7-氨基-4-苯基-1H-喹啉-2-酮 | 19841-02-2

• 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-4-苯基-1H-喹啉-2-酮
• 中文别名: 7-氨基-4-苯基喹啉-2(1H)-酮
• 英文名称: 7-amino-4-phenyl-2(1H)-quinolinone
• 英文别名: 7-amino-4-phenyl-1H-quinolin-2-one；7-amino-4-phenyl-1H-quinolin-2-one
• CAS: 19841-02-2
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: UMRAZINCLOYNLF-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: N,N-dimethylformamide (68-12-2); water (7732-18-5))
• 沸点：
  485.1±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-氨基-4-苯基-1H-喹啉-2-酮 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 4-Phenyl-7-hydroxy-2-chinolon
  参考文献：
  名称：

  简洁的区域特异性合成8,8-二甲基-2 H，8 H-吡喃并[6，5- h ]喹啉-2-酮及相关化合物

  摘要：

  描述了一种有效的方法，该方法通过克莱森重排进行8,8-二甲基-2 H，8 H-吡喃并[6,5 - h ]喹啉-2-酮和相关化合物的区域特异性合成。

  DOI：

  10.1016/s0040-4039(99)00821-7
• 作为产物：
  描述：

  N,N-diallyl-3-nitroaniline 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 1,3-二甲基巴比妥酸 、 铁粉 、 sodium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.0h， 生成 7-氨基-4-苯基-1H-喹啉-2-酮
  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

• Synthesis, Enzymatic Evaluation, and Docking Studies of Fluorogenic Caspase 8 Tetrapeptide Substrates
  作者：Przemysław Reszka、Riad Schulz、Karen Methling、Michael Lalk、Patrick J. Bednarski

  DOI：10.1002/cmdc.200900356

  日期：2010.1.4

  give the desired substrates in good yields and in high enantiomeric purity. Based on KM and Vmax values, the new compounds proved to be excellent substrates for recombinant human caspase 8. In contrast, the KM values for the same compounds as substrates for human caspase 3 were approximately 10–20‐fold higher. Molecular modeling studies based on the X‐ray crystal structures of both human caspases 3 and

  描述了对半胱天冬酶8具有选择性的新型荧光基四肽底物的合成，酶学评估和分子模型研究，该底物具有一般结构Ac-IETD-AXX。von Pechmann缩合反应合成了各种荧光报告基团（AXX），即3和4个取代的香豆素和quinolin-2（1 H ）-1 。随后在新开发的合成条件下将它们与caspase-8选择性四肽Ac-IETD-OH偶联，以高收率和高对映体纯度提供所需的底物。基于K M和V max值，新化合物被证明是重组人caspase 8的优良底物。相反， K M与人半胱天冬酶3的底物相同的化合物的值大约高10–20倍。基于人半胱氨酸蛋白酶3和8的X射线晶体结构的分子建模研究表明，两个活性位点中都有足够的空间容纳在荧光香豆素和喹啉3和4位中具有中等体积取代基的底物。 2（1小时）-那些。使用程序AutoDock 3将底物自动对接至人胱天蛋白酶3和8的活性位点，其结构类似于已公开的晶体学结
• Wasserlösliche faserreaktive Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
  申请人：DyStar Textilfarben GmbH & Co. Deutschland KG

  公开号：EP0838504B1

  公开（公告）日：2000-06-07
• US5834601A
  申请人：——

  公开号：US5834601A

  公开（公告）日：1998-11-10
• 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.
• A concise regiospecific synthesis of 8,8-dimethyl-2H, 8H-pyrano[6, 5-h]quinolin-2-oneand related compounds
  作者：Zheng-Yu Yang、Yi Xia、Peng Xia、Arnold Brossi、Kuo-Hsiung Lee

  DOI：10.1016/s0040-4039(99)00821-7

  日期：1999.6

  An efficient method for the regiospecific synthesis of 8,8-dimethyl-2H,8H-pyrano[6,5-h]quinolin-2-one and related compounds via a Claisen rearrangement is described.

  描述了一种有效的方法，该方法通过克莱森重排进行8,8-二甲基-2 H，8 H-吡喃并[6,5 - h ]喹啉-2-酮和相关化合物的区域特异性合成。