5-[2,2′:5′,2″]terthiophenyl-5-ylpyrimidine | 1438096-42-4

• 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-[2,2′:5′,2″]terthiophenyl-5-ylpyrimidine
• 英文别名: 5-[5-(5-Thiophen-2-ylthiophen-2-yl)thiophen-2-yl]pyrimidine
• CAS: 1438096-42-4
• 化学式: C₁₆H₁₀N₂S₃
• 分子量: 326.467
• InChiKey: UKKFTFBXSIIZFP-UHFFFAOYSA-N

物化性质

• 沸点：
  486.7±45.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  噻吩 、 5-(5-phenylthiophen-2-yl)pyrimidine 在 palladium diacetate 、 potassium carbonate 、 三环己基膦 作用下， 以 三氟乙酸 为溶剂， 反应 0.17h， 以87.2%的产率得到5-[2,2′:5′,2″]terthiophenyl-5-ylpyrimidine
  参考文献：
  名称：

  Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (SNH) in 5-bromopyrimidine by action of bithiophene and its analogues

  摘要：

  5-Bromopyrimidine reacts with 2,2'-bithiophene, [2,2':5',2 '']terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladium-catalyzed aryl-aryl C-C coupling. However 5-bromo-4-(het)aryl-pyrimidines have been prepared from the same starting materials through the S-N(H)-reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gas-liquid chromatography/mass-spectrometry. Evidence for the structure of 4- and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.062