(2R,3S,4R)-2-azido-3,4-isopropylidenedioxy-1-octadecanal | 1252975-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-2-azido-3,4-isopropylidenedioxy-1-octadecanal
• CAS: 1252975-46-4
• 化学式: C₂₁H₃₉N₃O₃
• 分子量: 381.559
• InChiKey: YFWWZEIKDKBDMP-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  27.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  84.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-2-azido-3,4-isopropylidenedioxy-1-octadecanal 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolane-4-carbonitrile
  参考文献：
  名称：

  Unexpected Cleavage of 2-Azido-2-(hydroxymethyl)oxetanes: Conformation Determines Reaction Pathway?

  摘要：

  An unanticipated cleavage of 2-azido-2-(hydroxymethyl)oxetanes is reported In attempts to oxidize the title oxetanyl alcohols to the corresponding carboxylic acids with RuO4, cleaved nitriles were formed as the sole isolable products, while a closely related tetrahydrofuran gave solely the expected carboxylic acid Quantum chemical calculations suggest that the divergent outcomes are governed by conformational differences in the azidoalcohols

  DOI：

  10.1021/jo101328c
• 作为产物：
  描述：

  (2R,3S,4R)-2-azido-3,4-isopropylidenedioxy-1-octadecanoic acid 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 3.5h， 以99%的产率得到(2R,3S,4R)-2-azido-3,4-isopropylidenedioxy-1-octadecanal
  参考文献：
  名称：

  Unexpected Cleavage of 2-Azido-2-(hydroxymethyl)oxetanes: Conformation Determines Reaction Pathway?

  摘要：

  An unanticipated cleavage of 2-azido-2-(hydroxymethyl)oxetanes is reported In attempts to oxidize the title oxetanyl alcohols to the corresponding carboxylic acids with RuO4, cleaved nitriles were formed as the sole isolable products, while a closely related tetrahydrofuran gave solely the expected carboxylic acid Quantum chemical calculations suggest that the divergent outcomes are governed by conformational differences in the azidoalcohols

  DOI：

  10.1021/jo101328c