Ethyl (3S)-3-{methyl[(1S)-1-phenylethyl]amino}butanoate | 644984-58-7

• 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: Ethyl (3S)-3-{methyl[(1S)-1-phenylethyl]amino}butanoate
• 英文别名: ethyl (3S)-3-[methyl-[(1S)-1-phenylethyl]amino]butanoate
• CAS: 644984-58-7
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: VPNRSRJOHFQVIW-STQMWFEESA-N

物化性质

• 沸点：
  314.0±25.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-(-)-N-甲基-1-苯基乙胺 、 反式-2-丁烯酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到Ethyl (3S)-3-{methyl[(1S)-1-phenylethyl]amino}butanoate
  参考文献：
  名称：

  Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine

  摘要：

  N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine (1)(1) is a key intermediate in the preparation of premafloxacin (2), which was under development as an antibiotic for use against pathogens of veterinary importance. This paper describes the development of a practical, efficient, and stereoselective process for the preparation of 1 from isobutyl (3S)-3-{methyl[(1S)-1-phenylethyl]amino}butanoate (5c). The key steps in the synthetic sequence are an asymmetric Michael addition, which yields 5c, and a stereoselective alkylation, which yields (3S,4S)-3-allyl-1,4-dimethylazetidin-2-one (17).

  DOI：

  10.1021/jo0349633

文献信息

• Synthesis of <i>N</i>-Methyl-<i>N</i>-{(1<i>S</i>)-1-[(3<i>R</i>)-pyrrolidin-3-yl]ethyl}amine
  作者：Thomas J. Fleck、William W. McWhorter,、Richard N. DeKam、Bruce A. Pearlman

  DOI：10.1021/jo0349633

  日期：2003.12.1

  N-Methyl-N-(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine (1)(1) is a key intermediate in the preparation of premafloxacin (2), which was under development as an antibiotic for use against pathogens of veterinary importance. This paper describes the development of a practical, efficient, and stereoselective process for the preparation of 1 from isobutyl (3S)-3-methyl[(1S)-1-phenylethyl]amino}butanoate (5c). The key steps in the synthetic sequence are an asymmetric Michael addition, which yields 5c, and a stereoselective alkylation, which yields (3S,4S)-3-allyl-1,4-dimethylazetidin-2-one (17).