1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-<(3'S,4'R)-2'-oxo-3'-phenoxy-4'-phenylazetidin-1'-yl>-4-phenylazetidin-2-one | 136778-91-1

• 英文名称: 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-<(3'S,4'R)-2'-oxo-3'-phenoxy-4'-phenylazetidin-1'-yl>-4-phenylazetidin-2-one
• CAS: 136778-91-1
• 化学式: C₃₁H₃₂N₂O₅
• 分子量: 512.605
• InChiKey: WHQIRPGRHLTYTR-AMDJRULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-<(3'S,4'R)-2'-oxo-3'-phenoxy-4'-phenylazetidin-1'-yl>-4-phenylazetidin-2-one 在 chlorohydroalane 作用下， 以 乙醚 为溶剂， 以77%的产率得到(2S,3S)-1-<(S)-1-methyl-2-hydroxyethyl>-2-phenyl-3-<(2'R,3'R)-2'-phenyl-3'-phenoxyazetidinyl>azetidine
  参考文献：
  名称：

  Azetidines and bisazetidines. Their synthesis and use as the key intermediates to enantiomerically pure diamines, amino alcohols, and polyamines

  摘要：

  Highly selective reductions of beta-lactams (1, 5), direct-tandem bis-beta-lactams (6), and tandem bis-beta-lactams (7) to the corresponding azetidines (13, 14) and bisazetidines (11, 12) are successfully performed by using diisobutylaluminum hydride (DIBAL-H), monochlorohydroalane (AlH2Cl) and dichloroalane (AlHCl2) as specific reducing agents: Enantiomerically pure azetidines and bisazetidines are readily synthesized without loss of enantiomeric purity. Possible mechanisms that can accommodate the unique selectivity realized by hydroalanes are discussed. Hydrogenolysis of 2-arylazetidines and 2,2'-diarylbisazetidines on palladium catalyst or Raney-Ni gives the corresponding diamines, amino alcohols, polyamino alcohols, and polyamino ethers in excellent yields, which may serve as useful chiral chelating agents as well as chiral building blocks for organic synthesis and for chiral macrocycles.

  DOI：

  10.1021/jo00018a012
• 作为产物：
  描述：

  1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-(benzylideneamino)-4-phenylazetidin-2-one 、 苯氧乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-<(3'S,4'R)-2'-oxo-3'-phenoxy-4'-phenylazetidin-1'-yl>-4-phenylazetidin-2-one 、 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-<(3'R,4'S)-2'-oxo-3'-phenoxy-4'-phenylazetidin-1'-yl>-4-phenylazetidin-2-one
  参考文献：
  名称：

  Azetidines and bisazetidines. Their synthesis and use as the key intermediates to enantiomerically pure diamines, amino alcohols, and polyamines

  摘要：

  Highly selective reductions of beta-lactams (1, 5), direct-tandem bis-beta-lactams (6), and tandem bis-beta-lactams (7) to the corresponding azetidines (13, 14) and bisazetidines (11, 12) are successfully performed by using diisobutylaluminum hydride (DIBAL-H), monochlorohydroalane (AlH2Cl) and dichloroalane (AlHCl2) as specific reducing agents: Enantiomerically pure azetidines and bisazetidines are readily synthesized without loss of enantiomeric purity. Possible mechanisms that can accommodate the unique selectivity realized by hydroalanes are discussed. Hydrogenolysis of 2-arylazetidines and 2,2'-diarylbisazetidines on palladium catalyst or Raney-Ni gives the corresponding diamines, amino alcohols, polyamino alcohols, and polyamino ethers in excellent yields, which may serve as useful chiral chelating agents as well as chiral building blocks for organic synthesis and for chiral macrocycles.

  DOI：

  10.1021/jo00018a012