tert-butyl (S)-2-((S)-N-(benzyloxycarbonyl)-1-aminoethyl)pent-4-enoate | 644984-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (S)-2-((S)-N-(benzyloxycarbonyl)-1-aminoethyl)pent-4-enoate
• 英文别名: tert-butyl (2S)-2-((1S)-1-{[(benzyloxy)carbonyl]amino}ethyl)pent-4-enoate；tert-butyl (2S)-2-[(1S)-1-(phenylmethoxycarbonylamino)ethyl]pent-4-enoate
• CAS: 644984-52-1
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: XBBQXHQZUXHUOW-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙醇 、 tert-butyl (S)-2-((S)-N-(benzyloxycarbonyl)-1-aminoethyl)pent-4-enoate 在 对甲苯磺酸 作用下， 反应 192.0h， 以72%的产率得到ethyl (2S)-2-((1S)-1-{[(benzyloxy)carbonyl]amino}ethyl)pent-4-enoate
  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：

  tert-butyl (3S,αS)-3-(N-benzyl-N-α-methylbenzylamino)butanoate 在 palladium dihydroxide 正丁基锂 、 氢气 、 potassium hydrogencarbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 乙酸乙酯 为溶剂， -78.0~10.0 ℃ 、206.84 kPa 条件下， 反应 43.59h， 生成 tert-butyl (S)-2-((S)-N-(benzyloxycarbonyl)-1-aminoethyl)pent-4-enoate
  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

• Asymmetric Synthesis of Intermediates for Otamixaban and Premafloxacin by the Chiral Ligand-Controlled Asymmetric Conjugate Addition of a Lithium Amide
  作者：Takeo Sakai、Yoshito Kawamoto、Kiyoshi Tomioka

  DOI：10.1021/jo060588d

  日期：2006.6.1

  A chiral ligand-controlled conjugate addition reaction of lithium benzyl(trimethylsilyl)amide with tert-butyl enoates gave the corresponding lithium enolates that were then treated with electrophiles, giving anti-alkylation products with high ee up to 98%. The benzyl group on the amino nitrogen was removed by the oxidation of secondary amines to imines and subsequent transoximation to give 3-aminoalkanoates

  苄基（三甲基甲硅烷基）氨基锂与叔丁基烯醇酸酯的手性配体控制的共轭加成反应，得到相应的烯醇锂，然后将其用亲电子试剂处理，得到具有高ee高达98％的抗烷基化产物。通过将仲胺氧化为亚胺，然后进行转肟作用，以良好的收率除去氨基氮上的苄基。该产品是otamixaban和premafloxacin的可能关键中间体。