1-<(S)-1-(benzyloxy)-4-methylpent-2-yl>-(3S,4R)-3-azido-4-phenylazetidin-2-one | 82101-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-<(S)-1-(benzyloxy)-4-methylpent-2-yl>-(3S,4R)-3-azido-4-phenylazetidin-2-one
• 英文别名: 1-[(S)-1-(benzyloxy)-4-methylpent-2-yl]-(3S,4R)-3-azido-4-phenylazetidin-2-one；(3S,4R)-3-azido-1-[(2S)-4-methyl-1-phenylmethoxypentan-2-yl]-4-phenylazetidin-2-one
• CAS: 82101-54-0
• 化学式: C₂₂H₂₆N₄O₂
• 分子量: 378.474
• InChiKey: PGAZXTNRFVHMRT-PCCBWWKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  78.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-<(S)-1-(benzyloxy)-4-methylpent-2-yl>-(3S,4R)-3-azido-4-phenylazetidin-2-one 在 palladium on activated charcoal 氢气 、 sodium sulfate 作用下， 以 甲醇 、 苯 为溶剂， 反应 6.0h， 生成 1-<(S)-1-(benzyloxy)-4-methylpent-2-yl>-(3S,4R)-3-(benzylideneamino)-4-phenylazetidin-2-one
  参考文献：
  名称：

  Remarkable effects of lone pair-lone pair interactions on the extremely stereoselective [2 + 2] cycloaddition of azidoketene to chiral 3-imino-.beta.-lactams

  摘要：

  DOI：

  10.1021/ja00240a033
• 作为产物：
  描述：

  L-亮氨醇 在 potassium hydride 、 sodium sulfate 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 20.5h， 生成 1-<(S)-1-(benzyloxy)-4-methylpent-2-yl>-(3S,4R)-3-azido-4-phenylazetidin-2-one
  参考文献：
  名称：

  Remarkable effects of lone pair-lone pair interactions on the extremely stereoselective [2 + 2] cycloaddition of azidoketene to chiral 3-imino-.beta.-lactams

  摘要：

  DOI：

  10.1021/ja00240a033

文献信息

• SYNTHESIS OF OPTICALLY PURE ENKEPHALIN ANALOG, [D-Ala², Leu⁵-ol]ENKEPHALIN, USING CHIRAL β-LACTAMS AS SYNTHETIC INTERMEDIATES
  作者：Naoto Hatanaka、Rumiko Abe、Iwao Ojima

  DOI：10.1246/cl.1982.445

  日期：1982.4.5

  Optically pure pentapeptide, l-Tyr-d-Ala-Gly-l-Phe-l-Leu-ol (1) which is an analog of opioid hormone, enkephalin, was successfully synthesized by using β-lactam building blocks as chiral synthons of peptide units.

  光学纯五肽 l-Tyr-d-Ala-Gly-l-Phe-l-Leu-ol (1) 是阿片类激素脑啡肽的类似物，通过将β-内酰胺结构单元作为肽单元的手性合成子成功合成。
• Azetidines and bisazetidines. Their synthesis and use as the key intermediates to enantiomerically pure diamines, amino alcohols, and polyamines
  作者：Iwao Ojima、Mangzhu Zhao、Takehiko Yamato、Kazuaki Nakahashi、Mitsuo Yamashita、Rumiko Abe

  DOI：10.1021/jo00018a012

  日期：1991.8

  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.
• OSIMA, IVAO;XATANAKA, NAOXITO;ABEH, RUMIKO
  作者：OSIMA, IVAO、XATANAKA, NAOXITO、ABEH, RUMIKO

  DOI：——

  日期：——