3',6'-diacetyl-2',7'-dichloro-6-(4-Coumarin-343-carboxybutyl)fluoresceinamide | 790661-02-8

• 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: 3',6'-diacetyl-2',7'-dichloro-6-(4-Coumarin-343-carboxybutyl)fluoresceinamide
• CAS: 790661-02-8
• 化学式: C₄₅H₃₆Cl₂N₂O₁₂
• 分子量: 867.693
• InChiKey: QWCGBFMCHZQWOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  61.0
• 可旋转键数：
  9.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  176.98
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 二甲基吡啶胺 、 3',6'-diacetyl-2',7'-dichloro-6-(4-Coumarin-343-carboxybutyl)fluoresceinamide 在 水 作用下， 以 乙腈 为溶剂， 反应 24.75h， 以33%的产率得到coumazin-1
  参考文献：
  名称：

  A Novel Two-Fluorophore Approach to Ratiometric Sensing of Zn²⁺

  摘要：

  We present a small molecule ratiometric Zn2+-sensing system based on two fluorophores excited by visible light, a Zn2+-insensitive reporter fluorophore, coumarin 343, and a Zn2+-sensitive fluorescein-based compound, ZPA-1. The two fluorophores are linked by an ester to give Coumazin-1, a membrane-permeable, essentially nonfluorescent compound. Upon exposure to esterases, Coumazin-1 is hydrolyzed to its constituent fluorophores. Measurement of the ratio of coumarin emission at 488 nm (lambdaexc = 445 nm) and comparison with ZPA-1 emission at 534 nm (lambdaexc = 505 nm) affords information about the amount of sensor present as well as the amount of Zn2+ present. A generally applicable synthetic route to amide-functionalized ZP1 sensors is also described. The Zn2+-sensing properties of one member of this class are similar to those of the parent ZP1 sensor, with slightly tighter binding and lower background signal.

  DOI：

  10.1021/ja0364930
• 作为产物：
  描述：

  3',6'-diacetyl-2',7'-dichloro-6-carboxyfluorescein pyridinium salt 在 草酰氯 、 偶氮二甲酸二异丙酯 、 碳酸氢钠 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 3',6'-diacetyl-2',7'-dichloro-6-(4-Coumarin-343-carboxybutyl)fluoresceinamide
  参考文献：
  名称：

  A Novel Two-Fluorophore Approach to Ratiometric Sensing of Zn²⁺

  摘要：

  We present a small molecule ratiometric Zn2+-sensing system based on two fluorophores excited by visible light, a Zn2+-insensitive reporter fluorophore, coumarin 343, and a Zn2+-sensitive fluorescein-based compound, ZPA-1. The two fluorophores are linked by an ester to give Coumazin-1, a membrane-permeable, essentially nonfluorescent compound. Upon exposure to esterases, Coumazin-1 is hydrolyzed to its constituent fluorophores. Measurement of the ratio of coumarin emission at 488 nm (lambdaexc = 445 nm) and comparison with ZPA-1 emission at 534 nm (lambdaexc = 505 nm) affords information about the amount of sensor present as well as the amount of Zn2+ present. A generally applicable synthetic route to amide-functionalized ZP1 sensors is also described. The Zn2+-sensing properties of one member of this class are similar to those of the parent ZP1 sensor, with slightly tighter binding and lower background signal.

  DOI：

  10.1021/ja0364930