5-chloro-2-(dimethylamino)-1-(4-methoxyphenyl)-1H-imidazole-4-carboxaldehyde | 215320-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-2-(dimethylamino)-1-(4-methoxyphenyl)-1H-imidazole-4-carboxaldehyde
• 英文别名: 5-Chloro-2-(dimethylamino)-1-(4-methoxyphenyl)imidazole-4-carbaldehyde
• CAS: 215320-62-0
• 化学式: C₁₃H₁₄ClN₃O₂
• 分子量: 279.726
• InChiKey: KDHOMMAHTLSCEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(dimethylamino)-1-(4-methoxyphenyl)-1H-imidazole-4-carboxaldehyde 在 盐酸 、 manganese(IV) oxide 、 氰化钠 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 N-[(E)-(4-bromophenyl)methylideneamino]-5-chloro-2-(dimethylamino)-1-(4-methoxyphenyl)imidazole-4-carboxamide
  参考文献：
  名称：

  新型抗伤害性N-取代-苯基咪唑基-4-酰基hydr衍生物的合成和药理评价。

  摘要：

  本文介绍了属于N-取代-苯基咪唑基-4-酰基hydr类（3a-o）的新型N-杂环官能化N-酰基hydr化合物（NAH）的设计，合成和药理学评估的最新结果。通过应用分子杂交策略对这些化合物进行规划，以提出对上述功能化的2-甲基-咪唑基-3-酰基ac类（2）的结构修饰，该类化合物具有重要的镇痛作用。为了研究N-杂芳族环和N-酰基hydr部分对镇痛活性的可能药效学贡献，合成了这个新系列（3）。化合物3g和3n是该系列中最有效的镇痛药，筛选剂量为100 mg / kg po和化合物3e，

  DOI：

  10.1016/s0014-827x(02)01286-7
• 作为产物：
  描述：

  2-氯-N-(4-甲氧基苯基)-乙酰胺 在 sodium azide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-chloro-2-(dimethylamino)-1-(4-methoxyphenyl)-1H-imidazole-4-carboxaldehyde
  参考文献：
  名称：

  Intramolecular Cyclization of Azides by Iminium Species. A Novel Method for the Construction of Nitrogen Heterocycles under Vilsmeier Conditions

  摘要：

  An unprecedented attack of the azide functionality by iminium species, generated in situ under Vilsmeier conditions, provided a novel route for the construction of nitrogen heterocycles. Thus, the treatment of 2-azidoacetophenones with Vilsmeier reagent under reflux conditions gave 5-aryloxazole-4-carboxaldehydes. One-pot synthesis of oxazole carboxaldehydes from 2-bromoacetophenones by dehaloazidation-Vilsmeier cyclization reaction sequence provided better yields. The susceptibility of the carbonyl group to undergo chloroformylation at room temperature without affecting the azide function was exploited to provide an attractive scheme for the synthesis of alpha-azido-beta-chlorovinyl azides from phenacyl azides. The synthesis of a series of N-aryl 5-chloro-2-(dimethylamino)imidazole-4-carboxaldehydes was accomplished by the Vilsmeier cyclization of N-aryl-2-azidoacetamides. The possible mechanisms for the reactions are also discussed.

  DOI：

  10.1021/jo971745z

文献信息

• Synthesis and pharmacological evaluation of novel antinociceptive N-substituted-phenylimidazolyl-4-acylhydrazone derivatives
  作者：Anna C Cunha、Jorge L.M Tributino、Ana L.P Miranda、Carlos A.M Fraga、Eliezer J Barreiro

  DOI：10.1016/s0014-827x(02)01286-7

  日期：2002.12

  This paper describes recent results of design, synthesis and pharmacological evaluation of new N-heterocyclic functionalized N-acylhydrazone compounds (NAH), belonging to the N-substituted-phenylimidazolyl-4-acylhydrazone class (3a-o). These compounds were planned by applying the molecular hybridization strategy to propose the structural modifications on the previously described functionalized 2-m

  本文介绍了属于N-取代-苯基咪唑基-4-酰基hydr类（3a-o）的新型N-杂环官能化N-酰基hydr化合物（NAH）的设计，合成和药理学评估的最新结果。通过应用分子杂交策略对这些化合物进行规划，以提出对上述功能化的2-甲基-咪唑基-3-酰基ac类（2）的结构修饰，该类化合物具有重要的镇痛作用。为了研究N-杂芳族环和N-酰基hydr部分对镇痛活性的可能药效学贡献，合成了这个新系列（3）。化合物3g和3n是该系列中最有效的镇痛药，筛选剂量为100 mg / kg po和化合物3e，
• Intramolecular Cyclization of Azides by Iminium Species. A Novel Method for the Construction of Nitrogen Heterocycles under Vilsmeier Conditions
  作者：Vattoly J. Majo、Paramasivan T. Perumal

  DOI：10.1021/jo971745z

  日期：1998.10.1

  An unprecedented attack of the azide functionality by iminium species, generated in situ under Vilsmeier conditions, provided a novel route for the construction of nitrogen heterocycles. Thus, the treatment of 2-azidoacetophenones with Vilsmeier reagent under reflux conditions gave 5-aryloxazole-4-carboxaldehydes. One-pot synthesis of oxazole carboxaldehydes from 2-bromoacetophenones by dehaloazidation-Vilsmeier cyclization reaction sequence provided better yields. The susceptibility of the carbonyl group to undergo chloroformylation at room temperature without affecting the azide function was exploited to provide an attractive scheme for the synthesis of alpha-azido-beta-chlorovinyl azides from phenacyl azides. The synthesis of a series of N-aryl 5-chloro-2-(dimethylamino)imidazole-4-carboxaldehydes was accomplished by the Vilsmeier cyclization of N-aryl-2-azidoacetamides. The possible mechanisms for the reactions are also discussed.