(1R,2S)-2-methyl-1-pentafluorophenyl-3-buten-1-ol | 694503-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-2-methyl-1-pentafluorophenyl-3-buten-1-ol
• 英文别名: (1R,2S)-2-methyl-1-pentafluorophenyl-but-3-en-1-ol；(1R,2S)-2-methyl-1-(2,3,4,5,6-pentafluorophenyl)but-3-en-1-ol
• CAS: 694503-78-1
• 化学式: C₁₁H₉F₅O
• 分子量: 252.184
• InChiKey: NYBWJKZZFVVSBM-AQPAIEDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-methyl-1-pentafluorophenyl-3-buten-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (5S,6R)-5-methyl-6-pentafluorophenyl-5,6-dihydropyran-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
• 作为产物：
  描述：

  五氟苯甲醛 、 (Z)-(-)-crotylbis(isopinocampheyl)borane 在 sodium hydroxide 、 双氧水 作用下， 生成 (1R,2S)-2-methyl-1-pentafluorophenyl-3-buten-1-ol
  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

• Asymmetric synthesis of γ-perfluoroalkyl(aryl) butyrolactones via organoboranes
  作者：P.Veeraraghavan Ramachandran、Kamlesh J. Padiya、Vivek Rauniyar、M.Venkat Ram Reddy、Herbert C. Brown

  DOI：10.1016/j.tetlet.2003.11.050

  日期：2004.1

  Asymmetric ‘allyl’boration of fluorinated aldehydes with α-pinene-based ‘allyl’ boranes provides the corresponding homoallylic alcohols in high ee and de, which upon hydroboration, followed by oxidation with TPAP/NMO furnish γ-perfluoroalkyl(aryl)-γ-butyrolactones.

  氟化醛与基于α-pine烯的“烯丙基”硼烷的不对称“烯丙基”硼化反应可在高ee和de中提供相应的均烯丙基醇，在氢硼化后，再用TPAP / NMO氧化可得到γ-全氟烷基（芳基）-γ-丁内酯。
• 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
  作者：P.Veeraraghavan Ramachandran、Kamlesh J Padiya、Vivek Rauniyar、M.Venkat Ram Reddy、Herbert C Brown

  DOI：10.1016/j.jfluchem.2004.01.005

  日期：2004.4

  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.
• 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.