(2S,5S)-(E)-1,6-bis-benzyloxy-2,5-difluorohex-3-ene | 921038-77-9

• 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,5S)-(E)-1,6-bis-benzyloxy-2,5-difluorohex-3-ene
• 英文别名: [(E,2S,5S)-2,5-difluoro-6-phenylmethoxyhex-3-enoxy]methylbenzene
• CAS: 921038-77-9
• 化学式: C₂₀H₂₂F₂O₂
• 分子量: 332.39
• InChiKey: GXRHNTSUSPINJV-ARZGSZHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S)-(E)-1,6-bis-benzyloxy-2,5-difluorohex-3-ene 在 ruthenium trichloride 、 palladium on activated charcoal 吡啶 、 potassium permanganate 、 sodium periodate 、 氯化亚砜 、 四丁基氟化铵 、 氢气 、 magnesium sulfate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 95.0h， 生成 (2R,3R,4R,5R)-2,4,5-trifluoro-hexane-1,3,6-triol
  参考文献：
  名称：

  Enantioselective Synthesis of an All-syn Four Vicinal Fluorine Motif

  摘要：

  Alkanes bearing multiple vicinal fluorine atoms at adjacent stereocenters may be considered intermediate between alkanes and perfluoroalkanes, and as a class, their chemistry and behavior remain to be explored. We report here a stereoselective synthesis of an all-syn four vicinal fluorine motif as a single enantiomer. The four vicinal fluorine compound was amenable to single-crystal X-ray analysis, and the resulting structure displays gauche relationships between all four fluorines, consistent with the fluorine gauche effect, and CF...HC hydrogen bonding between adjacent fluoroalkyl chains.

  DOI：

  10.1021/ja066188p
• 作为产物：
  描述：

  1-benzyloxy-2-fluoro-3-butene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2R,5S)-(E)-1,6-bis-benzyloxy-2,5-difluorohex-3-ene 、 (2S,5S)-(E)-1,6-bis-benzyloxy-2,5-difluorohex-3-ene
  参考文献：
  名称：

  Enantioselective Synthesis of an All-syn Four Vicinal Fluorine Motif

  摘要：

  Alkanes bearing multiple vicinal fluorine atoms at adjacent stereocenters may be considered intermediate between alkanes and perfluoroalkanes, and as a class, their chemistry and behavior remain to be explored. We report here a stereoselective synthesis of an all-syn four vicinal fluorine motif as a single enantiomer. The four vicinal fluorine compound was amenable to single-crystal X-ray analysis, and the resulting structure displays gauche relationships between all four fluorines, consistent with the fluorine gauche effect, and CF...HC hydrogen bonding between adjacent fluoroalkyl chains.

  DOI：

  10.1021/ja066188p

文献信息

• Synthesis and Conformation of Multi-Vicinal Fluoroalkane Diastereoisomers
  作者：Luke Hunter、Alexandra M. Z. Slawin、Peer Kirsch、David O'Hagan

  DOI：10.1002/anie.200701988

  日期：2007.10.15
• Enantioselective Synthesis of an All-<i>syn</i> Four Vicinal Fluorine Motif
  作者：Luke Hunter、David O'Hagan、Alexandra M. Z. Slawin

  DOI：10.1021/ja066188p

  日期：2006.12.1

  Alkanes bearing multiple vicinal fluorine atoms at adjacent stereocenters may be considered intermediate between alkanes and perfluoroalkanes, and as a class, their chemistry and behavior remain to be explored. We report here a stereoselective synthesis of an all-syn four vicinal fluorine motif as a single enantiomer. The four vicinal fluorine compound was amenable to single-crystal X-ray analysis, and the resulting structure displays gauche relationships between all four fluorines, consistent with the fluorine gauche effect, and CF...HC hydrogen bonding between adjacent fluoroalkyl chains.