17β-Bromoacetylamino-4-androsten-3-one

• 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-Bromoacetylamino-4-androsten-3-one
• 英文别名: 2-bromo-N-[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]acetamide
• 化学式: C₂₁H₃₀BrNO₂
• 分子量: 408.379
• InChiKey: ALELCXPHBFSCGQ-ZKHIMWLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲氧基雄甾-3,5-二烯-17-酮 在 盐酸 、 ammonium acetate 、 sodium cyanoborohydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 96.5h， 生成 17β-Bromoacetylamino-4-androsten-3-one
  参考文献：
  名称：

  Synthesis of 16α-bromoacetoxy androgens and 17 β-bromoacetylamino-4-androsten-3-one: Potential affinity labels of human placental aromatase

  摘要：

  A novel synthesis of 16 alpha-hydroxy-4-androstene-3,17-dione (3), 16 alpha-hydroxy-4-androstene-3,6,17-trione (4), 17 beta-amino-5-androsten-3 beta-o1 (10) and 17 beta-amino-4-androsten-3-one (14) is described. 16 alpha-Bromoacetoxy-4-androstene-3,17-dione (5), 16 alpha-bromoacetoxy-4-androstene-3,6,17-trione (6) and 17 beta-bromoacetylamino-4-androsten-3-one (15) were synthesized as potentially selective irreversible inhibitors of androgen aromatases. 16 alpha-Bromo-4-androstene-3,17-dione (1) and 16 alpha-bromo-4-androstene-3,6,17-trione (2) were converted to compounds 3 and 4 in 80-90% yield by controlled stereospecific hydrolysis using sodium hydroxide in aqueous pyridine. Reductive amination of 3 beta-hydroxy-5-androsten-17-one and 3-methoxy-3,5-androstadien-17-one (11) using ammonium acetate and sodium cyanohydridoborate (NaBH3CN) and a subsequent treatment with acid gave the amines 10 and 14 respectively, as a salt. The corresponding 17-imino compounds 9 and 13 were also isolated from the reaction mixtures when methanol was used as a solvent for the reaction. The 16 alpha-hydroxyl compounds 3 and 4 and the 17 beta-amino compound 14 were converted to the corresponding bromoacetyl derivatives, 5, 6, and 15, with bromoacetic acid and N,N'-dicyclohexylcarbodiimide.

  DOI：

  10.1016/0039-128x(81)90029-5

文献信息

• Synthesis of 16α-bromoacetoxy androgens and 17 β-bromoacetylamino-4-androsten-3-one: Potential affinity labels of human placental aromatase
  作者：Numazawa Mitsuteru、Osawa Yoshio

  DOI：10.1016/0039-128x(81)90029-5

  日期：1981.8

  A novel synthesis of 16 alpha-hydroxy-4-androstene-3,17-dione (3), 16 alpha-hydroxy-4-androstene-3,6,17-trione (4), 17 beta-amino-5-androsten-3 beta-o1 (10) and 17 beta-amino-4-androsten-3-one (14) is described. 16 alpha-Bromoacetoxy-4-androstene-3,17-dione (5), 16 alpha-bromoacetoxy-4-androstene-3,6,17-trione (6) and 17 beta-bromoacetylamino-4-androsten-3-one (15) were synthesized as potentially selective irreversible inhibitors of androgen aromatases. 16 alpha-Bromo-4-androstene-3,17-dione (1) and 16 alpha-bromo-4-androstene-3,6,17-trione (2) were converted to compounds 3 and 4 in 80-90% yield by controlled stereospecific hydrolysis using sodium hydroxide in aqueous pyridine. Reductive amination of 3 beta-hydroxy-5-androsten-17-one and 3-methoxy-3,5-androstadien-17-one (11) using ammonium acetate and sodium cyanohydridoborate (NaBH3CN) and a subsequent treatment with acid gave the amines 10 and 14 respectively, as a salt. The corresponding 17-imino compounds 9 and 13 were also isolated from the reaction mixtures when methanol was used as a solvent for the reaction. The 16 alpha-hydroxyl compounds 3 and 4 and the 17 beta-amino compound 14 were converted to the corresponding bromoacetyl derivatives, 5, 6, and 15, with bromoacetic acid and N,N'-dicyclohexylcarbodiimide.