(6S)-6-pentafluorophenyl-5,6-dihydropyran-2-one | 731850-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (6S)-6-pentafluorophenyl-5,6-dihydropyran-2-one
• CAS: 731850-97-8
• 化学式: C₁₁H₅F₅O₂
• 分子量: 264.152
• InChiKey: CSTUBCBKLSYCJN-BYPYZUCNSA-N

物化性质

• 沸点：
  258.1±40.0 °C(Predicted)
• 密度：
  1.531±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (6S)-6-pentafluorophenyl-5,6-dihydropyran-2-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 二苯基二硒醚 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 溶剂黄146 为溶剂， 反应 1.33h， 生成 (4R,6S)-4-hydroxy-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)-1-pentafluorophenyl-3-buten-1-ol 在 1,3-bismesyl-2-(Cl₂Rh=CHPh)imidazolidine 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (6S)-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