5β-Androst-1-ene-3,17-dione | 571-39-1

• 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: 5β-Androst-1-ene-3,17-dione
• 英文别名: 5β-Androst-1-ene-3,17-dion；5β-Androst-1-en-3,17-dion；5beta-Androst-1-ene-3,17-dione；(5R,8R,9S,10R,13S,14S)-10,13-dimethyl-5,6,7,8,9,11,12,14,15,16-decahydro-4H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 571-39-1
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: WJIQCDPCDVWDDE-QJISAEMRSA-N

物化性质

• 熔点：
  171-172 °C(Solv: ethanol (64-17-5))
• 沸点：
  418.8±45.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5β-Androst-1-ene-3,17-dione 在 potassium tri-sec-butyl-borohydride 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 以14%的产率得到5β-androst-1-ene-3β,17β-diol
  参考文献：
  名称：

  Steroidal isomers with uniform mass spectra of their per-TMS derivatives: Synthesis of 17-hydroxyandrostan-3-ones, androst-1-, and -4-ene-3,17-diols

  摘要：

  In human sports doping control analysis most of the steroids are analyzed after enzymatic hydrolysis of the glucuronides as per-trimethylsilyl (TMS) derivatives applying gas chromatography-mass spectrometry (GC-MS). According to the recommendations of the World Anti-Doping Agency the identification of analytes should be based on retention time and on mass spectrometric characterization. This study shows that the bis-TMS derivatives of 16 specific C19 steroids, namely the stereoisomers of S xi-androst-l-ene-3 xi,17 xi-diol (8 isomers), androst-4-ene-3 xi,17 xi-diol (4 isomers), and 17 xi-hydroxy-5 xi-androstan-3-one (4 isomers), reveal very similar mass spectra. As a rule, when taking the retention times, which are provided as Kovac indices for all these isomers, into account, a restriction to two or three possible isomers is possible. Reliable identification should additionally include a comparison of the retention times of the analytes with the reference compounds measured concomitantly. In some cases standard addition may be appropriate.Due to the limited availability; the above mentioned isomers were synthesized by reduction of the corresponding alpha,beta-unsaturated oxo, steroids either with K-Selectride or by catalytic hydrogenation (Pd/C as catalyst). The products of the reactions were identified by means of nuclear magnetic resonance (NMR) characterization and by further reduction to the corresponding 5 xi-androstane-3 xi,17 xi-diols and GC-MS comparison with commercially available reference standards. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.03.006
• 作为产物：
  描述：

  17-羟基-6-甲基雌甾-4-烯-3-酮 在 chromium(VI) oxide 作用下， 生成 5β-Androst-1-ene-3,17-dione
  参考文献：
  名称：

  Metabolism of 1-dehydroand rostanes in man

  摘要：

  DOI：

  10.1016/s0039-128x(71)80169-1

文献信息

• Unusual enolizations in 19-nor-3-ketosteroids
  作者：Yusuf J. Abul-Hajj

  DOI：10.1039/c39850001479

  日期：——

  The direction of enolization of 19-nor-3-ketosteroids was found to proceed predominantly towards C-2 irrespective of the ring junction at C-5.

  发现19-nor-3-ketosteroids的烯醇化方向主要朝C-2进行，而与C-5处的环结无关。
• Quantitative analysis of 3-oxo-5Beta-Steroid and reagent therefor
  申请人：DAIICHI PURE CHEMICALS CO. LTD.

  公开号：EP0269786A1

  公开（公告）日：1988-06-08

  A quantitative analysis of 3-oxo-5β-steroid which comprises acting 3-oxo-5β-steroidΔ⁴-dehydrogenase on a sample in the presence of a reducing chromophoric agent, and measuring the optical density of the chromophoric substance thereby produced. A typical reducing chromophoric agent is a tetrazolium compound. The invention also provides a reagent for the quantitative analysis of 3-oxo-5β-steroid comprising 3-oxo-5β-steroidΔ⁴-dehydrogenase and a tetrazolium compound. The analysis and reagent provide a simple and reliable method for a liver function test.

  一种 3-氧代-5β-类固醇的定量分析方法，包括在还原性发色剂存在下，将 3-氧代-5β-类固醇Δ⁴-脱氢酶作用于样品，并测量由此产生的发色物质的光密度。典型的还原性发色剂是四唑化合物。本发明还提供了一种用于定量分析 3-氧代-5β-类固醇的试剂，该试剂由 3-氧代-5β-类固醇Δ⁴-脱氢酶和四唑化合物组成。该分析和试剂为肝功能检测提供了一种简单可靠的方法。
• Pelc,B.; Hodkova,J., Collection of Czechoslovak Chemical Communications, 1967, vol. 32, p. 410 - 418
  作者：Pelc,B.、Hodkova,J.

  DOI：——

  日期：——
• Steroidal isomers with uniform mass spectra of their per-TMS derivatives: Synthesis of 17-hydroxyandrostan-3-ones, androst-1-, and -4-ene-3,17-diols
  作者：Maria K. Parr、Josef Zapp、Michael Becker、Georg Opfermann、Ulrike Bartz、Wilhelm Schänzer

  DOI：10.1016/j.steroids.2007.03.006

  日期：2007.6

  In human sports doping control analysis most of the steroids are analyzed after enzymatic hydrolysis of the glucuronides as per-trimethylsilyl (TMS) derivatives applying gas chromatography-mass spectrometry (GC-MS). According to the recommendations of the World Anti-Doping Agency the identification of analytes should be based on retention time and on mass spectrometric characterization. This study shows that the bis-TMS derivatives of 16 specific C19 steroids, namely the stereoisomers of S xi-androst-l-ene-3 xi,17 xi-diol (8 isomers), androst-4-ene-3 xi,17 xi-diol (4 isomers), and 17 xi-hydroxy-5 xi-androstan-3-one (4 isomers), reveal very similar mass spectra. As a rule, when taking the retention times, which are provided as Kovac indices for all these isomers, into account, a restriction to two or three possible isomers is possible. Reliable identification should additionally include a comparison of the retention times of the analytes with the reference compounds measured concomitantly. In some cases standard addition may be appropriate.Due to the limited availability; the above mentioned isomers were synthesized by reduction of the corresponding alpha,beta-unsaturated oxo, steroids either with K-Selectride or by catalytic hydrogenation (Pd/C as catalyst). The products of the reactions were identified by means of nuclear magnetic resonance (NMR) characterization and by further reduction to the corresponding 5 xi-androstane-3 xi,17 xi-diols and GC-MS comparison with commercially available reference standards. (c) 2007 Elsevier Inc. All rights reserved.
• Metabolism of 1-dehydroand rostanes in man
  作者：Ferdinando Galletti、Rinaldo Gardi

  DOI：10.1016/s0039-128x(71)80169-1

  日期：1971.7