N,N'-bis(N-Cbz-L-phenylalanyl)-1,4-diaminobutane | 553668-45-4

• 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: N,N'-bis(N-Cbz-L-phenylalanyl)-1,4-diaminobutane
• 英文别名: benzyl N-[(2S)-1-oxo-3-phenyl-1-[4-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]butylamino]propan-2-yl]carbamate
• CAS: 553668-45-4
• 化学式: C₃₈H₄₂N₄O₆
• 分子量: 650.775
• InChiKey: ZTHDPKKFLQDHME-HEVIKAOCSA-N

物化性质

• 熔点：
  219-220 °C(Solv: dichloromethane (75-09-2); methanol (67-56-1))
• 沸点：
  918.9±65.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(N-Cbz-L-phenylalanyl)-1,4-diaminobutane 在 氢溴酸 、 溶剂黄146 作用下， 以90%的产率得到1,4-bis(Phe-amino)butane
  参考文献：
  名称：

  U-Turn 预组织肽模拟物的有效大环化：分子内氢键和疏溶剂效应的作用

  摘要：

  源自氨基酸的简单拟肽分子在乙腈中与间位和对位双（溴甲基）苯反应，非常有效地产生大环结构。环化反应不需要高稀释技术，并且似乎对形成的大环的大小不敏感。通过 (1)H NMR、单晶 X 射线衍射、荧光测量和分子力学获得的数据分析表明，折叠构象可以预先组织系统以实现有效的环化。分析了在折叠构象存在下分子内氢键和疏溶剂效应所起的作用。

  DOI：

  10.1021/ja0284759
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 生成 N,N'-bis(N-Cbz-L-phenylalanyl)-1,4-diaminobutane
  参考文献：
  名称：

  A simple peptidomimetic that self-associates on the solid state to form a nanoporous architecture containing chiral π-channels

  摘要：

  源自苯丙氨酸的简单拟肽化合物晶体结构显示，形成了包含一维π通道的纳米多孔结构，其中芳香环作为手性通道壁的唯一组分。

  DOI：

  10.1039/b922172g

文献信息

• Homogeneous and Supported Copper Complexes of Cyclic and Open-Chain Polynitrogenated Ligands as Catalysts of Cyclopropanation Reactions
  作者：F. Adrián、M. I. Burguete、J. M. Fraile、J. I. García、J. García、E. García-España、S. V. Luis、J. A. Mayoral、A. J. Royo、M. C. Sánchez

  DOI：10.1002/(sici)1099-0682(199912)1999:12<2347::aid-ejic2347>3.0.co;2-7

  日期：1999.12
• Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acids
  作者：Belén Altava、M. Isabel Burguete、Noèlia Carbó、Jorge Escorihuela、Santiago V. Luis

  DOI：10.1016/j.tetasy.2010.05.010

  日期：2010.4

  A family of bis(amino amides) derived from natural amino acids has been synthesized and tested for the NMR enantiodiscrimination, as chiral solvating agents, for enantiomeric excess determination of some carboxylic acids. Those bis(amino amide) receptors contain different structural modifications and the splitting of the signals of the acids, after addition of the corresponding CSAs, depends on those structural variables. The influence of aminoacid side chain and the nature of the aliphatic spacer are important parameters to obtain good chiral discriminations. The results obtained clearly show the chiral recognition abilities of these bis(amino amide) ligands and suggest their advantageous use as chiral solvating agents for carboxylic acids. The binding between bis(amino amides) and carboxylic acids has been studied by ESI-MS, NMR, DSC, and molecular modeling. The data suggest that enantiodiscrimination involves the formation of an ionic pair after proton transfer from the carboxylic substrate to the bis(amino amides). (C) 2010 Elsevier Ltd. All rights reserved.
• Optically Active Tropocoronands Having Amino Acid Residues in Linker Chains: Syntheses, Metal Coordination Properties, and Their Abilities as an Asymmetric Catalyst
  作者：Ohki Sato、Akira Tanbo

  DOI：10.3987/com-04-s(p)35

  日期：——

  Optically active tropocoronands (7) having L-amino acid moieties were synthesized by stepwise and one-pot reactions of tropolone derivatives with amino acid linker chains. The coordination styles of their Ni(II) and Pd(II) complexes and the abilities as an asymmetric catalyst were investigated.
• Efficient Macrocyclization of U-Turn Preorganized Peptidomimetics:  The Role of Intramolecular H-Bond and Solvophobic Effects
  作者：Jorge Becerril、Michael Bolte、M. Isabel Burguete、Francisco Galindo、Enrique García-España、Santiago V. Luis、Juan F. Miravet

  DOI：10.1021/ja0284759

  日期：2003.6.1

  acetonitrile to very efficiently yield macrocyclic structures. The cyclization reaction does not require high dilution techniques and seems to be insensitive to the size of the formed macrocycle. The analysis of data obtained by (1)H NMR, single-crystal X-ray diffraction, fluorescence measurements, and molecular mechanics indicate that folded conformations can preorganize the system for an efficient cyclization

  源自氨基酸的简单拟肽分子在乙腈中与间位和对位双（溴甲基）苯反应，非常有效地产生大环结构。环化反应不需要高稀释技术，并且似乎对形成的大环的大小不敏感。通过 (1)H NMR、单晶 X 射线衍射、荧光测量和分子力学获得的数据分析表明，折叠构象可以预先组织系统以实现有效的环化。分析了在折叠构象存在下分子内氢键和疏溶剂效应所起的作用。
• A simple peptidomimetic that self-associates on the solid state to form a nanoporous architecture containing chiral π-channels
  作者：Jorge Becerril、Michael Bolte、M. Isabel Burguete、Jorge Escorihuela、Francisco Galindo、Santiago V. Luis

  DOI：10.1039/b922172g

  日期：——

  The crystal structure of a simple peptidomimetic compound, derived from phenylalanine, shows the formation of a nanoporous architecture containing monodimensional π-channels with the aromatic rings as the exclusive components of the chiral channel walls.

  源自苯丙氨酸的简单拟肽化合物晶体结构显示，形成了包含一维π通道的纳米多孔结构，其中芳香环作为手性通道壁的唯一组分。