(S)-methyl 2-methylene-5-oxo-3-phenyldecanoate | 1315340-18-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-methyl 2-methylene-5-oxo-3-phenyldecanoate
• 英文别名: methyl (3S)-2-methylidene-5-oxo-3-phenyldecanoate
• CAS: 1315340-18-1
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: FLFJHEXAZWKBIH-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  1-苯基-1-辛烯-3-酮 在 奎宁胺 、 BOC-L-脯氨酸 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 108.5h， 生成 (S)-methyl 2-methylene-5-oxo-3-phenyldecanoate
  参考文献：
  名称：

  Organocatalytic Asymmetric Michael-Type/Wittig Reaction of Phosphorus Ylides: Synthesis of Chiral α-Methylene-δ-Ketoesters

  摘要：

  An asymmetric Michael-type reaction of phosphorus ylides and alpha,beta-unsaturated ketones under the catalysis of a chiral ion pair catalyst has been described. The ion pair catalyst containing a chiral counteranion was prepared by simply mixing 9-amino-(9-deoxy)-epl-quinine with L-N-Boc-proline. The optically active alpha-methylene-delta-ketoesters could be obtained with good to excellent enantloselectivities (up to 95% ee) under mild reaction conditions.

  DOI：

  10.1021/ol201483s

文献信息

• Organocatalytic Asymmetric Michael-Type/Wittig Reaction of Phosphorus Ylides: Synthesis of Chiral α-Methylene-δ-Ketoesters
  作者：Aijun Lin、Junying Wang、Haibin Mao、Huiming Ge、Renxiang Tan、Chengjian Zhu、Yixiang Cheng

  DOI：10.1021/ol201483s

  日期：2011.8.19

  An asymmetric Michael-type reaction of phosphorus ylides and alpha,beta-unsaturated ketones under the catalysis of a chiral ion pair catalyst has been described. The ion pair catalyst containing a chiral counteranion was prepared by simply mixing 9-amino-(9-deoxy)-epl-quinine with L-N-Boc-proline. The optically active alpha-methylene-delta-ketoesters could be obtained with good to excellent enantloselectivities (up to 95% ee) under mild reaction conditions.