4,5-diphenyl-3-hydroxy-2(5H)-furanone | 4263-96-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,5-diphenyl-3-hydroxy-2(5H)-furanone
• 英文别名: 4,5-diphenyl-isotetronic acid；2-Keto-3,4-diphenyl-butyrolacton；4-hydroxy-2,3-diphenyl-2H-furan-5-one
• CAS: 4263-96-1
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: NJTYPFZEHCVTNE-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211 °C
• 沸点：
  470.5±45.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-diphenyl-3-hydroxy-2(5H)-furanone 、 氘代碘甲烷 在 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  The fragmentation of isotetronic acidO-methyl ethers under electron impact

  摘要：

  AbstractThe mass spectra of a series of methyl ethers of isotetronic acids have been examined and the modes of fragmentation rationalized on the basis of two general schemes.

  DOI：

  10.1002/oms.1210160204
• 作为产物：
  描述：

  苯丙酮酸 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5-diphenyl-3-hydroxy-2(5H)-furanone
  参考文献：
  名称：

  Novel 4,5-Diaryl-3-hydroxy-2(5H)-furanones as Anti-Oxidants and Anti-Inflammatory Agents

  摘要：

  In order to study the effect of phenol moieties on biological activities of ascorbic acid derivatives, we synthesized 13 novel 4,5-diaryl-3-liydroxy-2(5H)-furanones 5a m with various substitution patterns. Compound 5g bearing a 2,3-dihydroxy phenyl ring on the 5-position of the heterocycle appeared to be the most powerful anti-oxidant furanone with reducing activity against DPPH (IC50- 10.3 muM), superoxide anion quenching capacity (IC50=0.187 mM) and lipid peroxidation inhibitory effect (IC50 = 0.129 mM). To ascertain determinant molecular features for anti-oxidant activities, structure-activity relationship, were studied. Lipophilicity and molecular parameters related to electron distribution and structure (difference in heats of formation between the compound and its radical or its cation radical, energy of the highest occupied molecular orbital, HOMO) were found to correlate with the anti-oxidant action of compounds 5 in the different tests used. Oxygen-derived free radicals are known to contribute to inflammatory disorders; therefore we have investigated effects of compounds 5 in two models of inflammation: phorbol ester-induced car edema in mice (TPA-test) and carrageenan-induced paw edema in rat. At 100 mg/kg ip in the TPA-test, the anti-inflammatory activity of compounds 5 was potent compared with that of indomethacin and ketorolac and all the results suggested a cyclooxygenase inhibition in the emergence of such properties. The combined pharmacological actions of compounds 5 associated with a favorable therapeutic index prompt with interesting perspectives for their use in heart and brain disorders as well as in inflammatory diseases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00053-6

文献信息

• Boron-Catalyzed Direct Aldol Reactions of Pyruvic Acids
  作者：Doris Lee、Stephen G. Newman、Mark S. Taylor

  DOI：10.1021/ol902322r

  日期：2009.12.3

  Interactions between pyruvic acids and diphenylborinic acid form the basis of an efficient, direct, boron-catalyzed aldol reaction that takes place in water at room temperature with low catalyst loadings. Both boronic and borinic acids function as catalysts, with the latter demonstrating particularly high activity. A wide range of aldehydes, including enolizable species, may be employed, delivering

  丙酮酸和二苯基硼酸之间的相互作用形成了有效的，直接的，硼催化的羟醛反应的基础，该反应在室温下于水中以较低的催化剂负载量进行。硼酸和硼酸都起催化剂的作用，后者表现出特别高的活性。可以使用各种各样的醛，包括可烯醇的醛，以高收率递送有用的等渗酸衍生物。
• Novel 4,5-Diaryl-3-hydroxy-2(5H)-furanones as Anti-Oxidants and Anti-Inflammatory Agents
  作者：V Weber

  DOI：10.1016/s0968-0896(02)00053-6

  日期：2002.6

  In order to study the effect of phenol moieties on biological activities of ascorbic acid derivatives, we synthesized 13 novel 4,5-diaryl-3-liydroxy-2(5H)-furanones 5a m with various substitution patterns. Compound 5g bearing a 2,3-dihydroxy phenyl ring on the 5-position of the heterocycle appeared to be the most powerful anti-oxidant furanone with reducing activity against DPPH (IC50- 10.3 muM), superoxide anion quenching capacity (IC50=0.187 mM) and lipid peroxidation inhibitory effect (IC50 = 0.129 mM). To ascertain determinant molecular features for anti-oxidant activities, structure-activity relationship, were studied. Lipophilicity and molecular parameters related to electron distribution and structure (difference in heats of formation between the compound and its radical or its cation radical, energy of the highest occupied molecular orbital, HOMO) were found to correlate with the anti-oxidant action of compounds 5 in the different tests used. Oxygen-derived free radicals are known to contribute to inflammatory disorders; therefore we have investigated effects of compounds 5 in two models of inflammation: phorbol ester-induced car edema in mice (TPA-test) and carrageenan-induced paw edema in rat. At 100 mg/kg ip in the TPA-test, the anti-inflammatory activity of compounds 5 was potent compared with that of indomethacin and ketorolac and all the results suggested a cyclooxygenase inhibition in the emergence of such properties. The combined pharmacological actions of compounds 5 associated with a favorable therapeutic index prompt with interesting perspectives for their use in heart and brain disorders as well as in inflammatory diseases. (C) 2002 Elsevier Science Ltd. All rights reserved.
• The fragmentation of isotetronic acidO-methyl ethers under electron impact
  作者：C. C. Bonini、C. Iavarone、C. Trogolo、G. A. Poulton

  DOI：10.1002/oms.1210160204

  日期：1981.2

  AbstractThe mass spectra of a series of methyl ethers of isotetronic acids have been examined and the modes of fragmentation rationalized on the basis of two general schemes.