4-(5-phenylthiophen-2-yl)pyrimidine | 1438096-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4-(5-phenylthiophen-2-yl)pyrimidine
• 英文别名: 4-(5-Phenyl-2-thienyl)pyrimidine
• CAS: 1438096-57-1
• 化学式: C₁₄H₁₀N₂S
• 分子量: 238.313
• InChiKey: LCLIJPHDTQDHJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-phenylthiophen-2-yl)pyrimidine 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 53.0h， 生成 2-amino-6-(5-phenylthiophen-2-yl)pyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines

  摘要：

  开发了一种通过相应嘧啶的环变换高效合成6-噻吩基取代的2-氨基-3-氰基吡啶的方法。在室温空气中使用反式双（环己胺）钯（II）乙酸酯作为催化剂的条件下，对其获得的吡啶进行了进一步的修饰研究。

  DOI：

  10.1007/s11172-015-0920-8
• 作为产物：
  描述：

  嘧啶 、 2-苯基噻吩 在 三氟乙酸 、 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 生成 4-(5-phenylthiophen-2-yl)pyrimidine
  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

• 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。
• Synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines
  作者：E. V. Verbitskiy、E. M. Cheprakova、M. G. Pervova、G. G. Danagulyan、G. L. Rusinov、O. N. Chupakhin、V. N. Charushin

  DOI：10.1007/s11172-015-0920-8

  日期：2015.3

  An efficient method for the synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines by the ring transformation in the corresponding pyrimidines was developed. Further modification of the pyridines obtained under conditions of a room temperature aerobic Suzuki reaction in the presence of trans-bis(dicyclohexylamine)palladium(II) acetate as a catalyst was studied

  开发了一种通过相应嘧啶的环变换高效合成6-噻吩基取代的2-氨基-3-氰基吡啶的方法。在室温空气中使用反式双（环己胺）钯（II）乙酸酯作为催化剂的条件下，对其获得的吡啶进行了进一步的修饰研究。