16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester | 853904-67-3

• 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: 16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester
• 英文别名: 2-Carboxy 3-Hydroxy Madol Methyl Ester-d5；methyl (5S,8R,9S,10S,13S,14S,17S)-16,16-dideuterio-3,17-dihydroxy-10,13-dimethyl-17-(trideuteriomethyl)-4,5,6,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthrene-2-carboxylate
• CAS: 853904-67-3
• 化学式: C₂₂H₃₄O₄
• 分子量: 367.47
• InChiKey: QUTQPYZOFLCEEF-SCQDEYKUSA-N

物化性质

• 溶解度：
  溶于乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 23.0h， 以78%的产率得到(5alpha,17beta)-17-羟基-17-(甲基-d3)-2'H-雄甾-2-烯并[3,2-c]吡唑-5'(1'H)-酮-16,16-d2
  参考文献：
  名称：

  First synthesis of a pentadeuterated 3′-hydroxystanozolol—an internal standard in doping analysis

  摘要：

  The first synthesis of 16,16,20,20,20-pentadeuterio-3'-hydroxystanozolol (8) in 26% yield over nine steps is described using moderately priced starting materials and economic amounts of reagents. Compound 8 can be used as an internal standard in screening procedures for anabolic steroids as well as for the quantification of stanozolol metabolites via mass spectrometric techniques, such as LC-MS or gas chromatography-mass spectrometry (GC-MS). (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.10.002
• 作为产物：
  描述：

  16,16,20,20,20-pentadeuterio-17β-hydroxy-17α-methyl-5α-androstan-3-one 在 咪唑 、 六甲基磷酰三胺 、 正丁基锂 、 N-环己基异丙基胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 16,16,20,20,20-pentadeuterio-3,17β-dihydroxy-17α-methyl-androst-2-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  First synthesis of a pentadeuterated 3′-hydroxystanozolol—an internal standard in doping analysis

  摘要：

  The first synthesis of 16,16,20,20,20-pentadeuterio-3'-hydroxystanozolol (8) in 26% yield over nine steps is described using moderately priced starting materials and economic amounts of reagents. Compound 8 can be used as an internal standard in screening procedures for anabolic steroids as well as for the quantification of stanozolol metabolites via mass spectrometric techniques, such as LC-MS or gas chromatography-mass spectrometry (GC-MS). (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.10.002

文献信息

• First synthesis of a pentadeuterated 3′-hydroxystanozolol—an internal standard in doping analysis
  作者：Wolfgang Felzmann、Günter Gmeiner、Peter Gärtner

  DOI：10.1016/j.steroids.2004.10.002

  日期：2005.2

  The first synthesis of 16,16,20,20,20-pentadeuterio-3'-hydroxystanozolol (8) in 26% yield over nine steps is described using moderately priced starting materials and economic amounts of reagents. Compound 8 can be used as an internal standard in screening procedures for anabolic steroids as well as for the quantification of stanozolol metabolites via mass spectrometric techniques, such as LC-MS or gas chromatography-mass spectrometry (GC-MS). (C) 2004 Elsevier Inc. All rights reserved.