(2S)-2-hydroxy-1-(4-methoxyphenyl)-4-phenylpent-4-en-1-one | 1402975-37-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (2S)-2-hydroxy-1-(4-methoxyphenyl)-4-phenylpent-4-en-1-one
• CAS: 1402975-37-4
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: UBHSOFVYFYVLHX-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-hydroxy-1-(4-methoxyphenyl)-4-phenylpent-4-en-1-one 、 丙醛 在 iron(III) chloride 、 叔丁基二甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到
  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
• 作为产物：
  描述：

  2-(4-甲氧基苯基)-2-氧代乙醛 、 2-苯基-1-丙烯 在 (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 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以99%的产率得到(2S)-2-hydroxy-1-(4-methoxyphenyl)-4-phenylpent-4-en-1-one
  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