15α-bis(ethoxycarbonyl)methyl-4-androstene-3,17-dione | 85234-09-9

• 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: 15α-bis(ethoxycarbonyl)methyl-4-androstene-3,17-dione
• CAS: 85234-09-9
• 化学式: C₂₆H₃₆O₆
• 分子量: 444.568
• InChiKey: HCQKKLFTZOQPKF-FFSDMBQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  15α-bis(ethoxycarbonyl)methyl-4-androstene-3,17-dione 在 sodium hydroxide 、 sodium tetrahydroborate 、 硫酸 作用下， 以 乙醇 为溶剂， 生成 15α-Carboxymethyltestosterone
  参考文献：
  名称：

  Syntheses OF 15α- and 15β-carboxymethyltestosterone bovine serum albumin conjugates: Characteristics of the antisera to testosterone

  摘要：

  Syntheses of 15 alpha- and 15 beta-carboxymethyltestosterone (15 alpha- and 15 beta-CMT) were investigated in order to prepare testosterone-bovine serum albumin conjugates for radioimmunoassays of testosterone. A mixture of 15 alpha- and 15 beta-bis(ethoxycarbonyl)methyl-3 beta-hydroxy-5-androsten-17-one (IIa and IIb) obtained by a reaction of 3 beta-hydroxy-5,15-androstadien-17-one (I) and sodium diethyl malonate was oxidized to afford a mixture of 15 alpha- and 15 beta-bis(ethoxycarbonyl)methyl-4-androstene-3, 17-dione (Va and Vb). After the separation by silica gel chromatography, each epimer obtained was hydrolyzed by acid, followed by decarboxylation, and selective reduction of the 17-ketone to give 15 alpha- and 15 beta-CMT. The antisera, generated in rabbits by immunization with the bovine serum albumin (BSA) conjugates of 15 alpha- and 15 beta-CMT, respectively, exhibited high specificity for testosterone.

  DOI：

  10.1016/0039-128x(82)90037-x
• 作为产物：
  描述：

  15-bis(ethoxycarbonyl)methyl-3β-hydroxy-5-androsten-17-one 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以26%的产率得到15α-bis(ethoxycarbonyl)methyl-4-androstene-3,17-dione
  参考文献：
  名称：

  Syntheses OF 15α- and 15β-carboxymethyltestosterone bovine serum albumin conjugates: Characteristics of the antisera to testosterone

  摘要：

  Syntheses of 15 alpha- and 15 beta-carboxymethyltestosterone (15 alpha- and 15 beta-CMT) were investigated in order to prepare testosterone-bovine serum albumin conjugates for radioimmunoassays of testosterone. A mixture of 15 alpha- and 15 beta-bis(ethoxycarbonyl)methyl-3 beta-hydroxy-5-androsten-17-one (IIa and IIb) obtained by a reaction of 3 beta-hydroxy-5,15-androstadien-17-one (I) and sodium diethyl malonate was oxidized to afford a mixture of 15 alpha- and 15 beta-bis(ethoxycarbonyl)methyl-4-androstene-3, 17-dione (Va and Vb). After the separation by silica gel chromatography, each epimer obtained was hydrolyzed by acid, followed by decarboxylation, and selective reduction of the 17-ketone to give 15 alpha- and 15 beta-CMT. The antisera, generated in rabbits by immunization with the bovine serum albumin (BSA) conjugates of 15 alpha- and 15 beta-CMT, respectively, exhibited high specificity for testosterone.

  DOI：

  10.1016/0039-128x(82)90037-x