4-methoxybenzoyl-3-hydroxy-2(5H)-furanone | 35998-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxybenzoyl-3-hydroxy-2(5H)-furanone
• CAS: 35998-42-6
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: AFDGBYSVJNNPAO-UHFFFAOYSA-N

物化性质

• 沸点：
  458.5±45.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-methoxybenzoyl-3-hydroxy-2(5H)-furanone 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 1.5h， 以92%的产率得到E-4-(4-methoxybenzylidene)-(4H,5H)-2,3-furandione
  参考文献：
  名称：

  Zimmer, Hans; Manning, M. J.; Ventura, M., Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 199 - 202

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-methyl 2-hydroxy-4-(4-methoxylphenyl)-4-oxobut-2-enoate 、 聚合甲醛 生成 4-methoxybenzoyl-3-hydroxy-2(5H)-furanone
  参考文献：
  名称：

  PAYARD M.; PARIS J.; COUQUELET J., TRAV. SOC. PHARM. MONTPELLIER, 1976, 36, NO 2, 115-127

  摘要：

  DOI：

文献信息

• Effect on Free Radical Processes of Some Ascorbic Acid Analogues.
  作者：Pascal COUDERT、Fernand LEAL、Eliane DUROUX、Catherine RUBAT、Jacques COUQUELET

  DOI：10.1248/bpb.19.220

  日期：——

  Ascorbic acid, present in plasma from humans at concentrations of 50 to 200μmol/l, has multiple antioxidant properties. Structural modification of this vitamin by the introduction of lipophilic moieties has allowed to the development of ascorbate esters and ethers active as free radical quenchers. Thus, a new series of ascorbic acid analogues possessing one or two aromatic rings was prepared in an attempt to synthesize potent antioxidants with lipophilic properties. Substituted 3-hydroxy furan-2 (5H)-ones and in some cases, dihydrofuro [3, 4-b] pyrones were prepared. The synthesized compounds were evaluated for their antioxidant activity in vitro. So, 4-(4-methoxybenzoyl)-3-hydroxy-5-phenylfuran-2 (5H)-one 3e (IC50=3.06×10-4M) was found to be the most effective in scavenging the superoxide anion, whereas 4-benzoyl-3-hydroxy-5-(3, 4-dimethoxyphenyl) furan-2 (5H)-one 3d (IC50=1.38×10-4M) was the most active in inhibiting, lipid peroxidation.

  抗坏血酸在人类血浆中的浓度为50至200μmol/l，具有多种抗氧化特性。通过引入脂溶性基团对这种维生素进行结构修饰，使得抗坏血酸酯和醚的开发成为可能，这些化合物在清除自由基方面活性良好。因此，合成了一系列具有一个或两个芳香环的抗坏血酸类似物，以期合成具有强效抗氧化性能的脂溶性化合物。制备了取代的3-羟基呋喃-2(5H)-酮，某些情况下还制备了二氢呋喃[3, 4-b]吡喃酮。合成的化合物在体外评估了其抗氧化活性。因此，4-(4-甲氧基苯甲酰)-3-羟基-5-苯基呋喃-2(5H)-酮3e（IC50=3.06×10^-4M）被发现对超氧阴离子的清除最为有效，而4-苯甲酰-3-羟基-5-(3, 4-二甲氧基苯基)呋喃-2(5H)-酮3d（IC50=1.38×10^-4M）在抑制脂质过氧化方面最为活跃。
• Antioxidant Properties of Novel Lipophilic Ascorbic Acid Analogues
  作者：Valerie Weber、Pascal Coudert、Catherine Rubat、Eliane Duroux、Fernand Leal、Jacques Couquelet

  DOI：10.1211/0022357001774318

  日期：2010.2.18

  Structural modifications of ascorbic acid by the introduction of lipophilic moieties has led to derivatives with increased stability against thermal and oxidative degradation. Two series of new lipophilic ascorbic analogues were synthesized to obtain antioxidants devoid of autooxidant properties: 4-benzoyl-3-hydroxyfuran-2(5H)-ones (3a-j) and 4-acetyl-5-aryl-3,4-dihydrofuran-2(5H)ones(5a-f).

