咪唑四甲基铵盐 | 135284-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 咪唑四甲基铵盐
• 英文名称: imidazole tetramethylammonium salt
• 英文别名: tetramethylammonium imidazolate；Imidazol-3-ide;tetramethylazanium
• CAS: 135284-99-0
• 化学式: C₃H₃N₂*C₄H₁₂N
• 分子量: 141.216
• InChiKey: FFFIKOHFZDRFRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  13.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  咪唑四甲基铵盐 、 4-(2-Chloro-2,2-difluoroacetyl)-5-dimethylamino-11,11-difluoro-1,2,11,11a-tetrahydro-3aH-phenanthreno[1,2-b]furan-10-one 以 二甲基亚砜 为溶剂， 反应 10.0h， 以65%的产率得到4-(2-Chloro-2,2-difluoroacetyl)-11,11-difluoro-5-imidazolyl-1-yl-1,2,11,11a-tetrahydro-3aH-phenanthreno[1,2-b]furan-10-one
  参考文献：
  名称：

  氯二氟甲基化酮的电化学诱导自由基串联环化：在合成宝石-二氟杂环中的应用

  摘要：

  一系列chlorodifluoromethylated酮的合成1 - 6被呈现和这些酮的还原裂解的循环伏安法进行了研究，在Ñ，Ñ二甲基甲酰胺（DMF），在惰性电极。间接电化学还原（通过电致阴离子自由基的手段）在乙腈（CH 3 CN）或在ñ，Ñ二甲基甲酰胺（DMF），萘衍生chlorodifluoroacetylated化合物1和2在烯烃底材的存在7 - 10，生成新的宝石-二氟杂环化合物11 - 16一γ，γ-二氟烷基自由基的分子内环化后。α，α-difluoroketones的芳香亲核取代12和13，在无水二甲亚砜，用咪唑作为亲核试剂，在温和条件下进行，得到相应的氮-氮的几个四甲基铵盐交换产品17 - 23在中度至良好的产率。

  DOI：

  10.1016/s0022-1139(00)00372-9

文献信息

• Aromatic NN exchange reactions of N,N-dimethylamino gem-difluorinated heterocycles. A convenient synthesis of new 5-imidazol-1-yl α,α-difluoroketones
  作者：Maurice Médebielle

  DOI：10.1016/0040-4039(96)01064-7

  日期：1996.7

  Aromatic nucleophilic substitution reaction of N,N-dimethylamino α,α-difluoroketones 2 and 3 in anhydrous dimethylsulfoxide, with several tetramethylammonium salts of imidazole as nucleophiles including imidazole, benzimidazole, imidazole-2-carboxaldehyde, 2-(4′-methoxyphenyl)imidazole and 2-methyl-5-nitro imidazole proceeds under mild conditions to give the corresponding nitrogen-nitrogen exchanged

  N，N-二甲基氨基α，α-二氟酮2和3在无水二甲基亚砜中与几种咪唑四甲基铵盐作为亲核试剂的芳香亲核取代反应，包括咪唑，苯并咪唑，咪唑-2-甲醛，2-（4'-甲氧基苯基）咪唑2-甲基-5-硝基咪唑在温和的条件下进行，以中等至良好的收率得到相应的氮-氮交换产物4-12。
• 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.
• Electrochemically induced free-radical tandem cyclisation of chlorodifluoromethylated ketones
  作者：Philippe Hapiot、Maurice Médebielle

  DOI：10.1016/s0022-1139(00)00372-9

  日期：2001.2

  substrates 7–10, yields new gem-difluoro heterocyclic compounds 11–16 after intramolecular cyclisation of a γ,γ-difluoroalkyl radical. Aromatic nucleophilic substitution of α,α-difluoroketones 12 and 13, in anhydrous dimethylsulfoxide, with several tetramethylammonium salts of imidazole as nucleophiles, proceeds under mild conditions to give the corresponding nitrogen–nitrogen exchanged products 17–23 in

  一系列chlorodifluoromethylated酮的合成1 - 6被呈现和这些酮的还原裂解的循环伏安法进行了研究，在Ñ，Ñ二甲基甲酰胺（DMF），在惰性电极。间接电化学还原（通过电致阴离子自由基的手段）在乙腈（CH 3 CN）或在ñ，Ñ二甲基甲酰胺（DMF），萘衍生chlorodifluoroacetylated化合物1和2在烯烃底材的存在7 - 10，生成新的宝石-二氟杂环化合物11 - 16一γ，γ-二氟烷基自由基的分子内环化后。α，α-difluoroketones的芳香亲核取代12和13，在无水二甲亚砜，用咪唑作为亲核试剂，在温和条件下进行，得到相应的氮-氮的几个四甲基铵盐交换产品17 - 23在中度至良好的产率。