(1S,5S,8aS)-2-Benzyl-1-hydroxymethyl-8a-methyl-5-phenyl-tetrahydro-imidazo[5,1-c][1,4]oxazine-3,8-dione | 140705-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (1S,5S,8aS)-2-Benzyl-1-hydroxymethyl-8a-methyl-5-phenyl-tetrahydro-imidazo[5,1-c][1,4]oxazine-3,8-dione
• 英文别名: (1S,5S,8aS)-2-benzyl-1-(hydroxymethyl)-8a-methyl-5-phenyl-5,6-dihydro-1H-imidazo[5,1-c][1,4]oxazine-3,8-dione
• CAS: 140705-89-1
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: YUDCZMRBZQLQPY-OPYAIIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-3-((3S,4S)-4-Benzylamino-3-methyl-2-oxo-tetrahydro-furan-3-yl)-4-phenyl-oxazolidin-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(1S,5S,8aS)-2-Benzyl-1-hydroxymethyl-8a-methyl-5-phenyl-tetrahydro-imidazo[5,1-c][1,4]oxazine-3,8-dione
  参考文献：
  名称：

  Novel rearrangements of chiral 3-oxazolidinylazetidin-2-ones

  摘要：

  Reaction of a 3-oxazolininyl-4-hydroxymethylazetidin-2-one with excess NaOMe in refluxing methanol gives the corresponding 4-oxa-1,8-diazabicyclo[4.3.0]nonan-5,9-dione stereospecifically in nearly quantitative yield via a novel skeletal rearrangement, which includes a gamma-lactone as a key-intermediate; Possible mechanisms and similar rearrangement in a related system is discussed.

  DOI：

  10.1016/s0040-4039(00)91567-3