6-hydroxy-1,6-dimethylthieno[2',3':3,4]bicyclo[3.3.0]octan-2-one | 216145-02-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-hydroxy-1,6-dimethylthieno[2',3':3,4]bicyclo[3.3.0]octan-2-one
• 英文别名: 4-hydroxy-4,6a-dimethyl-5,6-dihydro-3bH-pentaleno[2,1-b]thiophen-7-one
• CAS: 216145-02-7
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: CFCVTXAWJONPFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-1,6-dimethylthieno[2',3':3,4]bicyclo[3.3.0]octan-2-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 24.0h， 以55%的产率得到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-(2-butanon-4-yl)-5-methyl-6H-cyclopenta[b]thiophen-6-one 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以54%的产率得到6-methylthieno[3',2':8,9]bicyclo[4.3.0]non-1(2)-en-3-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