17α-hydroperoxy-16α-methyl-20-oxopregn-5-en-3β-yl acetate | 115040-05-6

• 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: 17α-hydroperoxy-16α-methyl-20-oxopregn-5-en-3β-yl acetate
• 英文别名: 3β-Acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one；3β-acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one；3beta-Acetoxy-17alpha-hydroperoxy-16alpha-methylpregn-5-en-20-one；[(3S,8R,9S,10R,13S,14S,16R,17R)-17-acetyl-17-hydroperoxy-10,13,16-trimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 115040-05-6
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: WCCVKAYHSCWCEN-KSXMLDNHSA-N

物化性质

• 熔点：
  157.5 °C (decomp)
• 沸点：
  514.8±50.0 °C(predicted)
• 密度：
  1.16±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：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17α-hydroperoxy-16α-methyl-20-oxopregn-5-en-3β-yl acetate 在 potassium iodide 、 sodium sulfite 作用下， 以 丙酮 、 水 为溶剂， 反应 1.0h， 以98%的产率得到17α-hydroxy-16α-methyl-20-oxopregn-5-en-3β-yl acetate
  参考文献：
  名称：

  Autooxidation of Δ17(20)-20-hydroxy derivatives of steroids. Synthesis of 3β-acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one and its reduction to 17α-hydroxy derivative

  摘要：

  An efficient procedure was proposed for the synthesis of 3 beta-acetoxy-17 alpha-hydroperoxy-16 alpha-methyl-pregn-5-en-20-one. Optimal conditions were found for the combined process including 1,4-addition of methyl-magnesium bromide at the Delta(16)-20-oxo fragment of dehydropregnenolone acetate and autooxidation of resulting bromomagnesium 3 beta-acetoxy-16 alpha-methylpregna-5,17(20)-dien-20-olate. The subsequent reduction of the 17 alpha-hydroperoxy group and hydrolysis of the 3 beta-acetoxy group afforded 17 alpha-hydroxy-16 alpha-methyl-substituted dehydropregnenolone acetate and its 3-hydroxy analog in high yield.

  DOI：

  10.1134/s1070428011010052
• 作为产物：
  描述：

  甲基溴化镁 、 16-脱氢孕烯醇酮乙酸酯 在 copper(l) chloride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 0.33h， 以88%的产率得到17α-hydroperoxy-16α-methyl-20-oxopregn-5-en-3β-yl acetate
  参考文献：
  名称：

  Autooxidation of Δ17(20)-20-hydroxy derivatives of steroids. Synthesis of 3β-acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one and its reduction to 17α-hydroxy derivative

  摘要：

  An efficient procedure was proposed for the synthesis of 3 beta-acetoxy-17 alpha-hydroperoxy-16 alpha-methyl-pregn-5-en-20-one. Optimal conditions were found for the combined process including 1,4-addition of methyl-magnesium bromide at the Delta(16)-20-oxo fragment of dehydropregnenolone acetate and autooxidation of resulting bromomagnesium 3 beta-acetoxy-16 alpha-methylpregna-5,17(20)-dien-20-olate. The subsequent reduction of the 17 alpha-hydroperoxy group and hydrolysis of the 3 beta-acetoxy group afforded 17 alpha-hydroxy-16 alpha-methyl-substituted dehydropregnenolone acetate and its 3-hydroxy analog in high yield.

  DOI：

  10.1134/s1070428011010052

文献信息

• Products of the decomposition of 3β-acetoxy-17α-hydroperoxy-16α-methylpregn-5-en-20-one
  作者：T. S. Kolyvanova、V. I. Bayunova、G. A. Bogdanova、E. F. Kuleshova、G. S. Grinenko

  DOI：10.1007/bf00757968

  日期：1987.12