5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6-carbaldehyde | 27038-43-3

• 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-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6-carbaldehyde
• 英文别名: 5-hydroxy-4,7-dimethyl-6-formylcoumarin；5-Hydroxy-4,7-dimethyl-2-oxo-2H-chromen-6-carbaldehyd；5-hydroxy-4,7-dimethyl-2-oxochromene-6-carbaldehyde
• CAS: 27038-43-3
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: CGJLVTDZAAVCEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯胺-15N 、 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6-carbaldehyde 以 异丙醇 为溶剂， 反应 5.0h， 以55%的产率得到5-hydroxy-4,7-dimethyl-6-[(15N)phenyliminomethyl]-2H-chromen-2-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
• 作为产物：
  描述：

  5-hydroxy-4,7-dimethylcoumarin 、 N-甲基甲酰苯胺 在 邻二氯苯 、 三氯氧磷 作用下， 生成 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-8-carbaldehyde 、 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6-carbaldehyde
  参考文献：
  名称：

  Formylation of Benzopyrones. II. Formylation of Hydroxycoumarins with N-Methylformanilide¹

  摘要：

  DOI：

  10.1021/jo01363a025

文献信息

• Synthesis and photochromism of spiroindoline-2,2'-pyrano[2,3-f]coumarins
  作者：O. G. Nikolaeva、A. S. Cheprasov、A. V. Metelitsa、A. D. Dubonosov、V. A. Bren’、V. I. Minkin

  DOI：10.1134/s001250081512006x

  日期：2015.12

  Indoline spiropyrans containing a formylcoumarin moiety annulated to the 2H-pyran ring at the 6,5-position have been synthesized, and their structure and photochromism have been studied. It has been shown that the synthesized compounds exhibit better spectral-kinetic and photochromic properties as compared with other coumarin spiropyrans.