14-epi-2-methylene-1α,25-dihydroxy-19-nortachysterol | 1298075-91-8

• 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: 14-epi-2-methylene-1α,25-dihydroxy-19-nortachysterol
• 英文别名: (1R,3R)-5-[(E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl]ethenyl]-2-methylidenecyclohex-4-ene-1,3-diol
• CAS: 1298075-91-8
• 化学式: C₂₇H₄₂O₃
• 分子量: 414.629
• InChiKey: AGHGGWNXJODIIY-AMDICAQWSA-N

物化性质

• 沸点：
  575.7±50.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  14-epi-2-methylene-1α,25-dihydroxy-19-nortachysterol 在 Wilkinson's catalyst 、 氢气 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 以47%的产率得到14-epi-2β-methyl-1α,25-dihydroxy-19-nortachysterol
  参考文献：
  名称：

  Development of 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor

  摘要：

  In the study of the synthesis of 14-epi-19-norprevitamin D-3, we found 14-epi-19-nortachysterol derivatives through C6,7-cis/trans isomerization. We also succeeded in their chemical synthesis and revealed their marked stability and potent VDR binding affinity. To the best of our knowledge, this is the first isolation of stable tachysterol analogues. Surprisingly, 14-epi-19-nortachysterol derivatives exhibited an unprecedented binding configurations for the ligand binding pocket in hVDR, C5,6-s-trans and C7,8-s-trans triene configurations, which were opposite the natural C7,8-ene-configuration of 1 alpha,25(OH)(2)D-3.

  DOI：

  10.1021/ja201481j
• 作为产物：
  描述：

  methyl (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylenecyclohexanecarboxylate 在 吡啶 、 正丁基锂 、 tetra-n-propylammonium perruthenate. 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.75h， 生成 14-epi-2-methylene-1α,25-dihydroxy-19-nortachysterol
  参考文献：
  名称：

  Development of 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor

  摘要：

  In the study of the synthesis of 14-epi-19-norprevitamin D-3, we found 14-epi-19-nortachysterol derivatives through C6,7-cis/trans isomerization. We also succeeded in their chemical synthesis and revealed their marked stability and potent VDR binding affinity. To the best of our knowledge, this is the first isolation of stable tachysterol analogues. Surprisingly, 14-epi-19-nortachysterol derivatives exhibited an unprecedented binding configurations for the ligand binding pocket in hVDR, C5,6-s-trans and C7,8-s-trans triene configurations, which were opposite the natural C7,8-ene-configuration of 1 alpha,25(OH)(2)D-3.

  DOI：

  10.1021/ja201481j