ethyl 3-thiophen-3-ylhept-2-enoate | 188559-56-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-thiophen-3-ylhept-2-enoate
• CAS: 188559-56-0
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: AGYQSLZSGSCGCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-thiophen-3-ylhept-2-enoate 在 sodium hydroxide 、 sodium amalgam 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 生成 3-thiophen-3-ylheptanoyl chloride
  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
• 作为产物：
  描述：

  3-(1-hydroxypentyl)thiophene 在 chromium(VI) oxide 、 正丁基锂 作用下， 生成 ethyl 3-thiophen-3-ylhept-2-enoate
  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

• 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.