17β-hydroxy-5α-androstan[3,2-c]isoxazole | 100152-29-2

• 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-hydroxy-5α-androstan[3,2-c]isoxazole
• 英文别名: isofurazadrol；17β-Hydroxy-androstan<3.2-c>isoxazol；5α-Androstanol-(17β)-<3.2-c>-isoxazol；(5α)-androstano[3,2-c]isoxazol-17β-ol；17beta-Hydroxy-androstano[3,2-c]isoxazole；(1S,2S,10S,13R,14S,17S,18S)-2,18-dimethyl-6-oxa-7-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7-dien-17-ol
• CAS: 100152-29-2
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: YYWMPTGXJBPRND-YNZDMMAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-5α-androstan[3,2-c]isoxazole 在 三氧化硫吡啶 、 ammonium hydroxide 、 甲酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates

  摘要：

  Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or no availability hampering the development of analytical methods. We report simple protocols for the rapid synthesis and purification of steroid sulfates that are suitable for adoption by analytical laboratories. Central to this approach is the use of solid-phase extraction (SPE) for purification, a technique routinely used for sample preparation in analytical laboratories around the world. The sulfate conjugates of sixteen steroid compounds encompassing a wide range of steroid substitution patterns and configurations are prepared, including the previously unreported sulfate conjugates of the designer steroids furazadrol (17 beta-hydroxyandrostan[2,3-d]isoxazole), isofurazadrol (17 beta-hydroxyandrostan[3,2-c]isoxazole) and trenazone (17 beta-hydroxyestra-4,9-dien-3-one). Structural characterization data, together with NMR and mass spectra are reported for all steroid sulfates, often for the first time. The scope of this approach for small scale synthesis is highlighted by the sulfation of 1 mu g of testosterone (17 beta-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography-mass spectrometry (LCMS). (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.09.006
• 作为产物：
  描述：

  雄诺龙 在 吡啶 、 盐酸羟胺 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 4.5h， 生成 17β-hydroxy-5α-androstan[3,2-c]isoxazole
  参考文献：
  名称：

  A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates

  摘要：

  Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or no availability hampering the development of analytical methods. We report simple protocols for the rapid synthesis and purification of steroid sulfates that are suitable for adoption by analytical laboratories. Central to this approach is the use of solid-phase extraction (SPE) for purification, a technique routinely used for sample preparation in analytical laboratories around the world. The sulfate conjugates of sixteen steroid compounds encompassing a wide range of steroid substitution patterns and configurations are prepared, including the previously unreported sulfate conjugates of the designer steroids furazadrol (17 beta-hydroxyandrostan[2,3-d]isoxazole), isofurazadrol (17 beta-hydroxyandrostan[3,2-c]isoxazole) and trenazone (17 beta-hydroxyestra-4,9-dien-3-one). Structural characterization data, together with NMR and mass spectra are reported for all steroid sulfates, often for the first time. The scope of this approach for small scale synthesis is highlighted by the sulfation of 1 mu g of testosterone (17 beta-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography-mass spectrometry (LCMS). (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.09.006

文献信息

• Identification of steroid isoxazole isomers marketed as designer supplement
  作者：Maria K. Parr、Michael Gütschow、Jörg Daniels、Georg Opfermann、Mario Thevis、Wilhelm Schänzer

  DOI：10.1016/j.steroids.2008.11.006

  日期：2009.3

  The product Orastan-A from Gaspari Nutrition was analyzed for its steroid content. According to the labeling, it is supposed to contain "5a-Androstano[2,3-c]furazan-17b-tetrahydropyranol ether", also called furazadrol-THP ether. The GC-MS analyses of the liberated steroids (after extraction from the capsule matrix and cleavage of the THP ether, TMS-derivative and underivatized) revealed mass spectra

  分析了来自Gaspari Nutrition的产品Orastan-A的类固醇含量。根据标签，它应该包含“ 5a-Androstano [2,3-c] furazan-17b-四氢吡喃醚”，也称为呋喃唑醇-THP醚。所释放的类固醇的GC-MS分析（从胶囊基质中提取并裂解THP醚，TMS衍生物和未衍生的THP醚后）显示出两种成分的质谱，均与标记不一致。因此，类固醇通过质谱，核磁共振波谱和X射线晶体结构分析等不同的分析技术进行表征。它们被鉴定为17β-羟基雄甾烷[3,2-c]异恶唑和-[2,3-d]异恶唑。
• de Ruggieri,P. et al., Gazzetta Chimica Italiana, 1962, vol. 92, p. 768 - 798
  作者：de Ruggieri,P. et al.

  DOI：——

  日期：——
• Steroidal Heterocycles. VII.¹ Androstano[2,3-d]isoxazoles and Related Compounds
  作者：A. J. Manson、F. W. Stonner、H. C. Neumann、R. G. Christiansen、Robert L. Clarke、J. H. Ackerman、D. F. Page、J. W. Dean、D. K. Phillips、G. O. Potts、A. Arnold、A. L. Beyler、R. O. Clinton

  DOI：10.1021/jm00337a001

  日期：1963.1
• A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates
  作者：Christopher C. Waller、Malcolm D. McLeod

  DOI：10.1016/j.steroids.2014.09.006

  日期：2014.12

  Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or no availability hampering the development of analytical methods. We report simple protocols for the rapid synthesis and purification of steroid sulfates that are suitable for adoption by analytical laboratories. Central to this approach is the use of solid-phase extraction (SPE) for purification, a technique routinely used for sample preparation in analytical laboratories around the world. The sulfate conjugates of sixteen steroid compounds encompassing a wide range of steroid substitution patterns and configurations are prepared, including the previously unreported sulfate conjugates of the designer steroids furazadrol (17 beta-hydroxyandrostan[2,3-d]isoxazole), isofurazadrol (17 beta-hydroxyandrostan[3,2-c]isoxazole) and trenazone (17 beta-hydroxyestra-4,9-dien-3-one). Structural characterization data, together with NMR and mass spectra are reported for all steroid sulfates, often for the first time. The scope of this approach for small scale synthesis is highlighted by the sulfation of 1 mu g of testosterone (17 beta-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography-mass spectrometry (LCMS). (C) 2014 Elsevier Inc. All rights reserved.