1-Aza-2-oxa-1-<15N>nitroso-2-cyclohexene

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-Aza-2-oxa-1-<15N>nitroso-2-cyclohexene
• 英文别名: 4-(Oxoamino)-2,3-dihydro-1,4-oxazine
• 化学式: C₄H₆N₂O₂
• 分子量: 115.097
• InChiKey: MZUPVVFKRZSBKL-HOSYLAQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-<15N>Nitroso-2-hydroxymorpholine tosylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 1-Aza-2-oxa-1-<15N>nitroso-2-cyclohexene
  参考文献：
  名称：

  Acid-catalyzed rearrangements of N-nitrosodehydromorpholine

  摘要：

  N-Nitrosodehydromorpholine, a potential metabolic intermediate in the carcinogenic activation of N-nitrosodiethanolamine, and N-nitrosomorpholine, was prepared from the hemiacetal N-nitroso-2-hydroxymorpholine (2) by tosylation and in situ base-catalyzed elimination. The attempted acid-catalyzed hydration of 3 gives neither 2 nor the unstable alpha-hydroxynitrosamine, N-nitroso-3-hydroxymorpholine (4). The product of this transformation is N-(2-hydroxyethyl)-2-oximinoethanamide (5) as confirmed by an X-ray crystallographic determination. Treatment of 3 with gaseous HCl in CH2Cl2 gives 1-aza-4-oxa-3-oximinocyclohexene (6), which rearranges to 5 upon treatment with aqueous acid. The initial rearrangement was proven to be intermolecular by means of a crossover experiment employing (NO)-N-15 and C-5-D-2 isotopomers of 3.

  DOI：

  10.1021/jo00122a036