(S)-N-benzyl-3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanamide | 1332355-70-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-N-benzyl-3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanamide
• 英文别名: (2S)-N-benzyl-3-cyclopentyl-2-[4-(trifluoromethyl)imidazol-1-yl]propanamide
• CAS: 1332355-70-0
• 化学式: C₁₉H₂₂F₃N₃O
• 分子量: 365.398
• InChiKey: XAMKULBOTDKVII-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-3-cyclopentyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanoic acid 、 苄胺 在 吡啶 、 1-丙基磷酸酐 作用下， 以 乙酸乙酯 为溶剂， 以98%的产率得到(S)-N-benzyl-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