(3R)-2-tert-butyl-3-(4-methoxyphenyl)oxaziridine | 1385722-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3R)-2-tert-butyl-3-(4-methoxyphenyl)oxaziridine
• CAS: 1385722-20-2
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: RSBGOXJMPUJSCP-JTDNENJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-methoxybenzylidene)-2-methylpropan-2-amine 在 (2S)-2-bromo-3-methylbutanenitrile 、 双氧水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 2-tert-butyl-3-paramethoxyphenyloxaziridine 、 (3R)-2-tert-butyl-3-(4-methoxyphenyl)oxaziridine
  参考文献：
  名称：

  Enantio- and Diastereoselective Oxidation of N-Alkylimines Using Chiral α-Bromonitriles and Hydrogen Peroxide System

  摘要：

  Chiral alpha-bromonitriles were prepared with good chemical and optical yields starting from natural alpha-amino acids by dehydrating the corresponding alpha-bromoamides with thionyl chloride. The combined system alpha-bromonitriles/hydrogen peroxide was examined for the enantio- and diastereoselective oxidation of N-alkylimines in basic media at room temperature. The oxidation of N-tertiobutylarylimines leads to optically active oxaziridines with moderate enantiomeric excess. However, the oxidation of (S)-1-phenylethylarylimines affords the corresponding oxaziridines with good diasteromeric excess up to 97/3 as proved by gaseous-phase chromatography.

  DOI：

  10.1080/00397911.2011.573611