(3S,10R,13S,17S)-3-hydroxy-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide | 1360163-54-7

• 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: (3S,10R,13S,17S)-3-hydroxy-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
• 英文别名: (3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
• CAS: 1360163-54-7
• 化学式: C₂₂H₃₅NO₃
• 分子量: 361.525
• InChiKey: YWKFLEVHYFQOKN-SPHVDITISA-N

物化性质

• 沸点：
  467.9±55.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,10R,13S,17S)-3-hydroxy-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide 在 N-甲基咪唑 、 四丁基氟化铵 、 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-5-methylhexan-1-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Action of 20R-Hydroxyvitamin D3

  摘要：

  The non-naturally occurring 20R epimer of 20-hydroxyvitamin D3 is synthesized based on chemical design and hypothesis. The 20R isomer is separated by semipreparative HPLC, and its structure is characterized. A comparison of 20R isomer to its 20S counterpart in biological evaluation demonstrates that they have different behaviors in antiproliferative and metabolic studies.

  DOI：

  10.1021/jm201478e
• 作为产物：
  描述：

  3-羟基-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-17-羧酸 、 二甲羟胺盐酸盐 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以75.9%的产率得到(3S,10R,13S,17S)-3-hydroxy-N-methoxy-N,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Action of 20R-Hydroxyvitamin D3

  摘要：

  The non-naturally occurring 20R epimer of 20-hydroxyvitamin D3 is synthesized based on chemical design and hypothesis. The 20R isomer is separated by semipreparative HPLC, and its structure is characterized. A comparison of 20R isomer to its 20S counterpart in biological evaluation demonstrates that they have different behaviors in antiproliferative and metabolic studies.

  DOI：

  10.1021/jm201478e