methyl 4-(4-bromophenyl)-3-ethyl-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate | 1505519-42-5

• 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 4-(4-bromophenyl)-3-ethyl-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
• 英文别名: methyl (4S,5S)-4-(4-bromophenyl)-5-ethyl-6-oxo-5-phenyl-4H-pyran-2-carboxylate
• CAS: 1505519-42-5
• 化学式: C₂₁H₁₉BrO₄
• 分子量: 415.283
• InChiKey: ODHOZLFBCNTYET-LAUBAEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(4-bromophenyl)-2-oxo-3-butenoic acid methyl ester 、 2-苯基-1-丁烯-1-酮 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 7.5h， 以84%的产率得到methyl 4-(4-bromophenyl)-3-ethyl-2-oxo-3-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