ditert-butyl 2-[(2S)-4-oxopentan-2-yl]propanedioate | 177722-22-4

• 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: ditert-butyl 2-[(2S)-4-oxopentan-2-yl]propanedioate
• CAS: 177722-22-4
• 化学式: C₁₆H₂₈O₅
• 分子量: 300.395
• InChiKey: MYDRWAGYQPGIFQ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ditert-butyl 2-[(2S)-4-oxopentan-2-yl]propanedioate 在 盐酸 作用下， 生成 methyl (S)-(+)-3-methyl-5-oxohexanoate
  参考文献：
  名称：

  Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by l-Proline Rubidium Salt

  摘要：

  L-Proline rubidium salt catalyzes the asymmetric Michael addition of malonate anions to prochiral enones and enals. This method can be applied to a wide range of substrates to give adducts with a predictable absolute configuration: (S)-adducts from (E)-enones/enals and (R)-adducts from cyclic (Z)-enones. Both the secondary amine moiety and the carboxylate moiety are critical for the catalytic activity and asymmetric induction. Varying the countercation also affects the reaction course. High enantiomeric excesses were attained when di(tert-butyl) malonate was added to (E)-enones in the presence of CsF. The stereochemistry of the Michael reaction indicates that asymmetric induction takes place via enantioface discrimination involving the acceptor alpha-carbon atom rather than the beta-carbon atom.

  DOI：

  10.1021/jo960216c
• 作为产物：
  描述：

  丙二酸二叔丁酯 、 戊-3-烯-2-酮 在 4-甲基-3戊烯-2-酮 、 cesium fluoride 、 (L)-proline rubidium salt 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 、 ditert-butyl 2-[(2S)-4-oxopentan-2-yl]propanedioate
  参考文献：
  名称：

  Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by l-Proline Rubidium Salt

  摘要：

  L-Proline rubidium salt catalyzes the asymmetric Michael addition of malonate anions to prochiral enones and enals. This method can be applied to a wide range of substrates to give adducts with a predictable absolute configuration: (S)-adducts from (E)-enones/enals and (R)-adducts from cyclic (Z)-enones. Both the secondary amine moiety and the carboxylate moiety are critical for the catalytic activity and asymmetric induction. Varying the countercation also affects the reaction course. High enantiomeric excesses were attained when di(tert-butyl) malonate was added to (E)-enones in the presence of CsF. The stereochemistry of the Michael reaction indicates that asymmetric induction takes place via enantioface discrimination involving the acceptor alpha-carbon atom rather than the beta-carbon atom.

  DOI：

  10.1021/jo960216c

文献信息

• Asymmetric Michael Addition of Malonate Anions to Prochiral Acceptors Catalyzed by <scp>l</scp>-Proline Rubidium Salt
  作者：Masahiko Yamaguchi、Tai Shiraishi、Masahiro Hirama

  DOI：10.1021/jo960216c

  日期：1996.1.1

  L-Proline rubidium salt catalyzes the asymmetric Michael addition of malonate anions to prochiral enones and enals. This method can be applied to a wide range of substrates to give adducts with a predictable absolute configuration: (S)-adducts from (E)-enones/enals and (R)-adducts from cyclic (Z)-enones. Both the secondary amine moiety and the carboxylate moiety are critical for the catalytic activity and asymmetric induction. Varying the countercation also affects the reaction course. High enantiomeric excesses were attained when di(tert-butyl) malonate was added to (E)-enones in the presence of CsF. The stereochemistry of the Michael reaction indicates that asymmetric induction takes place via enantioface discrimination involving the acceptor alpha-carbon atom rather than the beta-carbon atom.