(5S)-5-isobutyl-2,4-dioxopyrrolidine | 53618-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S)-5-isobutyl-2,4-dioxopyrrolidine
• 英文别名: (S)-5-isobutylpyrrolidine-2,4-dione；(S)-5-(2-methylpropyl)-2,4-pyrrolidinedione；(5S)-5-(2-Methylpropyl)pyrrolidine-2,4-dione
• CAS: 53618-00-1
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: CPQISGPODAZNLC-LURJTMIESA-N

物化性质

• 熔点：
  89-92 °C
• 沸点：
  333.9±35.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-5-isobutyl-2,4-dioxopyrrolidine 在 aluminum nickel 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 (4S,5S)-5-isobutyl-4-hydroxy-2-oxopyrrolidine
  参考文献：
  名称：

  2-oxo-1-pyrrolidine carboxylic acid esters

  摘要：

  描述了一种改进的工艺，用于制备statine、statine的苯基类似物、statine的环己基类似物及其衍生物，以及在该工艺中使用的其他有价值的中间体。

  公开号：

  US05061808A1
• 作为产物：
  描述：

  (S)-2-Isobutyl-3,5-dioxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 反应 0.25h， 以85%的产率得到(5S)-5-isobutyl-2,4-dioxopyrrolidine
  参考文献：
  名称：

  Diastereofacial selectivity in reduction of chiral tetramic acids

  摘要：

  The reduction of (5S)-5-alkyl-2,4-dioxopyrrolidines, so-called tetramic acids, by NaBH4 gives only partial diastereofacial selectivity in the case of the N-substituted analogues 9f-i, unlike the carbamate derivatives 9a-3 which give the reduced cis-pyrrolidinones 10betaa-e. Increasing the steric hindrance of either the N- or C-5-substituents enhances the re-face selectivity. On the other hand, reduction of the heterobicyclic compound 9n leads to a dramatic reversal of the stereoselectivity. Preliminary calculations show that the N-atom of the ring is slightly pyramidalized; the direction of hydride addition could be a consequence of this finding.

  DOI：

  10.1021/jo00072a018

文献信息

• Synthesis of new chiral lactam-fused pyridine derivatives
  作者：Tetsuya Sengoku、Yusuke Murata、Chihiro Suzuki、Masaki Takahashi、Hidemi Yoda

  DOI：10.1039/c5ra16896a

  日期：——

  An acid promoted cyclisation of benzylidene-modified tetramic acid and various enamines followed by MnO₂ oxidation afforded the corresponding C₂-symmetric and unsymmetric lactam-fused pyridines in enantiomerically pure forms.

  一种酸促进的苯甲醛修饰的四酮酸和各种乙烯胺的环化反应，随后经过MnO₂氧化，形成了相应的对映纯的C₂-对称和非对称的内酰胺-融合吡啶。
• Short and efficient diastereoselective synthesis of pyrrolidinone-containing dipeptide analogues
  作者：Masood Hosseini、Jakob S. Grau、Kasper K. Sørensen、Inger Søtofte、David Tanner、Anthony Murray、Janne E. Tønder

  DOI：10.1039/b705093c

  日期：——

  The pyrrolidine-2,4-diones have been identified as a convenient starting point for the synthesis of peptide analogues. Herein we describe an optimized two-step reductive amination procedure, which provides a small library of pyrrolidinone-containing dipeptide analogues in high yield and excellent diastereoselectivity.

  吡咯烷-2，4-二酮已被鉴定为合成肽类似物的方便起点。在这里，我们描述了一种优化的两步还原胺化程序，该程序以高收率和出色的非对映选择性提供了一个小的含吡咯烷酮的二肽类似物文库。
• Process for statine and statine analogs
  申请人：Warner-Lambert Company

  公开号：US04876343A1

  公开（公告）日：1989-10-24

  An improved process for the preparation of statine, the phenyl analog of statine, the cyclohexyl analog of statine and derivatives thereof is described, as well as other valuable intermediates used in the process.

  本文描述了一种改进的工艺，用于制备statine，statine的苯基类似物，statine的环己基类似物及其衍生物，以及在该过程中使用的其他有价值的中间体。
• 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.
• Pyrrolinone–Pyrrolidine Oligomers as Universal Peptidomimetics
  作者：Arjun Raghuraman、Eunhwa Ko、Lisa M. Perez、Thomas R. Ioerger、Kevin Burgess

  DOI：10.1021/ja2033734

  日期：2011.8.17

  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.