eicosyl 3α-azido-7α,12α-bis-[(4-trifluoromethylphenyl)aminocarbonylamino]-5β-cholan-24-oate | 861399-65-7

• 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: eicosyl 3α-azido-7α,12α-bis-[(4-trifluoromethylphenyl)aminocarbonylamino]-5β-cholan-24-oate
• CAS: 861399-65-7
• 化学式: C₆₀H₈₉F₆N₇O₄
• 分子量: 1086.4
• InChiKey: PYKIICALIMHQKI-WXLHBKEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.96
• 重原子数：
  77.0
• 可旋转键数：
  28.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  157.32
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  eicosyl 3α-azido-7α,12α-bis-[(4-trifluoromethylphenyl)aminocarbonylamino]-5β-cholan-24-oate 在 三甲基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (R)-4-{(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-[3-(4-trifluoromethyl-phenyl)-ureido]-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid icosyl ester
  参考文献：
  名称：

  Substrate Discrimination by Cholapod Anion Receptors:  Geometric Effects and the “Affinity−Selectivity Principle”

  摘要：

  Cholapod anion receptors can achieve high affinities while maintaining compatibility with nonpolar media. Previously they have been shown to transport anions across cell and vesicle membranes. In the present work, the scope of the architecture is expanded and structure-selectivity relationships are investigated. Eight new receptors have been synthesized, with up to six H-bond donor centers. Using Cram's extraction method, these compounds plus five known examples have been tested for binding to seven monovalent anions (tetraethylammonium salts, wet chloroform as solvent). Association constants in excess of 10(10) M-1 have been measured for several pairings. Selectivities vary with receptor geometry, as expected. More remarkably, they also depend on receptor strength: more powerful receptors show a wider range of binding free energies, and therefore a greater spread of Ka(X-)/K-a(Y-). This "affinity-selectivity" effect can be derived from empirical relationships for H-bond strengths, and could prove widely operative in supramolecular chemistry.

  DOI：

  10.1021/ja0524144
• 作为产物：
  描述：

  eicosyl 3α-azido-7α,12α-di-[N-(t-butyloxycarbonyl)amino]-5β-cholan-24-oate 在 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 eicosyl 3α-azido-7α,12α-bis-[(4-trifluoromethylphenyl)aminocarbonylamino]-5β-cholan-24-oate
  参考文献：
  名称：

  Substrate Discrimination by Cholapod Anion Receptors:  Geometric Effects and the “Affinity−Selectivity Principle”

  摘要：

  Cholapod anion receptors can achieve high affinities while maintaining compatibility with nonpolar media. Previously they have been shown to transport anions across cell and vesicle membranes. In the present work, the scope of the architecture is expanded and structure-selectivity relationships are investigated. Eight new receptors have been synthesized, with up to six H-bond donor centers. Using Cram's extraction method, these compounds plus five known examples have been tested for binding to seven monovalent anions (tetraethylammonium salts, wet chloroform as solvent). Association constants in excess of 10(10) M-1 have been measured for several pairings. Selectivities vary with receptor geometry, as expected. More remarkably, they also depend on receptor strength: more powerful receptors show a wider range of binding free energies, and therefore a greater spread of Ka(X-)/K-a(Y-). This "affinity-selectivity" effect can be derived from empirical relationships for H-bond strengths, and could prove widely operative in supramolecular chemistry.

  DOI：

  10.1021/ja0524144