5-bromo-2-(4-(trifluoromethyl)phenyl)pyrimidine | 183437-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-2-(4-(trifluoromethyl)phenyl)pyrimidine
• 英文别名: 2-[4'-(Trifluoromethyl)phenyl]-5-bromopyrimidine；5-Bromo-2-(4-trifluoromethylphenyl)pyrimidine；5-bromo-2-[4-(trifluoromethyl)phenyl]pyrimidine
• CAS: 183437-80-1
• 化学式: C₁₁H₆BrF₃N₂
• 分子量: 303.081
• InChiKey: ZLRAHJFXQBBHBL-UHFFFAOYSA-N

物化性质

• 沸点：
  242.3±40.0 °C(Predicted)
• 密度：
  1.587±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4-(trifluoromethyl)phenyl)pyrimidine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 potassium acetate 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Identification of a novel conformationally constrained glucagon receptor antagonist

  摘要：

  Identification of orally active, small molecule antagonists of the glucagon receptor represents a novel treatment paradigm for the management of type 2 diabetes mellitus. The present work discloses novel glucagon receptor antagonists, identified via conformational constraint of current existing literature antagonists. Optimization of lipophilic ligand efficiency (LLE or LipE) culminated in enantiomers (+)-trans-26 and (-)-trans-27 which exhibit good physicochemical and in vitro drug metabolism profiles. In vivo, significant pharmacokinetic differences were noted with the two enantiomers, which were primarily driven through differences in clearance rates. Enantioselective oxidation by cytochrome P450 was ruled out as a causative factor for pharmacokinetic differences. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.090
• 作为产物：
  描述：

  4-三氟甲基苯硼酸 、 5-溴-2-碘嘧啶 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以22%的产率得到5-bromo-2-(4-(trifluoromethyl)phenyl)pyrimidine
  参考文献：
  名称：

  New n-Type Field-effect Transistors Based on Pyrimidine-containing Compounds with (Trifluoromethyl)phenyl Groups

  摘要：

  新型含有 pyrimidine 单元的共聚物已被制备。平面分子和 π-堆叠结构通过 X 射线结构分析揭示。基于它们的 FET 器件显示出良好的 n 型性能。

  DOI：

  10.1246/cl.2009.428

文献信息

• Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes
  作者：Kaitlyn M. Logan、Stephen R. Sardini、Sean D. White、M. Kevin Brown

  DOI：10.1021/jacs.7b12160

  日期：2018.1.10

  A Ni-catalyzed method for arylboration is disclosed. The method allows for highly stereoselective arylboration of unactivated alkenes. The reactions utilize a simple Ni-catalyst and work with a broad range of alkenes and aryl bromides. The products represent useful intermediates for chemical synthesis due to the versatility of the C-B bond. Preliminary mechanistic details of the method are also disclosed

  公开了一种用于芳基硼化的Ni催化方法。该方法允许未活化烯烃的高度立体选择性芳基硼化。该反应使用简单的 Ni 催化剂，并适用于广泛的烯烃和芳基溴化物。由于 CB 键的多功能性，这些产品代表了用于化学合成的有用中间体。还公开了该方法的初步机械细节。
• 5-Bromo-2-iodopyrimidine: a novel, useful intermediate in selective palladium-catalysed cross-coupling reactions for efficient convergent syntheses
  作者：John W. Goodby、Michael Hird、Robert A. Lewis、Kenneth J. Toyne

  DOI：10.1039/cc9960002719

  日期：——

  A simple synthesis of the novel 5-bromo-2-iodopyrimidine is described and examples are provided of the use of the compound in selective palladium-catalysed cross-coupling reactions with a wide range of arylboronic acids and alkynylzincs to give the efficient syntheses of many substituted pyrimidine compounds.

  描述了一种简单合成新型 5-溴-2-碘嘧啶的方法，并提供了该化合物在选择性钯催化的交叉偶联反应中与多种芳基硼酸和炔基锌的应用实例，以高效合成多种取代的嘧啶化合物。
• Pyrimidine compounds
  申请人：The Secretary of State for Defence in Her Britannic Majesty's a

  公开号：US05986096A1

  公开（公告）日：1999-11-16

  5-Bromo-2-iodopyrimidine is used to synthesize a range of chemical compounds including liquid crystalline compounds.

  5-溴-2-碘吡啶用于合成一系列化合物，包括液晶化合物。
• Pyridinone Derivatives Against Malaria
  申请人：Fiandor Roman Jose Maria

  公开号：US20080287461A1

  公开（公告）日：2008-11-20

  4-pyridone derivatives of Formula (1) and pharmaceutically acceptable derivatives thereof, processes for their preparation, pharmaceutical formulations thereof and their use in chemotherapy of certain parasitic infections such as malaria, are provided.

  本发明提供了式（1）的4-吡啶酮衍生物及其药学上可接受的衍生物，其制备过程，制药配方以及它们在治疗某些寄生虫感染（例如疟疾）的化疗中的应用。
• Pyridinone derivatives against malaria
  申请人：Glaxo Group Limited

  公开号：US07579353B2

  公开（公告）日：2009-08-25

  4-pyridone derivatives of Formula (I) and pharmaceutically acceptable derivatives thereof, processes for their preparation, pharmaceutical formulations thereof and their use in chemotherapy of certain parasitic infections such as malaria, are provided.

  本发明提供了公式(I)的4-吡啶酮衍生物及其药学上可接受的衍生物，其制备过程，药物配方以及它们在化疗某些寄生虫感染疾病如疟疾中的使用。