4-hydroxy-3-(4-methoxyphenyl)furan-2(5H)-one | 93831-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-hydroxy-3-(4-methoxyphenyl)furan-2(5H)-one
• 英文别名: 3-hydroxy-4-(4-methoxyphenyl)-2H-furan-5-one
• CAS: 93831-11-9
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: ABVCVXURBCZANH-UHFFFAOYSA-N

物化性质

• 熔点：
  228 °C
• 沸点：
  425.8±45.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(4-methoxyphenyl)furan-2(5H)-one 在 草酰溴 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以35%的产率得到3-(4-methoxyphenyl)-4-bromo-5H-furan-2-one
  参考文献：
  名称：

  4-Azidotetronic Acids: A New Class of Azido Derivatives

  摘要：

  4-Azidotetronic derivatives bearing different substituent groups on the carbon atom in position 3 were easily obtained by reaction of the corresponding 4-bromotetronic compounds with sodium azide in methanol at room temperature.

  DOI：

  10.1080/00397910008087364
• 作为产物：
  描述：

  4-甲氧基苯乙酸钠盐 在 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 4-hydroxy-3-(4-methoxyphenyl)furan-2(5H)-one
  参考文献：
  名称：

  Novel 3-arylfuran-2(5H)-one-fluoroquinolone hybrid: Design, synthesis and evaluation as antibacterial agent

  摘要：

  3-Arylfuran-2(5H)-one, a novel antibacterial pharmacophore targeting tyrosyl-tRNA synthetase (TyrRS), was hybridized with the clinically used fluoroquinolones to give a series of novel multi-target antimicrobial agents. Thus, twenty seven 3-arylfuran-2(5H)-one-fluoroquinolone hybrids were synthesized and evaluated for their antimicrobial activities. Some of the hybrids exhibited merits from both parents, displaying a broad spectrum of activity against resistant strains including both Gram-negative and Gram-positive bacteria. The most potent compound (11) in antibacterial assay shows MIC50 of 0.11μg/mL against Multiple drug resistant Escherichia coli, being about 51-fold more potent than ciprofloxacin. The enzyme assays reveal that 11 is a potent multi-target inhibitor with IC50 of 1.15±0.07μM against DNA gyrase and 0.12±0.04μM against TyrRS, respectively. Its excellent inhibitory activities against isolated enzymes and intact cells strongly suggest that 11 deserves to further research as a novel antibiotic.

  DOI：

  10.1016/j.bmc.2014.05.018

文献信息

• Synthesis of (E)- and (Z)-pulvinones
  作者：Alexander C. Campbell、Maurice S. Maidment、John H. Pick、Donald F. M. Stevenson

  DOI：10.1039/p19850001567

  日期：——

  one of which involves a novel Wittig reaction. For the first time, members of the E-series, including the parent (E)-pulvinone, are reported and the structural elucidation of the geometric isomers is described. A method for quantitatively converting (E)-pulvinones into (Z)-pulvinones is presented, together with a technique for differentiating between the isomers.

  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。
• 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。
• 3-Aryltetronic Acids: Efficient Preparation and Use as Precursors for Vulpinic Acids
  作者：Aurélie Mallinger、Thierry Le Gall、Charles Mioskowski

  DOI：10.1021/jo802038z

  日期：2009.2.6

  3-Aryltetronic acids were prepared in one step by treatment of a mixture of methyl arylacetates and methyl hydroxyacetates with potassium tert-butoxide, via tandem transesterification/Dieckmann condensation. Several mushroom or lichen pigments, vulpinic acids, were synthesized from 3-(4-methoxyphenyl)tetronic acid in three steps involving the reaction of the corresponding dianion with an α-ketoester

  通过串联酯交换反应/ Dieckmann缩合反应，用叔丁醇钾处理芳基乙酸甲酯和羟基乙酸甲酯的混合物，一步制得3-芳基酸。在三个步骤中，由3-（4-甲氧基苯基）tetronic酸合成了几种蘑菇或地衣颜料的硫化松香酸，这三个步骤涉及相应的二价阴离子与α-酮酸酯的反应以及所获得的叔醇的脱水成（E）的混合物-和（Z）-烯烃，它们在254nm的紫外线辐射下转化为天然（E）-异构体。樟脑酸，4,4'-二甲氧基硫代乙酸的合成，以及最近分离出的甲基3'，5'-dichloro-4,4'-di- O的首次合成因此，以有效的方式获得了苹果酸-草酸甲酯。
• Catalytic Undirected Intermolecular C–H Functionalization of Arenes with 3-Diazofuran-2,4-dione: Synthesis of 3-Aryl Tetronic Acids, Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate
  作者：Amarender Manchoju、Sunil V. Pansare

  DOI：10.1021/acs.orglett.6b03087

  日期：2016.11.18

  A variety of 3-aryl tetronic acids have been synthesized by an undirected, intermolecular C–H functionalization of arenes with 3-diazofuran-2,4-dione. This methodology featured as a key step in the synthesis of a series of naturally occurring 3-aryl-5-arylidene tetronic acids (pulvinates) from commercially available tetronic acid. Salient features of the pulvinic acid synthesis include a one-step,

  通过使用3-重氮呋喃-2,4-二酮对芳烃进行无方向的CH-H分子间官能化反应，已经合成了多种3-芳基tetronic酸。该方法学是从可商购的tetronic酸合成一系列天然存在的3-芳基-5-芳基亚芳基tetronic酸（pulvinates）的关键步骤。戊酸合成的显着特征包括C5芳基的一步一步立体选择性合成和C3芳基取代基的一步导入。
• One-Pot Synthesis of Tetronic Acids from Esters
  作者：Thierry Le Gall、Aurélie Mallinger、Charles Mioskowski

  DOI：10.1055/s-2008-1032061

  日期：2008.2

  Tetronic acids substituted by various groups were synthesized in one pot from the corresponding aryl- or heteroarylacetic acid esters and hydroxyacetic acid esters, by a tandem process involving a transesterification and a subsequent Dieckmann cyclization.

  通过涉及酯交换和随后的 Dieckmann 环化的串联方法，由相应的芳基-或杂芳基乙酸酯和羟基乙酸酯在一锅中合成被各种基团取代的 Tetronic 酸。