4-(4-bromophenyl)-6-(1-fluoroethyl)-2-methylpyrimidine | 1160586-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-bromophenyl)-6-(1-fluoroethyl)-2-methylpyrimidine
• 英文别名: 4-(4-Bromophenyl)-6-(1-fluoroethyl)-2-methylpyrimidine
• CAS: 1160586-97-9
• 化学式: C₁₃H₁₂BrFN₂
• 分子量: 295.154
• InChiKey: NLXLMQCNXBNMCT-UHFFFAOYSA-N

物化性质

• 熔点：
  45 °C
• 沸点：
  379.8±37.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)-6-(1-fluoroethyl)-2-methylpyrimidine 、 三丁基乙烯基锡 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 以95%的产率得到4-(1-fluoroethyl)-2-methyl-6-(4-vinylphenyl)pyrimidine
  参考文献：
  名称：

  Towards chemical libraries based on heterocyclic scaffolds with monofluorinated and difluoroalkyl side chains

  摘要：

  The preparation of focused chemical libraries, based on five- and six-membered heteroaromatic systems with mono- and gemdifluoroalkyl side chains, is described. Four heterocyclic scaffolds with a p-bromophenyl group have been easily prepared from readily available propargylic fluorides. Starting from these scaffolds, palladium-catalyzed reactions have been performed, including by automated procedures, to prepare libraries of molecules designed for biological applications. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.03.003
• 作为产物：
  描述：

  1-(6-(4-bromophenyl)-2-methylpyrimidin-4-yl)ethanol 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到4-(4-bromophenyl)-6-(1-fluoroethyl)-2-methylpyrimidine
  参考文献：
  名称：

  Flexible Synthesis of Pyrimidines with Chiral Monofluorinated and Difluoromethyl Side Chains

  摘要：

  Chiral pyrimidines with a fluorine atom in the benzylic position are easily accessible in high enantiomeric excesses from optically active propargylic intermediates by two complementary routes. Both the use of optically active propargylic fluorides and the fluorination of the chiral pyrimidine in the final stage give excellent results in terms of enantiocontrol. On the other hand, original pyrimidines with a difluoromethyl side chain are also obtained in a few steps from new propargylic ketones bearing a CHF2 substituent on the triple bond.

  DOI：

  10.1021/jo900674u

文献信息

• Flexible Synthesis of Pyrimidines with Chiral Monofluorinated and Difluoromethyl Side Chains
  作者：Pierre Bannwarth、Alain Valleix、Danielle Grée、René Grée

  DOI：10.1021/jo900674u

  日期：2009.6.19

  Chiral pyrimidines with a fluorine atom in the benzylic position are easily accessible in high enantiomeric excesses from optically active propargylic intermediates by two complementary routes. Both the use of optically active propargylic fluorides and the fluorination of the chiral pyrimidine in the final stage give excellent results in terms of enantiocontrol. On the other hand, original pyrimidines with a difluoromethyl side chain are also obtained in a few steps from new propargylic ketones bearing a CHF2 substituent on the triple bond.
• Towards chemical libraries based on heterocyclic scaffolds with monofluorinated and difluoroalkyl side chains
  作者：Pierre Bannwarth、Danielle Grée、Saibal Das、Jhillu Singh Yadav、René Grée

  DOI：10.1016/j.jfluchem.2011.03.003

  日期：2012.2

  The preparation of focused chemical libraries, based on five- and six-membered heteroaromatic systems with mono- and gemdifluoroalkyl side chains, is described. Four heterocyclic scaffolds with a p-bromophenyl group have been easily prepared from readily available propargylic fluorides. Starting from these scaffolds, palladium-catalyzed reactions have been performed, including by automated procedures, to prepare libraries of molecules designed for biological applications. (C) 2011 Elsevier B.V. All rights reserved.