10-Oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracene-9-carboxylic acid pentafluorophenyl ester | 292067-77-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 10-Oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracene-9-carboxylic acid pentafluorophenyl ester
• CAS: 292067-77-7
• 化学式: C₂₂H₁₄F₅NO₄
• 分子量: 451.349
• InChiKey: NSQNYCRBKVEXAD-UHFFFAOYSA-N

物化性质

• 沸点：
  618.2±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.75
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  10-Oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracene-9-carboxylic acid pentafluorophenyl ester 、 在 4-二甲氨基吡啶 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Detection and Mechanistic Studies of Multicomponent Assembly by Fluorescence Resonance Energy Transfer

  摘要：

  The kinetics and thermodynamics of multicomponent assembly in organic solution are investigated using fluorescence resonance energy transfer (FRET). Calix[4]arenes functionalized with ureas on their wider rims dimerize in organic solution, via intermolecular hydrogen bonding, to form encapsulation complexes. When one calixarene component is outfitted with a donor fluorophore and the other with an acceptor, dimerization brings the chromophores within 20 Angstrom, a distance suitable for efficient energy transfer to occur between them. Excitation of the donor results in two colors of emitted light: one fluorescence band at the donor emission wavelength, and a second at the acceptor emission wavelength signaling the noncovalent union of three species-donor, acceptor, and small-molecule guest. By monitoring these wavelengths, assembly and dissociation processes are observed in real time at nanomolar concentrations. Rate and association constants for assembly processes are determined for the first time, and they reveal unexpected contributions from the structure and concentration of the monomer. Finally, the combination of FRET and the molecular recognition capabilities of the encapsulation complexes provides a sensitive and specific method for small-molecule sensing.

  DOI：

  10.1021/ja994397m
• 作为产物：
  描述：

  香豆素 343 在 N,N-二甲基甲酰胺 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 10-Oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracene-9-carboxylic acid pentafluorophenyl ester
  参考文献：
  名称：

  Detection and Mechanistic Studies of Multicomponent Assembly by Fluorescence Resonance Energy Transfer

  摘要：

  The kinetics and thermodynamics of multicomponent assembly in organic solution are investigated using fluorescence resonance energy transfer (FRET). Calix[4]arenes functionalized with ureas on their wider rims dimerize in organic solution, via intermolecular hydrogen bonding, to form encapsulation complexes. When one calixarene component is outfitted with a donor fluorophore and the other with an acceptor, dimerization brings the chromophores within 20 Angstrom, a distance suitable for efficient energy transfer to occur between them. Excitation of the donor results in two colors of emitted light: one fluorescence band at the donor emission wavelength, and a second at the acceptor emission wavelength signaling the noncovalent union of three species-donor, acceptor, and small-molecule guest. By monitoring these wavelengths, assembly and dissociation processes are observed in real time at nanomolar concentrations. Rate and association constants for assembly processes are determined for the first time, and they reveal unexpected contributions from the structure and concentration of the monomer. Finally, the combination of FRET and the molecular recognition capabilities of the encapsulation complexes provides a sensitive and specific method for small-molecule sensing.

  DOI：

  10.1021/ja994397m