3-(2-oxo-5-phenethyl-cyclopentyl)-benzoic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-(2-oxo-5-phenethyl-cyclopentyl)-benzoic acid ethyl ester
• 英文别名: ethyl 3-[(1S,5S)-2-oxo-5-(2-phenylethyl)cyclopentyl]benzoate
• 化学式: C₂₂H₂₄O₃
• 分子量: 336.431
• InChiKey: VIBSPYOBUAGSKA-UWJYYQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-乙氧基-2-环戊烯酮 在 copper(l) chloride 二苯基硅烷 、 (±)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 18.0h， 生成 3-(2-oxo-5-phenethyl-cyclopentyl)-benzoic acid ethyl ester
  参考文献：
  名称：

  One-Pot Sequential Cu-Catalyzed Reduction and Pd-Catalyzed Arylation of Silyl Enol Ethers

  摘要：

  {graphic} Enantiomerically enriched beta-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to alpha-arylated cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The isolation of the intermediate, diphenylsilyl enol ethers is not necessary; the procedure can be carried out in one-pot.

  DOI：

  10.1021/ol048313c

文献信息

• One-Pot Sequential Cu-Catalyzed Reduction and Pd-Catalyzed Arylation of Silyl Enol Ethers
  作者：Junghyun Chae、Jaesook Yun、Stephen L. Buchwald

  DOI：10.1021/ol048313c

  日期：2004.12.1

  graphic} Enantiomerically enriched beta-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to alpha-arylated cycloalkanones with excellent levels of enantiomeric and diastereomeric purity. The isolation of the intermediate, diphenylsilyl enol ethers is not necessary; the procedure can be carried out in one-pot.