(R)-4-((S,E)-4-(benzyloxy)-1-fluorobut-2-enyl)-2,2-dimethyl-1,3-dioxolane | 1187768-75-7

• 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: (R)-4-((S,E)-4-(benzyloxy)-1-fluorobut-2-enyl)-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4R)-4-[(E,1S)-1-fluoro-4-phenylmethoxybut-2-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 1187768-75-7
• 化学式: C₁₆H₂₁FO₃
• 分子量: 280.339
• InChiKey: JOGNOIJMAJYFRM-OVPGCVMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-4-((S,E)-4-(benzyloxy)-1-fluorobut-2-enyl)-2,2-dimethyl-1,3-dioxolane 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 73.0h， 以37%的产率得到(1S,2S,3R)-4-(benzyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-fluorobutane-2,3-diol
  参考文献：
  名称：

  A regio- and stereoisomeric study of allylic alcohol fluorination with a range of reagents

  摘要：

  A range of dehydroxyfluorination reagents was reacted with separate diastereoisomers of a chiral allylic alcohol to explore both the regio- and stereoselectivity ratios of direct versus allylic fluorination. The allylic alcohol stereoisomers gave the same predominant fluorinated diastereoisomer indicating that the reaction proceeds with a significant S(N)1 component via an allylic carbocation intermediate, which is quenched by fluoride ion, predominantly from the least hindered face. None of the reagents displayed very high regio- or stereoselectivity, although in all cases the allylic fluorination products predominated. (c) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.03.003
• 作为产物：
  描述：

  (E)-4-(benzyloxy)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)but-2-en-1-ol 在 N,N-二甲基四氟乙胺 作用下， 以 二氯甲烷 为溶剂， 以11%的产率得到(R)-4-((S,E)-4-(benzyloxy)-1-fluorobut-2-enyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  A regio- and stereoisomeric study of allylic alcohol fluorination with a range of reagents

  摘要：

  A range of dehydroxyfluorination reagents was reacted with separate diastereoisomers of a chiral allylic alcohol to explore both the regio- and stereoselectivity ratios of direct versus allylic fluorination. The allylic alcohol stereoisomers gave the same predominant fluorinated diastereoisomer indicating that the reaction proceeds with a significant S(N)1 component via an allylic carbocation intermediate, which is quenched by fluoride ion, predominantly from the least hindered face. None of the reagents displayed very high regio- or stereoselectivity, although in all cases the allylic fluorination products predominated. (c) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.03.003

文献信息

• Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of d-glucose and d-altrose and assessment of their erythrocyte transmembrane transport
  作者：Stefano Bresciani、Tomas Lebl、Alexandra M. Z. Slawin、David O'Hagan

  DOI：10.1039/c0cc01128b

  日期：——

  The 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of D-glucose and D-altrose were prepared and characterised and these novel sugar analogues were explored by 2D-19F-EXSY NMR for their potential to cross erythrocyte (red blood cell) membranes, by comparison with the well known capacity of erythrocytes to transport D-glucose.

  我们制备了 2,3,4-三脱氧-2,3,4-三氟己糖类似物 D-葡萄糖和 D-麦芽糖，并对其进行了表征，通过二维-19F-EXSY NMR 对这些新型糖类似物进行了研究，通过与众所周知的红细胞转运 D-葡萄糖的能力进行比较，探讨了它们穿过红细胞膜的潜力。
• A regio- and stereoisomeric study of allylic alcohol fluorination with a range of reagents
  作者：Stefano Bresciani、Alexandra M.Z. Slawin、David O’Hagan

  DOI：10.1016/j.jfluchem.2009.03.003

  日期：2009.6

  A range of dehydroxyfluorination reagents was reacted with separate diastereoisomers of a chiral allylic alcohol to explore both the regio- and stereoselectivity ratios of direct versus allylic fluorination. The allylic alcohol stereoisomers gave the same predominant fluorinated diastereoisomer indicating that the reaction proceeds with a significant S(N)1 component via an allylic carbocation intermediate, which is quenched by fluoride ion, predominantly from the least hindered face. None of the reagents displayed very high regio- or stereoselectivity, although in all cases the allylic fluorination products predominated. (c) 2009 Elsevier B.V. All rights reserved.