(S)-benzyl 2-(3,5-dioxopyrrolidin-2-yl)acetate | 1316848-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-benzyl 2-(3,5-dioxopyrrolidin-2-yl)acetate
• 英文别名: benzyl 2-[(2S)-3,5-dioxopyrrolidin-2-yl]acetate
• CAS: 1316848-20-0
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: XKABYBQCWFDXRS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-(3,5-dioxopyrrolidin-2-yl)acetate 、 (S)-4-(tert-butoxy)-5-((S)-sec-butyl)-1-((S)-pyrrolidin-3-yl)-1H-pyrrol-2(5H)-one 在 原甲酸三甲酯 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以55%的产率得到benzyl 2-((S)-3-((S)-3-((S)-3-(tert-butoxy)-2-((S)-sec-butyl)-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)pyrrolidin-1-yl)-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)acetate
  参考文献：
  名称：

  Pyrrolinone–Pyrrolidine Oligomers as Universal Peptidomimetics

  摘要：

  Peptidomimetics 1-3 were prepared from amino acid-derived tetramic acids 7 as the key starting materials. Calculations show that preferred conformations of 1 can align their side-chain vectors with amino acids in common secondary structures more effectively than conformations of 3. A good fit was found for a preferred conformation of 2 (an extended derivative of 1) with a sheet/beta-turn/sheet motif.

  DOI：

  10.1021/ja2033734
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (S)-benzyl 2-(3,5-dioxopyrrolidin-2-yl)acetate
  参考文献：
  名称：

  Pyrrolinone–Pyrrolidine Oligomers as Universal Peptidomimetics

  摘要：

  Peptidomimetics 1-3 were prepared from amino acid-derived tetramic acids 7 as the key starting materials. Calculations show that preferred conformations of 1 can align their side-chain vectors with amino acids in common secondary structures more effectively than conformations of 3. A good fit was found for a preferred conformation of 2 (an extended derivative of 1) with a sheet/beta-turn/sheet motif.

  DOI：

  10.1021/ja2033734

文献信息

• Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics
  作者：Arjun Raghuraman、Dongyue Xin、Lisa M. Perez、Kevin Burgess

  DOI：10.1021/jo400323k

  日期：2013.5.17

  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.