1-乙基-2-甲基-4-硝基咪唑 | 89128-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-乙基-2-甲基-4-硝基咪唑
• 中文别名: 1-乙基-2-甲基-4-硝基-1H-咪唑
• 英文名称: 1-ethyl-2-methyl-4-nitro-1H-imidazole
• 英文别名: 1-ethyl-2-methyl-4-nitroimidazole
• CAS: 89128-07-4
• 化学式: C₆H₉N₃O₂
• mdl: MFCD00156146
• 分子量: 155.156
• InChiKey: AILAZDVPNOAKOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  1-乙基-2-甲基-4-硝基咪唑 在 溴 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以93%的产率得到5-Bromo-1-ethyl-2-methyl-4-nitro-1H-imidazole
  参考文献：
  名称：

  A new high-yielding method for the preparation of 2-alkyl- and 1,2-dialkyl-4-nitro-5-bromoimidazoles

  摘要：

  DOI：

  10.1021/jo00037a051
• 作为产物：
  描述：

  溴乙烷 、 2-甲基-4-硝基咪唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以82%的产率得到1-乙基-2-甲基-4-硝基咪唑
  参考文献：
  名称：

  Transition-Metal-Catalyzed Arylation of Nitroimidazoles and Further Transformations of Manipulable Nitro Group

  摘要：

  Pd- or Ni-catalyzed CH arylation of 4-nitroimidazole derivatives directed by a manipulable nitro group was developed. The reaction tolerates a wide range of substituted aryl halides and 4-nitroimidazoles. The experiments indicated that the nitro group has influence on regioselectivity of the reaction. In addition, we have shown that the efficiency of the SuzukiMiyaura cross-coupling reaction of nitroimidazoles is slightly lower in comparison to the direct CH arylation. The exploration of the chemical potential of the nitro group and a putative reaction mechanism are discussed.

  DOI：

  10.1021/jo5025927

文献信息

• Azoles. Part 43: Reactions of N-(Phenylsulphonylmethyl)- and N-(Phenylsulphinylmethyl)azoles with some Nitroarenes
  作者：Marek K Bernard

  DOI：10.1016/s0040-4020(00)00624-4

  日期：2000.9

  cleavage of the phenylsulphonyl group, whereas the t-BuOK/DMF system at low temperature promotes to a greater extent oxidation of the σ-adducts. When 1-(phenylsulphinylmethyl)azoles were used for the reaction only elimination of the phenylsulphinyl group was observed.

  在室温下，在KOH / DMSO系统中用1-（苯磺酰基甲基）唑对硝基芳烃进行处理通常会导致苯磺酰基的裂解，而在低温下的t- BuOK / DMF系统则会在更大程度上促进σ-的氧化。加合物。当将1-（苯基亚磺酰基甲基）唑用于反应时，仅观察到苯基亚磺酰基的消除。
• Rao, A. K. S. Bhujanga; Rao, C. Gundu; Singh, B. B., Journal of the Chemical Society. Perkin transactions I, 1994, # 17, p. 2399 - 2402
  作者：Rao, A. K. S. Bhujanga、Rao, C. Gundu、Singh, B. B.

  DOI：——

  日期：——
• Electrophilic Iodination of 4-Nitroimidazoles - a New High Yielding Method for the Synthesis of 4-Nitro-5-iodoimidazoles
  作者：Rao、Rao、Singh

  DOI：10.1080/00397919408011194

  日期：1994.2

  Electrophilic iodination of 4-nitroimidazoles employing the system KI-HN3-AcOH provided for the synthesis of 4-nitro-5-iodoimidazoles in high yields. With 2-unsubstituted-4-nitroimidazoles, 2,5-diiodo-4-nitro-imidazoles were obtained.
• A Facile High Yielding Method for Synthesis of N-Alkyl-4-Nitroimidazoles
  作者：A. K. S. Bhujanga Rao、C. Gundu Rao、B. B. Singh

  DOI：10.1080/00397919108016766

  日期：1991.2

  A high yielding and fast reaction for the synthesis of a variety of N-alkyl 4-nitroimidazoles has been described. This method involves reaction of 2-methyl-4(5)-nitro-1H-imidazole with suitable alkyl halides in K2CO3/DMF at 110-120-degrees-C.
• Solid — Liquid Phase — Transfer Catalytic Method for N-Alkylation of Nitroimidazole
  作者：Zhen-Zhong Liu、Heng-Chang Chen、Sheng-Li Cao、Run-Tao Li

  DOI：10.1080/00397919308012596

  日期：1993.9

  A variety of 1-alkyl-2-methyl-4-nitroimidazoles have been synthesized with a solid-liquid phase-transfer catalytic method in excellent yield.