5,5'-di(ethoxycarbonyl)-2,2'-bithiophene | 144433-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-di(ethoxycarbonyl)-2,2'-bithiophene
• 英文别名: Ethyl 5-(5-ethoxycarbonylthiophen-2-yl)thiophene-2-carboxylate
• CAS: 144433-88-5
• 化学式: C₁₄H₁₄O₄S₂
• 分子量: 310.395
• InChiKey: JZZURXSVEYSOIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-di(ethoxycarbonyl)-2,2'-bithiophene 在 高氯酸 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Perthienyl analogues of chichibabin's hydrocarbon. A new stable, highly amphoteric multistage redox system with low oxidation potentials.

  摘要：

  Perthienyl analogues of Chichibabin's hydrocarbon have been first synthesized as fairly stable substances, showing highly amphoteric multistage redox properties with considerably low oxidation potentials.

  DOI：

  10.1016/s0040-4039(00)79106-4
• 作为产物：
  描述：

  2-噻吩羧酸乙酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 氟化银 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以85%的产率得到5,5'-di(ethoxycarbonyl)-2,2'-bithiophene
  参考文献：
  名称：

  Palladium-Catalyzed C−H Homocoupling of Thiophenes:  Facile Construction of Bithiophene Structure

  摘要：

  Palladium-catalyzed C-H homocoupling of thiophene derivatives takes place in the presence of silver(I) fluoride or acetate. A variety of bithiophenes are obtained in good to excellent yields. In particular, the reaction of 2-bromothiophene proceeds at room temperature to afford 5,5'-dibromo-2,2'-bithiophene, where the bromine atom is completely intact in the palladium-catalyzed reaction. XRD analysis reveals that silver fluoride is reduced to silver(0) during the reaction.

  DOI：

  10.1021/ja031855p

文献信息

• Perthienyl analogues of chichibabin's hydrocarbon. A new stable, highly amphoteric multistage redox system with low oxidation potentials.
  作者：Takeshi Kawase、Nobuhiko Ueno、Masaji Oda

  DOI：10.1016/s0040-4039(00)79106-4

  日期：1992.9

  Perthienyl analogues of Chichibabin's hydrocarbon have been first synthesized as fairly stable substances, showing highly amphoteric multistage redox properties with considerably low oxidation potentials.
• Palladium-Catalyzed C−H Homocoupling of Thiophenes:  Facile Construction of Bithiophene Structure
  作者：Kentaro Masui、Haruka Ikegami、Atsunori Mori

  DOI：10.1021/ja031855p

  日期：2004.4.28

  Palladium-catalyzed C-H homocoupling of thiophene derivatives takes place in the presence of silver(I) fluoride or acetate. A variety of bithiophenes are obtained in good to excellent yields. In particular, the reaction of 2-bromothiophene proceeds at room temperature to afford 5,5'-dibromo-2,2'-bithiophene, where the bromine atom is completely intact in the palladium-catalyzed reaction. XRD analysis reveals that silver fluoride is reduced to silver(0) during the reaction.