| 1427512-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• CAS: 1427512-59-1
• 化学式: C₃₆H₂₉N₃O₇S
• 分子量: 647.708
• InChiKey: BUJFPXZZJVRMAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.65
• 重原子数：
  47.0
• 可旋转键数：
  3.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  131.4
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以90%的产率得到1-(3',6'-Dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)-3-[[7-hydroxy-8-(hydroxymethyl)-2-methylquinolin-4-yl]methyl]thiourea
  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：

  4-(iodomethyl)-2,8,8-trimethyl-10H-[1,3]dioxino[4,5-h]quinoline 在 sodium azide 、 5%-palladium/activated carbon 、 氢气 、 二异丙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 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