Butanoic acid, 3-[methyl[(1S)-1-phenylethyl]amino]-, methyl ester, (3S)- | 644984-56-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Butanoic acid, 3-[methyl[(1S)-1-phenylethyl]amino]-, methyl ester, (3S)-
• 英文别名: methyl (3S)-3-[methyl-[(1S)-1-phenylethyl]amino]butanoate
• CAS: 644984-56-5
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: RMPJGESTQIAGBC-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-formyl-1-phenylethylamine 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 Butanoic acid, 3-[methyl[(1S)-1-phenylethyl]amino]-, methyl ester, (3S)-
  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).