3-甲氧基-4-(4-甲氧基苯基)-2H-呋喃-5-酮 | 58368-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-甲氧基-4-(4-甲氧基苯基)-2H-呋喃-5-酮
• 英文名称: 4-Methoxy-3-(4-methoxyphenyl)-furan-2(5H)-one
• 英文别名: 4-methoxy-3-(4-methoxyphenyl)furan-2(5H)-one；methyl 2-(4-methoxyphenyl)tetronate；4-methoxy-3-(4-methoxy-phenyl)-5H-furan-2-one；4-methoxy-3-(4-methoxyphenyl)-5H-furan-2-one；3-methoxy-4-(4-methoxyphenyl)-2H-furan-5-one
• CAS: 58368-11-9
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: PLRSSMHBYNFYIS-UHFFFAOYSA-N

物化性质

• 沸点：
  444.5±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲氧基-4-(4-甲氧基苯基)-2H-呋喃-5-酮 在 4-二甲氨基吡啶 、 正丁基锂 、 ammonium chloride 、 乙酸酐 、 三乙胺 、 二异丙胺 、 三氟乙酸酐 、 magnesium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 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
• 作为产物：
  描述：

  (4-Methoxy-phenyl)-acetic acid ethoxycarbonylmethyl ester 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 丙酮 、 叔丁醇 为溶剂， 反应 2.0h， 生成 3-甲氧基-4-(4-甲氧基苯基)-2H-呋喃-5-酮
  参考文献：
  名称：

  （E）-和（Z）-pulvinones的合成

  摘要：

  已经开发出两种新的途径获得pulvinones，其中一种涉及新颖的Wittig反应。首次报道了E系列的成员，包括母体（E）-普尔维酮，并描述了几何异构体的结构。提出了一种将（E）-普尔维酮定量转化为（Z）-普尔维酮的方法，以及区分异构体的技术。

  DOI：

  10.1039/p19850001567

文献信息

• 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。
• Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
  作者：Xiaotan Yu、Xiaoxia Gu、Yunpeng Zhao、Fengqing Wang、Weiguang Sun、Changxing Qi、Lianghu Gu、Yonghui Zhang

  DOI：10.1039/d2ra08133d

  日期：——

  mild, modular and efficient synthetic method with broad substrate scope was developed for aspulvinones. Nine natural aspulvinones were synthesized, six of which were for the first time. The aldol condensation delivered Z-configuration products predominantly in MeCN. Meanwhile, alkoxy exchange occurred in MeOH and EtOH. Aspulvinone O and E, and substrate 49, 50, and 51 exhibited modest anti-SARS-CoV-2

  开发了一种温和、模块化、高效且底物适用范围广的阿斯普维酮合成方法。合成了九种天然阿斯普维酮，其中六种为首次合成。羟醛缩合主要在 MeCN 中提供 Z 构型产品。同时，MeOH和EtOH发生烷氧基交换。Aspulvinone O 和 E，以及底物 49、50 和 51 在高通量筛选和酶动力学测定中表现出适度的抗 SARS-CoV-2 活性。
• 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.
• Ramage, Robert; Griffiths, Gareth J.; Shutt, Fiona E., Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1539 - 1545
  作者：Ramage, Robert、Griffiths, Gareth J.、Shutt, Fiona E.、Sweeney, John N. A.

  DOI：——

  日期：——
• An efficient procedure for the synthesis of 3-aryl-4-methoxy-2(5H)-furanones by using the microwave-promoted Suzuki–Miyaura coupling reactions
  作者：Young Seob Song、Yun-Jeong Lee、Bum Tae Kim、Jung-Nyoung Heo

  DOI：10.1016/j.tetlet.2006.08.052

  日期：2006.10

  The Suzuki-Miyaura coupling reactions of 3-bromo-2(5H)-furanones with a variety of arylboronic acids, promoted by microwave heating, efficiently generate 3-aryl-2(5H)-furan ones. This remarkably rapid process serves as the foundation for a simple method to rapidly construct 3-aryl-2(5H)-furanone libraries. (c) 2006 Elsevier Ltd. All rights reserved.