benzyl N-[3-[(1S,3R,4R,5S,7S,8R,9S,12R,13R,18R,21S,22S,24R,25R,26S,28S,29R,30S,33R,34R,39R,42S,43S,45R,46R,47S,49S,50R,51S,54R,55R,60S,63R,66S)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-16,37,58,61-tetraoxo-17,38,59,62-tetrazatridecacyclo[61.3.1.118,22.139,43.04,9.05,66.08,12.021,26.025,30.029,33.042,47.046,51.050,54]nonahexacontan-60-yl]propyl]carbamate | 1374873-16-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: benzyl N-[3-[(1S,3R,4R,5S,7S,8R,9S,12R,13R,18R,21S,22S,24R,25R,26S,28S,29R,30S,33R,34R,39R,42S,43S,45R,46R,47S,49S,50R,51S,54R,55R,60S,63R,66S)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-16,37,58,61-tetraoxo-17,38,59,62-tetrazatridecacyclo[61.3.1.118,22.139,43.04,9.05,66.08,12.021,26.025,30.029,33.042,47.046,51.050,54]nonahexacontan-60-yl]propyl]carbamate
• CAS: 1374873-16-1
• 化学式: C₈₅H₁₃₃N₅O₁₂
• 分子量: 1417.02
• InChiKey: KMKIQKUTCVCYJL-JPFTXOCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  102
• 可旋转键数：
  7
• 环数：
  26.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  276
• 氢给体数：
  11
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  benzyl N-[3-[(1S,3R,4R,5S,7S,8R,9S,12R,13R,18R,21S,22S,24R,25R,26S,28S,29R,30S,33R,34R,39R,42S,43S,45R,46R,47S,49S,50R,51S,54R,55R,60S,63R,66S)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-16,37,58,61-tetraoxo-17,38,59,62-tetrazatridecacyclo[61.3.1.118,22.139,43.04,9.05,66.08,12.021,26.025,30.029,33.042,47.046,51.050,54]nonahexacontan-60-yl]propyl]carbamate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以80%的产率得到(1S,3R,4R,5S,7S,8R,9S,12R,13R,18R,21S,22S,24R,25R,26S,28S,29R,30S,33R,34R,39R,42S,43S,45R,46R,47S,49S,50R,51S,54R,55R,60S,63R,66S)-60-(3-aminopropyl)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-17,38,59,62-tetrazatridecacyclo[61.3.1.118,22.139,43.04,9.05,66.08,12.021,26.025,30.029,33.042,47.046,51.050,54]nonahexacontane-16,37,58,61-tetrone
  参考文献：
  名称：

  Aromatically Functionalized Cyclic Tricholate Macrocycles: Aggregation, Transmembrane Pore Formation, Flexibility, and Cooperativity

  摘要：

  The aggregation of macrocyclic oligocholates with introverted hydrophilic groups and aromatic side chains was studied by fluorescence spectroscopy and liposome leakage assays. Comparison between the solution and the membrane phase afforded insight into the solvophobically driven aggregation. The macrocycles stacked over one another in lipid membranes to form transmembrane nanopores, driven by a strong tendency of the water molecules in the interior of the amphiphilic macrocycles to aggregate in a nonpolar environment. The aromatic side chains provided spectroscopic signatures for stacking, as well as additional driving force for the aggregation. Smaller, more rigid macrocycles stacked better than larger, more flexible ones because the cholate building blocks in the latter could rotate outward and diminish the conformation needed for the water-templated hydrophobic stacking. The acceptor acceptor interactions among naphthalenediimide (NDI) groups were more effective than the pyrene NDI donor acceptor interactions in promoting the transmembrane pore formation of the oligocholate macrocycles.

  DOI：

  10.1021/jo3004056
• 作为产物：
  描述：

  在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以98%的产率得到benzyl N-[3-[(1S,3R,4R,5S,7S,8R,9S,12R,13R,18R,21S,22S,24R,25R,26S,28S,29R,30S,33R,34R,39R,42S,43S,45R,46R,47S,49S,50R,51S,54R,55R,60S,63R,66S)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-16,37,58,61-tetraoxo-17,38,59,62-tetrazatridecacyclo[61.3.1.118,22.139,43.04,9.05,66.08,12.021,26.025,30.029,33.042,47.046,51.050,54]nonahexacontan-60-yl]propyl]carbamate
  参考文献：
  名称：

  Aromatically Functionalized Cyclic Tricholate Macrocycles: Aggregation, Transmembrane Pore Formation, Flexibility, and Cooperativity

  摘要：

  The aggregation of macrocyclic oligocholates with introverted hydrophilic groups and aromatic side chains was studied by fluorescence spectroscopy and liposome leakage assays. Comparison between the solution and the membrane phase afforded insight into the solvophobically driven aggregation. The macrocycles stacked over one another in lipid membranes to form transmembrane nanopores, driven by a strong tendency of the water molecules in the interior of the amphiphilic macrocycles to aggregate in a nonpolar environment. The aromatic side chains provided spectroscopic signatures for stacking, as well as additional driving force for the aggregation. Smaller, more rigid macrocycles stacked better than larger, more flexible ones because the cholate building blocks in the latter could rotate outward and diminish the conformation needed for the water-templated hydrophobic stacking. The acceptor acceptor interactions among naphthalenediimide (NDI) groups were more effective than the pyrene NDI donor acceptor interactions in promoting the transmembrane pore formation of the oligocholate macrocycles.

  DOI：

  10.1021/jo3004056