| 134485-73-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 134485-73-7
• 化学式: C₁₃H₂₅NO
• 分子量: 212.34
• InChiKey: FTNALKHHPDFMOP-RJDDLKSPSA-N

反应信息

• 作为产物：
  描述：

  N,N-diisopropyl-2,3-dimethyl-4-pentenamide 在 氘代甲醇-d 、 四甲基乙二胺 、 仲丁基锂 作用下， 生成 、
  参考文献：
  名称：

  Complex induced proximity effects: .beta.-lithiations of carboxamides

  摘要：

  The R*,S* and the R*,R* diastereomers of N,N-diisopropyl-2,3-dideuterio-2-methyl-3-phenylpropanamide (5,6) have been used to investigate the diastereoselectivity of the beta-lithiation of N,N-diisopropyl-2-methyl-3-phenylpropanamide (4). The beta-lithiation of 4 is highly diastereoselective with the beta-proton that is in the same relative position as the beta-proton of diastereomer 6 being preferentially removed. The beta-lithio species derived from 4 is shown to be a pyramidal, organolithium reagent based on C-13 NMR. Lithiation of the R*,S* and the R*,R* diastereomers of N,N-diisopropyl-2-methyl-3-(phenylthio)butanamide (7, 8) and N,N-diisopropyl-2,3-dimethyl-4-pentenamide (9, 10) occur at the beta-position. Lithiation of the R*,S* and R*,R* diastereomers of N,N-diisopropyl-2-methyl-3-phenylbutanamide (11, 12) occurs at the beta-position for 11 and at the alpha-position for 12. A conformational model is shown to correlate with these observations. The beta-lithio species formed do not react diastereospecifically.

  DOI：

  10.1021/jo00016a025