methyl 4-[[4-[[[(2S)-6-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]methyl]phenyl]methyl]benzoate | 162554-07-6

• 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: methyl 4-[[4-[[[(2S)-6-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]methyl]phenyl]methyl]benzoate
• CAS: 162554-07-6
• 化学式: C₂₇H₃₇N₃O₅
• 分子量: 483.608
• InChiKey: MJAHMVPQGLTOJZ-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-[[4-[[[(2S)-6-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]methyl]phenyl]methyl]benzoate 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Stabilization of a Cis Amide Bond in a Host−Guest Complex

  摘要：

  Macrobicycle 12 has been synthesized and its binding properties with a range of N-acetyl amino acid carboxylates (as tetrabutylammonium salts) have been studied. While the binding results showed little selectivity for the various substrates investigated, detailed NMR studies have revealed that D-amino acid substrates bind predominantly on the outside of the macrobicycle cavity by a strong carboxylate-thiourea interaction, whereas L-amino acid substrates bind predominantly on the inside of the cavity also establishing a strong carboxylate-thiourea interaction but with the acetyl amide in a cis configuration. Molecular modeling studies suggest that the energetic penalty associated with adopting a cis amide configuration in the host-guest complex is compensated by intermolecular hydrogen bonds between the cis amide and the rim of the macrobicycle.

  DOI：

  10.1021/ja9607805
• 作为产物：
  描述：

  methyl 4-(4-cyanobenzyl)benzoate 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 4-[[4-[[[(2S)-6-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]methyl]phenyl]methyl]benzoate
  参考文献：
  名称：

  A novel receptor for amino acid derivatives

  摘要：

  一种新型大环分子被制备，其特征是在其结构中包含一个作为羧酸盐结合位点的硫脲，并且具有酰胺功能，以便与合适的客体提供进一步的氢键相互作用；本研究探讨了这种新型大环分子结合简单氨基酸衍生物的能力。

  DOI：

  10.1039/c39950000305

文献信息

• A novel receptor for amino acid derivatives
  作者：Glen J. Pernía、Jeremy D. Kilburn、Michael Rowley

  DOI：10.1039/c39950000305

  日期：——

  A novel macrobicycle featuring a thiourea as a carboxylate binding site, and amide functionality to provide further hydrogen-bonding interactions with suitable guests is prepared; the ability of this novel macrobicycle to bind simple amino acid derivatives is investigated.

  一种新型大环分子被制备，其特征是在其结构中包含一个作为羧酸盐结合位点的硫脲，并且具有酰胺功能，以便与合适的客体提供进一步的氢键相互作用；本研究探讨了这种新型大环分子结合简单氨基酸衍生物的能力。
• Stabilization of a <i>Cis</i> Amide Bond in a Host−Guest Complex
  作者：Glen J. Pernía、Jeremy D. Kilburn、Jonathan W. Essex、Russell J. Mortishire-Smith、Michael Rowley

  DOI：10.1021/ja9607805

  日期：1996.1.1

  Macrobicycle 12 has been synthesized and its binding properties with a range of N-acetyl amino acid carboxylates (as tetrabutylammonium salts) have been studied. While the binding results showed little selectivity for the various substrates investigated, detailed NMR studies have revealed that D-amino acid substrates bind predominantly on the outside of the macrobicycle cavity by a strong carboxylate-thiourea interaction, whereas L-amino acid substrates bind predominantly on the inside of the cavity also establishing a strong carboxylate-thiourea interaction but with the acetyl amide in a cis configuration. Molecular modeling studies suggest that the energetic penalty associated with adopting a cis amide configuration in the host-guest complex is compensated by intermolecular hydrogen bonds between the cis amide and the rim of the macrobicycle.