5,7-dihydroxy-4-methyl-2-oxo-2H-chromene-6,8-dicarbaldehyde | 1431043-38-7

• 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: 5,7-dihydroxy-4-methyl-2-oxo-2H-chromene-6,8-dicarbaldehyde
• 英文别名: 6,8-Diformyl-5,7-dihydroxy-4-methylcoumarin；5,7-dihydroxy-4-methyl-2-oxochromene-6,8-dicarbaldehyde
• CAS: 1431043-38-7
• 化学式: C₁₂H₈O₆
• 分子量: 248.192
• InChiKey: DRJHANRTTAZXAN-UHFFFAOYSA-N

物化性质

• 沸点：
  421.3±45.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯胺-15N 、 5,7-dihydroxy-4-methyl-2-oxo-2H-chromene-6,8-dicarbaldehyde 以 异丙醇 为溶剂， 反应 5.0h， 以45%的产率得到4-methyl-6,8-bis{[(15N)phenylamino]methylidene}-2H-chromene-2,5,7(6H,8H)-trione
  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
• 作为产物：
  描述：

  5,7-二羟基-4-甲基香豆素 、 原甲酸三乙酯 反应 5.0h， 以35%的产率得到5,7-dihydroxy-4-methyl-2-oxo-2H-chromene-6,8-dicarbaldehyde
  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

文献信息

• Synthesis of bis-spiropyrans based on 6,8-diformyl-5,7-dihydroxy-4-methylcoumarin and photochromic properties thereof
  作者：Olga G. Nikolaeva、Olga Yu. Karlutova、Alexander S. Cheprasov、Anatoly V. Metelitsa、Igor V. Dorogan、Alexander D. Dubonosov、Vladimir A. Bren’

  DOI：10.1007/s10593-015-1689-2

  日期：2015.3

  [GRAPHICS]Synthesis of new asymmetric bis-spiropyrans of indoline series based on 6,8-diformyl-5,7-dihydroxy-4-methylcoumarin was realized. Depending on the nature of the substituents in positions 1 and 5 of the indoline moiety the derived compounds may exist in solution in the spiro or merocyanine forms, or as a tautomeric mixture of these forms. UV irradiation of the cyclic forms leads to photocoloring associated with re-opening of one or both of the spiro moieties. The wide variability of spectral kinetic properties of bis-spiropyrans upon fluorescence of photoinduced forms allows one to consider them as molecular switches having absorptive and fluorescent signal functions with the possibility of practical application.
• Spectral-Luminescent and Ionochromic Properties of Azomethine Imine-Coumarin Conjugates
  作者：O. G. Nikolaeva、O. S. Popova、I. V. Dubonosova、O. Yu. Karlutova、A. D. Dubonosov、V. A. Bren、V. I. Minkin

  DOI：10.1134/s1070363222050139

  日期：2022.5
• Benzoid-quinoid tautomerism of Schiff bases and their structural analogs: LV. Crown-containing N-phenylimines derived from ortho-hydroxycarbaldehydes of the coumarin series
  作者：V. I. Minkin、A. D. Dubonosov、V. A. Bren’、O. G. Nikolaeva、A. V. Tsukanov、O. N. Burov、A. Yu. Fedyanina

  DOI：10.1134/s107042801303010x

  日期：2013.3

  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.