(16R)-spiro<3-methoxy-17-oxoestra-1,3,5(10)-triene-16,2'-oxirane> | 162301-52-2

• 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: (16R)-spiro<3-methoxy-17-oxoestra-1,3,5(10)-triene-16,2'-oxirane>
• CAS: 162301-52-2
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: MELZXSYATPMSSA-NLPMXTIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  38.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (16R)-spiro<3-methoxy-17-oxoestra-1,3,5(10)-triene-16,2'-oxirane> 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以96%的产率得到(16R)-spiro<17β-hydroxy-3-methoxyestra-1,3,5(10)-triene-16,2'-oxirane>
  参考文献：
  名称：

  Stereoselectivity in the epoxidation and cis-hydroxylation of 16-methylene-estra-1,3,5(10)-trienes

  摘要：

  Epoxidation of 3-methoxy-16-methylene-estra-1,3,5(10)-trien-17-one in the presence of alkaline hydrogen peroxide gives rise to (16R)- and (16S)-spiro[3-methoxy-17-oxoestra-1,3,5(10)-triene-16,2'-oxirane] in similar proportions. Epoxidation of the corresponding 16-methlene 17 beta-alcohol and 16-methylene-17 beta-acetate with m-chloroperbenzoic acid does not display any significant directing effects associated with allylic functionality, whereas Sharpless epoxidation of the 16-methylene 17 beta-alcohol is highly stereoselective, leading exclusively to the (16R) isomer. cis-Hydroxylation of the 16-methylene 17-ketone with osmium tetroxide/4-methylmorpholine-4-oxide proceeds stereoselectively to give mainly 16 alpha-hydroxy-16 beta-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17-one. The isomeric addition products derived from these reactions are correlated by appropriate interconversions, and the assignments are corroborated by comparative reactivity of derived products.

  DOI：

  10.1016/0039-128x(94)90018-3
• 作为产物：
  描述：

  3-methoxy-16-methylene-estra-1,3,5(10)-trien-17-one 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 (16S)-spiro<3-methoxy-17-oxoestra-1,3,5(10)-triene-16,2'-oxirane> 、 (16R)-spiro<3-methoxy-17-oxoestra-1,3,5(10)-triene-16,2'-oxirane>
  参考文献：
  名称：

  Stereoselectivity in the epoxidation and cis-hydroxylation of 16-methylene-estra-1,3,5(10)-trienes

  摘要：

  Epoxidation of 3-methoxy-16-methylene-estra-1,3,5(10)-trien-17-one in the presence of alkaline hydrogen peroxide gives rise to (16R)- and (16S)-spiro[3-methoxy-17-oxoestra-1,3,5(10)-triene-16,2'-oxirane] in similar proportions. Epoxidation of the corresponding 16-methlene 17 beta-alcohol and 16-methylene-17 beta-acetate with m-chloroperbenzoic acid does not display any significant directing effects associated with allylic functionality, whereas Sharpless epoxidation of the 16-methylene 17 beta-alcohol is highly stereoselective, leading exclusively to the (16R) isomer. cis-Hydroxylation of the 16-methylene 17-ketone with osmium tetroxide/4-methylmorpholine-4-oxide proceeds stereoselectively to give mainly 16 alpha-hydroxy-16 beta-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17-one. The isomeric addition products derived from these reactions are correlated by appropriate interconversions, and the assignments are corroborated by comparative reactivity of derived products.

  DOI：

  10.1016/0039-128x(94)90018-3