甲基2-氧杂-3-氮杂双环[2.2.1]庚烷-3-羧酸酯 | 188789-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 甲基2-氧杂-3-氮杂双环[2.2.1]庚烷-3-羧酸酯
• 英文名称: N-methyloxycarbonyl-2-aza-3-oxabicyclo[2.2.1]heptane
• 英文别名: Methyl 2-oxa-3-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS: 188789-38-0
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: YNIAYXZEFRMUOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-methyloxycarbonyl-2-aza-3-oxabicyclo[2.2.1]hept-5-ene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以92%的产率得到甲基2-氧杂-3-氮杂双环[2.2.1]庚烷-3-羧酸酯
  参考文献：
  名称：

  2-Aza-3-oxabicyclo[2.2.1]heptene hydrochloride: An exceptionally versatile synthon for carbocyclic sugars and nucleosides

  摘要：

  The transformation of cyclopentadiene to 5'-desmethylene 1'-aza carbocyclic sugars has been achieved in four steps: 1. Cycloaddition of chloronitrosocyclohexane to 2-aza-3-oxabicyclo[2.2.1]heptene hydrochloride in EtOH-Et(2)O, 2. Nitrogen functionalization, 3. cis hydroxylation and 4. N-O bond cleavage. The protocols provided enable practical access to a range of 5'-desmethylene carbocyclic sugar analogs whose utility has been illustrated with synthesis of a novel 5'-desmethylene analog of aristeromycin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00057-4

文献信息

• 2-Aza-3-oxabicyclo[2.2.1]heptene hydrochloride: An exceptionally versatile synthon for carbocyclic sugars and nucleosides
  作者：Subramania Ranganathan、K.Shaji George

  DOI：10.1016/s0040-4020(97)00057-4

  日期：1997.3

  The transformation of cyclopentadiene to 5'-desmethylene 1'-aza carbocyclic sugars has been achieved in four steps: 1. Cycloaddition of chloronitrosocyclohexane to 2-aza-3-oxabicyclo[2.2.1]heptene hydrochloride in EtOH-Et(2)O, 2. Nitrogen functionalization, 3. cis hydroxylation and 4. N-O bond cleavage. The protocols provided enable practical access to a range of 5'-desmethylene carbocyclic sugar analogs whose utility has been illustrated with synthesis of a novel 5'-desmethylene analog of aristeromycin. (C) 1997 Elsevier Science Ltd.