(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid icosyl ester | 266326-10-7

• 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: (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid icosyl ester
• 英文别名: icosyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-triamino-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 266326-10-7
• 化学式: C₄₄H₈₃N₃O₂
• 分子量: 686.162
• InChiKey: PXZMBEIQUMGULK-CWKBHGIBSA-N

物化性质

• 沸点：
  713.2±60.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  49
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异氰酸苯酯 、 (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid icosyl ester 以 四氢呋喃 为溶剂， 以75%的产率得到eicosyl 3α,7α,12α-tri-[(phenylaminocarbonyl)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：

  溴代二十烷 在 cesium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Triamino-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid icosyl ester
  参考文献：
  名称：

  An Extraction-Based Assay for Neutral Anionophores: The Measurement of High Binding Constants to Steroidal Receptors in a Nonpolar Solvent

  摘要：

  The extraction-hased protocol for measuring binding constants. developed by Cram and co-workers, has been extended for use with anionic substrates. The method is especially useful for high-affinity receptors, allowing very high binding constants to tic measured in nonpolar solvents. Distribution constants K, between chloroform and water have been obtained for tetraethylammonium chloride and bromide, thus calibrating the method for these two substrates. Application to steroidal podands 5-9 has confirmed the ability of electron-withdrawing groups to enhance hydrogen-bond donor capabilities. Binding constants of approximate to 3 x 10(7) M-1 have been measured for the most powerful receptor 7 An X-ray crystal structure of 15. the methyl ester analogue of 7, reveals a well-defined binding site preorganised for anion recognition.

  DOI：

  10.1002/1521-3765(20020503)8:9<2197::aid-chem2197>3.0.co;2-j

文献信息

• An Extraction-Based Assay for Neutral Anionophores: The Measurement of High Binding Constants to Steroidal Receptors in a Nonpolar Solvent
  作者：Alan J. Ayling、Shay Broderick、John P. Clare、Anthony P. Davis、M. Nieves Pérez-Payán、Maarit Lahtinen、Maija J. Nissinen、Kari Rissanen

  DOI：10.1002/1521-3765(20020503)8:9<2197::aid-chem2197>3.0.co;2-j

  日期：2002.5.3

  The extraction-hased protocol for measuring binding constants. developed by Cram and co-workers, has been extended for use with anionic substrates. The method is especially useful for high-affinity receptors, allowing very high binding constants to tic measured in nonpolar solvents. Distribution constants K, between chloroform and water have been obtained for tetraethylammonium chloride and bromide, thus calibrating the method for these two substrates. Application to steroidal podands 5-9 has confirmed the ability of electron-withdrawing groups to enhance hydrogen-bond donor capabilities. Binding constants of approximate to 3 x 10(7) M-1 have been measured for the most powerful receptor 7 An X-ray crystal structure of 15. the methyl ester analogue of 7, reveals a well-defined binding site preorganised for anion recognition.
• Substrate Discrimination by Cholapod Anion Receptors:  Geometric Effects and the “Affinity−Selectivity Principle”
  作者：John P. Clare、Alan J. Ayling、Jean-Baptiste Joos、Adam L. Sisson、Germinal Magro、M. Nieves Pérez-Payán、Timothy N. Lambert、Rameshwer Shukla、Bradley D. Smith、Anthony P. Davis

  DOI：10.1021/ja0524144

  日期：2005.8.1

  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.