methyl 3-ethyl-3-(naphthalen-2-yl)-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate | 1505519-40-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 3-ethyl-3-(naphthalen-2-yl)-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1505519-40-3
• 化学式: C₂₅H₂₂O₄
• 分子量: 386.447
• InChiKey: ZZNRMNKAKMVDBT-SQJMNOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 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：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-naphthyl ethyl ketene 、 methyl 4-phenyl-2-oxo-3-butenoate 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 、 yttrium(III) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 以99%的产率得到methyl 3-ethyl-3-(naphthalen-2-yl)-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones

  摘要：

  Highly diastereo- and enantioselective [2 + 2]- and [4 + 2]-cycloadditions of disubstituted ketenes were realized by chiral Lewis acid catalysis. A series of arylalkylketenes underwent the reaction smoothly with isatins and beta,gamma-unsaturated alpha-ketoesters, providing optically active beta-lactones and delta-lactones with vicinal chiral centers in excellent yields (up to 99%) and enantioselectivities (up to 99% ee), as well as exclusively high diastereoselectivities under 0.2-2 mol % catalyst loading.

  DOI：

  10.1021/ol4031217