(R)-4-{(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-[3-(4-nitro-phenyl)-ureido]-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester | 861399-64-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-4-{(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-[3-(4-nitro-phenyl)-ureido]-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester
• CAS: 861399-64-6
• 化学式: C₃₉H₅₃N₇O₈
• 分子量: 747.892
• InChiKey: ULYNBUXWTHHHPU-SHZUJHEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  54.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  220.86
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (R)-4-{(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-[3-(4-nitro-phenyl)-ureido]-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester 、 三氟乙酸酐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以44%的产率得到methyl 3α-[(trifluoromethylcarbonyl)amino]-7α,12α-di[N-(4-nitrophenylaminocarbonyl)amino]-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
• 作为产物：
  描述：

  (R)-4-{(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3-Azido-10,13-dimethyl-7,12-bis-[3-(4-nitro-phenyl)-ureido]-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester 在 三甲基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以97%的产率得到(R)-4-{(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-[3-(4-nitro-phenyl)-ureido]-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl 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