2-Methyl-2-(p-nitrophenyl)-3-oxazolin-5-one 3-oxide

• 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: 2-Methyl-2-(p-nitrophenyl)-3-oxazolin-5-one 3-oxide
• 英文别名: 2-Methyl-2-(4-nitrophenyl)-3-oxido-1,3-oxazol-3-ium-5-one
• 化学式: C₁₀H₈N₂O₅
• 分子量: 236.184
• InChiKey: YDUZMYIYYFFPPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  isonitroso Meldrum’s acid 、 对硝基苯乙酮 以 甲苯 为溶剂， 反应 3.0h， 以12%的产率得到2-Methyl-2-(p-nitrophenyl)-3-oxazolin-5-one 3-oxide
  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

文献信息

• A New Synthesis of Highly Functional Nitrones through a Nitrosoketene Intermediate and Their Use for the Stereoselective Synthesis of Amino Acids
  作者：Nobuya Katagiri、Hiroshi Sato、Ayumu Kurimoto、Makoto Okada、Akemi Yamada、Chikara Kaneko

  DOI：10.1021/jo00105a029

  日期：1994.12

  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.