1α,17β-dihydroxy-17α-methyl-5α-androst-2-ene | 13974-36-2

• 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: 1α,17β-dihydroxy-17α-methyl-5α-androst-2-ene
• 英文别名: 17-Methyl-androst-2-ene-1,17-diol, (1alpha,5alpha,17beta)-；(1S,5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-1,17-diol
• CAS: 13974-36-2
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: SJDLTXFILISTBP-DVEALZNXSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  420.7±45.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1α,17β-dihydroxy-17α-methyl-5α-androst-2-ene 在 sodium tetrahydroborate 、 Jones reagent 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.5h， 生成 1β,17β-dihydroxy-17α-methyl-5α-androst-2-ene
  参考文献：
  名称：

  Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes

  摘要：

  Desoxymethyltestosterone (DMT; 17 beta-hydroxy-17 alpha-methyl-5 alpha-androst-2-ene) is a designer steroid present in hormonal supplements distributed illegally as such or in combination with other steroids, for self-administration. It figures on the list of substances prohibited in sports and its detection in athlete's urine samples is based upon the presence of the parent compound or the main urinary metabolite, which has not been characterized yet. Following its isolation from cultures of human fresh hepatocytes and S9 fractions of liver homogenates, we were able to identify this metabolite as being 17 alpha-methyl-2 beta,3 alpha,17 beta-trihydroxy-5 alpha-androstane. Other minor metabolites were also characterized. The production, isolation, NMR, mass spectral analyses and chemical synthesis are presented. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.02.008
• 作为产物：
  描述：

  美雄诺龙 在 sodium peroxide 、 pyridinium hydrobromide perbromide 、 双氧水 、 lithium carbonate 、 一水合肼 、 lithium bromide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.92h， 生成 1α,17β-dihydroxy-17α-methyl-5α-androst-2-ene
  参考文献：
  名称：

  Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes

  摘要：

  Desoxymethyltestosterone (DMT; 17 beta-hydroxy-17 alpha-methyl-5 alpha-androst-2-ene) is a designer steroid present in hormonal supplements distributed illegally as such or in combination with other steroids, for self-administration. It figures on the list of substances prohibited in sports and its detection in athlete's urine samples is based upon the presence of the parent compound or the main urinary metabolite, which has not been characterized yet. Following its isolation from cultures of human fresh hepatocytes and S9 fractions of liver homogenates, we were able to identify this metabolite as being 17 alpha-methyl-2 beta,3 alpha,17 beta-trihydroxy-5 alpha-androstane. Other minor metabolites were also characterized. The production, isolation, NMR, mass spectral analyses and chemical synthesis are presented. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.02.008

文献信息

• Anabolic Agents. A-Ring Oxygenated Androstane Derivatives
  作者：P. D. Klimstra、R. Zigman、R. E. Counsell

  DOI：10.1021/jm00324a029

  日期：1966.11