(R)-ethyl 2-methylene-5-oxo-3-(thiophen-2-yl)hexanoate | 1315340-09-0

• 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: (R)-ethyl 2-methylene-5-oxo-3-(thiophen-2-yl)hexanoate
• 英文别名: ethyl (3R)-2-methylidene-5-oxo-3-thiophen-2-ylhexanoate
• CAS: 1315340-09-0
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: SQHNYBSTKCZCHI-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 (R)-ethyl 2-methylene-5-oxo-3-(thiophen-2-yl)hexanoate 、 (S)-ethyl 2-methylene-5-oxo-3-(thiophen-2-yl)hexanoate
  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.