15α-ethoxycarbonylmethyl-4-androstene-3,17-dione | 85234-11-3

• 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: 15α-ethoxycarbonylmethyl-4-androstene-3,17-dione
• 英文别名: ethyl 2-[(8R,9S,10R,13S,14S,15R)-10,13-dimethyl-3,17-dioxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-15-yl]acetate
• CAS: 85234-11-3
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: MGGHBLQOGHARST-ZGACRRMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  15α-ethoxycarbonylmethyl-4-androstene-3,17-dione 在 sodium hydroxide 、 sodium tetrahydroborate 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：

  15α-bis(ethoxycarbonyl)methyl-4-androstene-3,17-dione 在 硫酸 作用下， 生成 15α-ethoxycarbonylmethyl-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

文献信息

• 4,15-Disubstituierte 4-Androsten-3,17-dione und Verfahren zu deren Herstellung
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0286578A1

  公开（公告）日：1988-10-12

  1.) 4,15-Disubstituierte 4-Androsten-3,17-dione der allgemeinen Formel I worin Ra einen gesättigten oder ungesättigten, gegebenenfalls substituierten Alkylrest mit 1-10 Kohlenstoffatomen, wobei Ra in der α- oder β-Position steht, Rb ein Halogen, eine Azido-, eine -OR₁ oder -NR₂R₃ Gruppe, wobei R₁ ein Wasserstoffatom oder eine Acylgruppe mit 1-10 Kohlenstoffatomen und R₂ und R₃ gleich oder verschieden sind und jeweils ein Wasserstoffatom, eine Alkyl-oder Acylgruppe mit jeweils 1-10 Kohlenstoffatomen darstellen, bedeu­ten. Die neuen Verbindungen der allgemeinen Formel 1 sind zur Fertilitätskontrolle und zur Behandlung von Krankheiten geeignet, die durch Östrogene hervorgerufen werden.

  1.) 通式 I 的 4,15-二取代-4-雄烯-3,17-二酮 其中 Ra 是具有 1-10 个碳原子的饱和或不饱和、任选取代的烷基，Ra 位于 α 或 β 位、 Rb 是卤素、叠氮基、-OR₁ 或 -NR₂R₃ 基团，其中 R₁ 是氢原子或具有 1-10 个碳原子的酰基，R₂ 和 R₃ 相同或不同，各自代表氢原子、烷基或酰基，各自具有 1-10 个碳原子。 通式 1 的新化合物适用于控制生育和治疗由雌激素引起的疾病。
• Syntheses OF 15α- and 15β-carboxymethyltestosterone bovine serum albumin conjugates: Characteristics of the antisera to testosterone
  作者：Yoshinori Miyake、Yoshiaki Kubo、Setsuko Iwabuchi、Masaharu Kojima

  DOI：10.1016/0039-128x(82)90037-x

  日期：1982.9

  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.