervelt

  DOI：10.1021/j100012a011

  日期：1995.3

  We investigate the optical absorption spectra of aromatic isothianaphthene oligomers, from the monomer up to the tetramer, with a combined theoretical and experimental approach. Geometry optimizations are performed with the semiempirical Austin Model 1 method on disilylated isothianaphthene oligomers of increasing chain length. The calculated geometric parameters are compared to those obtained from the single-crystal structure of the 3,3'-bis(tert-butyldimethylsilyl)-1,1'-biisothianaphthene. We then use the intermediate neglect of differential overlap method, coupled to single configuration interaction, to simulate theoretically the optical absorption spectra of the oligomers. The corresponding experimental spectra are recorded in n-hexane solution, and their evolution with chain length is discussed on the basis of the theoretical data.