isobutyl (3S)-3-{methyl[(1S)-1-phenylethyl]amino}butanoate | 161011-01-4

• 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: isobutyl (3S)-3-{methyl[(1S)-1-phenylethyl]amino}butanoate
• 英文别名: 2-methylpropyl (3S)-3-[methyl-[(1S)-1-phenylethyl]amino]butanoate
• CAS: 161011-01-4
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: VNRBOXYBPZLBQH-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isobutyl (3S)-3-{methyl[(1S)-1-phenylethyl]amino}butanoate 在 palladium on activated charcoal sodium tetrahydroborate 、 正丁基锂 、 氢气 、 臭氧 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， -78.0~90.0 ℃ 、275.79 kPa 条件下， 反应 15.5h， 生成 (3S)-1-benzyl-3-[(1S)-1-(methylamino)ethyl]pyrrolidin-2-one
  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
• 作为产物：
  描述：

  (S)-(-)-N-甲基-1-苯基乙胺 、 巴豆酸异丁酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到isobutyl (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).