(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-naphthalen-1-ylpentanamide | 873796-96-4

• 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: (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-naphthalen-1-ylpentanamide
• CAS: 873796-96-4
• 化学式: C₃₄H₄₆N₄O₃
• 分子量: 558.764
• InChiKey: WOGNFSAUGAROBX-LXCBOGQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  83.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-naphthalen-1-ylpentanamide 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid naphthalen-1-ylamide
  参考文献：
  名称：

  Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities

  摘要：

  The hydroxyl at the C-3 of cholic acid was converted to an amino group, and the resulting aminofunctionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in solvent mixtures consisting of mostly nonpolar solvents such as carbon tetrachloride or ethyl acetate/hexane and 2-5% of a polar solvent such as methanol or DMSO. The conformations of the foldamers; were studied by UV, fluorescence, fluorescence quenching, and fluorescence resonance energy transfer. The nature of the polar/nonpolar solvents and their miscibility strongly influenced the folding reaction. Folding was cooperative, as evidenced by the sigmoidal curves in solvent denaturation experiments. The folded conformers became more stable with an increase in the chain length. The folding/unfolding equilibrium was highly sensitive toward the amount of polar solvent. One percent variation in the solvent composition could change the folding free energies by 0.5-1.4 kcal/mol.

  DOI：

  10.1021/ja056151p
• 作为产物：
  描述：

  胆酸甲酯 在 lithium hydroxide 、 sodium azide 、 高氯酸 、 草酰氯 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 62.5h， 生成 (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-naphthalen-1-ylpentanamide
  参考文献：
  名称：

  Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities

  摘要：

  The hydroxyl at the C-3 of cholic acid was converted to an amino group, and the resulting aminofunctionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in solvent mixtures consisting of mostly nonpolar solvents such as carbon tetrachloride or ethyl acetate/hexane and 2-5% of a polar solvent such as methanol or DMSO. The conformations of the foldamers; were studied by UV, fluorescence, fluorescence quenching, and fluorescence resonance energy transfer. The nature of the polar/nonpolar solvents and their miscibility strongly influenced the folding reaction. Folding was cooperative, as evidenced by the sigmoidal curves in solvent denaturation experiments. The folded conformers became more stable with an increase in the chain length. The folding/unfolding equilibrium was highly sensitive toward the amount of polar solvent. One percent variation in the solvent composition could change the folding free energies by 0.5-1.4 kcal/mol.

  DOI：

  10.1021/ja056151p