| 1427512-52-4

• 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
• CAS: 1427512-52-4
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: YYUHZZGGPXXGMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.58
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 咪唑 、 sodium azide 、 碘 、 4-甲基苯磺酸吡啶 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 4-(azidomethyl)-2,8,8-trimethyl-10H-[1,3]dioxino[4,5-h]quinoline
  参考文献：
  名称：

  A Bioorthogonal Ligation Enabled by Click Cycloaddition ofo-Quinolinone Quinone Methide and Vinyl Thioether

  摘要：

  There is an increasing interest in the use of bioorthogonal ligation to advance biomedical research through selective labeling of biomolecules in living systems. Accordingly, discovering new reactions to expand the toolbox of bioorthogonal chemistry is of particular interest to chemical biologists. Herein we report a new bioorthogonal ligation enabled by click hetero-Diels-Alder (HDA) cycloaddition of in situ-generated o-quinolinone quinone methides and vinyl thioethers. This reaction is highly selective and proceeds smoothly under aqueous conditions. The functionalized vinyl thioethers are small and chemically stable in vivo, making them suitable for use as bioorthogonal chemical reporters that can be effectively coupled to various biomolecules. We utilized this bioorthogonal ligation for site-specific labeling of proteins as well as imaging of bioactive small molecules inside live cells.

  DOI：

  10.1021/ja401989p
• 作为产物：
  描述：

  2-甲基-7-羟基喹啉 在 ferrous(II) sulfate heptahydrate 、 硫酸 、 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  A Bioorthogonal Ligation Enabled by Click Cycloaddition ofo-Quinolinone Quinone Methide and Vinyl Thioether

  摘要：

  There is an increasing interest in the use of bioorthogonal ligation to advance biomedical research through selective labeling of biomolecules in living systems. Accordingly, discovering new reactions to expand the toolbox of bioorthogonal chemistry is of particular interest to chemical biologists. Herein we report a new bioorthogonal ligation enabled by click hetero-Diels-Alder (HDA) cycloaddition of in situ-generated o-quinolinone quinone methides and vinyl thioethers. This reaction is highly selective and proceeds smoothly under aqueous conditions. The functionalized vinyl thioethers are small and chemically stable in vivo, making them suitable for use as bioorthogonal chemical reporters that can be effectively coupled to various biomolecules. We utilized this bioorthogonal ligation for site-specific labeling of proteins as well as imaging of bioactive small molecules inside live cells.

  DOI：

  10.1021/ja401989p