7-氨基-2-氧代-1,2-二氢喹啉-4-羧酸乙酯 | 502143-68-2

• 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
• 中文名称: 7-氨基-2-氧代-1,2-二氢喹啉-4-羧酸乙酯
• 英文名称: 7-amino-2-hydroxy-quinoline-4-carboxylic acid ethyl ester
• 英文别名: 7-Amino-2-hydroxy-chinolin-4-carbonsaeure-aethylester；ethyl 7-amino-2-oxo-1H-quinoline-4-carboxylate
• CAS: 502143-68-2
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: CDUDUCSKAXXQJC-UHFFFAOYSA-N

物化性质

• 熔点：
  262 °C
• 沸点：
  483.7±45.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-氨基-2-氧代-1,2-二氢喹啉-4-羧酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 7-amino-2-keto-4-quinolinic acid
  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：

  N,N-diallyl-3-nitroaniline 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 、 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.0h， 生成 7-氨基-2-氧代-1,2-二氢喹啉-4-羧酸乙酯
  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

文献信息

• Efficient Synthesis of 3,4-Dihydro-1<i>H</i>-Quinoxalin-2-ones and 1<i>H</i>-Quinolin-2-Ones and Evaluation of Their Anti-Bacterial Activity
  作者：Elham Zarenezhad、Mohammad Hossein Mosslemin、Alireaza Alborzi、Hossein Anaraki-Ardakani、Nasim Shams、Mehdi Mard Khoshnood、Ali Zarenezhad

  DOI：10.3184/174751914x13987604216112

  日期：2014.6

  Economical and environmentally friendly syntheses of three 3,4-dihydro-1H-quinoxalin-2-ones and six 1H-quinolin-2-ones have been developed by a 1: 1 reaction of o-, m-, or p-phenylenediamine with dialkyl acetylenedicarboxylates under solvent-free conditions. Some of the products were antibacterial towards both Gram positive and Gram negative microorganisms.

  通过邻苯二胺、间苯二胺和对苯二胺的 1:1 反应，开发了三种 3,4-dihydro-1H-quinoxalin-2-ones 和六个 1H-quinolin-2-ones 的经济且环保的合成方法。乙炔二羧酸二烷基酯在无溶剂条件下。一些产品对革兰氏阳性和革兰氏阴性微生物均具有抗菌作用。
• 38. Attempts to find new antimalarials. Part XVIII. Derivatives of m-phenanthroline
  作者：William O. Kermack、William Webster

  DOI：10.1039/jr9420000213

  日期：——
• Cocktails of Tb³⁺ and Eu³⁺ Complexes:  A General Platform for the Design of Ratiometric Optical Probes
  作者：Matthew S. Tremblay、Marlin Halim、Dalibor Sames

  DOI：10.1021/ja070867y

  日期：2007.6.1

  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.