6-nitro-9-oxo-9H-xanthen-3-yl trifluoromethanesulfonate | 1169852-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-nitro-9-oxo-9H-xanthen-3-yl trifluoromethanesulfonate
• 英文别名: (6-Nitro-9-oxoxanthen-3-yl) trifluoromethanesulfonate
• CAS: 1169852-12-3
• 化学式: C₁₄H₆F₃NO₇S
• 分子量: 389.265
• InChiKey: YJMQXQFRDJRPRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-nitro-9-oxo-9H-xanthen-3-yl trifluoromethanesulfonate 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以65%的产率得到3-nitro-6-(2-(trimethylsilyl)ethynyl)-9H-xanthen-9-one
  参考文献：
  名称：

  Rapid Synthesis, Screening, and Identification of Xanthone- and Xanthene-Based Fluorophores Using Click Chemistry

  摘要：

  A panel of new fluorophores with emission wavelengths from blue to yellow regions using the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of alkyne-functionalized xanthones and xanthenes with various azides have been synthesized. Screening of the "click" products led to the identification of "hit" fluorophores which showed a fluorescence increase upon triazole formation. These novel "click" fluorophores could potentially be used for bioconjugation and bioimaging purposes.

  DOI：

  10.1021/ol9010344
• 作为产物：
  描述：

  3-hydroxy-6-nitro-9H-xanthen-9-one 、 三氟甲磺酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到6-nitro-9-oxo-9H-xanthen-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Rapid Synthesis, Screening, and Identification of Xanthone- and Xanthene-Based Fluorophores Using Click Chemistry

  摘要：

  A panel of new fluorophores with emission wavelengths from blue to yellow regions using the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of alkyne-functionalized xanthones and xanthenes with various azides have been synthesized. Screening of the "click" products led to the identification of "hit" fluorophores which showed a fluorescence increase upon triazole formation. These novel "click" fluorophores could potentially be used for bioconjugation and bioimaging purposes.

  DOI：

  10.1021/ol9010344