benzyl (S)-3-(((S)-1-methoxy-1-oxopropan-2-yl)amino)pyrrolidine-1-carboxylate hydrochloride | 1433502-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (S)-3-(((S)-1-methoxy-1-oxopropan-2-yl)amino)pyrrolidine-1-carboxylate hydrochloride
• CAS: 1433502-99-8
• 化学式: C₁₆H₂₂N₂O₄*ClH
• 分子量: 342.823
• InChiKey: DRAGLSMADSMNJR-KYSPHBLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl (S)-3-(((S)-1-methoxy-1-oxopropan-2-yl)amino)pyrrolidine-1-carboxylate hydrochloride 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 75.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 生成 (S)-tert-butyl 2-((4-methoxybenzyl)amino)propanoate hydrochloride
  参考文献：
  名称：

  Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics

  摘要：

  Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains corresponding to genetically encoded proteins. This paper describes expansion of the synthetic scope of 1, the difficulties encountered in this process, particularly issues with epimerization and slow coupling rates, and methods to overcome them. Finally, spectroscopic and physicochemical properties as well as proteolytic stabilities of molecules in this series were measured; these data highlight the suitability of oligo-pyrrolinone-pyrrolidines for the development of pharmacological probes or pharmaceutical leads.

  DOI：

  10.1021/jo400323k
• 作为产物：
  描述：

  N-CBZ-3-(R)-羟基吡咯烷 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 benzyl (S)-3-(((S)-1-methoxy-1-oxopropan-2-yl)amino)pyrrolidine-1-carboxylate hydrochloride
  参考文献：
  名称：

  Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics

  摘要：

  Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains corresponding to genetically encoded proteins. This paper describes expansion of the synthetic scope of 1, the difficulties encountered in this process, particularly issues with epimerization and slow coupling rates, and methods to overcome them. Finally, spectroscopic and physicochemical properties as well as proteolytic stabilities of molecules in this series were measured; these data highlight the suitability of oligo-pyrrolinone-pyrrolidines for the development of pharmacological probes or pharmaceutical leads.

  DOI：

  10.1021/jo400323k