(2S,4R,5R,6R)-ethyl 4-hydroxy-5-methyl-6-(naphthalen-2-yl)-4-phenyltetrahydro-2H-pyran-2-carboxylate | 1402854-52-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: (2S,4R,5R,6R)-ethyl 4-hydroxy-5-methyl-6-(naphthalen-2-yl)-4-phenyltetrahydro-2H-pyran-2-carboxylate
• CAS: 1402854-52-7
• 化学式: C₂₅H₂₆O₄
• 分子量: 390.479
• InChiKey: UQNKWGVCOOOMBM-SGURQHNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  、 2-萘甲醛 在 iron(III) chloride 、 叔丁基二甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以63%的产率得到(2S,4R,5R,6R)-ethyl 4-hydroxy-5-methyl-6-(naphthalen-2-yl)-4-phenyltetrahydro-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