5-[2,2′]bithiophenyl-5-ylpyrimidine | 1332462-26-6

• 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′]bithiophenyl-5-ylpyrimidine
• 英文别名: 5-[2,2']bithiophenyl-5-yl-pyrimidine；5-[2,2'-Bithiophen]-5-ylpyrimidine；5-(5-thiophen-2-ylthiophen-2-yl)pyrimidine
• CAS: 1332462-26-6
• 化学式: C₁₂H₈N₂S₂
• 分子量: 244.341
• InChiKey: ZQYHJVIMAOMRKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴嘧啶 、 2,2'-联二噻吩 在 palladium diacetate 、 potassium carbonate 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-[2,2′]bithiophenyl-5-ylpyrimidine
  参考文献：
  名称：

  作为一个新的抗分枝杆菌化合物家族，C（4）和/或C（5）噻吩基取代的嘧啶的合成及其与结构-活性的关系

  摘要：

  铃木交叉偶联和亲核氢取代的结合（小号ñH）反应被证明是从市售的5-溴嘧啶合成C（4）和/或C（5）单（噻吩基）和二（噻吩基）取代的嘧啶的简便方法。所有新的嘧啶被发现是在微摩尔浓度的活性在体外针对ħ 37 RV，鸟，terrae，利福平的和异烟肼耐药的菌株结核分枝杆菌。对于这些化合物，已经获得了小鼠急性体内毒性的数据，这些化合物似乎是有希望的抗结核药。

  DOI：

  10.1016/j.ejmech.2015.05.007

文献信息

• Palladium‐Catalysed Direct Monoarylation of Bithiophenyl Derivatives or Bis(thiophen‐2‐yl)methanone with Aryl Bromides
  作者：Karima Si Larbi、Safia Djebbar、Henri Doucet

  DOI：10.1002/ejic.201100294

  日期：2011.8

  Arylated bithiophenes, which are useful compounds due to their coordination and/or physical properties, can be easily prepared by palladium-catalysed C–H bond activation of heteroaromatics followed by arylation using electron-deficient aryl bromides. A variety of 5-arylated 2,2′-bithiophenyl derivatives have been prepared. Good yields were generally obtained by using the air-stable [PdCl(dppb)(C3H5)]

  芳基化联噻吩由于其配位和/或物理性质而成为有用的化合物，可以通过钯催化的杂芳烃的 C-H 键活化，然后使用缺电子的芳基溴化物进行芳基化来轻松制备。已经制备了多种 5-芳基化 2,2'-联噻吩衍生物。通过使用空气稳定的 [PdCl(dppb)(C3H5)] 配合物作为催化剂，通常可以获得良好的产率。芳基溴上的一系列官能团，例如乙酰基、甲酰基、酯、腈、三氟甲基、氟和羟烷基，是可以容忍的。
• Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (SNH) in 5-bromopyrimidine by action of bithiophene and its analogues
  作者：Egor V. Verbitskiy、Ekaterina M. Cheprakova、Ekaterina F. Zhilina、Mikhail I. Kodess、Marina A. Ezhikova、Marina G. Pervova、Pavel A. Slepukhin、Julia O. Subbotina、Aleksandr V. Schepochkin、Gennady L. Rusinov、Oleg N. Chupakhin、Valery N. Charushin

  DOI：10.1016/j.tet.2013.04.062

  日期：2013.6

  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.
• Synthesis, and structure–activity relationship for C(4) and/or C(5) thienyl substituted pyrimidines, as a new family of antimycobacterial compounds
  作者：Egor V. Verbitskiy、Ekaterina M. Cheprakova、Pavel A. Slepukhin、Marionella A. Kravchenko、Sergey N. Skornyakov、Gennady L. Rusinov、Oleg N. Chupakhin、Valery N. Charushin

  DOI：10.1016/j.ejmech.2015.05.007

  日期：2015.6

  Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions proved to be a convenient method for the synthesis of C(4) and/or C(5) mono(thienyl) and di(thienyl) substituted pyrimidines from commercially available 5-bromopyrimidine. All new pyrimidines were found to be active in micromolar concentrations in vitro against H37Rv, avium, terrae, rifampicin

  铃木交叉偶联和亲核氢取代的结合（小号ñH）反应被证明是从市售的5-溴嘧啶合成C（4）和/或C（5）单（噻吩基）和二（噻吩基）取代的嘧啶的简便方法。所有新的嘧啶被发现是在微摩尔浓度的活性在体外针对ħ 37 RV，鸟，terrae，利福平的和异烟肼耐药的菌株结核分枝杆菌。对于这些化合物，已经获得了小鼠急性体内毒性的数据，这些化合物似乎是有希望的抗结核药。