(R)-2-(3,3-dimethyl-butyryl)-2-(3-oxobutyl)-cyclopentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-(3,3-dimethyl-butyryl)-2-(3-oxobutyl)-cyclopentanone
• 英文别名: (2R)-2-(3,3-dimethylbutanoyl)-2-(3-oxobutyl)cyclopentan-1-one
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: RAGBTJQDNMFBHC-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丁烯酮 、 2-(3,3-Dimethylbutanoyl)cyclopentan-1-one 在 (R)-tol-BINAP-Pd(OH₂)2⁽²⁺⁾*2TfO^(1-) 三氟甲磺酸 作用下， 以 氘代四氢呋喃 为溶剂， 反应 7.0h， 以99%的产率得到(R)-2-(3,3-dimethyl-butyryl)-2-(3-oxobutyl)-cyclopentanone
  参考文献：
  名称：

  Direct Generation of Nucleophilic Chiral Palladium Enolate from 1,3-Dicarbonyl Compounds:  Catalytic Enantioselective Michael Reaction with Enones

  摘要：

  Generation of chiral palladium enolates from 1,3-dicarbonyl compounds with the palladium aqua complex and its application to the highly efficient catalytic enantioselective Michael reaction with enones are described. The palladium aqua complexes are likely to supply Brønsted base and Brønsted acid successively during the reaction. The former activates the carbonyl compounds to give chiral palladium enolates, and the latter cooperatively activates enones. Using a catalytic amount (2-10 mol %) of the palladium complexes, the various 1,3-dicarbonyl compounds including diketones and beta-ketoesters were converted to the desired Michael adducts in good yields (69-92%) with excellent enantiomeric excesses (89-99% ee).

  DOI：

  10.1021/ja027075i

文献信息

• Direct Generation of Nucleophilic Chiral Palladium Enolate from 1,3-Dicarbonyl Compounds:  Catalytic Enantioselective Michael Reaction with Enones
  作者：Yoshitaka Hamashima、Daido Hotta、Mikiko Sodeoka

  DOI：10.1021/ja027075i

  日期：2002.9.1

  Generation of chiral palladium enolates from 1,3-dicarbonyl compounds with the palladium aqua complex and its application to the highly efficient catalytic enantioselective Michael reaction with enones are described. The palladium aqua complexes are likely to supply Brønsted base and Brønsted acid successively during the reaction. The former activates the carbonyl compounds to give chiral palladium enolates, and the latter cooperatively activates enones. Using a catalytic amount (2-10 mol %) of the palladium complexes, the various 1,3-dicarbonyl compounds including diketones and beta-ketoesters were converted to the desired Michael adducts in good yields (69-92%) with excellent enantiomeric excesses (89-99% ee).