cycle | 139033-63-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cycle
• 英文别名: cycle[Leuψ(CH2NH)Phe]；(3S,6S)-3-benzyl-6-(2-methylpropyl)piperazin-2-one
• CAS: 139033-63-9
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: AHZGWRSFVBUNGU-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-carbobenzoxy-L-leucinal 在 palladium on activated charcoal 盐酸 、 4 A molecular sieve 、 氢气 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 5.17h， 生成 cycle
  参考文献：
  名称：

  Studies on N-deprotection of ψ(CH₂NH) pseudodipeptide methyl esters. Cyclization to 2-ketopiperazines

  摘要：

  N-Deprotection of Z- and Boc-aminomethylene pseudodipeptide methyl esters yielded not only the expected linear deprotected compounds but also the 2-ketopiperazine cyclic analogues. The extent of lactamization was found to be dependent on the nature of the amino acid, the sequence order, and the deprotection conditions. Hydrogenation of Z-pseudodipeptides containing N-terminal basic amino acids in acidic media afforded linear compounds, while replacement of these basic residues by Leu gave mixtures of linear and cyclic pseudodipeptides. The reverse-sequence analogues, with Lys or Arg at the C-terminus, yielded the corresponding 2-ketopiperazines as the only reaction products. Opposite results were obtained for C-terminal Leu derivatives in which almost no cyclization occurred. Hydrogenation under neutral conditions gave mainly cyclic derivatives, while linear analogues were predominant after treatment of Boc-protected pseudodipeptides with trifluoroacetic acid or HCl.

  DOI：

  10.1039/p19910003117

文献信息

• Studies on N-deprotection of ψ(CH₂NH) pseudodipeptide methyl esters. Cyclization to 2-ketopiperazines
  作者：Ana Bravo、Isabel Gómez-Monterrey、Rosario González-Muñiz、M. Teresa García-López

  DOI：10.1039/p19910003117

  日期：——

  N-Deprotection of Z- and Boc-aminomethylene pseudodipeptide methyl esters yielded not only the expected linear deprotected compounds but also the 2-ketopiperazine cyclic analogues. The extent of lactamization was found to be dependent on the nature of the amino acid, the sequence order, and the deprotection conditions. Hydrogenation of Z-pseudodipeptides containing N-terminal basic amino acids in acidic media afforded linear compounds, while replacement of these basic residues by Leu gave mixtures of linear and cyclic pseudodipeptides. The reverse-sequence analogues, with Lys or Arg at the C-terminus, yielded the corresponding 2-ketopiperazines as the only reaction products. Opposite results were obtained for C-terminal Leu derivatives in which almost no cyclization occurred. Hydrogenation under neutral conditions gave mainly cyclic derivatives, while linear analogues were predominant after treatment of Boc-protected pseudodipeptides with trifluoroacetic acid or HCl.