tert-butyl (6R)-6-ethyl-1-((E)-{((1S)-1-(methoxymethyl)-2-methylpropyl)imino}(phenyl)methyl)-4-oxo-1,4,5,6-tetrahydropyridin-3-ylcarbamate | 904929-80-2

• 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: tert-butyl (6R)-6-ethyl-1-((E)-{((1S)-1-(methoxymethyl)-2-methylpropyl)imino}(phenyl)methyl)-4-oxo-1,4,5,6-tetrahydropyridin-3-ylcarbamate
• CAS: 904929-80-2
• 化学式: C₂₅H₃₇N₃O₄
• 分子量: 443.586
• InChiKey: BCVIGSVLTNVRDA-DVWYLRQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (6R)-6-ethyl-1-((E)-{((1S)-1-(methoxymethyl)-2-methylpropyl)imino}(phenyl)methyl)-4-oxo-1,4,5,6-tetrahydropyridin-3-ylcarbamate 在 lithium tri-t-butoxyaluminum hydride 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到tert-butyl-(6R)-6-ethyl-1-((E)-{((1S)-1-(methoxymethyl)-2-methylpropyl)imino}(phenyl)methyl)-4-oxopiperidin-3-ylcarbamate
  参考文献：
  名称：

  Stereoselective Synthesis of Pyridinones:  Application to the Synthesis of (−)-Barrenazines

  摘要：

  The stereoselective synthesis of pyridinones was accomplished by the nucleophilic addition of Grignard reagents to a chiral pyridinium salt derived from 4-methoxypyridine. This methodology was applied to an expedient synthesis of (-)-barrenazine A and B. After N-functionalization and 1,4-reduction of the pyridinone system, the corresponding alpha-amino piperidinones readily undergo dimerization to give the hexahydrodipyridinopyrazine skeleton of the barrenazine alkaloids.

  DOI：

  10.1021/ol0609006
• 作为产物：
  描述：

  在 copper(l) iodide 、 一氯化碘 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 39.0h， 生成 tert-butyl (6R)-6-ethyl-1-((E)-{((1S)-1-(methoxymethyl)-2-methylpropyl)imino}(phenyl)methyl)-4-oxo-1,4,5,6-tetrahydropyridin-3-ylcarbamate
  参考文献：
  名称：

  Stereoselective Synthesis of Pyridinones:  Application to the Synthesis of (−)-Barrenazines

  摘要：

  The stereoselective synthesis of pyridinones was accomplished by the nucleophilic addition of Grignard reagents to a chiral pyridinium salt derived from 4-methoxypyridine. This methodology was applied to an expedient synthesis of (-)-barrenazine A and B. After N-functionalization and 1,4-reduction of the pyridinone system, the corresponding alpha-amino piperidinones readily undergo dimerization to give the hexahydrodipyridinopyrazine skeleton of the barrenazine alkaloids.

  DOI：

  10.1021/ol0609006