<3,4-13C2>-17β-Hydroxy-4-estren-3-one | 82952-73-6

• 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: <3,4-13C2>-17β-Hydroxy-4-estren-3-one
• 英文别名: [3,4¹³C2]-19-nortestosterone；(8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 82952-73-6
• 化学式: C₁₈H₂₆O₂
• 分子量: 276.381
• InChiKey: NPAGDVCDWIYMMC-QKCUQBKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <3,4-13C2>-17β-Hydroxy-4-estren-3-one 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 <3,4-13C2>-4-estrene-3,17-dione
  参考文献：
  名称：

  Doping in sport—2. Quantification of the impurity 19-norandrostenedione in pharmaceutical preparations of norethisterone

  摘要：

  The finding of measurable amounts of 19-norandrostenedione in norethisterone tablets prompted us to develop an assay to quantify this steroid. 19-Norandrostenedione is an anabolic steroid whose use in sport is prohibited by the World Anti-Doping Agency (WADA). The assay was developed using isotope dilution and liquid chromatography-tandem mass spectrometry (LC-MS/MS) for the quantification of 19-norandrostenedione in norethisterone formulations, with [3,4(-13)C(2)]-19-norandrostenedione as the internal standard. The results showed amounts up to 1.01 +/- 0.01 mu g (mean +/- S.E.M.) per tablet in those containing S mg of norethisterone or norethisterone acetate (0.02%, w/w) and up to 0.5 +/- 0.01 mu g (mean S.E.M.) per tablet (0.05%, w/w) in oral contraceptive tablets containing 0.35-1.5 mg of norethisterone or norethisterone acetate. No tablet tested exceeded the British Pharmacopoeia limit of 0.1% for this impurity. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.10.006
• 作为产物：
  描述：

  2-<1',2'-13C2>acetyl-3-oxo-4-oxa-5(10)-estren-17β-yl benzoate 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以62%的产率得到<3,4-13C2>-17β-Hydroxy-4-estren-3-one
  参考文献：
  名称：

  Synthesis of 3,4-13C2 steroids

  摘要：

  A-ring enollactones la, lb, or 9 derived from 4-cholesten-3-one, testosterone benzoate or 3-oxo-4-estren-17 beta-yl benzoate were condensed with [1,2-13C2]acetyl chloride to give intermediates 2a, 2b, or 10. 2a and 2b were cyclized by acid or base to give 3,4 13c-labeled 4-cholesten-3-one and testosterone, respectively. [3,4-13c2 14-Cholesten-3-one was converted via reduction of its trimethylsilyl enol ether to [3,4-13C2] cholesterol. Acetyl enollactone 10 was cyclized in acetic acid to [3,4-13c2] 3-oxo-4-estren-17beta-yl benzoate followed by aromatization and hydrolysis to produce ]3,4-13c2] estradiol-17 beta. Alternatively, cyclization of 10 with base afforded [3,4-13c2-oxo-4-estren-17 beta-ol directly, which was then oxidized and aromatized to yield ]3,4-13c2] estrone. Ozonolysis of progesterone, conversion to the diketal ester 16 and acylation followed by acid hydrolysis furnished [3,4-13c2] progesterone.

  DOI：

  10.1016/0039-128x(82)90147-7