N-<(S)-1-phenylethyl>-5-phenyl-2-pyrrolidone-1-carboxamide | 90460-02-9

• 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: N-<(S)-1-phenylethyl>-5-phenyl-2-pyrrolidone-1-carboxamide
• 英文别名: (5R,1'S)-5-phenyl-1-(phenylethylaminocarbonyl)pyrrolidin-2-one；(5R)-N-{1-[(S)-phenylethyl]carbamoyl}-5-phenyl-2-pyrrolidone；N-((S)-1-phenylethyl)-5-phenyl-2-pyrrolidone-1-carboxamide；(5R)-2-oxo-5-phenyl-N-[(1S)-1-phenylethyl]pyrrolidine-1-carboxamide
• CAS: 90460-02-9
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: RYTCDXSSDJVOEZ-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-苯基-2-吡咯烷酮 、 (S)-(-)-1-苯乙基异氰酸酯 生成 N-<(S)-1-phenylethyl>-5-phenyl-2-pyrrolidone-1-carboxamide
  参考文献：
  名称：

  PIRKLE, W. H.;ROBERTSON, M. R.;HYUN, HO, MGUNG, J. ORG. CHEM., 1984, 49, N 13, 2433-2437

  摘要：

  DOI：

文献信息

• Chemical and microsomal oxidation of tertiary amides: regio- and stereoselective aspects
  作者：Jim Iley、Roberto Tolando、Luis Constantino

  DOI：10.1039/b102731j

  日期：——

  TPPFe/ButOOH reaction ring oxidation is preferred to N-demethylation, paralleling the relative stabilities of the corresponding intermediate carbon-centred radicals as calculated by the AM1 semi-empirical method. In contrast, the microsomal reaction of the N-methyllactams strongly favours N-demethylation, demonstrating that hydrogen atom abstraction from the alkyl group Z to the amide carbonyl oxygen atom is preferred

  构象受限 叔酰胺 N-甲基-2-吡咯烷酮 在图6中，N-甲基-2-哌啶酮7和N-甲基-ε-己内酰胺8被5,10,15,20-四苯基卟啉toiron（III）氯化物/氧化。叔丁基过氧化氢（TPPFe / Bu t OOH）和苯巴比妥诱导的大鼠肝微粒体。产物是N-去甲基化的内酰胺类以及类似的N-甲基酰亚胺和诺里米德。对于TPPFe / Bu t OOH反应环氧化作用与N-脱甲基化相比，“亚甲基”是优选的，其平行于通过AM1半经验方法计算的相应的以碳为中心的中间自由基的相对稳定性。相比之下，N-甲基内酰胺类的微粒体反应强烈促进N-脱甲基化，这表明从H-甲基内酰胺中提取氢原子烷基 Z到酰胺 羰氧原子是优选的。手性叔酰胺 N-甲基-N-（1-苯乙基）苯甲酰胺 9和N-甲基-5-苯基-2-吡咯烷酮 10也通过TPPFe /卜氧化吨OOH和由苯巴比妥诱导的大鼠肝微粒体。使用TPPPe / Bu t OOH，优选9的仲烷基的损失约为1倍。6
• Synthesis and Absolute Configuration of Novel <i>N</i>,<i>O</i>-Psiconucleosides Using (<i>R</i>)-<i>N</i>-Phenylpantolactam as a Resolution Agent
  作者：Pelayo Camps、Tània Gómez、Diego Muñoz-Torrero、Jordi Rull、Laura Sánchez、Francesca Boschi、Mauro Comes-Franchini、Alfredo Ricci、Teresa Calvet、Mercè Font-Bardia、Erik De Clercq、Lieve Naesens

  DOI：10.1021/jo800769m

  日期：2008.9.1

  A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2.3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.
• A liquid chromatographic method for resolving chiral lactams as their diastereomeric ureide derivatives
  作者：William H. Pirkle、Michael R. Robertson、Myung Ho Hyun

  DOI：10.1021/jo00187a027

  日期：1984.6