1,1'-(3,3'-dibromo-2,2'-bithiophene-5,5'-diyl)diethanone | 198566-39-1

• 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: 1,1'-(3,3'-dibromo-2,2'-bithiophene-5,5'-diyl)diethanone
• 英文别名: 5,5'-diacetyl-3,3'-dibromo-2,2'-bithiophene；1-[5-(5-Acetyl-3-bromothiophen-2-yl)-4-bromothiophen-2-yl]ethanone
• CAS: 198566-39-1
• 化学式: C₁₂H₈Br₂O₂S₂
• 分子量: 408.134
• InChiKey: FCTWUQYVCILJJL-UHFFFAOYSA-N

物化性质

• 沸点：
  525.3±50.0 °C(Predicted)
• 密度：
  1.781±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-(3,3'-dibromo-2,2'-bithiophene-5,5'-diyl)diethanone 在 1,1'-双(二苯基膦)二茂铁 、 potassium phosphate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 potassium thioacetate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 17.0h， 以43%的产率得到1,1'-(dithieno[3,2-b:2',3'-d]thiophene-2,6-diyl)diethanone
  参考文献：
  名称：

  Ambidextrous Catalytic Access to Dithieno[3,2-b:2′,3′-d]thiophene (DTT) Derivatives by Both Palladium-Catalyzed C–S and Oxidative Dehydro C–H Coupling

  摘要：

  A modular two-step synthesis of dithieno[3,2-b:2',3'-d]thiophene (DTT) derivatives by C-S cross-coupling and oxidative dehydro C-H coupling is herein described. Dibenzo[d,d']thieno[3,2-b;4,5-b']dithiophene (DBTDT) and associated two donor (anisyl) and acceptor (acetyl) substituted DTT derivatives were synthesized by palladium-catalyzed cross-coupling sequences in 17% to 71% yield over two steps. The 5,5'-disubstituted DTT derivatives were characterized in terms of their photophysical (UV and fluorescence spectroscopy) and electrophysical (cyclovoltammography) properties.

  DOI：

  10.1021/ol501752f
• 作为产物：
  描述：

  4-溴-2-乙酰基噻吩 在 potassium fluoride 、 bis(benzonitrile)palladium(II) chloride 、 silver nitrate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以84%的产率得到1,1'-(3,3'-dibromo-2,2'-bithiophene-5,5'-diyl)diethanone
  参考文献：
  名称：

  Ambidextrous Catalytic Access to Dithieno[3,2-b:2′,3′-d]thiophene (DTT) Derivatives by Both Palladium-Catalyzed C–S and Oxidative Dehydro C–H Coupling

  摘要：

  A modular two-step synthesis of dithieno[3,2-b:2',3'-d]thiophene (DTT) derivatives by C-S cross-coupling and oxidative dehydro C-H coupling is herein described. Dibenzo[d,d']thieno[3,2-b;4,5-b']dithiophene (DBTDT) and associated two donor (anisyl) and acceptor (acetyl) substituted DTT derivatives were synthesized by palladium-catalyzed cross-coupling sequences in 17% to 71% yield over two steps. The 5,5'-disubstituted DTT derivatives were characterized in terms of their photophysical (UV and fluorescence spectroscopy) and electrophysical (cyclovoltammography) properties.

  DOI：

  10.1021/ol501752f

文献信息

• Rhodium(I)-Mediated Synthesis of Benzo[2,1-b:3,4-b':5,6-c'']trithiophenes and Naphtho[2,1-b:3,4-b']dithiophenes
  作者：Uwe Dahlmann

  DOI：10.1055/s-1997-1310

  日期：1997.9

  The syntheses of carbonylated benzo[2,1-b:3,4-b':5,6-c'']trithiophenes 2 and naphtho[2,1-b:3,4-b']dithiophenes 3 are described. The treatment of 5,5'-dicarbonylated 3,3'-bis(phenylethynyl)-2,2'-bithiophenes 6 [readily available via Pd(II)-catalyzed alkynylation of the corresponding 3,3'-dibromo-2,2'-bithiophenes 5 in the presence of Cu(I) in (i-Pr)2NH] with chlorotris(triphenylphosphine)rhodium(I) yields the cyclic rhodium complexes 7 which smoothly react with sulfur and acetylenes to give 2 and 3 in good yields.

  描述了碳基化的苯并[2,1-b:3,4-b':5,6-c'']三噻吩 2 和萘[2,1-b:3,4-b']二噻吩 3 的合成。将5,5'-二羰基化的3,3'-双(苯乙炔)-2,2'-二噻吩 6 [通过 Pd(II) 催化相应的3,3'-二溴-2,2'-二噻吩 5 与 Cu(I) 在(i-Pr)2NH中进行的炔烃化反应易于获得] 与氯三(三苯基磷)铑(I) 反应，生成环状铑配合物 7，随后与硫和炔烃顺利反应，产出2和3，并具有良好的产率。