3-hydroxy-6-oxo-6H-benzo[c]chromene-4-carbaldehyde | 1208339-40-5

• 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-6-oxo-6H-benzo[c]chromene-4-carbaldehyde
• 英文别名: 3-Hydroxy-6-oxo-6h-benzo[c]chromene-4-carbaldehyde；3-hydroxy-6-oxobenzo[c]chromene-4-carbaldehyde
• CAS: 1208339-40-5
• 化学式: C₁₄H₈O₄
• 分子量: 240.215
• InChiKey: VZIKBHWNXQXIPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-hydroxy-6-oxo-6H-benzo[c]chromene-4-carbaldehyde 、 1,2,3,3-tetramethyl-3H-indolium perchlorate 在 三乙胺 作用下， 以 异丙醇 为溶剂， 以38%的产率得到1',3',3'-trimethyl-1',3'-dihydro-6H-spiro[benzo[c]pyrano[2,3-h]chromene-2,2'-indol]-6-one
  参考文献：
  名称：

  Synthesis and photochromic properties of spiropyrans containing a fused benzopyranone fragment

  摘要：

  New spiro compounds of the indole, phthalazine, isobenzofuran, and benzopyran series, containing a fused benzopyranone fragment in the chromene moiety, were synthesized. Indole derivatives were found to exhibit photochromic properties under stationary conditions at 293 K. The thermal stability of merocyanine isomers sharply decreases upon introduction of electron-withdrawing nitro group into the indole fragment and fusion of a benzene ring to the chromene fragment.

  DOI：

  10.1134/s1070428009070173
• 作为产物：
  描述：

  3-hydroxy-4-(4-methylphenyliminomethyl)-6H-benzo[c]chromen-6-one 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以78%的产率得到3-hydroxy-6-oxo-6H-benzo[c]chromene-4-carbaldehyde
  参考文献：
  名称：

  Synthesis and photochromic properties of spiropyrans containing a fused benzopyranone fragment

  摘要：

  New spiro compounds of the indole, phthalazine, isobenzofuran, and benzopyran series, containing a fused benzopyranone fragment in the chromene moiety, were synthesized. Indole derivatives were found to exhibit photochromic properties under stationary conditions at 293 K. The thermal stability of merocyanine isomers sharply decreases upon introduction of electron-withdrawing nitro group into the indole fragment and fusion of a benzene ring to the chromene fragment.

  DOI：

  10.1134/s1070428009070173

文献信息

• 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.
• 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
• Synthesis and photochromic properties of spiropyrans containing a fused benzopyranone fragment
  作者：O. G. Nikolaeva、E. B. Gaeva、E. N. Shepelenko、A. V. Tsukanov、A. V. Metelitsa、B. S. Luk’yanov、A. D. Dubonosov、V. A. Bren’、V. I. Minkin

  DOI：10.1134/s1070428009070173

  日期：2009.7

  New spiro compounds of the indole, phthalazine, isobenzofuran, and benzopyran series, containing a fused benzopyranone fragment in the chromene moiety, were synthesized. Indole derivatives were found to exhibit photochromic properties under stationary conditions at 293 K. The thermal stability of merocyanine isomers sharply decreases upon introduction of electron-withdrawing nitro group into the indole fragment and fusion of a benzene ring to the chromene fragment.