(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-Chloro-acetylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester | 452303-18-3

• 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-(2-Chloro-acetylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester
• CAS: 452303-18-3
• 化学式: C₄₆H₈₂ClNO₅
• 分子量: 764.614
• InChiKey: NGTFGJSILACPQK-KARBEAARSA-N

物化性质

• 沸点：
  803.2±65.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.31
• 重原子数：
  53.0
• 可旋转键数：
  25.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  95.86
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  氯乙酰异氰酸酯 、 (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-Chloro-acetylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester 在 三甲基氯硅烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以82%的产率得到eicosyl 3α-(chloroacetylamido)-7α,12α-bis(chloroacetylaminocarbonyloxy)-5β-cholan-24-oate
  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
• 作为产物：
  描述：

  胆酸 在 N,N-二甲基丙烯基脲 、 sodium azide 、 caesium carbonate 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 168026.0h， 生成 (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-Chloro-acetylamino)-7,12-dihydroxy-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