3,3-ethylenedioxy-7-oximino-5-androsten-17β-yl acetate | 81623-96-3

• 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: 3,3-ethylenedioxy-7-oximino-5-androsten-17β-yl acetate
• 英文别名: 17β-Acetoxy-3-ethylendioxy-7-syn-oxyimino-5-androsten
• CAS: 81623-96-3
• 化学式: C₂₃H₃₃NO₅
• 分子量: 403.519
• InChiKey: ZMBBAQBFTMVFQE-BJYRRAHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.35
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,3-ethylenedioxy-7-oximino-5-androsten-17β-yl acetate 在 sodium 作用下， 反应 3.0h， 生成 7β-hemisuccinamido-3,3-ethylenedioxy-5-androsten-17β-ol methyl ester
  参考文献：
  名称：

  Synthesis and stereochemistry of 7β- and 7α-amino-, acetamido-, hemisuccinamido- and terephthalamido derivatives of testosterone

  摘要：

  The reduction of 3-ethylenedioxy-7-oximino-5-androsten-17 beta-yl acetate and of its 17 beta-tetrahydropyranyl ether analog with sodium in ethanol, followed by thin-layer chromatography, allowed the isolation of the corresponding 17 beta-hydroxy- and 17 beta-tetrahydropyranyloxy-5-en-7 beta- and 7 alpha-amines which were also characterized as 7-acetamides. The acylation of the two epimeric 17 beta-hydroxy-5-en-7-amines with succinic anhydride followed by selective saponification of the 17 beta-hemisuccinate group and diazomethane esterification, gave the corresponding 17 beta-hydroxy-5-en-7 beta- and 7 alpha-hemisuccinamido methyl esters characterized also as 17 beta-acetates. On the other hand, the acylation of the two 17 beta-tetrahydropyranyloxy-5-en-7-amines with the acid chloride of terephthalic acid monomethyl ester led to the more rigid 7 beta- and 7 alpha-terephthalamido methyl ester side-chains. The acidolysis of the 3-ethyleneketal protecting group of the preceding 5-en-7-N-acyl derivatives regenerated the 4-en-3-oxo function while the 17 beta-tetrahydropyranyl ether group was cleaved simultaneously into the 17 beta-alcohol. The four desired 7 beta- and 7 alpha-hemisuccinamido- and terephthalamido carboxylic side-chain derivatives of 17 beta-hydroxy-4-androsten-3-one (testosterone) were finally obtained by saponification of the corresponding methyl esters.

  DOI：

  10.1016/0039-128x(81)90082-9
• 作为产物：
  描述：

  3,3-ethylenedioxy-7-oxo-5-androsten-17β-yl acetate 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 以97%的产率得到3,3-ethylenedioxy-7-oximino-5-androsten-17β-yl acetate
  参考文献：
  名称：

  Synthesis and stereochemistry of 7β- and 7α-amino-, acetamido-, hemisuccinamido- and terephthalamido derivatives of testosterone

  摘要：

  The reduction of 3-ethylenedioxy-7-oximino-5-androsten-17 beta-yl acetate and of its 17 beta-tetrahydropyranyl ether analog with sodium in ethanol, followed by thin-layer chromatography, allowed the isolation of the corresponding 17 beta-hydroxy- and 17 beta-tetrahydropyranyloxy-5-en-7 beta- and 7 alpha-amines which were also characterized as 7-acetamides. The acylation of the two epimeric 17 beta-hydroxy-5-en-7-amines with succinic anhydride followed by selective saponification of the 17 beta-hemisuccinate group and diazomethane esterification, gave the corresponding 17 beta-hydroxy-5-en-7 beta- and 7 alpha-hemisuccinamido methyl esters characterized also as 17 beta-acetates. On the other hand, the acylation of the two 17 beta-tetrahydropyranyloxy-5-en-7-amines with the acid chloride of terephthalic acid monomethyl ester led to the more rigid 7 beta- and 7 alpha-terephthalamido methyl ester side-chains. The acidolysis of the 3-ethyleneketal protecting group of the preceding 5-en-7-N-acyl derivatives regenerated the 4-en-3-oxo function while the 17 beta-tetrahydropyranyl ether group was cleaved simultaneously into the 17 beta-alcohol. The four desired 7 beta- and 7 alpha-hemisuccinamido- and terephthalamido carboxylic side-chain derivatives of 17 beta-hydroxy-4-androsten-3-one (testosterone) were finally obtained by saponification of the corresponding methyl esters.

  DOI：

  10.1016/0039-128x(81)90082-9