α-Hydroxy-β-benzoyl-γ-phenyl-Δα,β-butenolid | 21053-84-9

• 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: α-Hydroxy-β-benzoyl-γ-phenyl-Δα,β-butenolid
• 英文别名: α-Hydroxy-β-benzoyl-γ-phenyl-Δ^α,β-butenolid
• CAS: 21053-84-9
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: IBLSDYDFLPXUPW-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  495.3±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  α-Hydroxy-β-benzoyl-γ-phenyl-Δα,β-butenolid 在 zinc diacetate 作用下， 以 乙二醇 为溶剂， 反应 3.0h， 以88%的产率得到反式-查耳酮
  参考文献：
  名称：

  Bonadies, Francesco; Scarpati, M. Luisa; Savagnone, Fulvio, Gazzetta Chimica Italiana, 1982, vol. 112, # 1/2, p. 1 - 4

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 、 2,4-二氧代-4-苯丁酸甲酯 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 10.0h， 以15.2%的产率得到α-Hydroxy-β-benzoyl-γ-phenyl-Δα,β-butenolid
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 4-aroyl-3-hydroxy-2,5-dihydrofuran-2-ones and their derivatives

  摘要：

  DOI：

  10.1007/bf02524633

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。
• Enols as Feasible Acid Components in the Ugi Condensation
  作者：Teresa G. Castellano、Ana G. Neo、Stefano Marcaccini、Carlos F. Marcos

  DOI：10.1021/ol302976g

  日期：2012.12.21

  Heterocyclic enols are used for the first time as acid components in an Ugi-type multicomponent condensation. For that purpose, we have chosen enols containing a Michael acceptor, in order to facilitate an irreversible rearrangement of the primary Ugi adduct. The new four-component process leads readily and efficiently to heterocyclic enamines containing at least six elements of diversity.
• Acyl pyruvates as synthons in the Biginelli reaction
  作者：Sergey V. Ryabukhin、Andrey S. Plaskon、Semen S. Bondarenko、Eugeniy N. Ostapchuk、Oleksandr O. Grygorenko、Oleg V. Shishkin、Andrey A. Tolmachev

  DOI：10.1016/j.tetlet.2010.06.032

  日期：2010.8

  Chlorotrimethylsilane-promoted Biginelli-type reaction of ethyl 2,4-dioxo-4-phenylbutanoate, benzaldehyde, and various (thio)ureas is explored. The outcome of the reaction depends on the structure of the (thio)urea used and is strongly affected by the acceptor electronic properties of the COOEt substituent in the molecule of the starting beta-dicarbonyl compound. The di- and tetrahydropyrimidine derivatives obtained possess two functional groups with orthogonal reactivity, and thus represent promising building blocks for drug discovery. (C) 2010 Elsevier Ltd. All rights reserved.
• KURIHARA T.; SAKAMOTO Y.; KOBAYASHI T.; MORI M., J. HETEROCYCL. CHEM., 1978, 15, NO 5, 737-743
  作者：KURIHARA T.、 SAKAMOTO Y.、 KOBAYASHI T.、 MORI M.

  DOI：——

  日期：——
• Synthesis and antimicrobial activity of 4-aroyl-3-hydroxy-2,5-dihydrofuran-2-ones and their derivatives
  作者：V. L. Gein、L. F. Gein、É. N. Bezmaternykh、E. V. Voronina

  DOI：10.1007/bf02524633

  日期：2000.5