N-allyl-N-methyl-3β-(2-naphthylcarbamoyl)oxy-7β,12β-dihydroxy-5β-cholan-24-amide | 473530-01-7

• 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: N-allyl-N-methyl-3β-(2-naphthylcarbamoyl)oxy-7β,12β-dihydroxy-5β-cholan-24-amide
• CAS: 473530-01-7
• 化学式: C₃₉H₅₄N₂O₅
• 分子量: 630.868
• InChiKey: SFHFMTPUGLMUIK-WUOTWJTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.42
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.1
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-allyl-N-methyl-3β-(2-naphthylcarbamoyl)oxy-7β,12β-dihydroxy-5β-cholan-24-amide 在 4-二甲氨基吡啶 、 偶氮二异丁腈 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 52.0h， 生成 N-methyl-N-[3-(3-(trimethoxysilyl)propylthio)propyl]-3β,7β-bis((2-naphthylcarbamoyl)oxy)-12β-((3,5-dinitrophenyl)carbamoyl)oxy-5β-cholan-24-amide
  参考文献：
  名称：

  Synthesis of four cholic acid-based CSPs containing 2-naphthoyl carbamate and 3,5-dinitrophenylcarbamate moieties and their evaluation in the HPLC resolution of racemic compounds

  摘要：

  Four new chiral selectors, obtained by derivatising the hydroxy groups of cholic acid with 2-naphthylisocyanate and 3,5-dinitrophenylisocyanate have been prepared and linked to silica gel to obtain new chiral stationary phases (CSPs) for the HPLC separation of enantiomers. The CSP containing only 2-naphthylcarbamate groups is able to separate the enantiomers of pi-acidic substrates, whereas the CSPs containing one 3,5-dinitrophenylcarbamate group and two 2-naphthyl carbamate moieties resolve pi-acidic racemic compounds as well as pi-basic substrates, with the observed enantiodiscriminating capabilities depending on the arrangement of the different carbamoyl units on the cholestanic backbone. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00317-8
• 作为产物：
  描述：

  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 16.17h， 生成 N-allyl-N-methyl-3β-(2-naphthylcarbamoyl)oxy-7β,12β-dihydroxy-5β-cholan-24-amide
  参考文献：
  名称：

  Synthesis of four cholic acid-based CSPs containing 2-naphthoyl carbamate and 3,5-dinitrophenylcarbamate moieties and their evaluation in the HPLC resolution of racemic compounds

  摘要：

  Four new chiral selectors, obtained by derivatising the hydroxy groups of cholic acid with 2-naphthylisocyanate and 3,5-dinitrophenylisocyanate have been prepared and linked to silica gel to obtain new chiral stationary phases (CSPs) for the HPLC separation of enantiomers. The CSP containing only 2-naphthylcarbamate groups is able to separate the enantiomers of pi-acidic substrates, whereas the CSPs containing one 3,5-dinitrophenylcarbamate group and two 2-naphthyl carbamate moieties resolve pi-acidic racemic compounds as well as pi-basic substrates, with the observed enantiodiscriminating capabilities depending on the arrangement of the different carbamoyl units on the cholestanic backbone. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00317-8