10-(2-Oxa-3-aza-bicyclo[2.2.1]hept-5-en-3-yl)-10-oxo-decanoic acid methyl ester | 188789-26-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 10-(2-Oxa-3-aza-bicyclo[2.2.1]hept-5-en-3-yl)-10-oxo-decanoic acid methyl ester
• CAS: 188789-26-6
• 化学式: C₁₆H₂₅NO₄
• 分子量: 295.379
• InChiKey: WEQGGKQQOCGMRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  10-(2-Oxa-3-aza-bicyclo[2.2.1]hept-5-en-3-yl)-10-oxo-decanoic acid methyl ester 在 盐酸 、 potassium diazodicarboxylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以99%的产率得到
  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
• 作为产物：
  描述：

  10-氯-10-氧代癸酸甲酯 、 2-oxa-3-azabicyclo[2.2.1]hept-5-ene hydrochloride 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 以59%的产率得到10-(2-Oxa-3-aza-bicyclo[2.2.1]hept-5-en-3-yl)-10-oxo-decanoic acid methyl ester
  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