2-N-benzoylamino-4(5)-trifluoromethyl-5(4)-benzoyl-imidazole | 1021875-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-N-benzoylamino-4(5)-trifluoromethyl-5(4)-benzoyl-imidazole
• 英文别名: N-[4-benzoyl-5-(trifluoromethyl)-1H-imidazol-2-yl]benzamide
• CAS: 1021875-59-1
• 化学式: C₁₈H₁₂F₃N₃O₂
• 分子量: 359.307
• InChiKey: DCKHVHFJDWZVEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-N-benzoylamino-4(5)-trifluoromethyl-5(4)-benzoyl-imidazole 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以72%的产率得到2-N-benzoylamino-4(5)-trifluoromethyl-5(4)-hydroxy(phenyl)methyl-imidazole
  参考文献：
  名称：

  Synthesis of trifluoromethylated 2-benzoyl- and 2-aminoimidazoles from ring rearrangement of 1,2,4-oxadiazole derivatives

  摘要：

  Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated beta-dicarbonyl compounds and subsequent base-induced Boulton-Katritzky Rearrangement (BKR) of the isolated beta-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.047
• 作为产物：
  描述：

  3-氨基-5-苯基-1,2,4-噁二唑 、 苯甲酰三氟丙酮 在 Montmorillonite K₁₀ 作用下， 以 甲苯 为溶剂， 以36%的产率得到2-N-benzoylamino-4(5)-trifluoromethyl-5(4)-benzoyl-imidazole
  参考文献：
  名称：

  Synthesis of trifluoromethylated 2-benzoyl- and 2-aminoimidazoles from ring rearrangement of 1,2,4-oxadiazole derivatives

  摘要：

  Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated beta-dicarbonyl compounds and subsequent base-induced Boulton-Katritzky Rearrangement (BKR) of the isolated beta-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.047