2-amino-N-(pyren-1-yl)acetamide 2,2,2-trifluoroacetate | 1332221-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 2-amino-N-(pyren-1-yl)acetamide 2,2,2-trifluoroacetate
• 英文别名: 2-oxo-2-(pyren-1-ylamino)ethanaminium 2,2,2-trifluoroacetate
• CAS: 1332221-77-8
• 化学式: C₂HF₃O₂*C₁₈H₁₄N₂O
• 分子量: 388.346
• InChiKey: WZTOBYSPPSMGTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  92.42
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-amino-N-(pyren-1-yl)acetamide 2,2,2-trifluoroacetate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-((8-nitro-2-((2-oxo-2-(pyren-1-ylamino)ethyl)carbamoyl)quinolin-4-yl)oxy)propan-1-aminium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA

  摘要：

  Two novel pyrene - quinoline conjugates differing in the linker flexibility between aryls were prepared. In comparison with referent pyrene derivative, both conjugates showed intramolecular pyrene - quinoline stacking in aqueous medium, much more efficient for rigid conjugate. Consequently, only rigid conjugate showed excimer fluorescence with exceptionally strong bathochromic shift (+ 55 nm) of emission maximum in respect to referent pyrene analogue and flexible conjugate. All studied compounds showed similar, 10 mu mol dm(-3) affinity toward ds - DNA, characterised in general by fluorescence quenching. The flexible conjugate showed at large excess of DNA over dye formation of pyrene - quinoline excimer, while rigid conjugate retained excimer emission throughout all DNA concentrations. Lack of significant thermal stabilisation of ds - DNA by studied compounds and minor changes in CD spectrum of DNA supported non - specific agglomeration of both conjugates and referent pyrene analogue within hydrophobic DNA grooves as the dominant binding mode.

  DOI：

  10.5562/cca3269
• 作为产物：
  描述：

  tert-butyl (2-oxo-2-(pyren-1-ylamino)ethyl)carbamate 在 三氟乙酸 作用下， 反应 2.0h， 生成 2-amino-N-(pyren-1-yl)acetamide 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Impact of the Supramolecular Organisation of Pyrene – Quinoline Conjugates on their Interaction with ds – DNA

  摘要：

  Two novel pyrene - quinoline conjugates differing in the linker flexibility between aryls were prepared. In comparison with referent pyrene derivative, both conjugates showed intramolecular pyrene - quinoline stacking in aqueous medium, much more efficient for rigid conjugate. Consequently, only rigid conjugate showed excimer fluorescence with exceptionally strong bathochromic shift (+ 55 nm) of emission maximum in respect to referent pyrene analogue and flexible conjugate. All studied compounds showed similar, 10 mu mol dm(-3) affinity toward ds - DNA, characterised in general by fluorescence quenching. The flexible conjugate showed at large excess of DNA over dye formation of pyrene - quinoline excimer, while rigid conjugate retained excimer emission throughout all DNA concentrations. Lack of significant thermal stabilisation of ds - DNA by studied compounds and minor changes in CD spectrum of DNA supported non - specific agglomeration of both conjugates and referent pyrene analogue within hydrophobic DNA grooves as the dominant binding mode.

  DOI：

  10.5562/cca3269