(5S,6S)-5-methyl-6-pentafluorophenyl-5,6-dihydropyran-2-one | 731851-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (5S,6S)-5-methyl-6-pentafluorophenyl-5,6-dihydropyran-2-one
• CAS: 731851-08-4
• 化学式: C₁₂H₇F₅O₂
• 分子量: 278.178
• InChiKey: PKVHMFGEERVNNG-GPWCVORUSA-N

物化性质

• 沸点：
  267.8±40.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-methyl-6-pentafluorophenyl-5,6-dihydropyran-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以94%的产率得到(5S,6S)-5-methyl-6-pentafluorophenyl-tetrahydropyran-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 6-(2′,3′,4′,5′,6′-pentafluorophenyl)-δ-lactones via “allyl”boranes: application for the synthesis of fluorinated analog of key pharmacophore of statin drugs

  摘要：

  Asymmetric "allyl"boration of pentafluorobenzaldehyde with various alpha-pinene based "allyl"boranes provides homoallylic alcohols in high de and ee; the alcohols have been converted into delta-lactones via acryloylation, ring-closing metathesis and hydrogenation. Pentafluorophenyl analog of key pharmacophore of statin drugs has been synthesized using diastereoselective epoxidation and regioselective reduction as key steps. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.01.005
• 作为产物：
  描述：

  (1S,2S)-2-methyl-1-pentafluorophenyl-3-butenyl prop-2-enoate 在 1,3-bismesyl-2-(Cl₂Rh=CHPh)imidazolidine 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以96%的产率得到(5S,6S)-5-methyl-6-pentafluorophenyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Asymmetric synthesis of 6-(2′,3′,4′,5′,6′-pentafluorophenyl)-δ-lactones via “allyl”boranes: application for the synthesis of fluorinated analog of key pharmacophore of statin drugs

  摘要：

  Asymmetric "allyl"boration of pentafluorobenzaldehyde with various alpha-pinene based "allyl"boranes provides homoallylic alcohols in high de and ee; the alcohols have been converted into delta-lactones via acryloylation, ring-closing metathesis and hydrogenation. Pentafluorophenyl analog of key pharmacophore of statin drugs has been synthesized using diastereoselective epoxidation and regioselective reduction as key steps. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.01.005

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.