4,5-dihydro-5-(2-butanon-4-yl)-5-methyl-6H-cyclopenta[b]thiophen-6-one | 216144-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-dihydro-5-(2-butanon-4-yl)-5-methyl-6H-cyclopenta[b]thiophen-6-one
• 英文别名: 5-methyl-5-(3-oxobutyl)-4H-cyclopenta[b]thiophen-6-one
• CAS: 216144-99-9
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: FSBWBSGUIBYNDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-5-(2-butanon-4-yl)-5-methyl-6H-cyclopenta[b]thiophen-6-one 在 sodium ethanolate 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 25.0h， 生成 1,6-dimethylthieno[2',3':3,4]bicyclo[3.3.0]oct-6(7)-en-2-one
  参考文献：
  名称：

  Bridged 1,6-Dithienylhexa-1,3,5-trienes as Highly Photoluminescent and Stable Thiophene-Based π-Conjugated Systems

  摘要：

  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.

  DOI：

  10.1021/jo981176a
• 作为产物：
  描述：

  4,5-dihydro-5-methyl-6H-cyclopentathiophen-6-one 、 丁烯酮 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以53%的产率得到4,5-dihydro-5-(2-butanon-4-yl)-5-methyl-6H-cyclopenta[b]thiophen-6-one
  参考文献：
  名称：

  Bridged 1,6-Dithienylhexa-1,3,5-trienes as Highly Photoluminescent and Stable Thiophene-Based π-Conjugated Systems

  摘要：

  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.

  DOI：

  10.1021/jo981176a

文献信息

• 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.