(-)-1-(2-methoxyphenyl)-2-naphthalen-2-yl-2,3-dihydro-1H-pyridin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-1-(2-methoxyphenyl)-2-naphthalen-2-yl-2,3-dihydro-1H-pyridin-4-one
• 英文别名: (2R)-1-(2-methoxyphenyl)-2-naphthalen-2-yl-2,3-dihydropyridin-4-one
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: AWUZFWHWTUDEQQ-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 (2-methoxyphenyl)naphthalen-2-ylmethyleneamine 在 (+)-2-[(2-Ph₂PPhC=)N]-3-methylpentanoic acid 4-MeOPh-amide 、 silver(I) acetate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 12.0h， 生成 (-)-1-(2-methoxyphenyl)-2-naphthalen-2-yl-2,3-dihydro-1H-pyridin-4-one 、 (+)-1-(2-methoxyphenyl)-2-naphthalen-2-yl-2,3-dihydro-1H-pyridin-4-one
  参考文献：
  名称：

  Efficient and Practical Ag-Catalyzed Cycloadditions between Arylimines and the Danishefsky Diene

  摘要：

  An efficient Ag-catalyzed method for asymmetric addition of the Danishefsky diene to various aryl imines to afford cycloadducts in > or =89% ee and > or =85% isolated yield is reported. Reactions are effected with 0.1-1 mol % catalyst (4 degrees C), and the chiral ligand is readily prepared from commercially available materials, including the inexpensive i-Leu. These catalytic asymmetric cycloadditions can be carried out without the use of solvent or with undistilled THF in air. A first generation supported chiral catalyst that effectively promotes the cycloaddition reaction and can be recycled (five cycles) is described.

  DOI：

  10.1021/ja030033p

文献信息

• Efficient and Practical Ag-Catalyzed Cycloadditions between Arylimines and the Danishefsky Diene
  作者：Nathan S. Josephsohn、Marc L. Snapper、Amir H. Hoveyda

  DOI：10.1021/ja030033p

  日期：2003.4.1

  An efficient Ag-catalyzed method for asymmetric addition of the Danishefsky diene to various aryl imines to afford cycloadducts in > or =89% ee and > or =85% isolated yield is reported. Reactions are effected with 0.1-1 mol % catalyst (4 degrees C), and the chiral ligand is readily prepared from commercially available materials, including the inexpensive i-Leu. These catalytic asymmetric cycloadditions can be carried out without the use of solvent or with undistilled THF in air. A first generation supported chiral catalyst that effectively promotes the cycloaddition reaction and can be recycled (five cycles) is described.