tetramethylammonium salt of uracil | 146489-97-6

• 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: tetramethylammonium salt of uracil
• 英文别名: tetramethylammonium salt of uracyl；6-oxo-1H-pyrimidin-2-olate;tetramethylazanium
• CAS: 146489-97-6
• 化学式: C₄H₃N₂O₂*C₄H₁₂N
• 分子量: 185.226
• InChiKey: KXMFKZBLIFZYBD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
  参考文献：
  名称：

  A Convenient Synthesis of Perfluoroalkylated and Fluorinated-Aryl Nitrogen Bases by Electrochemically Induced S_RN1 Substitution

  摘要：

  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.

  DOI：

  10.1021/jo9515541

文献信息

• Perfluoroalkylation of purine and pyrimidine bases by electrochemically induced SRN1 substitution.
  作者：Maurice Médebielle、Jean Pinson、Jean-Michel Savéant

  DOI：10.1016/s0040-4039(00)60185-5

  日期：1992.11

  Indirect electrochemical reduction, by means of an aromatic anion mediator, of perfluoroalkyl iodides in the presence of purine and pyrimidine anions yields the correspon C-perfluoroalkylated purines and pyrimidines by an SRN1 mechanism.

  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。
• A new convenient synthesis of 5-aryl uracils using SRN1 aromatic nucleophilic substitution
  作者：Maurice Médebielle、Mehmet Ali Oturan、Jean Pinson、Jean-Michel Savéant

  DOI：10.1016/s0040-4039(00)79168-4

  日期：1993.5

  Direct and indirect electrochemical reduction of aryl halides in the presence of the uracil anion in dimethylsulfoxide yields the corrsponding 5-aryl uracils by an SRN1 mechanism.

  在二甲基亚砜中存在尿嘧啶阴离子的情况下，直接和间接电化学还原芳基卤化物可通过S RN 1机理产生相应的5-芳基尿嘧啶。