(9ci)-2-(3-吡啶)-1H-咪唑-4-羧醛 | 279251-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (9ci)-2-(3-吡啶)-1H-咪唑-4-羧醛
• 英文名称: 2-(3-pyridyl)-1H-4-imidazolcarbaldehyde
• 英文别名: 4-formyl-2-(pyridin-3-yl)-1H-imidazole；2-(Pyridin-3-yl)-1H-imidazole-5-carbaldehyde；2-pyridin-3-yl-1H-imidazole-5-carbaldehyde
• CAS: 279251-09-1
• 化学式: C₉H₇N₃O
• 分子量: 173.174
• InChiKey: FDJLINNUQPJPPX-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  464.3±25.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-叔丁基羟胺盐酸盐 、 (9ci)-2-(3-吡啶)-1H-咪唑-4-羧醛 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以60%的产率得到
  参考文献：
  名称：

  Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones

  摘要：

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.

  DOI：

  10.1021/jm991154w
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以16.1 mg的产率得到(9ci)-2-(3-吡啶)-1H-咪唑-4-羧醛
  参考文献：
  名称：

  Highly Efficient, Environment-Friendly, One-Pot Synthesis of 2-Substituted 4-Formylimidazoles from 4-Acylaminoisoxazoles

  摘要：

  A highly efficient and environment-friendly one-pot synthesis of 2-substituted 4-formylimidazoles was accomplished. Raney nickel catalyzed hydrogenation of 4-acylaminoisoxazoles in ethanol, followed by sodium hydroxide promoted recyclization of the ring-opened intermediates, afforded the functionalized imidazoles.

  DOI：

  10.1055/s-0034-1379201