11-(2-benzo[b]thienyl)cyclopenta-[1,2-b:4,3-b']-dibenzothiophene | 503835-62-9

• 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: 11-(2-benzo[b]thienyl)cyclopenta-[1,2-b:4,3-b']-dibenzothiophene
• 英文别名: 6-benzo[b]thien-2-yl-6H-cyclopenta[1,2-b:4,3-b']bis[1]benzothiophene；11-(1-Benzothiophen-2-yl)-9,13-dithiapentacyclo[10.7.0.02,10.03,8.014,19]nonadeca-1(12),2(10),3,5,7,14,16,18-octaene
• CAS: 503835-62-9
• 化学式: C₂₅H₁₄S₃
• 分子量: 410.584
• InChiKey: PQSDFAIHAUBQFE-UHFFFAOYSA-N

物化性质

• 熔点：
  228-229 °C(Solv: chloroform (67-66-3))
• 沸点：
  620.7±50.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-(2-benzo[b]thienyl)cyclopenta-[1,2-b:4,3-b']-dibenzothiophene 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 11-(1-Benzothiophen-2-yl)-11-[11-(1-benzothiophen-2-yl)-9,13-dithiapentacyclo[10.7.0.02,10.03,8.014,19]nonadeca-1(12),2(10),3,5,7,14,16,18-octaen-11-yl]-9,13-dithiapentacyclo[10.7.0.02,10.03,8.014,19]nonadeca-1(12),2(10),3,5,7,14,16,18-octaene
  参考文献：
  名称：

  Endo, Hiroyuki; Nagashima, Kinji; Wakabayashi, Hidetsugu, Heterocycles, 2007, vol. 71, # 11, p. 2389 - 2395

  摘要：

  DOI：
• 作为产物：
  描述：

  tris(2-benzo[b]thienyl)methyl alcohol 在 对甲苯磺酸 作用下， 生成 11-(2-benzo[b]thienyl)cyclopenta-[1,2-b:4,3-b']-dibenzothiophene
  参考文献：
  名称：

  三（2-苯并[ b ]噻吩基）甲醇的新型分子内光环化

  摘要：

  在乙腈中对三（2-苯并[ b ]噻吩基）甲醇进行光辐照，得到环戊酮化合物和苯并[ b ]噻吩缩合的托酮衍生物。前者被解释为通过使用两个噻吩环中的不饱和键进行二-π-甲烷重排而产生，而后者则是通过三个噻吩环中的不饱和键的三聚而产生的。

  DOI：

  10.1016/s0040-4039(02)02161-5

文献信息

• Novel intramolecular photocyclization of tris(2-benzo[b]thienyl)methyl alcohol
  作者：Naoki Tanifuji、Honghua Huang、Yoko Shinagawa、Keiji Kobayashi

  DOI：10.1016/s0040-4039(02)02161-5

  日期：2002.11

  Photoirradiation of tris(2-benzo[b]thienyl)methyl alcohol in acetonitrile afforded a cyclopentanone compound and a benzo[b]thiophene-condensed tropone derivative. The former is interpreted to originate via the di-π-methane rearrangement using the unsaturated bonds in two thiophene rings, while the latter via trimerization of the unsaturated bonds in three thiophene rings.

  在乙腈中对三（2-苯并[ b ]噻吩基）甲醇进行光辐照，得到环戊酮化合物和苯并[ b ]噻吩缩合的托酮衍生物。前者被解释为通过使用两个噻吩环中的不饱和键进行二-π-甲烷重排而产生，而后者则是通过三个噻吩环中的不饱和键的三聚而产生的。
• Electronic and Structural Characterization of a Piezochromic Indigoid:  11-(3‘-Oxodihydrobenzothiophen-2‘-ylidene)cyclopenta[1,2-b:4,3-b‘]dibenzothiophene
  作者：J. Mizuguchi、N. Tanifuji、K. Kobayashi

  DOI：10.1021/jp030692o

  日期：2003.11.1

  The title compound, a novel thioindigoid, undergoes a color change in the solid state from red to black due to mechanical shearing ("piezochromism"), and the color is also recovered either by heat or solvent treatment. The mechanism of the piezochromic effect has been studied in the present investigation on the basis of the crystal structure and thermal analysis. The absorption band in the initial red state is found to be similar to the one in solution, indicating that the molecular nature is well preserved even in the solid state. The color change (red --> black) is then induced by mechanical shearing, accompanied by an additional, new band around 750 nm. The new band covers the whole visible region together with the band in the red phase to make the color black. The new band has been interpreted as arising from excitonic interactions between transition dipoles based on the re-organized molecular arrangement caused by mechanical shearing.
• Endo, Hiroyuki; Nagashima, Kinji; Wakabayashi, Hidetsugu, Heterocycles, 2007, vol. 71, # 11, p. 2389 - 2395
  作者：Endo, Hiroyuki、Nagashima, Kinji、Wakabayashi, Hidetsugu、Kanazumi, Makoto、Kato, Tatsuhisa、Kobayashi, Keiji

  DOI：——

  日期：——