3-(3,5-dimethylphenyl)carbamoyl-N-allyl-deoxycholan-24-amide | 251091-76-6

• 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: 3-(3,5-dimethylphenyl)carbamoyl-N-allyl-deoxycholan-24-amide
• 英文别名: [(3R,5R,8R,9S,10S,12S,13R,14S,17R)-12-hydroxy-10,13-dimethyl-17-[(2R)-5-oxo-5-(prop-2-enylamino)pentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-(3,5-dimethylphenyl)carbamate
• CAS: 251091-76-6
• 化学式: C₃₆H₅₄N₂O₄
• 分子量: 578.836
• InChiKey: OCJBDSIVABPYDI-QSEFOZQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,5-dimethylphenyl)carbamoyl-N-allyl-deoxycholan-24-amide 在 偶氮二异丁腈 作用下， 以 甲苯 为溶剂， 反应 44.0h， 生成 3-bis-(3,5-dimethylphenyl)carbamoyl-12-(3,5-dichlorophenyl)carbamoyl-N-(3-trimethoxysilylpropylthio)propyl-deoxycholan-24-amide
  参考文献：
  名称：

  Synthesis of a new family of four deoxycholic acid derived chiral stationary phases and their evaluation in the HPLC resolution of racemic compounds

  摘要：

  Four new chiral selectors obtained by suitable derivatization of the hydroxyl groups of the deoxycholic acid with two identical (homoderivatized) or different (heteroderivatized) arylisocyanates have been prepared and linked covalently to silica gel to obtain new chiral stationary phases (CSPs) for the HPLC separation of enantiomers. The CSPs containing two identical substituents are able to enantiodiscriminate different classes of racemic compounds, or the same racemates to a different extent, a property which depends on the different electronic character of the arylcarbamate moieties. The heteroderivatized CSPs retain the character of the two homoderivatized phases: however, the relative position of the two different arylcarbamate moieties on the deoxycholic backbone strongly affects the enantiodiscrimination capability of these two CSPs. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00337-7
• 作为产物：
  描述：

  去氧胆酸 在 4-二甲氨基吡啶 、 三正丁胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 18.17h， 生成 3-(3,5-dimethylphenyl)carbamoyl-N-allyl-deoxycholan-24-amide
  参考文献：
  名称：

  Synthesis of a new family of four deoxycholic acid derived chiral stationary phases and their evaluation in the HPLC resolution of racemic compounds

  摘要：

  Four new chiral selectors obtained by suitable derivatization of the hydroxyl groups of the deoxycholic acid with two identical (homoderivatized) or different (heteroderivatized) arylisocyanates have been prepared and linked covalently to silica gel to obtain new chiral stationary phases (CSPs) for the HPLC separation of enantiomers. The CSPs containing two identical substituents are able to enantiodiscriminate different classes of racemic compounds, or the same racemates to a different extent, a property which depends on the different electronic character of the arylcarbamate moieties. The heteroderivatized CSPs retain the character of the two homoderivatized phases: however, the relative position of the two different arylcarbamate moieties on the deoxycholic backbone strongly affects the enantiodiscrimination capability of these two CSPs. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00337-7