endo-N,N-bis[(4-methoxyphenyl)methyl]-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-ethanesulfonamide

• 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: endo-N,N-bis[(4-methoxyphenyl)methyl]-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-ethanesulfonamide
• 英文别名: N,N-bis[(4-methoxyphenyl)methyl]-2-[(1R,2S,4R)-4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanyl]ethanesulfonamide
• 化学式: C₂₈H₃₇NO₅S
• 分子量: 499.671
• InChiKey: BNGIOWDYUIVMAF-OARDWFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  白樟油 、 N,N-bis(4-methoxybenzyl)ethenesulfonamide 在 双(三甲基硅烷基)氨基钾 作用下， 生成 exo-N,N-bis[(4-methoxyphenyl)methyl]-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-ethanesulfonamide 、 endo-N,N-bis[(4-methoxyphenyl)methyl]-4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-ethanesulfonamide
  参考文献：
  名称：

  Synthesis and Reactions of exo-Camphorylsulfonyloxaziridine

  摘要：

  The first example of an exo-camphorylsulfonyloxaziridine 4a was prepared by m-CPBA oxidation of camphor imine 9. This surprising result is due to the conformation of the imine which apparently prevents attack of the peracid from the endo direction. Similar oxidations of all other camphorsulfonylimines result in the endo-oxaziridine exclusively. Asymmetric oxidation of sulfides to sulfoxides and the alpha-hydroxylation of enolates by 4 can be interpreted in terms of open transition states where nonbonded interactions are minimized. These results support earlier conclusions and predictions of the stereoselectivity and mechanisms of molecular recognition by the N-sulfonyloxaziridine class of oxidizing reagents.

  DOI：

  10.1021/jo961991v

文献信息

• Synthesis and Reactions of <i>exo</i>-Camphorylsulfonyloxaziridine
  作者：Franklin A. Davis、Rajarathnam E. Reddy、Parimala V. N. Kasu、Padma S. Portonovo、Patrick J. Carroll

  DOI：10.1021/jo961991v

  日期：1997.5.1

  The first example of an exo-camphorylsulfonyloxaziridine 4a was prepared by m-CPBA oxidation of camphor imine 9. This surprising result is due to the conformation of the imine which apparently prevents attack of the peracid from the endo direction. Similar oxidations of all other camphorsulfonylimines result in the endo-oxaziridine exclusively. Asymmetric oxidation of sulfides to sulfoxides and the alpha-hydroxylation of enolates by 4 can be interpreted in terms of open transition states where nonbonded interactions are minimized. These results support earlier conclusions and predictions of the stereoselectivity and mechanisms of molecular recognition by the N-sulfonyloxaziridine class of oxidizing reagents.