17β-acetoxy-5α-androstan-3,6-dione | 25469-53-8

• 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: 17β-acetoxy-5α-androstan-3,6-dione
• 英文别名: 17β-acetoxy-5α-androstane-3,6-dione；17β-Acetoxy-5α-androstan-3,6-dion；5α-Androstan-17β-ol-3,6-dion-acetat；17β-Acetoxy-5α-androstan-3.6-dion；17beta-Acetoxy-5alpha-androstane-3,6-dione；[(5S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3,6-dioxo-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
• CAS: 25469-53-8
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: GYIQNKQDGKJVEB-UWJAUCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  17β-acetoxy-5α-androstan-3,6-dione 在 盐酸 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 17b-羟基-5a-雄甾烷-3,6-二酮
  参考文献：
  名称：

  Mancini,F.; Sciaky,R., Gazzetta Chimica Italiana, 1967, vol. 97, p. 431 - 441

  摘要：

  DOI：
• 作为产物：
  描述：

  醋酸睾酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 3.0h， 生成 17β-acetoxy-5α-androstan-3,6-dione
  参考文献：
  名称：

  Synthesis and some reactions of 6-bromoandrogens: Potential affinity ligand and inactivator of estrogen synthetase

  摘要：

  The synthesis of epimeric 6-bromo-4-androstene-3,17-dione (1a and 1b), 6-bromotestosterone (2a and 2b) and its acetate (3a and 3b), and 6-bromo-16 alpha-acetoxy-4-androstene-3,17-dione (5a and 5b), and 6 beta-bromo-16 alpha-hydroxy-4-androstene-3,17-dione (4) is described. The interconversions among compounds 1, 2, and 3 are also studied. The 6 beta-isomer (1b, 2b, and 3b) was epimerized to the 6 alpha-isomer (1a, 2a and 3a) in carbon tetrachloride or chloroform-methanol (9:1) and the 6 alpha-isomer was isolated by fractional crystallization from the epimeric mixture. 6 alpha-Bromo isomer 1a was also epimerized back to 6 beta-bromo isomer 1b in chloroform-methanol (9:1). Two polymorphic forms of 6 beta-bromotestosterone acetate (3b) were isolated (mp. 114--117 degrees and 138--141 degrees). The 6 beta-bromo isomers were found to be unstable in methanol and decomposed to give 5 alpha-androstane-3,6-dione derivative (6). The results of irreversible inactivation of human placental androgen aromatase with some of these 6-bromoandrogens are discussed.

  DOI：

  10.1016/0039-128x(79)90085-0

文献信息

• Secoandrostansäuren als enantiomere prostaglandin-analoga—II
  作者：M. Baumgarth、K. Irmscher

  DOI：10.1016/0040-4020(75)80159-1

  日期：1975.1

  A synthesis of the enantiomeric tetrahydro-PGA1 analogue 48 is described. In addition the homoacid 50, its pentanor analogue 39 and its epimer 51, the 6-deoxy compounds 13 and 16 as well as the lactones 14, 53, 56 and 68 were prepared as compounds closely related to 48. Simple androstane derivatives served as starting materials for the syntheses. Key intermediates were 4, 32 and 63.

  描述了对映体四氢-PGA 1类似物48的合成。另外homoacid 50，其pentanor类似物39及其差向异构体51，所述6-脱氧化合物13和16以及内酯类14，53，56和68制备为密切相关的化合物48。简单的雄烷烷衍生物用作合成的起始材料。关键中间体是4、32和63。
• Szczepek, Wojciech J.; Gumulka, Jerzy; Jagodzinski, Jacek J., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1980, vol. 28, # 3, p. 165 - 172
  作者：Szczepek, Wojciech J.、Gumulka, Jerzy、Jagodzinski, Jacek J.

  DOI：——

  日期：——
• Morisawa,Y.; Tanabe,K., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 6, p. 1212 - 1217
  作者：Morisawa,Y.、Tanabe,K.

  DOI：——

  日期：——
• Synthesis and some reactions of 6-bromoandrogens: Potential affinity ligand and inactivator of estrogen synthetase
  作者：Mitsuteru Numazawa、Yoshio Osawa

  DOI：10.1016/0039-128x(79)90085-0

  日期：1979.9

  The synthesis of epimeric 6-bromo-4-androstene-3,17-dione (1a and 1b), 6-bromotestosterone (2a and 2b) and its acetate (3a and 3b), and 6-bromo-16 alpha-acetoxy-4-androstene-3,17-dione (5a and 5b), and 6 beta-bromo-16 alpha-hydroxy-4-androstene-3,17-dione (4) is described. The interconversions among compounds 1, 2, and 3 are also studied. The 6 beta-isomer (1b, 2b, and 3b) was epimerized to the 6 alpha-isomer (1a, 2a and 3a) in carbon tetrachloride or chloroform-methanol (9:1) and the 6 alpha-isomer was isolated by fractional crystallization from the epimeric mixture. 6 alpha-Bromo isomer 1a was also epimerized back to 6 beta-bromo isomer 1b in chloroform-methanol (9:1). Two polymorphic forms of 6 beta-bromotestosterone acetate (3b) were isolated (mp. 114--117 degrees and 138--141 degrees). The 6 beta-bromo isomers were found to be unstable in methanol and decomposed to give 5 alpha-androstane-3,6-dione derivative (6). The results of irreversible inactivation of human placental androgen aromatase with some of these 6-bromoandrogens are discussed.
• Mancini,F.; Sciaky,R., Gazzetta Chimica Italiana, 1967, vol. 97, p. 431 - 441
  作者：Mancini,F.、Sciaky,R.

  DOI：——

  日期：——