1-(1H-imidazol-2-yl)-2-nitroethanol | 1223431-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(1H-imidazol-2-yl)-2-nitroethanol
• CAS: 1223431-57-9
• 化学式: C₅H₇N₃O₃
• 分子量: 157.129
• InChiKey: SXWRZDWCXLZNAO-UHFFFAOYSA-N

物化性质

• 沸点：
  454.0±40.0 °C(predicted)
• 密度：
  1.498±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硝基甲烷 、 2-咪唑甲醛 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到1-(1H-imidazol-2-yl)-2-nitroethanol
  参考文献：
  名称：

  NMR Characterization of Hydrate and Aldehyde Forms of Imidazole-2-carboxaldehyde and Derivatives

  摘要：

  The existence and stability of the aldehyde-hydrate form of imidazole-2-carboxaldehyde (4) were studied using FTIR together with solution- and solid-state NMR experiments. The results allowed us to conclude that the hydrate form was stable and precipitated at pH = 8.0 and that the aldehyde form was isolated at p = 6.5 and 9.5. Moreover, the presence of the aldehyde-hydrate form was studied through NMR experiments in D2O at both alkaline and acidic pH. In addition, the tautomeric forms of the 2-substituted imidazole compounds were also analyzed to investigate the influence of the hybridization on the carbon adjacent to the imidazole ring, by C-13 NMR in DMSO-d(6), acetone-d(6), and CDCl3. The presence of the syn- and anti-isomers of oxime 8 obtained from 4 were characterized by solid-state NMR and variable-temperature NMR experiments in acetone-d(6).

  DOI：

  10.1021/jo902588s

文献信息

• NMR Characterization of Hydrate and Aldehyde Forms of Imidazole-2-carboxaldehyde and Derivatives
  作者：Juan Manuel Lázaro Martínez、Pablo Nicolás Romasanta、Ana Karina Chattah、Graciela Yolanda Buldain

  DOI：10.1021/jo902588s

  日期：2010.5.21

  The existence and stability of the aldehyde-hydrate form of imidazole-2-carboxaldehyde (4) were studied using FTIR together with solution- and solid-state NMR experiments. The results allowed us to conclude that the hydrate form was stable and precipitated at pH = 8.0 and that the aldehyde form was isolated at p = 6.5 and 9.5. Moreover, the presence of the aldehyde-hydrate form was studied through NMR experiments in D2O at both alkaline and acidic pH. In addition, the tautomeric forms of the 2-substituted imidazole compounds were also analyzed to investigate the influence of the hybridization on the carbon adjacent to the imidazole ring, by C-13 NMR in DMSO-d(6), acetone-d(6), and CDCl3. The presence of the syn- and anti-isomers of oxime 8 obtained from 4 were characterized by solid-state NMR and variable-temperature NMR experiments in acetone-d(6).