6-ethynyl-9-(o-tolyl)-3H-xanthen-3-one | 1169852-06-5

• 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-ethynyl-9-(o-tolyl)-3H-xanthen-3-one
• CAS: 1169852-06-5
• 化学式: C₂₂H₁₄O₂
• 分子量: 310.352
• InChiKey: ZSURLZCETAJDHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-azidomethyl-2,3-dihydro-1,4-benzodioxine 、 6-ethynyl-9-(o-tolyl)-3H-xanthen-3-one 在 sodium ascorbate 、 copper(II) sulfate 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 12.0h， 生成 C₃₁H₂₃N₃O₄
  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-methoxy-9-(o-tolyl)-6-((trimethylsilyl)ethynyl)-9H-xanthen-9-ol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以27.3 mg的产率得到6-ethynyl-9-(o-tolyl)-3H-xanthen-3-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