4(1H)-Pyridinone,2-[6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]hexyl]-2,3-dihydro-5-iodo-1-[(E)-[[(1S)-1-(methoxymethyl)-2-methylpropyl]imino]phenylmethyl]-, (2R)- | 904930-00-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4(1H)-Pyridinone,2-[6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]hexyl]-2,3-dihydro-5-iodo-1-[(E)-[[(1S)-1-(methoxymethyl)-2-methylpropyl]imino]phenylmethyl]-, (2R)-
• CAS: 904930-00-3
• 化学式: C₃₀H₄₉IN₂O₃Si
• 分子量: 640.721
• InChiKey: JHTHHPSECGTEKL-IEHOBWAOSA-N

物化性质

• 沸点：
  581.4±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.13
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4(1H)-Pyridinone,2-[6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]hexyl]-2,3-dihydro-5-iodo-1-[(E)-[[(1S)-1-(methoxymethyl)-2-methylpropyl]imino]phenylmethyl]-, (2R)- 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以1.75 g的产率得到(2R)-2-(6-hydroxyhexyl)-5-iodo-1-((E)-{((1S)-1-(methoxymethyl)-2-methylpropyl)imino}(phenyl)methyl)-2,3-dihydropyridin-4(1H)-one
  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：

  4-甲氧基吡啶 在 叔丁基锂 、 一氯化碘 、 caesium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 5.0h， 生成 4(1H)-Pyridinone,2-[6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]hexyl]-2,3-dihydro-5-iodo-1-[(E)-[[(1S)-1-(methoxymethyl)-2-methylpropyl]imino]phenylmethyl]-, (2R)-
  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