(2R,3S,4R)-1,1-difluoro-5-methylenecyclopentane-2,3,4-triol | 1359718-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-1,1-difluoro-5-methylenecyclopentane-2,3,4-triol
• 英文别名: methylene-1,1-difluoro-2,3,4-tris(hydroxy)-cyclopentane；(1R,2S,3R)-4,4-difluoro-5-methylidenecyclopentane-1,2,3-triol
• CAS: 1359718-10-7
• 化学式: C₆H₈F₂O₃
• 分子量: 166.125
• InChiKey: DRKTVHSCGDVCHL-MROZADKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,1-difluoro-1-(phenylselanyl)-hex-5-yne-2,3,4-triol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 叔丁醇 为溶剂， 反应 1.75h， 以64%的产率得到(2R,3S,4R)-1,1-difluoro-5-methylenecyclopentane-2,3,4-triol
  参考文献：
  名称：

  Synthesis of exo-methylenedifluorocyclopentanes as precursors of fluorinated carbasugars by 5-exo-dig radical cyclization

  摘要：

  The synthesis of polyhydroxylated 1,1-difluoro-5-methylenecyclopentanes is described. The sequence involves an addition of PhSeCF2TMS to a tartrate-derived aldehyde or its corresponding tert-butanesulfinylimines followed by a radical cyclization. The use of a benzyl protected substrate led to an unproductive 1,5-hydrogen transfer after cyclization but the desired compound was eventually obtained from the unprotected substrate. A hydroboration/oxidation sequence was investigated on these 1,1-difluoro-5-methylenecyclopentanes as it would provide fluorinated carbasugars, a new and promising class of glycomimetics. Unfortunately, this reaction was poorly efficient and its regioselectivity not the expected one. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.02.015