4-butyl-4,5-dihydro-6H-cyclopenta[b]thiophene-6-one | 188559-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-butyl-4,5-dihydro-6H-cyclopenta[b]thiophene-6-one
• 英文别名: 4-Butyl-4,5-dihydrocyclopenta[b]thiophen-6-one
• CAS: 188559-57-1
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: UEPCFTIUPUAJHM-UHFFFAOYSA-N

物化性质

• 沸点：
  281.4±19.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-butyl-4,5-dihydro-6H-cyclopenta[b]thiophene-6-one 在 硫酸 、 四氯化钛 、 锌 作用下， 生成 (10E)-2-butyl-10-(2-butyl-12-methyl-6-thiatetracyclo[9.3.1.01,8.03,7]pentadeca-3(7),4,8,12-tetraen-10-ylidene)-12-methyl-6-thiatetracyclo[9.3.1.01,8.03,7]pentadeca-3(7),4,8,12-tetraene
  参考文献：
  名称：

  Pontage du 1,6-dithiényl hexa-1,3,5-triène : vers la rigidification de polyènes

  摘要：

  合成了结构 2 化合物，即 1,6-二噻吩基六-1,3,5-三烯 1 的硬化类似物。比较研究表明，刚性化既能降低氧化电位，又能稳定氧化物。此外，还观察到电子析出得到改善，光致发光得到增强。

  DOI：

  10.1051/jcp:1998261
• 作为产物：
  描述：

  3-噻吩甲醛 在 chromium(VI) oxide 、 sodium hydroxide 、 sodium amalgam 、 正丁基锂 、 三氯化铝 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 生成 4-butyl-4,5-dihydro-6H-cyclopenta[b]thiophene-6-one
  参考文献：
  名称：

  Bandgap control through reduction of bond length alternation in bridged poly(diethienylethylene)s

  摘要：

  一项新型刚性双噻吩乙烯的X射线结构分析显示，观察到的HOMO-LUMO间隙的缩小是由于键长交替的放松所致。

  DOI：

  10.1039/a607890g

文献信息

• Fine Tuning of the Electronic Properties of Linear π-Conjugated Oligomers by Covalent Bridging
  作者：Philippe Blanchard、Patrick Verlhac、Laurent Michaux、Pierre Frère、Jean Roncali

  DOI：10.1002/chem.200500853

  日期：2006.1.23

  that the sites of fixation of the bridges on the pi-conjugated backbone exert a determining effect on the relative stability of the cation radical and dication. Examination of these various results in the light of theoretical calculations shows that in addition to a local control of bond length alternation, and hence of the HOMO-LUMO gap, the fixation of covalent bridges at selected positions of the pi-conjugated

  已经通过多步合成方法构建了一系列的低聚噻吩亚乙烯基，即通过连接在共轭主链的不同位置的乙烯桥而刚性化的π-共轭低聚物。电子吸收光谱显示，与开链参考化合物的光谱相比，共轭体系的刚性产生最大吸收的红移和HOMO-LUMO能隙的缩小。所有低聚物的循环伏安图显示，这些化合物可被可逆地氧化成其阳离子自由基和阳离子，而刚性化作用则使第一氧化电位产生较大的负移，这表明HOMO含量显着增加。电化学数据证实，共价桥接强烈影响HOMO和LUMO的水平，这些数据表明，在pi共轭骨架上的桥固定位点对阳离子自由基和离子的相对稳定性起决定性作用。根据理论计算检查这些各种结果表明，除了局部控制键长交替以及HOMO-LUMO间隙外，共价桥固定在π共轭体系的选定位置还限制了变形。 π共轭结构在氧化成带电态时的结构。
• Bridged Dithienylethylenes as Precursors of Small Bandgap Electrogenerated Conjugated Polymers
  作者：Philippe Blanchard、Hugues Brisset、Bertrand Illien、Amédée Riou、Jean Roncali

  DOI：10.1021/jo9623447

  日期：1997.4.1

  Bridged dithienylethylenes (DTEs) bearing solubilizing alkyl chains at various positions (2-5) have been synthesized by McMurry dimerization of cyclopenta[b]thiophen-6-ones. In order to introduce alkyl substituents at different positions of the DTE molecule, the precursor ketones have been prepared by different strategies based on a combination of Mannich or Wittig-Horner reaction and Friedel-Craft intramolecular cyclization. The position and the length of the alkyl substituents exert a strong effect on the ability of the precursor to undergo electrochemical polymerization. Thus, whereas substitution at the alpha-position of the ethylene linkage (3) results in a rapid inhibition of electropolymerization, introduction of alkyl chains at the beta-position (4, 5) greatly improves the efficiency of the polymerization process. The analysis of the electrochemical and optical properties of the polymers shows that rigidification of the DTE molecule leads to a significant decrease of the oxidation potential and bandgap. A comparative analysis of DTE and its bridged analogues by means of X-ray diffraction reveals, in agreement with experimental and theoretical results, that the observed reduction of both the HOMO-LUMO gap of the precursor and the bandgap of the corresponding polymers are related to a relaxation of bond length alternation in the DTE moiety.
• Bridged 1,6-Dithienylhexa-1,3,5-trienes as Highly Photoluminescent and Stable Thiophene-Based π-Conjugated Systems
  作者：Philippe Blanchard、Hugues Brisset、Amédée Riou、Rolland Hierle、Jean Roncali

  DOI：10.1021/jo981176a

  日期：1998.11.1

  Bi- and tricyclic bridged dithienyl-1,3,5-hexatrienes (2 and 3) have been synthesized by McMurry dimerization of fused multicyclic ketones. The experimental conditions for the preparation of the precursor ketones have been established through a detailed analysis of the Robinson annulation of cyclopenta[b]thiophen-6-ones. The structures and electrochemical and optical properties of compounds 2 and 3 have been investigated using the open-chain analogue 1 as a reference. Whereas X-ray data confirm the highly conjugated and rigid structure of the bridged compounds, cyclic voltammetry and W-vis and photoluminescence spectroscopy show that rigidification of the pi-conjugated system produces a significant decrease in oxidation potential and HOMO-LUMO gap and a considerable enhancement of the photoluminescence quantum yield and thermal, stability.
• Electrosynthesis of a Low Band Gap π-Conjugated Polymer from a Multibridged Dithienylethylene
  作者：Philippe Blanchard、Amédée Riou、Jean Roncali

  DOI：10.1021/jo980778r

  日期：1998.10.1