(2S,3R,5R,6S)-2,3,4,5,6-pentafluoroheptane-1,7-diol | 1187425-89-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2S,3R,5R,6S)-2,3,4,5,6-pentafluoroheptane-1,7-diol
• CAS: 1187425-89-3
• 化学式: C₇H₁₁F₅O₂
• 分子量: 222.155
• InChiKey: GLAUVDDHLZLELZ-UNTFVMJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,5R,6S)-2,3,4,5,6-pentafluoroheptane-1,7-diol 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(2S,3R,5R,6S)-2,3,4,5,6-pentafluoroheptane-1,7-diol 1,7-ditosylate
  参考文献：
  名称：

  Diastereoselective Synthesis of 2,3,4,5,6-Pentafluoroheptanes

  摘要：

  A stereocontrolled synthesis of alkanes containing five contiguous fluorine atoms is presented. The compounds were prepared by sequential fluorination of diastereoisomeric alcohol-diepoxides. The chemistry involved epoxide ring-opening with HF-NEt3 and deshydroxyfluorination reactions of free alcohols with Deoxo-Fluor, The fluorination reactions were all highly stereospecific, with all five fluorines being incorporated in three sequential steps. Three different diastereoisomers of the 2,3,4,5,6-pentafluoroheptyl motif were prepared as heptane-1,7-diol derivatives, a structural format amenable for incorporation of the vicinal pentafluoro scaffold into larger molecular architectures.

  DOI：

  10.1021/jo901360e
• 作为产物：
  描述：

  (2S,3R,5R,6S)-1,7-di-O-benzyl-2,3,4,5,6-pentafluoroheptane-1,7-diol 在 10% palladium on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2S,3R,5R,6S)-2,3,4,5,6-pentafluoroheptane-1,7-diol
  参考文献：
  名称：

  Diastereoselective Synthesis of 2,3,4,5,6-Pentafluoroheptanes

  摘要：

  A stereocontrolled synthesis of alkanes containing five contiguous fluorine atoms is presented. The compounds were prepared by sequential fluorination of diastereoisomeric alcohol-diepoxides. The chemistry involved epoxide ring-opening with HF-NEt3 and deshydroxyfluorination reactions of free alcohols with Deoxo-Fluor, The fluorination reactions were all highly stereospecific, with all five fluorines being incorporated in three sequential steps. Three different diastereoisomers of the 2,3,4,5,6-pentafluoroheptyl motif were prepared as heptane-1,7-diol derivatives, a structural format amenable for incorporation of the vicinal pentafluoro scaffold into larger molecular architectures.

  DOI：

  10.1021/jo901360e