  These compounds were submitted to three different tests: reduction of the stable free radical, 1,1-diphenyl-2-picrylhydrazyl (DPPH); superoxide-anion scavenging assay; and lipid-peroxidation assay. Most compounds interacted with DPPH: at a concentration of 5 times 10−3 M, the reducing activity of 4-benzoyl derivatives, 3c and 3h, was more than 50%; under the same conditions, the rate of inhibition for 4-acetylbutanolides, 5a and 5f, reached 60.6% and 87.3%, respectively; 93.3% inhibition was observed with ascorbic acid. In the superoxide-anion scavenging assay, at a concentration of 1 mg mL−1, 4-benzoyl derivatives, 3g and 3i, exhibited a good activity, with IC50 (dose resulting in 50% inhibition) values of 1.45 and 1.35 times 10−3 M, respectively. 4-Acetylbutanolide, 5f, significantly inhibited the Fe2+/ADP/ascorbate-induced lipid peroxidation of rat liver microsomes with an IC50 of 4.9 times 10−4 M.

  This study demonstrates that enol functions in the structure of ascorbic acid analogues are not absolutely essential to bring about antioxidant effects.

  摘要：通过引入亲脂性基团对抗坏血酸进行结构修饰，导致衍生物对热和氧化降解具有增强的稳定性。合成了两系列新的亲脂性抗坏血酸类似物，以获得不具有自氧化性质的抗氧化剂：4-苯甲酰基-3-羟基呋喃-2(5H)-酮（3a-j）和4-乙酰基-5-芳基-3,4-二氢呋喃-2(5H)-酮（5a-f）。 这些化合物经过三种不同的测试：稳定自由基1,1-二苯基-2-苯基苦基肼（DPPH）的还原；超氧阴离子清除试验；和脂质过氧化试验。大多数化合物与DPPH发生相互作用：在浓度为5倍10-3 M时，4-苯甲酰衍生物3c和3h的还原活性超过50%；在相同条件下，4-乙酰基丁醇酯5a和5f的抑制率分别达到60.6%和87.3%；抗坏血酸的抑制率为93.3%。在超氧阴离子清除试验中，在浓度为1 mg mL-1时，4-苯甲酰衍生物3g和3i表现出良好的活性，IC50（导致50%抑制的剂量）值分别为1.45和1.35倍10-3 M。4-乙酰基丁醇酯5f显著抑制了Fe2+/ADP/抗坏血酸诱导的大鼠肝微粒体脂质过氧化，IC50为4.9倍10-4 M。 这项研究表明，抗坏血酸类似物结构中的烯醇功能并非绝对必要以产生抗氧化效果。
• Complexing ability of some γ-lactone derivatives. Thermal, magnetic and spectral studies on cobalt(II), nickel(II) and copper(II) complexes and their base adducts
  作者：Ali El-Dissouky、Ahmed Fahmy、Adel Amer

  DOI：10.1016/s0020-1693(00)87785-3

  日期：1987.10

  Abstract The complexes of some γ-lactone derivatives with cobalt(II), nickel(II) and copper(II) have been synthesized and formulated as [ML 2 ]· n H 2 O, M = Co 2+ , Ni 2+ or Cu 2+ , n = 2 or 3 and L = anion of the corresponding ligand. Their structures have been suggested on the basis of analysis, spectral (UV-Vis, IR) and magnetic susceptibility data. The thermal analysis revealed the non-coordinated

  摘要合成了一些γ-内酯衍生物与钴（II），镍（II）和铜（II）的配合物，并配制成[ML 2]·n H 2 O，M = Co 2+，Ni 2+或Cu 2+，n ＝ 2或3，L ＝相应配体的阴离子。根据分析，光谱（UV-Vis，IR）和磁化率数据提出了它们的结构。热分析表明这些配合物中水不协调。红外光谱表明存在与氢键配位的水分子，并且γ-内酯是通过苯甲酰基羰基和去质子化的羟基氧原子与金属离子配位的一元二齿双齿。内酯在配合物结构上的体积和电子性质从电子光谱数据中得到合理化。用分光光度法研究了具有不同路易斯基础的配合物之间的相互作用。计算出配体场参数并与配体分子的体积效应有关。这些参数指示基本分子的轴向连接，并且赤道平面被MO 4占据，M = Co 2+，Ni 2+或Cu 2+发色团。电子间排斥参数表明这些配合物的离子性质。还讨论了理想结构的变形程度。发色团。电子间排斥参数表明这些配合物的离子性
• Zimmer, Hans; Amer, Adel; Ho, Douglas, Journal of Heterocyclic Chemistry, 1991, vol. 28, # 6, p. 1501 - 1510
  作者：Zimmer, Hans、Amer, Adel、Ho, Douglas、Palmer-Sungail, R.

  DOI：——

  日期：——