N-[(6-bromo-7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]nicotinamide | 1364455-64-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-[(6-bromo-7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]nicotinamide
• 英文别名: N-[(6-bromo-7-hydroxy-2-oxochromen-4-yl)methyl]pyridine-3-carboxamide
• CAS: 1364455-64-0
• 化学式: C₁₆H₁₁BrN₂O₄
• 分子量: 375.178
• InChiKey: BVECLCCYVPAREF-UHFFFAOYSA-N

物化性质

• 熔点：
  >230 °C
• 沸点：
  650.6±55.0 °C(predicted)
• 密度：
  1.640±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-溴-4-(氯甲基)-7-羟基-2H-色烯-2-酮 在 ammonium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-[(6-bromo-7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]nicotinamide
  参考文献：
  名称：

  Synthesis, Photophysical, Photochemical, and Computational Studies of Coumarin-Labeled Nicotinamide Derivatives

  摘要：

  The syntheses and photophysical/photochemical properties of two amide-tethered coumarin-labeled nicotinamides are described. Photochemical studies of 6-bromo-7-hydroxycoumarin-4-ylmethylnicotinamide (BHC-nicotinamide) revealed an unexpected solvent effect. This result is rationalized by computational studies of the different protonation states using TD-DFT with the M06L/6-311+G** method with implicit and explicit solvation models. Molecular orbital energies responsible for the lambda(max) excitation show that the functionalization of the coumarin ring results in a strong red-shift from 330 to 370 nm when the pH of solution is increased from 3.06 to 8.07. From this MO analysis, a model for solvent interactions has been proposed. The BHC-nicotinamide proved to be photochemically stable, which is also interpreted in terms of NBO calculations. The results provide a set of principles for the rational design of either photostable labeling reagents or photolabile cage compounds.

  DOI：

  10.1021/jo2025527

文献信息

• Synthesis, Photophysical, Photochemical, and Computational Studies of Coumarin-Labeled Nicotinamide Derivatives
  作者：Pauline Bourbon、Qian Peng、Guillermo Ferraudi、Cynthia Stauffacher、Olaf Wiest、Paul Helquist

  DOI：10.1021/jo2025527

  日期：2012.3.16

  The syntheses and photophysical/photochemical properties of two amide-tethered coumarin-labeled nicotinamides are described. Photochemical studies of 6-bromo-7-hydroxycoumarin-4-ylmethylnicotinamide (BHC-nicotinamide) revealed an unexpected solvent effect. This result is rationalized by computational studies of the different protonation states using TD-DFT with the M06L/6-311+G** method with implicit and explicit solvation models. Molecular orbital energies responsible for the lambda(max) excitation show that the functionalization of the coumarin ring results in a strong red-shift from 330 to 370 nm when the pH of solution is increased from 3.06 to 8.07. From this MO analysis, a model for solvent interactions has been proposed. The BHC-nicotinamide proved to be photochemically stable, which is also interpreted in terms of NBO calculations. The results provide a set of principles for the rational design of either photostable labeling reagents or photolabile cage compounds.