(1S,2R,3S,4R)-4-acetoxy-2,3-difluorocyclopentan-1-ol | 159752-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3S,4R)-4-acetoxy-2,3-difluorocyclopentan-1-ol
• 英文别名: [(1R,2S,3R,4S)-2,3-difluoro-4-hydroxycyclopentyl] acetate
• CAS: 159752-15-5
• 化学式: C₇H₁₀F₂O₃
• 分子量: 180.151
• InChiKey: HLUFOOTVKZTSGH-WNJXEPBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-4-acetoxy-2,3-difluorocyclopentan-1-ol 在 chromium(VI) oxide 、 溶剂黄146 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 (R)-4-acetoxy-2-fluoro-2-cyclopenten-1-one
  参考文献：
  名称：

  Synthesis of enantiomerically pure 4-acetoxy-2-fluoro-2-cyclopenten-1-one

  摘要：

  Addition of molecular fluorine to cis-2-cyclopentene-1,4-diol gave the cis-anti adduct stereoselectively. This meso diol was dissymmetrized by means of acetylation under lipase catalysis to afford the monoacetate with a high enatiomeric purity. Oxidation of the monoacetate followed by elimination of hydrogen fluoride under basic conditions furnished the titled compound which is an attractive building block for chiral fluorinated molecules.

  DOI：

  10.1016/0957-4166(94)80047-2
• 作为产物：
  描述：

  顺式-4-环戊烯-1,3-二醇 在 fluorine 作用下， 以 乙醇 、 氯仿 、 一氟三氯甲烷 为溶剂， 反应 9.0h， 生成 (1S,2R,3S,4R)-4-acetoxy-2,3-difluorocyclopentan-1-ol
  参考文献：
  名称：

  Synthesis of enantiomerically pure 4-acetoxy-2-fluoro-2-cyclopenten-1-one

  摘要：

  Addition of molecular fluorine to cis-2-cyclopentene-1,4-diol gave the cis-anti adduct stereoselectively. This meso diol was dissymmetrized by means of acetylation under lipase catalysis to afford the monoacetate with a high enatiomeric purity. Oxidation of the monoacetate followed by elimination of hydrogen fluoride under basic conditions furnished the titled compound which is an attractive building block for chiral fluorinated molecules.

  DOI：

  10.1016/0957-4166(94)80047-2