rel-(3aR,5S)-3-Oxo-5-<(trimethylsilyl)methyl>-3,3a,4,5-tetrahydroisoxazolo<2,3-c>oxazole-1,1'-spirocyclohexane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: rel-(3aR,5S)-3-Oxo-5-<(trimethylsilyl)methyl>-3,3a,4,5-tetrahydroisoxazolo<2,3-c>oxazole-1,1'-spirocyclohexane
• 英文别名: (2S,3aR)-2-(trimethylsilylmethyl)spiro[3,3a-dihydro-2H-[1,3]oxazolo[3,4-b][1,2]oxazole-6,1'-cyclohexane]-4-one
• 化学式: C₁₄H₂₅NO₃Si
• 分子量: 283.443
• InChiKey: RBFZHEAMHOLBMQ-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rel-(3aR,5S)-3-Oxo-5-<(trimethylsilyl)methyl>-3,3a,4,5-tetrahydroisoxazolo<2,3-c>oxazole-1,1'-spirocyclohexane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以53%的产率得到rel-(3R,5S)-3-(Hydroxymethyl)-2-cyclohexyl-5-<(trimethylsilyl)methyl>isoxazolidine
  参考文献：
  名称：

  A New Synthesis of Highly Functional Nitrones through a Nitrosoketene Intermediate and Their Use for the Stereoselective Synthesis of Amino Acids

  摘要：

  Reaction of 5-isonitroso-2,2-dimethyl-1,3-dioxane-4,6-dione with various ketones under reflux in toluene gives 3-oxazolin-5-one 3-oxides (cyclic nitrones) via a nitrosoketene intermediate generated from the isonitroso derivative. The cyclic nitrones can be used for the stereoselective [3 + 2] dipolar cycloaddition to electron-rich olefins under high pressure to produce fused isoxazolidines. These isoxazolidines, in turn, are versatile intermediates for the stereoselective preparation of substituted alpha-amino acids.

  DOI：

  10.1021/jo00105a029
• 作为产物：
  描述：

  4-Aza-2-oxo-1-oxaspiro<5.4>dec-3-ene 4-oxide 、 烯丙基三甲基硅烷 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 rel-(3aR,5S)-3-Oxo-5-<(trimethylsilyl)methyl>-3,3a,4,5-tetrahydroisoxazolo<2,3-c>oxazole-1,1'-spirocyclohexane
  参考文献：
  名称：

  A New Synthesis of Highly Functional Nitrones through a Nitrosoketene Intermediate and Their Use for the Stereoselective Synthesis of Amino Acids

  摘要：

  Reaction of 5-isonitroso-2,2-dimethyl-1,3-dioxane-4,6-dione with various ketones under reflux in toluene gives 3-oxazolin-5-one 3-oxides (cyclic nitrones) via a nitrosoketene intermediate generated from the isonitroso derivative. The cyclic nitrones can be used for the stereoselective [3 + 2] dipolar cycloaddition to electron-rich olefins under high pressure to produce fused isoxazolidines. These isoxazolidines, in turn, are versatile intermediates for the stereoselective preparation of substituted alpha-amino acids.

  DOI：

  10.1021/jo00105a029