4-fluoro-2-(2-naphthyl)quinoline | 159788-74-6

• 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: 4-fluoro-2-(2-naphthyl)quinoline
• 英文别名: 4-Fluoro-2-naphthalen-2-yl-quinoline；4-fluoro-2-naphthalen-2-ylquinoline
• CAS: 159788-74-6
• 化学式: C₁₉H₁₂FN
• 分子量: 273.309
• InChiKey: BJXVLQOAHSUUFR-UHFFFAOYSA-N

物化性质

• 沸点：
  442.9±35.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(二甲基氨基)乙硫醇钠 、 4-fluoro-2-(2-naphthyl)quinoline 以 乙醇 为溶剂， 反应 48.0h， 以40%的产率得到N,N-dimethyl-2-(2-naphthalen-2-ylquinolin-4-yl)sulfanylethanamine
  参考文献：
  名称：

  DNA三重螺旋特异性嵌入剂的合成及结构-DNA结合关系分析。

  摘要：

  在喹啉的位置2和4周围具有构象自由度的4- [N-（氨基烷基）氨基] -2-芳基喹啉可以稳定地稳定聚（dT.dA.dT）（三链DNA），并与聚-（dA.dT）弱结合。 （双链DNA）。喹啉N1的碱性与这些化合物与三螺旋DNA结构的相互作用强度平行，表明喹啉N1在与DNA三链体复合物中质子化。实验结果支持了先前提出的交互模型。

  DOI：

  10.1021/jm9603734
• 作为产物：
  描述：

  2-萘乙酮 、 邻氨基三氟甲苯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 4-fluoro-2-(2-naphthyl)quinoline
  参考文献：
  名称：

  The o-Amino-Trifluoromethyl Functionality as a Novel Synthon for 4-Fluoroquinolines

  摘要：

  2-Substituted 4-fluoroquinolines 3 are obtained by the reaction of 2-(trifluoromethyl)aniline (1) with lithium enolates 2 derived from methylketones. A similar reaction of 1 with lithium enolate of acetaldehyde produces 4-fluoroquinoline. 1-Fluoro-3-phenyl-4,6-phenanthroline (18) is obtained by treatment of Lithium enolate of acetophenone with 4-(trifluoromethyl)quinolin-3-amine (17). By contrast, (Z)-N-[2-(1-fluoroalkenyl)phenyl]carboxamides 10 and 12 are the products of the reaction of 1 with the respective enolate ions derived from 3-pentanone and isobutyl phenyl ketone. A unified mechanism for the formation of quinolines and carboxamides is proposed.

  DOI：

  10.1021/jo00099a014

文献信息

• A facile synthesis of 2-substituted N-tert-butoxycarbonyl-N-methyl-1,3-propanediamines, key intermediates for the preparation of triplex DNA-specific intercalators
  作者：Lucjan Strekowski、Yuri Gulevich、Koen Van Aken、David W Wilson、Keith R Fox

  DOI：10.1016/0040-4039(94)02228-4

  日期：1995.1

  N-substituted 2-(2-naphthyl)quinolin-4-amines 4b,c are superior to other DNA intercalators reported to date in the ability to selectively stabilize triple helix DNA in the presence of duplex DNA. A facile synthesis of the title diamines 1 required for the preparation of 4 is based on a novel addition reaction of metallated tert-butyl N,N-dimethylcarbamate [Boc-N(Me)CH2M; 7, MLi; 8, MMgBr; 9, MCu(CN)ZnCl]

  N-取代的2-（2-萘基）喹啉-4-胺4b，c在双链体DNA存在下能够选择性稳定三螺旋DNA方面优于迄今为止报道的其他DNA嵌入剂。制备4所需的标题二胺1的简便合成是基于金属化的N，N-二甲基氨基甲酸叔丁酯[Boc-N（Me）CH 2 M; 7，MLi；8，MMgBr；9，M ＝ Cu（CN）ZnCl]与硝基烯烃。
• Strekowski, Lucjan; Parker, Alesia N; Hojjat, Maryam, Acta poloniae pharmaceutica, 2004, vol. 61 Suppl, p. 70 - 72
  作者：Strekowski, Lucjan、Parker, Alesia N、Hojjat, Maryam、Say, Martial、Zegrocka-Stendel, Oliwia、Patterson, Steven E、Tanious, Farial A、Wilson, W David

  DOI：——

  日期：——
• Strekowski Lucjan, Kiselyov Alexander S., Hojjat Maryam, J. Org. Chem, 59 (1994) N 20, S 5886-5890
  作者：Strekowski Lucjan, Kiselyov Alexander S., Hojjat Maryam

  DOI：——

  日期：——
• The o-Amino-Trifluoromethyl Functionality as a Novel Synthon for 4-Fluoroquinolines
  作者：Lucjan Strekowski、Alexander S. Kiselyov、Maryam Hojjat

  DOI：10.1021/jo00099a014

  日期：1994.10

  2-Substituted 4-fluoroquinolines 3 are obtained by the reaction of 2-(trifluoromethyl)aniline (1) with lithium enolates 2 derived from methylketones. A similar reaction of 1 with lithium enolate of acetaldehyde produces 4-fluoroquinoline. 1-Fluoro-3-phenyl-4,6-phenanthroline (18) is obtained by treatment of Lithium enolate of acetophenone with 4-(trifluoromethyl)quinolin-3-amine (17). By contrast, (Z)-N-[2-(1-fluoroalkenyl)phenyl]carboxamides 10 and 12 are the products of the reaction of 1 with the respective enolate ions derived from 3-pentanone and isobutyl phenyl ketone. A unified mechanism for the formation of quinolines and carboxamides is proposed.
• Synthesis and Structure−DNA Binding Relationship Analysis of DNA Triple-Helix Specific Intercalators
  作者：Lucjan Strekowski、Yuri Gulevich、Timothy C. Baranowski、Alesia N. Parker、Alexander S. Kiselyov、Shou-Yuan Lin、Farial A. Tanious、W. David Wilson

  DOI：10.1021/jm9603734

  日期：1996.1.1

  quinoline stabilize strongly poly(dT.dA.dT) (triplex DNA) and bind weakly to poly-(dA.dT) (duplex DNA). Basicity of N1 of the quinoline parallels the interaction strength of these compounds with the triple-helical DNA structure suggesting that N1 of the quinoline is protonated in the complex with the DNA triplex. The experimental results support the interaction model suggested previously.

  在喹啉的位置2和4周围具有构象自由度的4- [N-（氨基烷基）氨基] -2-芳基喹啉可以稳定地稳定聚（dT.dA.dT）（三链DNA），并与聚-（dA.dT）弱结合。 （双链DNA）。喹啉N1的碱性与这些化合物与三螺旋DNA结构的相互作用强度平行，表明喹啉N1在与DNA三链体复合物中质子化。实验结果支持了先前提出的交互模型。