2-(6-diethylaminobenzo[b]furan-2-yl)-3-hydroxychromone | 386736-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(6-diethylaminobenzo[b]furan-2-yl)-3-hydroxychromone
• 英文别名: 4H-1-Benzopyran-4-one, 2-[6-(diethylamino)-2-benzofuranyl]-3-hydroxy-；2-[6-(diethylamino)-1-benzofuran-2-yl]-3-hydroxychromen-4-one
• CAS: 386736-84-1
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: CYLPHAUGZHZYJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(6-diethylaminobenzo[b]furan-2-yl)-3-hydroxychromone 、 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Toward Point-of-Care Detection of Mycobacterium tuberculosis: A Brighter Solvatochromic Probe Detects Mycobacteria within Minutes

  摘要：

  DOI：

  10.1021/jacsau.1c00173
• 作为产物：
  描述：

  6-diethylaminobenzo[b]furan-2-carbaldehyde 在 氢氧化钾 、 双氧水 作用下， 以 乙醇 为溶剂， 生成 2-(6-diethylaminobenzo[b]furan-2-yl)-3-hydroxychromone
  参考文献：
  名称：

  A 3-hydroxychromone with dramatically improved fluorescence properties

  摘要：

  A new 3-hydroxychromone derivative, 2-(6-diethylaminobenzo[b]furan-2-yl)-3-hydroxychromone. has been synthesized by a concise route. Possessing dual emission common for 3-hydroxyflavones, it exhibits strong red shifts of both absorption and fluorescence spectra, which makes it the longest wavelength fluorescent dye among all known chromones. It also demonstrates a significant increase in fluorescence quantum yield in aprotic solvents and shift in solvent-polarity-dependent switch between normal and tautomer emissive forms. This derivative offers new possibilities in designing novel molecular sensors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01723-3

文献信息

• Modulation of the solvent-dependent dual emission in 3-hydroxychromones by substituents
  作者：Andrey S. Klymchenko、Vasyl G. Pivovarenko、Turan Ozturk、Alexander P. Demchenko

  DOI：10.1039/b302965d

  日期：——

  electron-donor substituents, introduced on opposite sides of the chromophore, were compared in solvents of different polarities. The substitution of 2-phenyl for 2-(2-benzo[b]furanyl) and introduction of electron donors on the 2-aryl group not only shift the absorption and fluorescence spectra to the red, but also strongly modulate the ESIPT behavior, resulting in a dramatic increase of the intensity ratio of the

  3-Hydroxychromones（3HCs）是 荧光染料，以回应 溶剂通过在发射光谱中两个分离良好的谱带的相对强度的变化和变化来扰动。这些条带源自分子内的激发态质子转移 （ESIPT）反应，可以通过不同的因素进行调节，包括3HC的修饰 发色团。鉴于3HC作为分子传感器的潜在基本元素的重要性，我们对3HC结构与光谱性质之间的相关性进行了首次系统研究。在电子束的相反侧引入了两个系列的已知和新合成的2-苯基-3-羟基色酮和具有不同电子给体取代基的2-（2-苯并[ b ]呋喃基）-3-羟基色酮。发色团，在中进行了比较 溶剂不同的极性。用2-苯基取代2-（2-苯并[ b ]呋喃基）并引入电子给体 在2-芳基上不仅会改变吸收和 荧光光谱为红色，但也强烈调节ESIPT行为，导致两个发射带I N * / I T *的强度比急剧增加。相反，引入7-甲氧基导致完全相反的光谱效应。所有研究过的3HC染料证明ln（I
• Dipolar 3-methoxychromones as bright and highly solvatochromic fluorescent dyes
  作者：Oleksandr A. Kucherak、Ludovic Richert、Yves Mély、Andrey S. Klymchenko

