(4R,5R,6R)-4-hydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5R,6R)-4-hydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one
• 英文别名: (4R,5R,6R)-4-hydroxy-5-methyl-6-(2,3,4,5,6-pentafluorophenyl)oxan-2-one
• 化学式: C₁₂H₉F₅O₃
• 分子量: 296.194
• InChiKey: COUVHSFAKGMBKG-OKRIULSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  五氟苯甲醛 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 、 sodium hydroxide 、 四氧化锇 、 N-甲基吲哚酮 、 偶氮二异丁腈 、 双氧水 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 14.0h， 生成 (4R,5R,6R)-4-hydroxy-5-methyl-6-pentafluorophenyltetrahydropyran-2-one
  参考文献：
  名称：

  Diastereoselective Dihydroxylation and Regioselective Deoxygenation of Dihydropyranones:  A Novel Protocol for the Stereoselective Synthesis of C₁−C₈ and C₁₅−C₂₁ Subunits of (+)-Discodermolide

  摘要：

  Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective alpha-deoxygenation provides 1,3-trans-beta-hydroxy-delta-lactones stereoselectively. This protocol has been applied for the synthesis of C-1-C-8 and C-15-C-21 subunits of (+)-discodermolide.

  DOI：

  10.1021/jo0492416

文献信息

• Diastereoselective Dihydroxylation and Regioselective Deoxygenation of Dihydropyranones:  A Novel Protocol for the Stereoselective Synthesis of C₁−C₈ and C₁₅−C₂₁ Subunits of (+)-Discodermolide
  作者：P. Veeraraghavan Ramachandran、Bodhuri Prabhudas、J. Subash Chandra、M. Venkat Ram Reddy

  DOI：10.1021/jo0492416

  日期：2004.9.1

  Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective alpha-deoxygenation provides 1,3-trans-beta-hydroxy-delta-lactones stereoselectively. This protocol has been applied for the synthesis of C-1-C-8 and C-15-C-21 subunits of (+)-discodermolide.