(5S)-5-[2-(3-Fluorophenyl)-1-hydroxyethyl]oxolan-2-one | 926292-92-4

• 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: (5S)-5-[2-(3-Fluorophenyl)-1-hydroxyethyl]oxolan-2-one
• 英文别名: (5S)-5-[(1R)-2-(3-fluorophenyl)-1-hydroxyethyl]oxolan-2-one
• CAS: 926292-92-4
• 化学式: C₁₂H₁₃FO₃
• 分子量: 224.232
• InChiKey: PBNUFSQWIOLKRQ-MNOVXSKESA-N

物化性质

• 沸点：
  399.4±17.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Oxone 、 potassium;(E)-6-(3-fluorophenyl)hex-4-enoate 在 Shi's ketone 、 硫酸 、 potassium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以86%的产率得到
  参考文献：
  名称：

  An Epoxidation Approach to a Chiral Lactone:  Application of the Shi Epoxidation

  摘要：

  The large-scale epoxidation of the alkene 7 with the organocatalyst, Epoxone (10), and Oxone as the oxidant is described. This is the first large-scale application of the Shi epoxidation methodology. The large-scale preparation of the catalyst 10 is also described. The potassium salt of the unsaturated acid precursor 7 was prepared by a Suzuki coupling from 3-fluorobenzyl chloride and the vinylborane 8 derived from 4-pentynoic acid.

  DOI：

  10.1021/op060140e

文献信息

• An Epoxidation Approach to a Chiral Lactone:  Application of the Shi Epoxidation
  作者：David J. Ager、Ken Anderson、Eric Oblinger、Yian Shi、James VanderRoest

  DOI：10.1021/op060140e

  日期：2007.1.1

  The large-scale epoxidation of the alkene 7 with the organocatalyst, Epoxone (10), and Oxone as the oxidant is described. This is the first large-scale application of the Shi epoxidation methodology. The large-scale preparation of the catalyst 10 is also described. The potassium salt of the unsaturated acid precursor 7 was prepared by a Suzuki coupling from 3-fluorobenzyl chloride and the vinylborane 8 derived from 4-pentynoic acid.