2-bromo-1-[(2S,4S)-4-fluoro-2-(5-{1,1-dimethyl-propyl}-[1,3,4]oxadiazole-2-carbonyl)-pyrrolidine-1]-ethanone | 851028-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-bromo-1-[(2S,4S)-4-fluoro-2-(5-{1,1-dimethyl-propyl}-[1,3,4]oxadiazole-2-carbonyl)-pyrrolidine-1]-ethanone
• CAS: 851028-94-9
• 化学式: C₁₄H₁₉BrFN₃O₃
• 分子量: 376.226
• InChiKey: QWHODLORTGHMDC-IUCAKERBSA-N

物化性质

• 沸点：
  494.8±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 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：
  0.71
• 拓扑面积：
  76.3
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-bromo-1-[(2S,4S)-4-fluoro-2-(5-{1,1-dimethyl-propyl}-[1,3,4]oxadiazole-2-carbonyl)-pyrrolidine-1]-ethanone 、 叔丁胺 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 2-tert-butylamino-1-{(2S,4S)-2-[5-(1,1-dimethyl-propyl)-[1,3,4]oxadiazole-2-carbonyl]-4-fluoro-pyrrolidine-1-yl}-ethanone
  参考文献：
  名称：

  Synthesis, SAR, and X-ray structure of novel potent DPPIV inhibitors: Oxadiazolyl ketones

  摘要：

  Synthesis of a novel series of DPPIV inhibitors with 1,2,4- and 1,3,4-oxadiazolyl ketone derivatives and its structure-activity relationships are discussed. Compound 18h showed good inhibitory activity against DPPIV and favorable pharmacokinetic properties. In vivo pharmacodynamic efficacy and co-crystal structure of compound 18h with DPPIV is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.046
• 作为产物：
  描述：

  (2S,4S)-1-tert-butoxycarbonyl-4-fluoro-2-(methoxy(methyl)carbamoyl)pyrrolidine 在 盐酸 、 正丁基锂 、 三乙胺 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 2-bromo-1-[(2S,4S)-4-fluoro-2-(5-{1,1-dimethyl-propyl}-[1,3,4]oxadiazole-2-carbonyl)-pyrrolidine-1]-ethanone
  参考文献：
  名称：

  Synthesis, SAR, and X-ray structure of novel potent DPPIV inhibitors: Oxadiazolyl ketones

  摘要：

  Synthesis of a novel series of DPPIV inhibitors with 1,2,4- and 1,3,4-oxadiazolyl ketone derivatives and its structure-activity relationships are discussed. Compound 18h showed good inhibitory activity against DPPIV and favorable pharmacokinetic properties. In vivo pharmacodynamic efficacy and co-crystal structure of compound 18h with DPPIV is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.046