3-hydroxy-2-phenyl-2,3-dihydroquinolin-4(1H)-one

• 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: 3-hydroxy-2-phenyl-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 3-hydroxy-2-phenyl-2H, 3H, 4H-1-benzopyridin-4-one；3-hydroxy-2-phenyl-2,3-dihydro-1H-quinolin-4-one
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: BLNJJQJVGIDTSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-phenyl-2,3-dihydroquinolin-4(1H)-one 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 为溶剂， 生成 3-羟基-2-苯基-2,3-二氢-4(1H)-喹啉酮
  参考文献：
  名称：

  Synthesis and fluorescence properties of 2-aryl-3-hydroxyquinolones, a new class of dyes displaying dual fluorescence

  摘要：

  A series of 2-aryl-3-hydroxyquinolones (3HQs) with different electron donating aryl substituents at the position 2 were synthesized. Their absorption and fluorescence properties were studied in solvents of medium and high polarity. Almost all the synthesized 3HQs display dual fluorescence in the tested solvents, in line with an excited state intramolecular proton transfer reaction. For N-methyl substituted compounds, the intensity ratio of the two emission bands was found to be exquisitely sensitive to solvent polarity, with a two orders of magnitude change from toluene to dimethylsulfoxide. Consequently, these compounds appear as prospective polarity fluorescent labels for proteins and nucleic acids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.160
• 作为产物：
  描述：

  2'-Aminochalcone Epoxide 以 正丁醇 为溶剂， 生成 3-hydroxy-2-phenyl-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Gao, Feng; Johnson, Kurtis F.; Schlenoff, Joseph B., Journal of the Chemical Society. Perkin transactions II, 1996, # 2, p. 269 - 274

  摘要：

  DOI：

文献信息

• Design, synthesis and anti-inflammatory activity of dihydroflavonol derivatives
  作者：Chunling Hu、Zongbao Zhou、Yuanhang Xiang、Xiaoying Song、Hong Wang、Kaiqi Tao、Xiaochuan Ye

  DOI：10.1007/s00044-017-2054-z

  日期：2018.1

  Thirty dihydroflavonol derivatives (D1–D30) were designed and synthesized, meanwhile the synthesized compounds were characterized on the basis of spectroscopic analyzes. Their inhibitory activity against the pro-inflammatory inducible interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophages were evaluated and

  设计并合成了三十种二氢黄酮醇衍生物（D1 - D30），同时在光谱分析的基础上对合成的化合物进行了表征。它们对脂多糖（LPS）刺激的鼠RAW 264.7巨噬细胞中促炎性诱导白介素1β（IL-1β），白介素6（IL-6）和肿瘤坏死因子-α（TNF-α）的抑制活性为评估并显示出各种效率。化合物D1 - D30在20μM的浓度下对RAW 264.7细胞无毒作用；其中，化合物D9，D13和D19通过降低IL-1β，IL-6和TNF-α表现出最佳的抗炎活性。此外，初步讨论了它们的结构-活性关系。
• Proton-transfer, low self-absorbing chromophores for use in scintillators
  申请人：Florida State University

  公开号：US05552551A1

  公开（公告）日：1996-09-03

  Proton-transfer, low self-absorbing chromophores of the formula: ##STR1## wherein R.sub.2 and R.sub.3 are independently hydrogen, alkyl, aryl, cyano, nitro, halo or an ether group, R.sub.4 is O or N--H, and R.sub.5 is thienyl, naphthyl, furanyl, pyrrolyl, phenyl vinyl, diphenyl vinyl, phenyl ethynyl, hydroxy chromonyl phenyl, didecyloxy hydroxy chromonyl phenyl, phenyl or ##STR2## wherein R.sub.1 is vinyl, vinyl phenyl, vinyl benzyl, alkyl ethenyl, or alkyl phenyl ethenyl, provided that when R.sub.5 is phenyl and R.sub.2 and R.sub.3 are hydrogen, R.sub.4 is N--H.

  质子转移，公式为：##STR1## 其中R.sub.2和R.sub.3独立地为氢，烷基，芳基，氰基，硝基，卤素或醚基，R.sub.4为O或N--H，R.sub.5为噻吩基，萘基，呋喃基，吡咯基，苯基乙烯基，二苯基乙烯基，苯基乙炔基，羟基色酮基苯基，二癸氧基羟基色酮基苯基，苯基或##STR2## 其中R.sub.1为乙烯基，乙烯基苯基，乙烯基苯甲基，烷基乙烯基或烷基苯基乙烯基，但当R.sub.5为苯基且R.sub.2和R.sub.3为氢时，R.sub.4为N--H。
• Gao, Feng; Johnson, Kurtis F.; Schlenoff, Joseph B., Journal of the Chemical Society. Perkin transactions II, 1996, # 2, p. 269 - 274
  作者：Gao, Feng、Johnson, Kurtis F.、Schlenoff, Joseph B.

  DOI：——

  日期：——
• Synthesis and fluorescence properties of 2-aryl-3-hydroxyquinolones, a new class of dyes displaying dual fluorescence
  作者：Dmytro A. Yushchenko、Mykhailo D. Bilokin’、Oleksandr V. Pyvovarenko、Guy Duportail、Yves Mély、Vasyl G. Pivovarenko

  DOI：10.1016/j.tetlet.2005.11.160

  日期：2006.2

  A series of 2-aryl-3-hydroxyquinolones (3HQs) with different electron donating aryl substituents at the position 2 were synthesized. Their absorption and fluorescence properties were studied in solvents of medium and high polarity. Almost all the synthesized 3HQs display dual fluorescence in the tested solvents, in line with an excited state intramolecular proton transfer reaction. For N-methyl substituted compounds, the intensity ratio of the two emission bands was found to be exquisitely sensitive to solvent polarity, with a two orders of magnitude change from toluene to dimethylsulfoxide. Consequently, these compounds appear as prospective polarity fluorescent labels for proteins and nucleic acids. (c) 2005 Elsevier Ltd. All rights reserved.