N,N-dimethyl-4-(6-(oxiran-2-ylmethoxy)quinolin-2-yl)aniline | 1587709-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N,N-dimethyl-4-(6-(oxiran-2-ylmethoxy)quinolin-2-yl)aniline
• CAS: 1587709-90-7
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: UBHDNZJZKDDGDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-4-(6-(oxiran-2-ylmethoxy)quinolin-2-yl)aniline 在 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 、 乙腈 、 叔丁醇 为溶剂， 反应 12.0h， 以74%的产率得到THK-5105
  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：

  4-(6-(methoxymethoxy)quinolin-2-yl)-N,N-dimethylaniline 在 盐酸 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 12.0h， 生成 N,N-dimethyl-4-(6-(oxiran-2-ylmethoxy)quinolin-2-yl)aniline
  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