17β-羟基-17α-甲基-5β-雄烷-3-酮 | 3275-58-9

• 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
• 中文名称: 17β-羟基-17α-甲基-5β-雄烷-3-酮
• 英文名称: 17β-Hydroxy-17α-methyl-5β-androstan-3-one
• 英文别名: 17β-hydroxy-17-methyl-5β-androstan-3-one；17α-methyl-5β-dihydrotestosterone；17β-Hydroxy-17α-methyl-5β-androstan-3-on；17-Methyl-17β-hydroxy-5β-androstan-3-on；5beta-Mestanolone；(5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 3275-58-9
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: WYZDXEKUWRCKOB-IHTGJJIASA-N

物化性质

• 熔点：
  746 °C
• 沸点：
  416.1±38.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17β-羟基-17α-甲基-5β-雄烷-3-酮 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 以277 mg的产率得到17α-methyl-5β-androstane-3β,17β-diol
  参考文献：
  名称：

  Proton magnetic resonance spectra of 17ξ-Hydroxy-17ξ-methyl-5ξ-androstane C-3 ketone and c-3ξ alcohol isomers in chloroform-d and pyridine-d5

  摘要：

  17 alpha-Hydroxy-17 beta-methyl-5 beta-androstan-3-one,17 beta-methyl-5 alpha-androstane-3 alpha,17 alpha-diol,17 beta-methyl-5 alpha-androstane-3 beta,17 alpha-diol,17 alpha-methyl-5 beta-androstane-3 beta,17 beta-diol,17 beta-methyl-5 beta-androstane-3 alpha,17 alpha-diol and 17 beta-methyl-5 beta-androstane-3 beta,17 alpha-diol were synthesized for the first time. 1H NMR spectra of all four 17 xi-hydroxy/17 xi-methyl C-3 ketones and all eight C-3 alcohols were recorded in chloroform-d and pyridine-d5. Pyridine-induced chemical shifts are discussed. Thin-layer chromatographic data are given.

  DOI：

  10.1016/0039-128x(83)90088-0
• 作为产物：
  描述：

  17-甲睾酮 在 Lindlar's catalyst 氢气 作用下， 以 吡啶 为溶剂， 以21.8 g的产率得到17β-羟基-17α-甲基-5β-雄烷-3-酮
  参考文献：
  名称：

  Proton magnetic resonance spectra of 17ξ-Hydroxy-17ξ-methyl-5ξ-androstane C-3 ketone and c-3ξ alcohol isomers in chloroform-d and pyridine-d5

  摘要：

  17 alpha-Hydroxy-17 beta-methyl-5 beta-androstan-3-one,17 beta-methyl-5 alpha-androstane-3 alpha,17 alpha-diol,17 beta-methyl-5 alpha-androstane-3 beta,17 alpha-diol,17 alpha-methyl-5 beta-androstane-3 beta,17 beta-diol,17 beta-methyl-5 beta-androstane-3 alpha,17 alpha-diol and 17 beta-methyl-5 beta-androstane-3 beta,17 alpha-diol were synthesized for the first time. 1H NMR spectra of all four 17 xi-hydroxy/17 xi-methyl C-3 ketones and all eight C-3 alcohols were recorded in chloroform-d and pyridine-d5. Pyridine-induced chemical shifts are discussed. Thin-layer chromatographic data are given.

  DOI：

  10.1016/0039-128x(83)90088-0

文献信息

• 3-Spiroandrostene-substituted 1,3,4-thiadiazolines
  作者：Alexander V. Komkov、Leonid G. Menchikov、Andrey S. Dmitrenok、Natalya G. Kolotyrkina、Igor V. Zavarzin

  DOI：10.1007/s10593-024-03317-z

  日期：2024.4

  A method for the synthesis of 1,3,4-thiadiazoline spiro steroids via ring A by the reaction of steroid 3-ketones with oxamic acid thiohydrazides was developed. It was shown that if a keto group was present both in ring A and in ring D of the precursor steroid, the reaction occurred only at the keto group of ring A. A number of new steroidal 3-spiroandrostene-substituted 1,3,4-thiadiazolines were obtained

  建立了一种通过3-甾体酮与草酸硫代酰肼反应经A环合成1,3,4-噻二唑啉螺环甾体的方法。结果表明，如果前体类固醇的A环和D环中都存在酮基，则反应仅发生在A环的酮基上。许多新的甾体3-螺雄烯取代的1,3,4得到了-噻二唑啉，噻二唑NH基团很容易被乙酰化。
• Draczynska, Bozena; Tlomak, Elzbieta; Dmochowska-Gladysz, Jadwiga, Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1982, vol. 30, # 1-12, p. 13 - 21
  作者：Draczynska, Bozena、Tlomak, Elzbieta、Dmochowska-Gladysz, Jadwiga、Siewinski, Antoni

  DOI：——

  日期：——
• Anti-androgenic activity of 17,17-dimethyl-18-norandrost-13-enes
  作者：Albert Segaloff、R. Bruce Gabbard

  DOI：10.1016/0039-128x(64)90156-4

  日期：1964.9
• Metabolism of 17α-methyl-5β-dihydrotestosterone in the rabbit
  作者：John F. Templeton、Jackson Chung-Ja Choi

  DOI：10.1016/0039-128x(83)90089-2

  日期：1983.4

  17 alpha-Methyl-5 beta-androstane-3 alpha,17 beta-diol together with the hydroxylated metabolites 17 alpha-methyl-5 beta-androstane-1 beta,3 alpha,17 beta-triol, 17 alpha-methyl-5 beta-androstane-3 alpha,12 beta,17 beta-triol, 17 alpha-methyl-5 beta-androstane-3 alpha,16 alpha,17 beta-triol and 17 alpha-methyl-5 beta-androstane-3 alpha,16 beta,17 beta-triol were isolated and identified in the urine of rabbits orally dosed with 17 alpha-methyl-5 beta-dihydrotestosterone. Biotransformations differ from the 5 alpha-series where hydroxylation occurred at C-6 and C-15. In both series, the C-3 equatorial epimer was the major urinary excretion product among the non-hydroxylated metabolites. The 5 beta-compound was more resistant to metabolic hydroxylation than the 5 alpha-compound. No evidence for epimerization at the C-17 position was observed.