2,6-difluoro-4-hydroxy-3-methoxybenzaldehyde | 152434-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-difluoro-4-hydroxy-3-methoxybenzaldehyde
• 英文别名: Benzaldehyde, 2,6-difluoro-4-hydroxy-3-methoxy-
• CAS: 152434-97-4
• 化学式: C₈H₆F₂O₃
• 分子量: 188.131
• InChiKey: XCGGYDMDMRNJKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  308.4±37.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-difluoro-4-hydroxy-3-methoxybenzaldehyde 在 lithium aluminium tetrahydride 、 potassium carbonate 、 zinc(II) iodide 作用下， 以 乙醚 、 氯仿 、 丙酮 为溶剂， 反应 2.0h， 生成 2,6-difluoro-3,4-dimethoxyphenethanolamine
  参考文献：
  名称：

  Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity

  摘要：

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.

  DOI：

  10.1021/jm00076a024
• 作为产物：
  描述：

  3,5-二氟-2-甲氧基苯甲醛 在 咪唑 、 盐酸 、 氢氧化钾 、 仲丁基锂 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2,6-difluoro-4-hydroxy-3-methoxybenzaldehyde
  参考文献：
  名称：

  Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity

  摘要：

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.

  DOI：

  10.1021/jm00076a024

文献信息

• Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity
  作者：George T. Chen、Michael King、Fabian Gusovsky、Cyrus R. Creveling、John W. Daly、Bang Hua Chen、Jun Ying Nie、Kenneth L. Kirk

  DOI：10.1021/jm00076a024

  日期：1993.11

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.