2H-1,4-噁嗪-2-酮,5,6-二氢-5-(1-甲基乙基)-3-苯基-,(S)- | 175226-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 中文名称: 2H-1,4-噁嗪-2-酮,5,6-二氢-5-(1-甲基乙基)-3-苯基-,(S)-
• 英文名称: (5S)-5-isopropyl-3-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (3S)-5-phenyl-3-propan-2-yl-2,3-dihydro-1,4-oxazin-6-one
• CAS: 175226-71-8
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: AORVRCNEBNKCCK-LLVKDONJSA-N

物化性质

• 沸点：
  311.1±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2H-1,4-噁嗪-2-酮,5,6-二氢-5-(1-甲基乙基)-3-苯基-,(S)- 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以15%的产率得到
  参考文献：
  名称：

  Diastereoselective Reduction of α-Imino Esters with Tris(trimethylsilyl)aluminum

  摘要：

  Tris(trimethylsilyl)aluminum was found to be a good chemoselective reducing reagent for alpha-imino esters to give alpha-amino esters in good yields. Application to the reduction of 3,5-disubstituted 5,6-dihyro-2H-1,4-oxazine2-ones realized a stereoselective conversion into cis-3,5-disubstituted morpholine-2-ones.

  DOI：

  10.3987/com-06-s(k)23
• 作为产物：
  描述：

  噁唑,4,5-二氢-4-(1-甲基乙基)-2-(苯基甲基)-,(S)- 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以74%的产率得到2H-1,4-噁嗪-2-酮,5,6-二氢-5-(1-甲基乙基)-3-苯基-,(S)-
  参考文献：
  名称：

  Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2H-1,4-oxazin-2-ones and Morpholin-2-ones

  摘要：

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.

  DOI：

  10.1021/jo952144f