ethyl 7-(2-(1,4,7,10-tetraazacyclododecan-1-yl)acetamido)-2-oxo-1,2-dihydroquinoline-4-carboxylate | 944149-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 7-(2-(1,4,7,10-tetraazacyclododecan-1-yl)acetamido)-2-oxo-1,2-dihydroquinoline-4-carboxylate
• CAS: 944149-94-4
• 化学式: C₂₂H₃₂N₆O₄
• 分子量: 444.534
• InChiKey: NPJIGOKDVRJOLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  127.59
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 7-(2-(1,4,7,10-tetraazacyclododecan-1-yl)acetamido)-2-oxo-1,2-dihydroquinoline-4-carboxylate 、 2-溴乙酰胺 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到ethyl 2-oxo-7-[[2-[4,7,10-tris(2-amino-2-oxoethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetyl]amino]-1H-quinoline-4-carboxylate
  参考文献：
  名称：

  Cocktails of Tb³⁺ and Eu³⁺ Complexes:  A General Platform for the Design of Ratiometric Optical Probes

  摘要：

  Fluorescent and luminescent reporters that signal molecular events of interest by modulating the ratio of peaks in their emission profile have advantages over reporters that simply modulate their emission intensity, since ratiometric measurement is concentration-independent and allows them to be effective in complex contexts, such as living cells or sensor microarrays. We herein describe a general platform for the design of ratiometric probes based on a heterometallic Tb3+/Eu3+ bis-lanthanide ensemble, consisting of a mixture, or "cocktail", of otherwise identical heterometalated chelates. The chelate contains an organic photon antenna that sensitizes the Tb3+/Eu3+ luminescence. The contributions of the two metals to the composite luminescence spectrum can be tuned to the same relative scale by adjusting the stoichiometry of the cocktail, allowing subtle changes in their ratio to be accurately measured. Importantly, the ratio responds to chemical and environmental changes experienced by the photon antenna, making the system an ideal platform for the design of chemical and enzymatic probes. As proofs of concept, we describe a ratiometric probe for esterase activity and a polarity-responsive ratiometric sensor.

  DOI：

  10.1021/ja070867y
• 作为产物：
  描述：

  7-(diallylamino)-4-hydroxyquinolin-2(1H)-one 在 palladium diacetate 、 四(三苯基膦)钯 1,1'-双(二苯基膦)二茂铁 、 1,3-二甲基巴比妥酸 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.17h， 生成 ethyl 7-(2-(1,4,7,10-tetraazacyclododecan-1-yl)acetamido)-2-oxo-1,2-dihydroquinoline-4-carboxylate
  参考文献：
  名称：

  Cocktails of Tb³⁺ and Eu³⁺ Complexes:  A General Platform for the Design of Ratiometric Optical Probes

  摘要：

  Fluorescent and luminescent reporters that signal molecular events of interest by modulating the ratio of peaks in their emission profile have advantages over reporters that simply modulate their emission intensity, since ratiometric measurement is concentration-independent and allows them to be effective in complex contexts, such as living cells or sensor microarrays. We herein describe a general platform for the design of ratiometric probes based on a heterometallic Tb3+/Eu3+ bis-lanthanide ensemble, consisting of a mixture, or "cocktail", of otherwise identical heterometalated chelates. The chelate contains an organic photon antenna that sensitizes the Tb3+/Eu3+ luminescence. The contributions of the two metals to the composite luminescence spectrum can be tuned to the same relative scale by adjusting the stoichiometry of the cocktail, allowing subtle changes in their ratio to be accurately measured. Importantly, the ratio responds to chemical and environmental changes experienced by the photon antenna, making the system an ideal platform for the design of chemical and enzymatic probes. As proofs of concept, we describe a ratiometric probe for esterase activity and a polarity-responsive ratiometric sensor.

  DOI：

  10.1021/ja070867y