2-(2-溴四氟乙基)吡咯 | 1005776-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-(2-溴四氟乙基)吡咯
• 英文名称: 2-(2-bromotetrafluoroethyl)pyrrole
• 英文别名: 2-(2-bromo-1,1,2,2-tetrafluoroethyl)-1H-pyrrole
• CAS: 1005776-40-8
• 化学式: C₆H₄BrF₄N
• 分子量: 246.002
• InChiKey: GUZAWEXXERMNKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  32-36 °C(Press: 6 Torr)
• 密度：
  1.802±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吡咯 、 1,1,2,2-四氟-1,2-二溴乙烷 在 2,5-二甲基吡啶 、 二氧化硫 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到2-(2-溴四氟乙基)吡咯
  参考文献：
  名称：

  Polyfluoroalkylation of pyrrole with 1,2-dibromotetrafluoroethane activated by sulfur dioxide

  摘要：

  展示了使用亚硝基-二氧化硫系统用氟利昂 BrCF2CF2Br 进行吡咯均相催化氟烷基化的可能性。研究了碱基的pKa 对这些过程发生的影响。该过程的离子自由基机制得到证实。

  DOI：

  10.1007/s11172-010-0135-y

文献信息

• Sodium dithionite initiated fluoroalkylation of trimethoxybenzenes, mesitylene and pyrroles with BrCF2CF2Br
  作者：Wojciech Dmowski、Krystyna Piasecka-Maciejewska

  DOI：10.1016/j.jfluchem.2010.01.009

  日期：2010.7

  Sodium dithionite initiated reaction of 1,2-dibromotetrafluoroethane with 1,3,5-trimethoxybenzene (la) in an acetonitrile-water mixture proceeded efficiently at ambient temperature to give 1-(2-bromotetrafluoroethyl)-2,4,6-trimethoxybenzene (2) almost quantitatively. Similar reaction with 1,2,3-trimethoxybenzene (1b) gave only reasonable yield of regioisomers of (2-bromotetrafluoroethyl)-trimethoxybenzenes 3 and 4 and small amount of a substitution product of the central trimethoxy group, 1-(2-bromotetrafluoroethyl)-2,6-dimethoxybenzene (5). The reaction with mesitylene (6) gave complex mixtures from which, depending on the temperature and a mesitylene/BrCF2CF2Br ratio, the expected (2-bromotetrafluoroethyl)mesitylene (8) or a dimeric product, 4,4'-bis(2-bromo-1,1,2,2-tetrafluoroethyl)-1,3,5,1',3',5'-hexamethylbicyclohexyl-2,5,2',5'-tetraene (7), were isolated in a yield of 18 and 13%, respectively. The reactions of BrCF2CF2Br with pyrrole (9) and 1-methylpyrrole (11) gave the respective alkylated compounds, 2-(2-bromotetrafluoroethyl)pyrrole (10) and 2-(2-bromotetrafluoroethyl)-1-methylpyrrole (12) in over 70% yields; the former was found to be fairly unstable. The reactivity of the terminal bromine atom in 1-(2-bromotetrafluoroethyl)-2,4,6-trimethoxybenzene (2) was also investigated. (C) 2010 Elsevier B.V. All rights reserved.
• Activation of free-radical polyfluoroalkylation of organic substrates with freon BrCF2CF2Br using a system of organic base-electron transfer mediator
  作者：Vyacheslav G. Koshechko、Lydiya A. Kiprianova、Ludmyla I. Kalinina

  DOI：10.1016/j.jfluchem.2009.11.003

  日期：2010.2

  A polyfluoroalkylation of pyrrole and phenols with freon BrCF2CF2Br using sulfur dioxide-substituted pyridine activating system proceeds at the aromatic nucleus by a free-radical mechanism. The essential influence of the basicity of the medium is demonstrated and discussed. (C) 2009 Elsevier B.V. All rights reserved.