4,5-bis-(2-benzyloxy-1-fluoroethyl)-[1,3,2]dioxathiolane 2,2-dioxide | 921038-79-1

• 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: 4,5-bis-(2-benzyloxy-1-fluoroethyl)-[1,3,2]dioxathiolane 2,2-dioxide
• 英文别名: (4S,5S)-4,5-bis[(1R)-1-fluoro-2-phenylmethoxyethyl]-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 921038-79-1
• 化学式: C₂₀H₂₂F₂O₆S
• 分子量: 428.454
• InChiKey: QDKAZMDDNMABAE-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,5-bis-(2-benzyloxy-1-fluoroethyl)-[1,3,2]dioxathiolane 2,2-dioxide 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 四丁基氟化铵 、 氢气 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 160.0h， 生成 (2R,3S,4S,5R)-2,3,4,5-tetrafluorohexane-1,6-diol ditosylate
  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：

  (2R,3S,4S,5R)-1,6-bis-benzyloxy-2,5-difluorohexane-3,4-diol 在 ruthenium trichloride 吡啶 、 sodium periodate 、 氯化亚砜 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 4,5-bis-(2-benzyloxy-1-fluoroethyl)-[1,3,2]dioxathiolane 2,2-dioxide
  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

• 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.