(S)-N-isopropyl-3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanamide | 1332355-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-N-isopropyl-3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanamide
• CAS: 1332355-72-2
• 化学式: C₁₅H₂₂F₃N₃O
• 分子量: 317.354
• InChiKey: RDPPKFAUXHJWFD-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.92
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (S)-3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanoic acid 、 异丙胺 在 吡啶 、 1-丙基磷酸酐 作用下， 以 乙酸乙酯 为溶剂， 生成 (R)-N-isopropyl-3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanamide 、 (S)-N-isopropyl-3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanamide
  参考文献：
  名称：

  General and Scalable Amide Bond Formation with Epimerization-Prone Substrates Using T3P and Pyridine

  摘要：

  The mild combination of T3P (n-propanephosphonic acid anhydride) and pyridine has been developed for low-epimerization amide bond formation and implemented for the synthesis of a key intermediate to a glucokinase activator. This robust method is general for the coupling of various racemization-prone acid substrates and amines, including relatively non-nucleophilic anilines, and provides amides in high yields with very low epimerization. With easy reaction setup and product isolation, this protocol offers several practical and experimental benefits.

  DOI：

  10.1021/ol201875q