(2R,3S)-1-fluoro-4-[(4-methoxyphenyl)methoxy]butane-2,3-diol | 1169863-35-7

• 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: (2R,3S)-1-fluoro-4-[(4-methoxyphenyl)methoxy]butane-2,3-diol
• CAS: 1169863-35-7
• 化学式: C₁₂H₁₇FO₄
• 分子量: 244.263
• InChiKey: CLBCKNUIZZYCAV-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-fluoro-4-[(4-methoxyphenyl)methoxy]butane-2,3-diol 、 环己酮 在 对甲苯磺酸 、 copper(II) sulfate 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Allylic fluorination via an unusual alkene Z/E isomerisation

  摘要：

  The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)- 1 -chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective Substrate in Sharpless asymmetric dihydroxylation (AD) reactions, delivering highly enantiomerically enriched fluorinated butene triol building blocks. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.068
• 作为产物：
  描述：

  1-[[(E)-4-fluorobut-2-enoxy]methyl]-4-methoxybenzene 在 AD-mix-α 、 K₂OsO₄ 、 甲基磺酰胺 、 (DHQ)₂PHAL 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以79%的产率得到(2R,3S)-1-fluoro-4-[(4-methoxyphenyl)methoxy]butane-2,3-diol
  参考文献：
  名称：

  Allylic fluorination via an unusual alkene Z/E isomerisation

  摘要：

  The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)- 1 -chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective Substrate in Sharpless asymmetric dihydroxylation (AD) reactions, delivering highly enantiomerically enriched fluorinated butene triol building blocks. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.068

文献信息

• Allylic fluorination via an unusual alkene Z/E isomerisation
  作者：James A.B. Laurenson、Sebastien Meiries、Jonathan M. Percy、Ricard Roig

  DOI：10.1016/j.tetlet.2009.03.068

  日期：2009.7

  The isomerisation of readily available (Z)-4-(para-methoxybenzyloxy)- 1 -chloro-2-butene was achieved under mild conditions to afford the much less accessible E-diastereoisomer. This was an effective Substrate in Sharpless asymmetric dihydroxylation (AD) reactions, delivering highly enantiomerically enriched fluorinated butene triol building blocks. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.