naphthalen-2-yl 2-(oxiran-2-yl)acetate | 1587709-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-2-yl 2-(oxiran-2-yl)acetate
• CAS: 1587709-86-1
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: MCSAYALFIRVIAT-UHFFFAOYSA-N

物化性质

• 沸点：
  385.9±15.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  naphthalen-2-yl 2-(oxiran-2-yl)acetate 在 叔丁基过氧化氢 、 六氟异丙醇 、 苯甲酰氟 、 1,5-二氮杂双环[4.3.0]壬-5-烯 、 C₇₃H₁₀₀Co₂N₄O₇ 作用下， 以 癸烷 、 甲基叔丁基醚 、 叔丁醇 为溶剂， 反应 12.0h， 以58%的产率得到naphthalen-2-yl 4-fluoro-3-hydroxybutanoate
  参考文献：
  名称：

  Enantioselective Radiosynthesis of Positron Emission Tomography (PET) Tracers Containing [¹⁸F]Fluorohydrins

  摘要：

  Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [F-18](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [F-18]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

  DOI：

  10.1021/ja5025645
• 作为产物：
  描述：

  naphthalen-2-yl but-3-enoate 在 sodium sulfate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以86%的产率得到naphthalen-2-yl 2-(oxiran-2-yl)acetate
  参考文献：
  名称：

  Enantioselective Radiosynthesis of Positron Emission Tomography (PET) Tracers Containing [¹⁸F]Fluorohydrins

  摘要：

  Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [F-18](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [F-18]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

  DOI：

  10.1021/ja5025645