4-(tridecafluorohexyl)-1H-imidazole | 81769-54-2

• 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-(tridecafluorohexyl)-1H-imidazole
• 英文别名: 4(5)-(tridecafluorohexyl)imidazole；4-Perfluorohexyl imidazole；4-perfluorohexylimidazole；Imidazole, 4-tridecafluorohexyl-；5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-1H-imidazole
• CAS: 81769-54-2
• 化学式: C₉H₃F₁₃N₂
• 分子量: 386.115
• InChiKey: RKFABGHMQGCKGI-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C(Solv: methanol (67-56-1))
• 沸点：
  236.7±40.0 °C(Predicted)
• 密度：
  1.666±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  全氟己基碘烷 、 咪唑钠 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以68.7%的产率得到4-(tridecafluorohexyl)-1H-imidazole
  参考文献：
  名称：

  氟烷基化和氟烷氧基化的研究。氟烷基化咪唑的区域选择性合成

  摘要：

  在温和的条件下，通过咪唑阴离子与氟代烷基碘化物或溴化物的反应，区域选择性地获得高产率的4-氟代烷基咪唑。提出了一种S RN 1机制。

  DOI：

  10.1039/c39870001240

文献信息

• Photochemical perfluoroalkylation of imidazoles
  作者：Hiroshi Kimoto、Shozo Fujii、Louis A. Cohen

  DOI：10.1021/jo00136a010

  日期：1982.7
• Fluoroalkylation of aromatic compounds with per(poly)fluoroalkyl chlorides initiated by sodium dithionite in DMSO
  作者：Xiao-Ting Huang、Zheng-Yu Long、Qing-Yun Chen

  DOI：10.1016/s0022-1139(01)00442-0

  日期：2001.10

  Treatment of electron-rich aromatic and heteroaromatic. compounds with per(poly)fluoroalkyl chlorides in the presence of sodium dithionite in DMSO gives the corresponding fluoroalkylated products in moderate to good yields. The structures and yields of products depend mainly on the position and electron-donating ability of the substituents on the aromatic compounds. (C) 2001 Elsevier Science B.V. All rights reserved.
• 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.
• MEDEBIELLE, MAURICE;PINSON, JEAN;SAVEANT, JEAN-MICHEL, TETRAHEDRON LETT., 31,(1990) N, C. 1279-1282
  作者：MEDEBIELLE, MAURICE、PINSON, JEAN、SAVEANT, JEAN-MICHEL

  DOI：——

  日期：——