(Z)-1-(2-Hydroxy-phenyl)-3-(4-methoxy-phenyl)-propenone | 58202-24-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-1-(2-Hydroxy-phenyl)-3-(4-methoxy-phenyl)-propenone
• 英文别名: 2-Propen-1-one, 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-；(Z)-1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 58202-24-7
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: NXBNYUSXDBHELA-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-(2-Hydroxy-phenyl)-3-(4-methoxy-phenyl)-propenone 在 双氧水 作用下， 生成 3-羟基-4-甲氧基黄酮
  参考文献：
  名称：

  Excited State and Ground State Proton Transfer Rates of 3-Hydroxyflavone and Its Derivatives Studied by Shpol'skii Spectroscopy:  The Influence of Redistribution of Electron Density

  摘要：

  We studied the mechanisms of excited-state intramolecular proton transfer (ESIPT) and ground-state back proton transfer (BPT) in 3-hydroxyflavone (3HF) at cryogenic temperatures. The focus was on substituents that change the distribution of electronic density on the chromophore and their influence on these reaction rates. Shpol'skii spectroscopy was applied for comparative studies of three compounds: 3HF, 3-hydroxy-4'-methoxyflavone (3HF-4'OMe), and 2-furyl-3-hydroxychromone (3HC-F). By comparing the spectral bandwidths with those of deuterated analogues, we could distinguish the lifetime broadening components in the high-resolution excitation and emission spectra, from which the time constants of the ESIPT and BPT reactions were calculated. The time constants for the ESIPT reaction were 0.093 ps for 3HF, 0.21 ps for 3HF-4'OMe, and slower than 0.6 ps for 3HC-F. For the same compounds, the BPT rates were 0.21, 0.47, and >2 ps, respectively. No change in bandwidth was observed over the temperature range 4-20 K, in agreement with a tunneling mechanism. Estimates for the barrier heights and proton-transfer distances are given. In addition, a systematic change in O-H bond strengths between ground and excited states was calculated from the isotope effect, observed as the shifts of the 0-0 bands in the excitation and emission spectra upon deuteration. The substantial effect of electron donating substituents on the rates of ESIPT and BPT reactions is in agreement with these changes.

  DOI：

  10.1021/jp048925e
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 4-甲氧基苯甲醛 生成 (Z)-1-(2-Hydroxy-phenyl)-3-(4-methoxy-phenyl)-propenone
  参考文献：
  名称：

  Excited State and Ground State Proton Transfer Rates of 3-Hydroxyflavone and Its Derivatives Studied by Shpol'skii Spectroscopy:  The Influence of Redistribution of Electron Density

  摘要：

  We studied the mechanisms of excited-state intramolecular proton transfer (ESIPT) and ground-state back proton transfer (BPT) in 3-hydroxyflavone (3HF) at cryogenic temperatures. The focus was on substituents that change the distribution of electronic density on the chromophore and their influence on these reaction rates. Shpol'skii spectroscopy was applied for comparative studies of three compounds: 3HF, 3-hydroxy-4'-methoxyflavone (3HF-4'OMe), and 2-furyl-3-hydroxychromone (3HC-F). By comparing the spectral bandwidths with those of deuterated analogues, we could distinguish the lifetime broadening components in the high-resolution excitation and emission spectra, from which the time constants of the ESIPT and BPT reactions were calculated. The time constants for the ESIPT reaction were 0.093 ps for 3HF, 0.21 ps for 3HF-4'OMe, and slower than 0.6 ps for 3HC-F. For the same compounds, the BPT rates were 0.21, 0.47, and >2 ps, respectively. No change in bandwidth was observed over the temperature range 4-20 K, in agreement with a tunneling mechanism. Estimates for the barrier heights and proton-transfer distances are given. In addition, a systematic change in O-H bond strengths between ground and excited states was calculated from the isotope effect, observed as the shifts of the 0-0 bands in the excitation and emission spectra upon deuteration. The substantial effect of electron donating substituents on the rates of ESIPT and BPT reactions is in agreement with these changes.

  DOI：

  10.1021/jp048925e