(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,60R,63R,66S)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-60-(prop-2-ynylsulfanylmethyl)-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 | 1429615-66-6

• 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: (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,60R,63R,66S)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-60-(prop-2-ynylsulfanylmethyl)-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
• CAS: 1429615-66-6
• 化学式: C₇₈H₁₂₄N₄O₁₀S
• 分子量: 1309.93
• InChiKey: JHSBTWFOEAPMPP-RAFIQJNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  93
• 可旋转键数：
  3
• 环数：
  25.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  263
• 氢给体数：
  10
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (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,60R,63R,66S)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-60-(prop-2-ynylsulfanylmethyl)-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 、 dimethyl 2-azidoterephthalate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Tuning Nanopore Formation of Oligocholate Macrocycles by Carboxylic Acid Dimerization in Lipid Membranes

  摘要：

  Oligocholate macrocycles self-assemble into transmembrane nanopores by the associative interactions of water molecules inside the amphiphilic macrocycles. Macrocycles functionalized with a terephthalic a acid "side chain" displayed significantly higher transport activity for glucose across lipid bilayers than the corresponding methyl ester derivative. Changing the 1,4-substitution of the carboxylic acid to 1,3-substitution lowered the activity. Combining the hydrophobic interactions and the hydrogen-bond-based carboxylic acid dimerization was an effective strategy to tune the structure and activity of self-assembled nanopores in lipid membranes.

  DOI：

  10.1021/jo400455x
• 作为产物：
  描述：

  methyl (2R)-2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-amino-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]pentanoyl]amino]-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]pentanoyl]amino]-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]pentanoyl]amino]-3-prop-2-ynylsulfanylpropanoate 在 lithium hydroxide 、 (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60%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,60R,63R,66S)-3,7,24,28,45,49-hexahydroxy-8,13,21,29,34,42,50,55,66-nonamethyl-60-(prop-2-ynylsulfanylmethyl)-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：

  Tuning Nanopore Formation of Oligocholate Macrocycles by Carboxylic Acid Dimerization in Lipid Membranes

  摘要：

  Oligocholate macrocycles self-assemble into transmembrane nanopores by the associative interactions of water molecules inside the amphiphilic macrocycles. Macrocycles functionalized with a terephthalic a acid "side chain" displayed significantly higher transport activity for glucose across lipid bilayers than the corresponding methyl ester derivative. Changing the 1,4-substitution of the carboxylic acid to 1,3-substitution lowered the activity. Combining the hydrophobic interactions and the hydrogen-bond-based carboxylic acid dimerization was an effective strategy to tune the structure and activity of self-assembled nanopores in lipid membranes.

  DOI：

  10.1021/jo400455x