16α-Acetoxy-androst-4-en-3,17-dion | 69389-91-9

• 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: 16α-Acetoxy-androst-4-en-3,17-dion
• 英文别名: 16α-Acetoxy-androsten-(4)-dion-(3,17)；16α-acetoxy-androst-4-ene-3,17-dione
• CAS: 69389-91-9
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: VIRIFYASJOZYTL-SBPVMYIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  16α-Acetoxy-androst-4-en-3,17-dion 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 6β-Bromo-16α-acetoxy-4-androsten-3,17-dion
  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
• 作为产物：
  描述：

  16α-Acetoxy-3β-formyloxy-androst-5-en-17-on 在 aluminum isopropoxide 作用下， 以 环己酮 为溶剂， 生成 16α-Acetoxy-androst-4-en-3,17-dion
  参考文献：
  名称：

  Sanda,V.; Fajkos,J., Collection of Czechoslovak Chemical Communications, 1961, vol. 26, p. 2734 - 2738

  摘要：

  DOI：

文献信息

• Gardi,R.; Gandolfi,R., Gazzetta Chimica Italiana, 1961, vol. 91, p. 1258 - 1267
  作者：Gardi,R.、Gandolfi,R.

  DOI：——

  日期：——