3β-hydroxy-13α-androst-5-en-17-one | 571-35-7

• 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: 3β-hydroxy-13α-androst-5-en-17-one
• 英文别名: 3beta-Hydroxy-13alpha-androst-5-en-17-one；(3S,8R,9S,10R,13R,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 571-35-7
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: FMGSKLZLMKYGDP-JLZSVDHQSA-N

物化性质

• 熔点：
  187.5-189 °C
• 沸点：
  426.7±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  3β-hydroxy-13α-androst-5-en-17-one 在 环己酮 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 反应 1.25h， 以91%的产率得到(8R,9S,10R,13R,14S)-10,13-二甲基-2,6,7,8,9,11,12,14,15,16-十氢-1H-环戊二烯并[a]菲-3,17-二酮
  参考文献：
  名称：

  脱氢氯甲基睾丸酮代谢产物的合成与结构解析†

  摘要：

  迄今为止，已通过GC / MS检测到常见掺杂剂DHCMT的人类尿液长期代谢物“ M3”（4-氯-17β-羟甲基-17α-甲基-18-norandrost-13-en-3-ol）-MS，造成有关其绝对配置的歧义。通过合成所有八个具有17β-羟甲基构型的立体异构体，阐明了其结构。合成的亮点包括对4β-chloro-5β化合物采用新颖的第一代方法以及发散途径，该途径可轻松获得其余的A环氯醇。

  DOI：

  10.1039/c8ob00122g
• 作为产物：
  描述：

  3β-acetoxy-androst-5-en-17-one oxime 在 偶氮二异丁腈 盐酸 、 三丁基膦 、 三正丁基氢锡 作用下， 以 吡啶 、 甲醇 、 环己烷 为溶剂， 反应 6.08h， 生成 3β-hydroxy-13α-androst-5-en-17-one
  参考文献：
  名称：

  亚氨基自由基：第二部分。环丁基和环戊基亚胺基的开环。

  摘要：

  缓慢地将三丁基锡烷加到亚磺酰基亚胺2中，得到相应的环亚氨基基团3，该环亚氨基基团3可以开环，该过程很容易并入复杂的反应序列中。

  DOI：

  10.1016/s0040-4020(01)80850-4

文献信息

• The synthesis of 4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrosta-4,13-diene-3α-ol – Proposed long term metabolite (M4) of oralturinabol
  作者：D. Yu. Shostko、A.I. Liubina、Yu.Yu. Kozyrkov、S.A. Beliaev

  DOI：10.1016/j.steroids.2020.108601

  日期：2020.6

  metabolites of oralturinabol (anabolic androgenic steroid restricted in sport). The synthesis of 4-chloro-17β-(hydroxymethyl)-17α-methyl-18-norandrosta-4,13-diene-3α-ol was achieved. Isomerisation of configuration of 13-carbon was used for construction of 17β-(hydroxymethyl)-17α-methyl fragment. The proposed route of synthesis allows to obtain 3β-hydroxy isomer as well .

  4-Chloro-17β-(羟甲基)-17α-methyl-18-norandrosta-4,13-diene-3α-ol 是一种建议的长期口服尿嘧啶代谢物（运动中限制合成代谢雄激素类固醇）。合成了4-chloro-17β-(hydroxymethyl)-17α-methyl-18-norandrosta-4,13-diene-3α-ol。13-碳构型的异构化用于构建17β-(羟甲基)-17α-甲基片段。建议的合成路线也允许获得 3β-羟基异构体。
• Synthesis of two epimeric long-term metabolites of oxandrolone
  作者：Nicolas Kratena、Berthold Stöger、Matthias Weil、Valentin S. Enev、Peter Gärtner

  DOI：10.1016/j.tetlet.2017.02.048

  日期：2017.3

  of the work reported herein, was the synthesis of two C-17-epimeric substances which have been found to be long-term urinary metabolites of the prescription drug and anabolic steroid oxandrolone. These 17-hydroxymethyl-17-methyl-18-nor-2-oxaandrost-13-en-3-ones have been used as markers to trace oxandrolone abuse in professional athletes since 2013. Our synthesis relied on an ozonolysis/lactonisation

  本文报道的工作目标是合成两种C-17-表异构物质，发现它们是处方药和合成代谢类固醇氧雄酮的长期尿代谢产物。自2013年以来，这些17-羟甲基-17-甲基-18-nor-2-oxaandrost-13-en-3-ones一直用作跟踪职业运动员中氧杂雄酮滥用的标记。我们的合成依赖于臭氧分解/内酯化策略，并且呈酸性螺环氧化物的重排。据我们所知，尚未公开任何一种物质的化学合成方法。
• The Preparation of Some 13α-Androstanes
  作者：James R. Hanson、A. Christy Hunter、Sandrine Roquier

  DOI：10.1135/cccc19981646

  日期：——

  The preparation of 17a-oxa-5α,13α-androstane-3,17-dione, 5α,13α-androstane-3,7,17-trione, 4-chloro- and 4-hydroxy-13α-androst-4-ene-3,17-dione and 13α-androst-4-ene-3,6,17-trione is described.

  描述了17a-氧-5α,13α-雄烷-3,17-二酮，5α,13α-雄烷-3,7,17-三酮，4-氯-和4-羟基-13α-雄烷-4-烯-3,17-二酮以及13α-雄烷-4-烯-3,6,17-三酮的制备方法。
• An efficient one-pot synthesis generating 4-ene-3,6-dione functionalised steroids from steroidal 5-en-3β-ols using a modified Jones oxidation methodology
  作者：A. Christy Hunter、Shelley-Marie Priest

  DOI：10.1016/j.steroids.2005.07.007

  日期：2006.1

  Steroids with 4-ene-3,6-dione functionality have application in natural product chemistry, as synthetic intermediates and as aromatase inhibitors. Here, we report a two-phase oxidation of a range of steroidal 5-en-3 beta-ols into corresponding 4-ene-3,6-diones using a modified Jones oxidation. The new reaction affords high yields (77-89%) of product in relatively short reaction times (1-2 h). The simplicity of this reaction gives significant advantages over previously reported methodologies. (c) 2005 Elsevier Inc. All rights reserved.
• α-Selective synthesis of 2-deoxy-glycosides and disaccharides
  作者：Guofang Yang、Xiaosheng Luo、Hong Guo、Qingbing Wang、Jiafen Zhou、Tianyun Huang、Jie Tang、Junjie Shan、Jianbo Zhang

  DOI：10.1080/07328303.2018.1439498

  日期：2018.3.24

  A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0 degrees C to form glycosides, glycoconjugates, and disaccharides with excellent alpha-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.