16α,19-dihydroxy-4-androstene-3,17-dione | 60385-81-1

• 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,19-dihydroxy-4-androstene-3,17-dione
• 英文别名: 16,19-Dihydroxy-4-androsten-3,17-dione；(8R,9S,10S,13S,14S,16R)-16-hydroxy-10-(hydroxymethyl)-13-methyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 60385-81-1
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: AWFCHTZPCGZPQD-ROSLGNJOSA-N

物化性质

• 沸点：
  530.9±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  16α,19-dihydroxy-4-androstene-3,17-dione 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以50%的产率得到17β,19-dihydroxy-4-androstene-3,16-dione
  参考文献：
  名称：

  Synthesis of 16α,19-dihydroxy-4-androstene-3,17-dione and 3β,16α,19-trihydroxy-5-androsten-17-one and their 17β-hydroxy-16-keto isomers

  摘要：

  3 beta,16 alpha,19-Trihydroxy-5-androsten-17-one and 16 alpha,17-dihydroxy-4-androstene-3,17-dione were synthesized from the 5 alpha-bromo-6 beta,19-epoxy-17-ketone derivative 1, using the bromination at C-16 alpha of the 17-ketone 1 and the controlled alkaline hydrolysis of the 16 alpha-bromo-17-ketones 2 and 11 as key reactions. Zinc dust reductive cleavage of the 6 beta,19-epoxy-16 alpha-hydroxy-17-ketones 4 and 12, produced by controlled hydrolysis, gave the corresponding 19-alcohol derivatives 6 and 14, which were rearranged to the 17 beta-hydroxy-16-ketones 7 and 15 when treated with sodium hydroxide. The 3 beta,16 alpha,17 beta,19-tetrol 8 was obtained from the 16 alpha-ketol 6 by reaction with sodium borohydride.

  DOI：

  10.1016/0039-128x(87)90002-x
• 作为产物：
  描述：

  5α,16α-dibromo-3β-hydroxy-6β,19-oxidoandrostan-17-one 在 chromium(VI) oxide 、 sodium hydroxide 、 锌 作用下， 以 吡啶 、 乙醇 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 7.0h， 生成 16α,19-dihydroxy-4-androstene-3,17-dione
  参考文献：
  名称：

  Synthesis of 16α,19-dihydroxy-4-androstene-3,17-dione and 3β,16α,19-trihydroxy-5-androsten-17-one and their 17β-hydroxy-16-keto isomers

  摘要：

  3 beta,16 alpha,19-Trihydroxy-5-androsten-17-one and 16 alpha,17-dihydroxy-4-androstene-3,17-dione were synthesized from the 5 alpha-bromo-6 beta,19-epoxy-17-ketone derivative 1, using the bromination at C-16 alpha of the 17-ketone 1 and the controlled alkaline hydrolysis of the 16 alpha-bromo-17-ketones 2 and 11 as key reactions. Zinc dust reductive cleavage of the 6 beta,19-epoxy-16 alpha-hydroxy-17-ketones 4 and 12, produced by controlled hydrolysis, gave the corresponding 19-alcohol derivatives 6 and 14, which were rearranged to the 17 beta-hydroxy-16-ketones 7 and 15 when treated with sodium hydroxide. The 3 beta,16 alpha,17 beta,19-tetrol 8 was obtained from the 16 alpha-ketol 6 by reaction with sodium borohydride.

  DOI：

  10.1016/0039-128x(87)90002-x

文献信息

• Synthesis of 16α,19-dihydroxy-4-androstene-3,17-dione and 3β,16α,19-trihydroxy-5-androsten-17-one and their 17β-hydroxy-16-keto isomers
  作者：Mitsuteru Numazawa、Ayako Mutsumi、Mieko Ogata、Yoshio Osawa

  DOI：10.1016/0039-128x(87)90002-x

  日期：1987.4

  3 beta,16 alpha,19-Trihydroxy-5-androsten-17-one and 16 alpha,17-dihydroxy-4-androstene-3,17-dione were synthesized from the 5 alpha-bromo-6 beta,19-epoxy-17-ketone derivative 1, using the bromination at C-16 alpha of the 17-ketone 1 and the controlled alkaline hydrolysis of the 16 alpha-bromo-17-ketones 2 and 11 as key reactions. Zinc dust reductive cleavage of the 6 beta,19-epoxy-16 alpha-hydroxy-17-ketones 4 and 12, produced by controlled hydrolysis, gave the corresponding 19-alcohol derivatives 6 and 14, which were rearranged to the 17 beta-hydroxy-16-ketones 7 and 15 when treated with sodium hydroxide. The 3 beta,16 alpha,17 beta,19-tetrol 8 was obtained from the 16 alpha-ketol 6 by reaction with sodium borohydride.