17β,19-dihydroxy-4-androstene-3,16-dione | 116506-58-2

• 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,19-dihydroxy-4-androstene-3,16-dione
• 英文别名: 17β,19-dihydroxyandrost-4-ene-3,16-dione
• CAS: 116506-58-2
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: RBSNJGVVZQRLFQ-UOMXVPEFSA-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)：
  2.03
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 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：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  16α-hydroxy-6β,19-epoxyandrost-4-ene-3,17-dione 在 sodium hydroxide 、 锌 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 52.0h， 生成 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

文献信息

• Synthesis of 3β,16β,19-trihydroxyandrost -5-en-17-one and 16β3,19-dihydroxyandrost-4-ene-3,17-dione and their 19-oxo derivatives
  作者：Numazawa Mitsuteru、Mutsumi Ayako、Hoshi Kumiko、Ishimura Shigechika、Shoji Satomi、Sekihara Hisahiko

  DOI：10.1016/0039-128x(90)90095-s

  日期：1990.9

  Abstract 3β,l6β,l9-Trihydroxyandrost-5-en-17-one (12) was synthesized from 5α-bromo-3β-acetoxy-6β,19-ep-oxyandrostan -17-one ( 2 ) through acetoxylation at C-16β of the enol acetate 4 with lead tetraacetate and reductive cleavage of the epoxide ring with une dust yielding the 3β,I6β-diacetoxy-19-hydroxy steroid 11 , followed by hydrolysis of the acetoxy groups with sulfuric acid. Jones oxidation of

  摘要 3β,l6β,l9-Trihydroxyandrost-5-en-17-one (12) 由 5α-bromo-3β-acetoxy-6β,19-ep-oxyandrostan -17-one ( 2 ) 通过 C-16β 的乙酰氧基化合成烯醇乙酸酯 4 与四乙酸铅和环氧化物环与 une 粉尘的还原裂解产生 3β,I6β-二乙酰氧基-19-羟基类固醇 11，然后用硫酸水解乙酰氧基。化合物 11 的琼斯氧化，然后酸水解得到 19-氧代甾体 15。5α-Bromo-3β-hydroxy-16β-acetoxy-6β, 19-epoxyandrostan-17-one ( 8 )，通过用氢氧化铵选择性水解 3-甲酸酯 5 获得，用琼斯试剂氧化得到 3-oxo类固醇 16，通过锌粉处理转化为 19-羟基衍生物 17。16β,19-Dihydroxyandrost-4-ene-3, 17-二酮