4'-(N,N-Dimethylamino)-α-naphthyl-3-hydroxychromone | 173289-77-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4'-(N,N-Dimethylamino)-α-naphthyl-3-hydroxychromone
• 英文别名: 2-[4-(Dimethylamino)naphthalen-1-yl]-3-hydroxychromen-4-one
• CAS: 173289-77-5
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: APVXKRIUZGNRTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-(N,N-Dimethylamino)-α-naphthyl-3-hydroxychromone 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4'-(N,N-Dimethylamino)-α-naphthyl-3-methoxychromone
  参考文献：
  名称：

  Torsional and Proton Transfer Dynamics in Substituted 3-Hydroxyflavones

  摘要：

  The role of torsional motion in proton transfer dynamics of 4'-(N,N-dimethylamino)-alpha-naphthyl-3-hydroxychromone has been studied using time-resolved emission spectroscopy. Excited state proton transfer (ESPT) rates in hydrocarbon solvents of varying viscosities are obtained. The viscosity is varied so that ESPT rate prior to, and following, torsional relaxation may be determined. The results show that as the aryl 'torsional relaxation proceeds, the exothermicity of proton transfer decreases and the proton transfer rate increases; thus, the system exhibits ''Marcus inverted'' behavior. These results are interpreted in terms of torsional potentials. These potential energy surfaces are constructed from solvent-dependent static absorption and emission spectra and time-dependent Stokes shift measurements. Potential energy surfaces are constructed for the normal and tautomeric forms af the molecule in both torsionally relaxed and unrelaxed states. From these surfaces, a ratio of reaction rates is obtained, which is in good agreement with experimentally determined value.

  DOI：

  10.1021/jp9520106
• 作为产物：
  描述：

  (E)-3-(4-Dimethylamino-naphthalen-1-yl)-1-phenyl-propenone 在 双氧水 作用下， 以 乙醇 为溶剂， 生成 4'-(N,N-Dimethylamino)-α-naphthyl-3-hydroxychromone
  参考文献：
  名称：

  Torsional and Proton Transfer Dynamics in Substituted 3-Hydroxyflavones

  摘要：

  The role of torsional motion in proton transfer dynamics of 4'-(N,N-dimethylamino)-alpha-naphthyl-3-hydroxychromone has been studied using time-resolved emission spectroscopy. Excited state proton transfer (ESPT) rates in hydrocarbon solvents of varying viscosities are obtained. The viscosity is varied so that ESPT rate prior to, and following, torsional relaxation may be determined. The results show that as the aryl 'torsional relaxation proceeds, the exothermicity of proton transfer decreases and the proton transfer rate increases; thus, the system exhibits ''Marcus inverted'' behavior. These results are interpreted in terms of torsional potentials. These potential energy surfaces are constructed from solvent-dependent static absorption and emission spectra and time-dependent Stokes shift measurements. Potential energy surfaces are constructed for the normal and tautomeric forms af the molecule in both torsionally relaxed and unrelaxed states. From these surfaces, a ratio of reaction rates is obtained, which is in good agreement with experimentally determined value.

  DOI：

  10.1021/jp9520106