3-(4-Methoxyphenyl)-6-methylfuro[3,2-b]furan-2,5-dione | 1092557-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-Methoxyphenyl)-6-methylfuro[3,2-b]furan-2,5-dione
• 英文别名: 6-(4-Methoxyphenyl)-3-methylfuro[3,2-b]furan-2,5-dione
• CAS: 1092557-61-3
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: UGQPSLULZAHERB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxyphenyl)-6-methylfuro[3,2-b]furan-2,5-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  戊二酸衍生物的合成及辐射防护性能

  摘要：

  高通量筛选方法突显了某些pulvinic酸衍生物（PAD）在γ和UV辐射以及类Fenton条件下对胸腺嘧啶核苷氧化的显着抗氧化活性。在这里，我们报告了一系列新的亲水性PADs的合成及其在细胞培养中的辐射防护功效的评估。使用基于细胞的荧光测定法，我们表明其中一些化合物具有明显的防止辐射引起的细胞死亡并随后恢复增殖的能力。因此，PAD可被认为是一类新型的辐射防护剂。

  DOI：

  10.1002/cmdc.201000391
• 作为产物：
  描述：

  2-(3-Hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-propanoic acid 在 乙酸酐 作用下， 以 乙酸酐 为溶剂， 反应 1.0h， 以94%的产率得到3-(4-Methoxyphenyl)-6-methylfuro[3,2-b]furan-2,5-dione
  参考文献：
  名称：

  A new series of Cs+, K+ and Na+ chelators: Synthesis, kinetics, thermodynamics and modeling

  摘要：

  The synthesis of two molecules, B1 and B2, based on elements of norbadione A, the natural Cs+ chelator in mushrooms, associated, in the case of B2, with an 18-crown-6 ether is reported. Thermodynamic and kinetic analyses performed in water, ethanol and ethanol/water 9/1 v/v (M1) show in M1 and ethanol that B1 and B2 form stable complexes with Na+, K+ and Cs+. Affinity constants, measured spectrophotometrically in ethanol and M1, by the use of the SPECFIT program, are in the 10(5) and 10(6) range for B1 and B2, respectively. The second-order rate constants are in the 10(6)-10(7) M-1 s(-1) range and the first-order rate constants about unity. The ratios of the second-order/first-order rate constants confirm the thermodynamic results in EtOH. The kinetic processes become much too fast to allow runs in M1. Molecular simulations in EtOH imply the existence of two isomers for each of the Cs+/B1 and Cs+/B2 complexes. With B1, the more stable one is that in which the two enolates are parallel and mimic the alkali-metal inclusion cavity already envisaged for norbadione A. With B2, two similar structures are extracted, in both of which Cs+ is included in the crown ether and capped by the enolate. The affinity of B1 for Cs+ is comparable to that of norbadione A, whereas that of B2 is higher. These results are encouraging as they introduce a new series of alkali chelators which can lead to molecules capable of complexing Cs-137(+) for radioactive decontamination. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.08.009

文献信息

• Evaluation of Antioxidant Properties of Monoaromatic Derivatives of Pulvinic Acids
  作者：Damien Habrant、Stéphane Poigny、Muriel Ségur-Derai、Yves Brunel、Benoît Heurtaux、Thierry Le Gall、Axelle Strehle、Régis Saladin、Stéphane Meunier、Charles Mioskowski、Alain Wagner

  DOI：10.1021/jm801500h

  日期：2009.4.23

  natural mushroom pigment Norbadione A and three other pulvinic acids were shown by our group to display very efficient antioxidant properties by comparison with a collection of potent molecules including catechols, flavonoids, stilbenes, or coumarins. Despite numerous publications on robust and straightforward synthetic access to pulvinic acids by us and others, no report has been made to unravel the

