1,1,3,3-四氯-2-苯并噻吩 | 13169-42-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 1,1,3,3-四氯-2-苯并噻吩
• 英文名称: 1,1,3,3-tetrachlorothiophthalan
• 英文别名: 1,1,3,3-tetrachloro-1,3-dihydro-benzo[c]thiophene；1,1,3,3-Tetrachlor-thiophthalan；Benzo[c]thiophene, 1,1,3,3-tetrachloro-1,3-dihydro-；1,1,3,3-tetrachloro-2-benzothiophene
• CAS: 13169-42-1
• 化学式: C₈H₄Cl₄S
• 分子量: 273.998
• InChiKey: WHFXPMCWVCLWLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1,3,3-四氯-2-苯并噻吩 在 正丁基锂 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-chloro-3-(methoxycarbonyl)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
• 作为产物：
  描述：

  1,3-二氢-2-苯并噻吩-1,3-二酮 在 五氯化磷 、 三氯氧磷 作用下， 反应 15.0h， 以83.2%的产率得到1,1,3,3-四氯-2-苯并噻吩
  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

• Novel electron acceptors derived from isothianaphthene
  作者：Dominique Lorcy、Kerry D. Robinson、Yoshihiro Okuda、Jerry L. Atwood、Michael P. Cava

  DOI：10.1039/c39930000345

  日期：——

  The synthesis and properties of 1,3-dihydro-1,3-bis(dicyanomethylene)isothianaphthene 1 and its higher homologue 1,3-bis(1,3-dicyanovinylene)isothianaphthene 2 are reported; these compounds, which are the first electron acceptors of the isothianaphthene series, show electrochemical behaviour that contrasts with that of their thiophene analogues; the molecular structure of 1 was determined by X-ray analysis.

  报告了 1,3-二氢-1,3-双（二氰基亚甲基）异噻吩 1 及其高同系物 1,3-双（1,3-二氰基乙烯基）异噻吩 2 的合成和性质；这些化合物是异噻吩系列的第一个电子受体，其电化学行为与其噻吩类似物形成鲜明对比；通过 X 射线分析确定了 1 的分子结构。
• 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.
• US5530139A
  申请人：——

  公开号：US5530139A

  公开（公告）日：1996-06-25
• US5648453A
  申请人：——

  公开号：US5648453A

  公开（公告）日：1997-07-15
• US5688873A
  申请人：——

  公开号：US5688873A

  公开（公告）日：1997-11-18