4-Nitro-5-perfluorohexyl imidazole | 109135-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-Nitro-5-perfluorohexyl imidazole
• 英文别名: 4-nitro-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-1H-imidazole
• CAS: 109135-29-7
• 化学式: C₉H₂F₁₃N₃O₂
• 分子量: 431.113
• InChiKey: AMRIGKUBNJDWSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  全氟己基碘烷 、 4(5)-nitroimidazole anion 生成 4-Nitro-5-perfluorohexyl imidazole
  参考文献：
  名称：

  MEDEBIELLE, MAURICE;PINSON, JEAN;SAVEANT, JEAN-MICHEL, TETRAHEDRON LETT., 31,(1990) N, C. 1279-1282

  摘要：

  DOI：

文献信息

• Perfluoroalkylation of imidazoles by electrochemically induced srn1 substitution.
  作者：Maurice Medebielle、Jean Pinson、Jean-Michel Savéant

  DOI：10.1016/s0040-4039(00)88785-7

  日期：1990.1

  Indirect electrochemical reduction, by means of aromatic anion radical mediators, of perfluoroalkyl halides in the presence of imidazolate or of substituted imidazolate anions yields the corresponding perfluoroalkylated imidazoles along an SRN1 mechanism.

  在咪唑或取代的咪唑阴离子的存在下，通过芳族阴离子自由基介体间接电化学还原全氟烷基卤化物，沿着S RN 1机理产生相应的全氟烷基化的咪唑。
• 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.
• Electrochemically induced nucleophilic substitution of perfluoroalkyl halides. An example of a dissociative electron-transfer-induced chemical reaction
  作者：Maurice Medebielle、Jean Pinson、Jean Michel Saveant

  DOI：10.1021/ja00018a025

  日期：1991.8

  Nucleophilic substitution of perfluoroalkyl halides can be induced electrochemically. The reaction mechanism is a slightly modified version of the classical S(RN)1 mechanism in which the reaction is triggered by dissociative electron transfer, not involving the intermediacy of the anion radical of the substrate. Direct electrochemical induction is possible in principle with the iodides but not with the bromides because the reduction potentials of the substrate and of the perfluoroalkyl radical are too close in the latter case. This impossibility can be overcome by using as inductor an electrochemically generated outer-sphere electron donor. Thiolates react at the sulfur atom whereas phenoxide as well as imidazolate ions react at ring carbons rather than at the negatively charged heteroatom.