17β-hydroxy-17α-methyl-1α,2α-spirooxirane-5α-androst-3-one | 7745-34-8

• 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-hydroxy-17α-methyl-1α,2α-spirooxirane-5α-androst-3-one
• 英文别名: 1α,2α-Epoxy-17α-methyl-5α-androstanol-(17β)-on-(3)
• CAS: 7745-34-8
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: WVNWFVUVUNGLEH-XGPWCGCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  49.83
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-17α-methyl-1α,2α-spirooxirane-5α-androst-3-one 在 氢溴酸 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 2-Brom-3β,17β-dihydroxy-17α-methyl-5α-androsten-(1)
  参考文献：
  名称：

  Counsell,R.E.; Klimstra,P.D., Journal of medicinal and pharmaceutical chemistry, 1962, vol. 5, p. 477 - 483

  摘要：

  DOI：
• 作为产物：
  描述：

  17Alpha-甲基-5Alpha-雄甾-3Β,17Β-二醇 在 sodium peroxide 、 Jones reagent 、 pyridinium hydrobromide perbromide 、 双氧水 、 lithium carbonate 、 lithium bromide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 9.5h， 生成 17β-hydroxy-17α-methyl-1α,2α-spirooxirane-5α-androst-3-one
  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

• Pelc,B.; Hodkova,J., Collection of Czechoslovak Chemical Communications, 1967, vol. 32, p. 410 - 418
  作者：Pelc,B.、Hodkova,J.

  DOI：——

  日期：——