(2S,3S,5S,6S)-1,7-di-O-benzyl-2,4,6-trifluoroheptane-1,3,5,7-tetraol | 1187425-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,5S,6S)-1,7-di-O-benzyl-2,4,6-trifluoroheptane-1,3,5,7-tetraol
• 英文别名: (2S,3S,5S,6S)-2,4,6-trifluoro-1,7-bis(phenylmethoxy)heptane-3,5-diol
• CAS: 1187425-93-9
• 化学式: C₂₁H₂₅F₃O₄
• 分子量: 398.422
• InChiKey: YFORFUAUUWBBCU-QIJZPMMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,5S,6S)-1,7-di-O-benzyl-2,4,6-trifluoroheptane-1,3,5,7-tetraol 在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(2S,3R,5R,6S)-1,7-di-O-benzyl-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
• 作为产物：
  描述：

  (5S,6R)-1,7-di-O-benzyl-2,3,5,6-diepoxy-4-fluoroheptane-1,7-diol 在 triethylamine tris(hydrogen fluoride) 作用下， 以23%的产率得到(2S,3S,5S,6S)-1,7-di-O-benzyl-2,4,6-trifluoroheptane-1,3,5,7-tetraol
  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