(S)-(+)-3,4-dihydroxy-5-phenyl-2(5H)-furanone | 124400-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-(+)-3,4-dihydroxy-5-phenyl-2(5H)-furanone
• 英文别名: (2S)-3,4-dihydroxy-2-phenyl-2H-furan-5-one
• CAS: 124400-08-4
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: JTJHHCGTUJXRQU-VIFPVBQESA-N

物化性质

• 熔点：
  142-143 °C
• 沸点：
  425.3±45.0 °C(Predicted)
• 密度：
  1.553±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (S)-(+)-2-phenyl-2-<(phenylmethoxy)acetoxy>-ethanoate 在 palladium on activated charcoal lithium dicyclohexylamide 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.17h， 生成 (S)-(+)-3,4-dihydroxy-5-phenyl-2(5H)-furanone
  参考文献：
  名称：

  Efficient syntheses for optically pure stereogenically labile 4-substituted-2-hydroxytetronic acids

  摘要：

  DOI：

  10.1021/jo00290a059

文献信息

• Synthesis of optically pure 4-aryl-2-hydroxytetronic acids
  申请人：The Ohio State University Research Foundation

  公开号：US05399721A1

  公开（公告）日：1995-03-21

  The present invention relates to a method for synthesis of optically pure stereogenically labile 4-aryl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase. the invention further relates to the pharmaceutical use of such compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis.

  本发明涉及一种从光学纯醛合成光学纯立体不稳定4-芳基-2-羟基四氢呋喃酸的方法。本发明进一步涉及将这种光学纯化合物作为通过在环氧合酶水平上作用的高效血小板聚集抑制剂的使用。本发明进一步涉及这种化合物在治疗冠状动脉疾病中的药物使用，特别是在治疗和/或预防动脉粥样硬化中的使用。
• Synthesis of Enantiomerically Pure Stereogenically Labile 4-Aryl-2-hydroxytetronic Acids from Enantiomerically Pure Silyl-Protected Mandelaldehydes: aci-Reductone Analogs of Propionic Acid Nonsteroidal Anti-inflammatory Agents
  作者：Allen T. Hopper、Donald T. Witiak

  DOI：10.1021/jo00116a015

  日期：1995.6

  Enantiomerically pure 4-aryl-2-hydroxytetronic acids (3) are expected to be useful tools for determining the mechanism by which corresponding racemic aci-reductones produce their multiple biological effects. Our published synthetic methods for the construction of the title compounds were only useful for the preparation of 4-alkyl analogues owing to facile racemization of the chiral benzylic proton with 4-aryl systems. The synthesis of these enantiomerically pure 4-aryl aci-reductones has now been accomplished in four steps by condensing enantiomerically pure tert-butyldimethylsilyl protected mandelaldehydes 16a-c with the anion of ethyl 1,3-dithiane-2-carboxylate in the presence of pivaloyl chloride to yield protected beta,gamma-dihydroxy-alpha-ketobutanoates 22a-c after dithiane hydrolysis. Reaction of 22a-c with tetrabutylammonium fluoride :resulted in silyl deprotection, cyclization, and pivaloyl migration to afford 2-(pivaloyloxy)tetronic acids 25a-c. Pivaloate deprotection by either acid hydrolysis or selective hydride reduction produced enantiopure targets 3a-c.
• WITIAK, DONALD T.;TEHIM, ASHOK K., J. ORG. CHEM., 55,(1990) N, C. 1112-1114
  作者：WITIAK, DONALD T.、TEHIM, ASHOK K.

  DOI：——

  日期：——
• OPTICALLY PURE 4-ARYL-2-HYDROXYTETRONIC ACIDS
  申请人：THE OHIO STATE UNIVERSITY RESEARCH FOUNDATION

  公开号：EP0746551A1

  公开（公告）日：1996-12-11
• US5095126A
  申请人：——

  公开号：US5095126A

  公开（公告）日：1992-03-10