(S)-6-methyl-1-(2,3,4,5,6-pentafluorobenzyl)piperazine-2,5-dione | 1059189-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-6-methyl-1-(2,3,4,5,6-pentafluorobenzyl)piperazine-2,5-dione
• 英文别名: (S)-1-(2,3,4,5,6-pentafluorobenzyl)-6-methylpiperazine-2,5-dione；(6S)-6-methyl-1-[(2,3,4,5,6-pentafluorophenyl)methyl]piperazine-2,5-dione
• CAS: 1059189-78-4
• 化学式: C₁₂H₉F₅N₂O₂
• 分子量: 308.208
• InChiKey: QSEOIIFQUOGRKF-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (S)-2-[2-chloro-N-(2,3,4,5,6-pentafluorobenzyl)acetylamino]propanoate 在 氨 作用下， 以 甲醇 为溶剂， 生成 (S)-6-methyl-1-(2,3,4,5,6-pentafluorobenzyl)piperazine-2,5-dione
  参考文献：
  名称：

  (S)-N-Benzyl-3(6)-methylpiperazine-2,5-diones as chiral solvating agents for N-acylamino acid esters

  摘要：

  Three closely related diketopiperazines, (S)-1-benzyl-6-methylpiperazine-2,5-dione (S)-1a, (S)-1-benzyl-3-methylpiperazine-2,5-dione (S)-1b, and (S)-6-methyl-1-(pentafluorobenzyl)piperazine-2,5-dione (S)-1c, were prepared and screened as potential chiral solvating agents in NMR spectroscopy. The H-1 NMR spectra of 13 racemic alpha-amino acid derivatives (RS)-5a-5m were taken in CDCl3 in the presence of equimolar amounts of enantiopure diketopiperazines (S)-1a-1c at 29 degrees C, 0 degrees C, and -20 degrees C. Cornpound (S)-1a exhibited the strongest chiral solvating properties for racemic alpha-amino acid derivatives (RS)-5a-5m and was recognized as a suitable CSA for the determination of their enantiomer composition. Weaker interactions of diketopiperazines (S)-1b and (S)-1c with compounds (RS)-5a-5m indicate that the position and properties of substituents play an important role in the binding affinity of diketopiperazines 1 towards amino acid derivatives 5. Association constants for binding of (S)-1a to each enantiomer of the leucine derivative (RS)-5d in CDCl3 at -20 degrees C were also determined by NMR titration. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.013