Acetic acid (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(R)-3-(allyl-methyl-carbamoyl)-1-methyl-propyl]-12-(3,5-dinitro-phenylcarbamoyloxy)-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester | 874212-72-3

• 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: Acetic acid (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(R)-3-(allyl-methyl-carbamoyl)-1-methyl-propyl]-12-(3,5-dinitro-phenylcarbamoyloxy)-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
• CAS: 874212-72-3
• 化学式: C₃₇H₅₂N₄O₁₀
• 分子量: 712.841
• InChiKey: WIQYZNYJBMHROK-SMAFMHIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.65
• 重原子数：
  51.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  191.45
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(R)-3-(allyl-methyl-carbamoyl)-1-methyl-propyl]-12-(3,5-dinitro-phenylcarbamoyloxy)-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 在 盐酸 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 25.0h， 生成 N-allyl-N-methyl-3-hydroxy-7-(2-naphthyl)carbamoyloxy-12-(3,5-dinitriphenyl)carbamoyloxycholan-24-amide
  参考文献：
  名称：

  Effect of the presence of a free hydroxyl group on the enantiodiscrimination properties of cholic acid based CSPs bearing 2-naphthylcarbamate and 3,5-dinitrophenylcarbamate moieties in the HPLC resolution of racemic compounds

  摘要：

  Two new chiral selectors, obtained by derivatizing two of the three hydroxyl groups of cholic acid with 2-naphthylisocyanate and 3,5-dinitrophenylisocyanate, have been prepared and linked to silica gel to obtain chiral stationary phases (CSPs) for the HPLC separation of enantiomers. The enantiodiscriminating capability of the two CSPs has been compared to that of the analogous CSP obtained from an exhaustively derivatized cholic acid based selector, in order to establish the effect of the presence of a free hydroxyl group on the enantiodiscrimination properties of this kind of selector. The chromatographic results demonstrate that the enantio selectivity of these selectors strongly depends on the position of the hydroxyl group on the cholestanic backbone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.036
• 作为产物：
  描述：

  3,5-二异氰酸硝基苯 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 Acetic acid (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(R)-3-(allyl-methyl-carbamoyl)-1-methyl-propyl]-12-(3,5-dinitro-phenylcarbamoyloxy)-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Effect of the presence of a free hydroxyl group on the enantiodiscrimination properties of cholic acid based CSPs bearing 2-naphthylcarbamate and 3,5-dinitrophenylcarbamate moieties in the HPLC resolution of racemic compounds

  摘要：

  Two new chiral selectors, obtained by derivatizing two of the three hydroxyl groups of cholic acid with 2-naphthylisocyanate and 3,5-dinitrophenylisocyanate, have been prepared and linked to silica gel to obtain chiral stationary phases (CSPs) for the HPLC separation of enantiomers. The enantiodiscriminating capability of the two CSPs has been compared to that of the analogous CSP obtained from an exhaustively derivatized cholic acid based selector, in order to establish the effect of the presence of a free hydroxyl group on the enantiodiscrimination properties of this kind of selector. The chromatographic results demonstrate that the enantio selectivity of these selectors strongly depends on the position of the hydroxyl group on the cholestanic backbone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.036