2-tert-butyl-3-paramethoxyphenyloxaziridine | 43052-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-tert-butyl-3-paramethoxyphenyloxaziridine
• 英文别名: 2-tert-butyl-3-(4-methoxy-phenyl)-oxaziridine；(3S)-2-tert-butyl-3-(4-methoxyphenyl)oxaziridine
• CAS: 43052-01-3；67504-72-7；82079-47-8
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: RSBGOXJMPUJSCP-AMGKYWFPSA-N

物化性质

• 沸点：
  269.0±50.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

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

文献信息

• Enantio- and Diastereoselective Oxidation of <i>N</i>-Alkylimines Using Chiral <font>α</font>-Bromonitriles and Hydrogen Peroxide System
  作者：Najeh Tka、Jamil Kraïem、Béchir Ben Hassine

  DOI：10.1080/00397911.2011.573611

  日期：2012.10.15

  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.