3-[(4-hydroxyphenyl)methyl]-2H-1-benzopyran-2-one | 149030-47-7

• 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: 3-[(4-hydroxyphenyl)methyl]-2H-1-benzopyran-2-one
• 英文别名: 3-[(4-Hydroxyphenyl)methyl]chromen-2-one
• CAS: 149030-47-7
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: WYBZDBQRDQXQGF-UHFFFAOYSA-N

物化性质

• 沸点：
  481.3±33.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  3-[(4-hydroxyphenyl)methyl]-2H-1-benzopyran-2-one 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 以87%的产率得到3-[(3-Bromo-4-hydroxyphenyl)methyl]chromen-2-one
  参考文献：
  名称：

  Majumdar, Krishna C.; Saha, Subrata; De, Rathindra N., Journal of the Chemical Society. Perkin transactions I, 1993, # 6, p. 715 - 718

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(Phenoxymethyl)chromen-2-one 以 二苯醚 为溶剂， 反应 4.0h， 以88%的产率得到3-[(4-hydroxyphenyl)methyl]-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Majumdar, Krishna C.; Saha, Subrata; De, Rathindra N., Journal of the Chemical Society. Perkin transactions I, 1993, # 6, p. 715 - 718

  摘要：

  DOI：

文献信息

• Synthesis, biochemical evaluation, and molecular modeling of organophosphate-coumarin hybrids as potent and selective butyrylcholinesterase inhibitors
  作者：Lee J. Macklin、Jason P. Schwans

  DOI：10.1016/j.bmcl.2020.127213

  日期：2020.7

  A small library of new organophosphorylated warfarins and 3-benzylcoumarins were synthesized and evaluated for in vitro cholinesterase inhibition by Ellman's method. Most of the compounds were found to be selective for butyrylcholinesterase (BChE) over acetylcholinesterase (AChE), with IC50 values ranging from 0.363 mu M to 53.0 mu M determined after 15 s of enzyme exposure. Comparison of the most potent compound, 3b with its constitutional isomer 2b revealed the high importance of phosphate positioning. Reversed selectivity and a 100-fold reduction in anti-BChE activity was observed when the organophosphate was attached to the benzyl instead of the coumarin. Docking calculations suggest that 3b binds initially as a transition state mimic with nearoptimal phosphate orientation relative to S198 and occupation of the oxyanion hole prior to phosphorylation. These results might inspire the design of a new type of non-neuropathic and irreversible coumarin-based inhibitor against BChE.
• Studies on sigmatropic rearrangements: Thermal rearrangement of 3-(meta-substituted aryloxymethyl) coumarins
  作者：K. C. Majumdar、G. H. Jana、S. K. Ghosh、S. Saha

  DOI：10.1007/bf00807595

  日期：——

  At elevated temperatures, the 3-(meta-substituted aryloxymethyl) coumarins 3a-e and 3g-k undergo sigmatropic rearrangements to give the hydroxylated 3-benzylcoumarins 4a-e and 4g-k. Upon methylation and subsequent oxidation with N-bromo succinimide, the 3-(chlorosubstituted benzyl) coumarins 4a, 4m and 4n afford 3-(chlorosubstituted benzoyl) coumarins 8a, 8m, and 8n.
• Majumdar, Krishna C.; Saha, Subrata; De, Rathindra N., Journal of the Chemical Society. Perkin transactions I, 1993, # 6, p. 715 - 718
  作者：Majumdar, Krishna C.、Saha, Subrata、De, Rathindra N.、Ghosh, Santosh K.

  DOI：——

  日期：——