  DOI：10.1039/c2cp23037b

  日期：——

  Herein, three environment-sensitive (solvatochromic) fluorescent dyes presenting a strong electron acceptor 3-methoxychromone unit and varied electron donor 2-aryl were developed. All three dyes showed remarkable polarity-dependent shifts of the emission maximum, which increase with extension of the dye conjugation. For the 3-methoxychromone bearing a 7-(diethylamino)-9,9-dimethylfluoren-2-yl donor group the difference between the excited and the ground state dipole moments, estimated from the Lippert–Mataga expression, reached 20 D, which is among the largest reported for neutral dipolar fluorophores. Moreover, the new dyes are characterized by significant two-photon absorption cross-section (up to 450 GM) and large fluorescence quantum yields. The strong decrease in the fluorescence quantum yields of the dyes in polar protic solvents was observed together with the increase in the non-radiative deactivation rates, which can originate from twisted intramolecular charge transfer and intermolecular proton transfer phenomena. In comparison to the parent 3-hydroxychromone derivatives, the new dyes presented significantly improved photostability, which confirms that photodegradation of 3-hydroxychromones occurs from a product of the excited-state intramolecular proton transfer (phototautomer). Finally, an application of the new dyes for probing local binding site polarity of serum albumin was shown. This new class of fluorescent dyes may serve as attractive building blocks for future molecular sensors utilizing environment-sensitive fluorophores.

  在此，开发了三种环境敏感（溶剂致变色）荧光染料，它们具有强电子受体 3-甲氧基色酮单元和不同的电子供体 2-芳基。所有三种染料均表现出显着的发射最大值的极性依赖性变化，这种变化随着染料缀合的延长而增加。对于带有 7-(二乙氨基)-9,9-二甲基芴-2-基供体基团的 3-甲氧基色酮，根据 Lippert-Mataga 表达式估计，激发态偶极矩与基态偶极矩之间的差异达到 20 D，即其中最大的中性偶极荧光团报道之一。此外，新型染料还具有显着的双光子吸收截面（高达 450 GM）和大的荧光量子产率。观察到染料在极性质子溶剂中的荧光量子产率急剧下降，同时非辐射失活率增加，这可能源于扭曲的分子内电荷转移和分子间质子转移现象。与母体3-羟基色酮衍生物相比，新染料的光稳定性显着提高，这证实了3-羟基色酮的光降解是由激发态分子内质子转移（光互变异构体）的产物发生的。最后，展示了新染料在探测血清白蛋白局部结合位点极性中的应用。这种新型荧光染料可以作为未来利用环境敏感荧光团的分子传感器的有吸引力的构建模块。
• A 3-hydroxychromone with dramatically improved fluorescence properties
  作者：Andrey S Klymchenko、Turan Ozturk、Vasyl G Pivovarenko、Alexander P Demchenko

  DOI：10.1016/s0040-4039(01)01723-3

  日期：2001.11

  A new 3-hydroxychromone derivative, 2-(6-diethylaminobenzo[b]furan-2-yl)-3-hydroxychromone. has been synthesized by a concise route. Possessing dual emission common for 3-hydroxyflavones, it exhibits strong red shifts of both absorption and fluorescence spectra, which makes it the longest wavelength fluorescent dye among all known chromones. It also demonstrates a significant increase in fluorescence quantum yield in aprotic solvents and shift in solvent-polarity-dependent switch between normal and tautomer emissive forms. This derivative offers new possibilities in designing novel molecular sensors. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Toward Point-of-Care Detection of <i>Mycobacterium tuberculosis</i>: A Brighter Solvatochromic Probe Detects Mycobacteria within Minutes
  作者：Mireille Kamariza、Samantha G. L. Keyser、Ashley Utz、Benjamin D. Knapp、Christopher Ealand、Green Ahn、C. J. Cambier、Teresia Chen、Bavesh Kana、Kerwyn Casey Huang、Carolyn R. Bertozzi

  DOI：10.1021/jacsau.1c00173

  日期：2021.9.27