tetramethylammonium 4-nitroimidazolate | 135284-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tetramethylammonium 4-nitroimidazolate
• 英文别名: 4-nitroimidazol-1-ide;tetramethylazanium
• CAS: 135284-97-8
• 化学式: C₃H₂N₃O₂*C₄H₁₂N
• 分子量: 186.214
• InChiKey: XINLFMMRVYYIMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  70.13
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  全氟己基碘烷 、 tetramethylammonium 4-nitroimidazolate 在 4-硝基吡啶-N-氧化物 、 tetrabutylammonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 生成 4-Nitro-5-perfluorohexyl imidazole 、 4-Nitro-2-perfluorohexyl imidazole
  参考文献：
  名称：

  Electrochemically induced nucleophilic substitution of perfluoroalkyl halides. An example of a dissociative electron-transfer-induced chemical reaction

  摘要：

  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.

  DOI：

  10.1021/ja00018a025
• 作为产物：
  描述：

  4-硝基-3H-咪唑 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以91%的产率得到tetramethylammonium 4-nitroimidazolate
  参考文献：
  名称：

  寻找结合有偶氮酸盐阴离子的离子液体。

  摘要：

  28种新型盐，分别与四甲基，四乙基和四丁基铵和1-丁基-3-甲基咪唑鎓阳离子与3,5-二硝基-1,2,4-三重氮酸酯，4-硝基-1,2,3-三重氮酸酯配对分别使用差示扫描量热法（DSC），热重分析（TGA）和单晶制备了2,4-二硝基咪唑盐，4,5-二硝基咪唑盐，4,5-二氰基咪唑盐，4-硝基咪唑盐和四唑酸盐阴离子并进行了表征。 X射线晶体学。阳离子和阴离子的类型和结构对所得盐（包括几种离子液体）的物理化学性质的影响已得到研究和讨论。使用1-丁基-3-甲基咪唑鎓阳离子（[C（4）mim]（+））和杂环偶氮根阴离子的所有组合获得离子液体（定义为mp <100摄氏度）。以及四乙基或四丁基铵阳离子和偶氮根阴离子的几种组合。[C（4）mim]（+）偶氮盐在室温下呈液态，表现出较大的液体范围，并在玻璃化转变温度为-53至-82摄氏度的条件下冷却时形成玻璃（3,5- mp 33℃的二硝基1,1,2,4-

  DOI：

  10.1002/chem.200500840

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.