(1S*,2R*,3S*,4R*)-2,3-difluorocyclopentane-1,4-diol | 159752-14-4

• 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*)-2,3-difluorocyclopentane-1,4-diol
• 英文别名: 1,3-Cyclopentanediol, 4,5-difluoro-, (1I+/-,3I+/-,4I(2),5I(2))-；(1S,3R,4S,5R)-4,5-difluorocyclopentane-1,3-diol
• CAS: 159752-14-4
• 化学式: C₅H₈F₂O₂
• 分子量: 138.114
• InChiKey: ZSTJADOUVHBMTE-YPVPKEFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S*,2R*,3S*,4R*)-2,3-difluorocyclopentane-1,4-diol 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 13.0h， 生成 Acetic acid (1R,2S,3R)-2,3-difluoro-4-oxo-cyclopentyl ester
  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， 以24%的产率得到(1S*,2R*,3S*,4R*)-2,3-difluorocyclopentane-1,4-diol
  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

文献信息

• Polar alicyclic rings: synthesis and structure of all cis-1,2,3,4-tetrafluorocyclopentane
  作者：Zeguo Fang、Nawaf Al-Maharik、Alexandra M. Z. Slawin、Michael Bühl、David O'Hagan

  DOI：10.1039/c6cc01348a

  日期：——

  The all-cis isomer of 1,2,3,4-tetrafluorocyclopentane is prepared and characterised by NMR and X-ray crystallography and the experimental structure compared with theory. The structure has a similarly high polarity to all-cis...

  制备了1,2,3,4-四氟环戊烷的全顺式异构体，并通过NMR和X射线晶体学表征，并与理论比较了实验结构。该结构具有与全顺式类似的高极性。