4-methyl-4,5-dihydro-6H-cyclopentathiophen-6-one | 13191-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-4,5-dihydro-6H-cyclopentathiophen-6-one
• 英文别名: 4,5-dihydro-4-methyl-cyclopentathiophen-6-one；4-methyl-4,5-dihydro-cyclopenta[b]thiophen-6-one；4-Methyl-4,5-dihydro-6H-cyclopentathiophen-6-on；4,5-Dihydro-4-methyl-6H-cyclopenta[b]thiophen-6-one；4-methyl-4,5-dihydrocyclopenta[b]thiophen-6-one
• CAS: 13191-31-6
• 化学式: C₈H₈OS
• 分子量: 152.217
• InChiKey: AXJOWUPRJUJACD-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  230.2±19.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-methyl-4,5-dihydro-6H-cyclopentathiophen-6-one 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到(6E)-4-methyl-6-(4-methyl-4,5-dihydrocyclopenta[b]thiophen-6-ylidene)-4,5-dihydrocyclopenta[b]thiophene
  参考文献：
  名称：

  Bridged Dithienylethylenes as Precursors of Small Bandgap Electrogenerated Conjugated Polymers

  摘要：

  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.

  DOI：

  10.1021/jo9623447
• 作为产物：
  描述：

  3-乙酰基噻吩 在 sodium hydroxide 、 sodium amalgam 、 正丁基锂 、 三氯化铝 、 氯化亚砜 作用下， 以 二硫化碳 、 乙醚 、 乙醇 、 水 为溶剂， 反应 74.5h， 生成 4-methyl-4,5-dihydro-6H-cyclopentathiophen-6-one
  参考文献：
  名称：

  Bridged Dithienylethylenes as Precursors of Small Bandgap Electrogenerated Conjugated Polymers

  摘要：

  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.

  DOI：

  10.1021/jo9623447

文献信息

• El-Khagawa, Ahmed M.; El-Zohry, Maher F.; Ismail, Mohamed T., Phosphorus and Sulfur and the Related Elements, 1987, vol. 33, p. 25 - 32
  作者：El-Khagawa, Ahmed M.、El-Zohry, Maher F.、Ismail, Mohamed T.

  DOI：——

  日期：——
• US9711728B1
  申请人：——

  公开号：US9711728B1

  公开（公告）日：2017-07-18
• 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.