  与一组有效的分子（包括儿茶酚，类黄酮，芪，香豆素）相比，天然蘑菇色素Norbadione A和其他三种豆蔻酸显示出非常有效的抗氧化性能。尽管我们和其他人发表了大量关于鲁棒性和直接合成pulvinic acid的途径，但尚未有报道阐明控制显着抗氧化剂活性的结构-活性关系。本文介绍了18种不同的蔚氨酸衍生物的合成，并通过四种不同的测定方法对其自由基清除能力进行了研究。研究了两个苯环，其取代基和侧链中的每一个对抗氧化剂性能的影响，以揭示具有优异活性的简化结构。这些结果，
• Synthesis of Pulvinic Derivatives via TBAF-Mediated Regioselective Opening of an Unsymmetrical Monoaromatic Pulvinic Dilactone
  作者：Damien Habrant、Antoine Le Roux、Stéphane Poigny、Stéphane Meunier、Alain Wagner、Charles Mioskowski

  DOI：10.1021/jo801817s

  日期：2008.12.5

  The synthesis of the monoaromatic pulvinic dilactone I from a tetronic acid derivative is reported. The reaction of 1 with various amines was found to provide the two pulvinamides regioisomers 2a and 2b. Using tetrabutylammonium fluoride (TBAF) as an activator, pulvinamides 2a could be obtained with excellent regioselectivities and good yields. Additions of alcohols to I are also studied, leading to similar observations.
• A new series of Cs+, K+ and Na+ chelators: Synthesis, kinetics, thermodynamics and modeling
  作者：Alexandre Korovitch、Antoine Le Roux、Florent Barbault、Miryana Hémadi、Nguyêt-Thanh Ha-Duong、Claude Lion、Alain Wagner、Jean-Michel El Hage Chahine

  DOI：10.1016/j.ica.2012.08.009

  日期：2013.1

  The synthesis of two molecules, B1 and B2, based on elements of norbadione A, the natural Cs+ chelator in mushrooms, associated, in the case of B2, with an 18-crown-6 ether is reported. Thermodynamic and kinetic analyses performed in water, ethanol and ethanol/water 9/1 v/v (M1) show in M1 and ethanol that B1 and B2 form stable complexes with Na+, K+ and Cs+. Affinity constants, measured spectrophotometrically in ethanol and M1, by the use of the SPECFIT program, are in the 10(5) and 10(6) range for B1 and B2, respectively. The second-order rate constants are in the 10(6)-10(7) M-1 s(-1) range and the first-order rate constants about unity. The ratios of the second-order/first-order rate constants confirm the thermodynamic results in EtOH. The kinetic processes become much too fast to allow runs in M1. Molecular simulations in EtOH imply the existence of two isomers for each of the Cs+/B1 and Cs+/B2 complexes. With B1, the more stable one is that in which the two enolates are parallel and mimic the alkali-metal inclusion cavity already envisaged for norbadione A. With B2, two similar structures are extracted, in both of which Cs+ is included in the crown ether and capped by the enolate. The affinity of B1 for Cs+ is comparable to that of norbadione A, whereas that of B2 is higher. These results are encouraging as they introduce a new series of alkali chelators which can lead to molecules capable of complexing Cs-137(+) for radioactive decontamination. (C) 2012 Elsevier B. V. All rights reserved.
• Synthesis and Radioprotective Properties of Pulvinic Acid Derivatives
  作者：Antoine Le Roux、Stéphane Meunier、Thierry Le Gall、Jean‐Marc Denis、Pierre Bischoff、Alain Wagner

  DOI：10.1002/cmdc.201000391

  日期：2011.3.7

  A high‐throughput screening method has highlighted the marked antioxidant activity of some pulvinic acid derivatives (PADs) towards oxidation of thymidine, under γ and UV irradiation, and Fenton‐like conditions. Here, we report the synthesis of a series of new hydrophilic PADs and the evaluation of their radioprotective efficacy in cell culture. Using a cell‐based fluorescent assay, we show that some

  高通量筛选方法突显了某些pulvinic酸衍生物（PAD）在γ和UV辐射以及类Fenton条件下对胸腺嘧啶核苷氧化的显着抗氧化活性。在这里，我们报告了一系列新的亲水性PADs的合成及其在细胞培养中的辐射防护功效的评估。使用基于细胞的荧光测定法，我们表明其中一些化合物具有明显的防止辐射引起的细胞死亡并随后恢复增殖的能力。因此，PAD可被认为是一类新型的辐射防护剂。