cyclo[L-His-L-(αMe)Phe]

• 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: cyclo[L-His-L-(αMe)Phe]
• 英文别名: (3S,6S)-3-benzyl-6-(1H-imidazol-5-ylmethyl)-3-methylpiperazine-2,5-dione
• 化学式: C₁₆H₁₈N₄O₂
• 分子量: 298.345
• InChiKey: CHFYPXPAMAQQEH-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  alpha-甲基-DL-苯丙氨酸 在 palladium on activated charcoal N-甲基吗啉 、 氯化亚砜 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 114.5h， 生成 cyclo[L-His-L-(αMe)Phe]
  参考文献：
  名称：

  Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(α-Me)Phe as catalyst

  摘要：

  Two cyclo-dipeptides based on His and the unnatural (alpha Me)Phe have been examined as catalysts in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxy-benzaldehyde. The synthesis, catalytic activity and NMR study towards the mechanism of this reaction are presented. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00178-x

文献信息

• Studies on cyclic dipeptides, II. Methylated modifications ofcyclo-[Phe-His]
  作者：C. R. Noe、A. Weigand、S. Pirker、P. Liepert

  DOI：10.1007/bf00807896

  日期：1997.3

  Synthesis of seven new cyclic dipeptides and their conformational analysis based on H-1 NMR spectra is reported as well as their application as models to elucidate the mechanism of cyclic dipeptide catalysis in enantioselective mandelonitrile formation. Further evidence is presented to support the view that a highly ordered supramolecular complex of dipeptides acts as catalyst.
• Catalytic enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxybenzaldehyde using cyclo-His-(α-Me)Phe as catalyst
  作者：Ron Hulst、Quirinus B. Broxterman、Johan Kamphuis、Fernando Formaggio、Marco Crisma、Claudio Toniolo、Richard M. Kellogg

  DOI：10.1016/s0957-4166(97)00178-x

  日期：1997.6

  Two cyclo-dipeptides based on His and the unnatural (alpha Me)Phe have been examined as catalysts in the enantioselective addition of hydrogen cyanide to benzaldehyde and p-methoxy-benzaldehyde. The synthesis, catalytic activity and NMR study towards the mechanism of this reaction are presented. (C) 1997 Elsevier Science Ltd.