(-)-(2R,3S)-2-azido-3-octanol | 152380-16-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (-)-(2R,3S)-2-azido-3-octanol
• 英文别名: (2R,3S)-2-azidooctan-3-ol
• CAS: 152380-16-0
• 化学式: C₈H₁₇N₃O
• 分子量: 171.242
• InChiKey: RPRGXEOOBYBQQZ-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3S)-2-azido-3-octanol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以93%的产率得到(-)-(2R,3S)-2-amino-3-octanol
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral β-azidoalcohols. Application to the preparation of chiral aziridines and aminoalcohols

  摘要：

  From the microbiological reduction of 3-azido-2-octanone, 3-azido-4-phenyl-2-butanone and 1-azido-1-phenyl-2-propanone, homochiral isomers of the corresponding beta-azidoalcohols were prepared. These ''alpha-bichiral'' synthons were used to prepare all the stereoisomers of 2-methyl-3-n-pentylaziridine and 2-methyl-3-benzylaziridine and some homochiral aminoalcohols.

  DOI：

  10.1016/0957-4166(94)80084-7
• 作为产物：
  描述：

  (2S,3S)-2,3-octanediol 在 氯化亚砜 、 叠氮化锂 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (-)-(2R,3S)-2-azido-3-octanol
  参考文献：
  名称：

  Chemoenzymatic synthesis of “α-bichiral” synthons. Application to the preparation of chiral epoxides

  摘要：

  Microbiological reduction of 3-bromo-2-octanone and 3-azido-2-octanone led to all the stereoisomers of 3-bromo-2-octanol and 3-azido-2-octanol. Chiral 2,3-epoxyoctanes were prepared from the 3-bromo-2-octanols.

  DOI：

  10.1016/s0957-4166(00)80239-6

文献信息

• Chemoenzymatic synthesis of “α-bichiral” synthons. Application to the preparation of chiral epoxides
  作者：Pascale Besse、Henri Veschambre

  DOI：10.1016/s0957-4166(00)80239-6

  日期：1993.6

  Microbiological reduction of 3-bromo-2-octanone and 3-azido-2-octanone led to all the stereoisomers of 3-bromo-2-octanol and 3-azido-2-octanol. Chiral 2,3-epoxyoctanes were prepared from the 3-bromo-2-octanols.
• Chemoenzymatic synthesis of chiral β-azidoalcohols. Application to the preparation of chiral aziridines and aminoalcohols
  作者：Pascle Besse、Henri Veschambre、Robert Chênevert、Michael Dickman

  DOI：10.1016/0957-4166(94)80084-7

  日期：1994.9

  From the microbiological reduction of 3-azido-2-octanone, 3-azido-4-phenyl-2-butanone and 1-azido-1-phenyl-2-propanone, homochiral isomers of the corresponding beta-azidoalcohols were prepared. These ''alpha-bichiral'' synthons were used to prepare all the stereoisomers of 2-methyl-3-n-pentylaziridine and 2-methyl-3-benzylaziridine and some homochiral aminoalcohols.