5-Iodo perfluorobutane uracil | 146305-08-0

• 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: 5-Iodo perfluorobutane uracil
• CAS: 146305-08-0
• 化学式: C₈H₃F₈IN₂O₂
• 分子量: 438.016
• InChiKey: PSIIBZZZGAOHJJ-UHFFFAOYSA-N

物化性质

• 密度：
  2.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.72
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,4-二碘全氟丁烷 、 tetramethylammonium salt of uracil 在 N,N,N,N-tetraethylammonium tetrafluoroborate 、 硝基苯 作用下， 以 二甲基亚砜 为溶剂， 以35%的产率得到5-Iodo perfluorobutane uracil
  参考文献：
  名称：

  嘌呤和嘧啶碱基的全氟烷基化通过电化学诱导的S RN 1取代。

  摘要：

  在嘌呤和嘧啶阴离子存在下，通过芳香族阴离子介体间接电化学还原全氟烷基碘，通过S RN 1机理产生相应的C-全氟烷基化嘌呤和嘧啶。

  DOI：

  10.1016/s0040-4039(00)60185-5

文献信息

• A Convenient Synthesis of Perfluoroalkylated and Fluorinated-Aryl Nitrogen Bases by Electrochemically Induced S_RN1 Substitution
  作者：Maurice Médebielle、Mehmet Ali Oturan、Jean Pinson、Jean-Michel Savéant

  DOI：10.1021/jo9515541

  日期：1996.1.1

  Indirect electrochemical reduction, by means of an aromatic anion mediator, of perfluoroalkyl halides (CF3Br, n-C4F9I, n-C6F13I, I(CF2)(4)I) in the presence of imidazole, 4(5)-nitroimidazole, 2-methyl-5-nitroimidazole, 2-(4'-methoxyphenyl)imidazole, imidazole-2-carboxaldehyde, 4(5)-nitroimidazole-2-carboxaldehyde, 5(6)-nitrobenzimidazole, purines (adenine, hypoxanthine, xanthine, theophylline, lumazine) and pyrimidine anions (uracil, cytosine, barbituric acid) yields the corresponding C-perfluoroalkylated nitrogen bases by an S(RN)1 mechanism. Aromatic nucleophilic substitution of some fluorinated aryl halides 1-iodo-2-(trifluoromethyl)benzene and 1-(4'-iodo-tetrafluorophenyl)-imidazole was also investigated and it was found that 1-iodo-2-(trifluoromethyl)benzene could react successfully under redox-catalyzed conditions with imidazole, 2-(4'-methoxyphenyl)imidazole anion, and uracil anion to give the corresponding 5-(fluorinated-aryl) nitrogen bases. In the case of 1-(4'iodo-tetrafluorophenyl)imidazole, direct electrochemical radical nucleophilic substitution with 2-methyl-5-nitroimidazole and uracil was possible in DMSO. In this way new, 4-[2',3',5',6'-tetrafluoro-4'-(imidazol-1 ''-yl)phenyl] nitrogen bases were obtained in good yields.