3-hydroxy-4-[(2,3,5,6,8,9,11,12-octahydrobenzo-[b][1,4,7,10,13]pentaoxacyclopentadecin-15-yl)-iminomethyl]-6H-benzo[c]chromen-6-one | 1431038-86-6

• 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-hydroxy-4-[(2,3,5,6,8,9,11,12-octahydrobenzo-[b][1,4,7,10,13]pentaoxacyclopentadecin-15-yl)-iminomethyl]-6H-benzo[c]chromen-6-one
• CAS: 1431038-86-6
• 化学式: C₂₈H₂₇NO₈
• 分子量: 505.524
• InChiKey: RKSRRINLOHAOEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  37.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  108.95
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4'-氨基苯并-15-冠-5-醚 、 3-hydroxy-6-oxo-6H-benzo[c]chromene-4-carbaldehyde 以 异丙醇 为溶剂， 反应 5.0h， 以56%的产率得到3-hydroxy-4-[(2,3,5,6,8,9,11,12-octahydrobenzo-[b][1,4,7,10,13]pentaoxacyclopentadecin-15-yl)-iminomethyl]-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Benzoid-quinoid tautomerism of Schiff bases and their structural analogs: LV. Crown-containing N-phenylimines derived from ortho-hydroxycarbaldehydes of the coumarin series

  摘要：

  Schiff bases were synthesized from 3-hydroxy-6-oxo-6H-benzo[c]chromene-4-carbaldehyde, 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6-carbaldehyde, 6,7-dihydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde, 5,7-dihydroxy-4-methyl-2-oxo-2H-chromene-6,8-dicarbaldehyde, and 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6,8-dicarbaldehyde and (N-15)aniline or aminobenzo-15-crown-5 (2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecin-15-amine), and tautomeric equilibrium between the hydroxy enimino and keto enamino forms of the 4- and 8-iminomethyl derivatives in solution was revealed by 1H NMR and electronic spectroscopy. Addition of alkaline earth cations to their solutions in acetonitrile displaced the tautomeric equilibrium toward the hydroxy enimino structure due to complex formation with the crown ether fragment.

  DOI：

  10.1134/s107042801303010x