5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6,8-dicarbaldehyde | 100374-64-9

• 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-6,8-dicarbaldehyde
• 英文别名: 5-hydroxy-4,7-dimethyl-2-oxochromene-6,8-dicarbaldehyde
• CAS: 100374-64-9
• 化学式: C₁₃H₁₀O₅
• 分子量: 246.219
• InChiKey: OSJMESZCGXPRNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6,8-dicarbaldehyde 、 对甲氧基苯甲酰肼 以 异丙醇 为溶剂， 反应 1.5h， 以54%的产率得到5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6,8-dicarbaldehyde bis-N-(4-methoxybenzoyl)hydrazone
  参考文献：
  名称：

  Bifunctional fluorescent and colorimetric ‘naked eye’ aroylhydrazone chemosensors for Hg2+ and F– ions detection

  摘要：

  Bis-aroylhydrazones of 5-hydroxy-4,7-dimethy1-2-oxo-2H-chromene-6,8-dicarbaldehyde display the properties of bifunctional fluorescent and colorimetric 'naked-eye' chemosensors for mercury(II) cations and fluoride anions detection.

  DOI：

  10.1016/j.mencom.2016.09.012
• 作为产物：
  描述：

  5-hydroxy-4,7-dimethylcoumarin 、 乌洛托品 在 溶剂黄146 作用下， 生成 5-hydroxy-4,7-dimethyl-2-oxo-2H-chromene-6,8-dicarbaldehyde
  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 studies of new photochromic spiropyrans containing a formylcoumarin fragment
  作者：O. G. Nikolaeva、A. V. Metelitsa、A. S. Cheprasov、O. Yu. Karlutova、A. G. Starikov、A. D. Dubonosov、V. A. Bren´、V. I. Minkin

  DOI：10.1007/s11172-016-1396-x

  日期：2016.4

  A computer search for new photoactive compounds among indoline spiropyrans of coumarin series was carried out using DFT B3LYP/6-31G(d,p) method. Based on the data obtained, the spiropyrans containing a formylcoumarin fragment annulated to the 2H-pyran ring and possessing photochromic properties were synthesized. The structure and photochromism of these compounds were studied by 1H NMR, IR, and UV/Vis

  使用 DFT B3LYP/6-31G(d,p) 方法在香豆素系列二氢吲哚螺吡喃中寻找新的光活性化合物。根据获得的数据，合成了含有与 2H-吡喃环成环的甲酰香豆素片段并具有光致变色特性的螺吡喃。通过1H NMR、IR和UV/Vis光谱研究了这些化合物的结构和光致变色。将甲酰基引入螺吡喃的香豆素部分导致部花青异构体的长波长吸收最大值发生红移，并显着延长其寿命。
• Novel photochromic indolinospiropyrans of coumarin series with high level of colorability
  作者：Anatoly V. Metelitsa、Olga G. Nikolaeva、Alexander S. Cheprasov、Olga Yu. Karlutova、Anastasia A. Burtseva、Alexander D. Dubonosov、Vladimir A. Bren、Vladimir I. Minkin

  DOI：10.1016/j.jphotochem.2016.01.019

  日期：2016.5

  Indolinospiropyrans containing coumarin moiety annulated to the 2H-pyran ring at the 6,5-position exhibit positive photochromism under normal conditions and are characterized by exceptionally high values of colorability. Both strong electron donating and electron withdrawing 5-R substituents in the indoline moiety provide for the noticeable decrease of colorability. Negative solvatochromism of merocyanine

  在正常条件下，含有在6,5-位环成2 H-吡喃环的香豆素部分的吲哚螺并吡喃并显示出正的光致变色现象，并且其着色力值极高。二氢吲哚部分中的强供电子和吸电子5-R取代基都显着降低了可着色性。合成的螺吡喃的花菁异构体的负溶剂溶变现象表明其偶极结构，这通过增加溶剂极性时再循环速率常数的降低来体现。
• 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.
• 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.