(2S,4S,6R)-ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-4-hydroxytetrahydro-2H-pyran-2-carboxylate | 1402854-32-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,6R)-ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-4-hydroxytetrahydro-2H-pyran-2-carboxylate
• 英文别名: ethyl (2S,4S,6R)-6-(4-bromophenyl)-4-(4-fluorophenyl)-4-hydroxyoxane-2-carboxylate
• CAS: 1402854-32-3
• 化学式: C₂₀H₂₀BrFO₄
• 分子量: 423.279
• InChiKey: RGLVBMVVPPQSBR-HBFSDRIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氟-Alpha-甲基苯乙烯 在 iron(III) chloride 、 (2S)-N-[2,6-di(propan-2-yl)phenyl]-1-[3-[(2S)-2-[[2,6-di(propan-2-yl)phenyl]carbamoyl]-1-oxidopiperidin-1-ium-1-yl]propyl]-1-oxidopiperidin-1-ium-2-carboxamide 、 nickel(II) tetrafluoroborate hexahydrate 、 叔丁基二甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-4-hydroxytetrahydro-2H-pyran-2-carboxylate 、 (2S,4S,6R)-ethyl 6-(4-bromophenyl)-4-(4-fluorophenyl)-4-hydroxytetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Completely OH-Selective FeCl₃-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans

  摘要：

  The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl3-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.5:0.5 er) were obtained for a remarkably broad range of substrates under mild reaction conditions. The control experiments, including NOE effects and O-18-labeling studies, as well as DFT calculations were conducted to provide fundamental insights into the mechanism of the reaction. A different [2 + 2] cycloaddition process was suggested to rationalize the observed OH-selectivity.

  DOI：

  10.1021/ja3062002

文献信息

• Completely OH-Selective FeCl₃-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans
  作者：Ke Zheng、Xiaohua Liu、Song Qin、Mingsheng Xie、Lili Lin、Changwei Hu、Xiaoming Feng

  DOI：10.1021/ja3062002

  日期：2012.10.24

  The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl3-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.5:0.5 er) were obtained for a remarkably broad range of substrates under mild reaction conditions. The control experiments, including NOE effects and O-18-labeling studies, as well as DFT calculations were conducted to provide fundamental insights into the mechanism of the reaction. A different [2 + 2] cycloaddition process was suggested to rationalize the observed OH-selectivity.