16-methylene-17α-methyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene | 2436-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 16-methylene-17α-methyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene
• CAS: 2436-36-4
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: OIJQDVNIQZBOJJ-MJCUULBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  16-methylene-17α-methyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene 在 N-溴代丁二酰亚胺(NBS) 、 高氯酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以45%的产率得到16α-methyl-16β-bromomethyl-3-methoxy-1,3,5(10)-estratrien-17-one
  参考文献：
  名称：

  Steroids 35: Synthesis of 16,16-dimethyl-17β-hydroxysteroids

  摘要：

  The reaction of 16-methylene-17-ketosteroids (Ia), (Ic) and (Ie) with methyl magnesium iodide yields 16-methylene-17 alpha-methyl-17 beta-hydroxysteroids (IIa), (IIb) and (IId). These are subjected to the addition of hypobromous acid and the subsequent anionotropic rearrangement to convert them into 16 alpha-methyl-16 beta-bromomethyl-17-ketosteroids (Va), (Vb) and (Vd). These were reduced with LiA1H4 to obtain 16,16-dimethyl-17 beta-hydroxysteroids (VIa), (VIb) and (VId). Compounds (VIIa) and (VIIe) were selectively deacetylated yielding (VIIb) and (VIId); these were then oxidized and hydrolyzed to convert them into (VIf) and (VIg).

  DOI：

  10.1016/0039-128x(88)90021-9
• 作为产物：
  描述：

  甲基碘化镁 、 3-methoxy-16-methylene-estra-1,3,5(10)-trien-17-one 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到16-methylene-17α-methyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene
  参考文献：
  名称：

  Steroids 35: Synthesis of 16,16-dimethyl-17β-hydroxysteroids

  摘要：

  The reaction of 16-methylene-17-ketosteroids (Ia), (Ic) and (Ie) with methyl magnesium iodide yields 16-methylene-17 alpha-methyl-17 beta-hydroxysteroids (IIa), (IIb) and (IId). These are subjected to the addition of hypobromous acid and the subsequent anionotropic rearrangement to convert them into 16 alpha-methyl-16 beta-bromomethyl-17-ketosteroids (Va), (Vb) and (Vd). These were reduced with LiA1H4 to obtain 16,16-dimethyl-17 beta-hydroxysteroids (VIa), (VIb) and (VId). Compounds (VIIa) and (VIIe) were selectively deacetylated yielding (VIIb) and (VIId); these were then oxidized and hydrolyzed to convert them into (VIf) and (VIg).

  DOI：

  10.1016/0039-128x(88)90021-9