17Alpha-甲基-5Alpha-雄甾-3Β,17Β-二醇 | 641-83-8

• 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
• 中文名称: 17Alpha-甲基-5Alpha-雄甾-3Β,17Β-二醇
• 中文别名: 17Α-甲基-5Α-雄甾-3Β,17Β-二醇；17-甲基-5alpha-雄甾烷-3beta,17beta-二醇；-甲基-5&alpha；-雄甾-3&beta；-二醇
• 英文名称: ZINC05223451
• 英文别名: 17α-methyl-3β,17β-dihydroxy-5α-androstane；3β,17β-dihydroxy-17α-methyl-5α-androstane；17α-Methyl-5α-androstane-3β,17β-diol；17α-methyl-5α-androstan-3β,17β-diol；5α-17α-methylandrostan-3β,17β-diol；17α-methyl-5α-androstane-3β,17-diol；17-Methyl-5alpha-androstane-3beta,17beta-diol；(3S,5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 641-83-8
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: QGKQXZFZOIQFBI-UYEYMFBJSA-N

物化性质

• 熔点：
  206-209 °C
• 沸点：
  418.1±18.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

制备方法与用途

化学性质：结晶（乙酸乙酯），熔点为210-211℃。

用途：作为去氢甲基睾丸素的中间体。

生产方法：可通过海可吉宁经由乙酰化、还原、开环、氧化、消除、肟化、重排、水解、加成和水解等多步反应制得。

反应信息

• 作为反应物：
  描述：

  17Alpha-甲基-5Alpha-雄甾-3Β,17Β-二醇 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以88%的产率得到美雄诺龙
  参考文献：
  名称：

  Efficient Oxidizing Methods for the Synthesis of Oxandrolone Intermediates

  摘要：

  在相转移条件下，使用三种不同的试剂，即在 65 °C、次氯酸钠和 H2O2/Na2WO4 中的五价碘试剂 2-iodoxy benzoic acid (IBX)，对 17α-甲基雄甾烷-3β-17β-二醇（1）进行了温和、高效和环保的氧化研究，以得到药物中间体 17β-羟基-17α-甲基雄甾烷-3-酮（美雄酮 2）作为氧化产物。H2O2/Na2WO4/PTC 得到的美雄诺龙收率高、纯度高，而次氯酸钠/PTC 体系在得到美雄诺龙的同时也得到了一些氯化物质。然而，在类似的反应条件下，1 与 2.5 等量的 IBX 可生成 17β-羟基-17α-甲基-Δ1-雄烯-3-酮（3），收率高，且为一步反应。

  DOI：

  10.1248/cpb.52.989
• 作为产物：
  描述：

  美雄诺龙 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以50 mg的产率得到17Alpha-甲基-5Alpha-雄甾-3Β,17Β-二醇
  参考文献：
  名称：

  Proton magnetic resonance spectra of 17ξ-Hydroxy-17ξ-methyl-5ξ-androstane C-3 ketone and c-3ξ alcohol isomers in chloroform-d and pyridine-d5

  摘要：

  17 alpha-Hydroxy-17 beta-methyl-5 beta-androstan-3-one,17 beta-methyl-5 alpha-androstane-3 alpha,17 alpha-diol,17 beta-methyl-5 alpha-androstane-3 beta,17 alpha-diol,17 alpha-methyl-5 beta-androstane-3 beta,17 beta-diol,17 beta-methyl-5 beta-androstane-3 alpha,17 alpha-diol and 17 beta-methyl-5 beta-androstane-3 beta,17 alpha-diol were synthesized for the first time. 1H NMR spectra of all four 17 xi-hydroxy/17 xi-methyl C-3 ketones and all eight C-3 alcohols were recorded in chloroform-d and pyridine-d5. Pyridine-induced chemical shifts are discussed. Thin-layer chromatographic data are given.

  DOI：

  10.1016/0039-128x(83)90088-0

文献信息

• Tris(3,6-dioxaheptyl)amine: A superior complexing agent for dissolving metal reactions
  作者：Ajay K. Bose、Pietro Mangiaracina

  DOI：10.1016/s0040-4039(00)95452-2

  日期：1987.1

  Commercially available tris(3,6-dioxaheptyl)amine (TDA-1) is an effective phase transfer catalyst for reactions with sodium-potassium alloy in tetrahydrofuran. Deoxygenation of acetates, dehalogenation, and hydrolysis of tosylates and mesylates proceed in high yield. The use of a deuterated alcohol during deoxygenation reactions leads to site-specific deuteration.

  市售的三（3,6-二氧杂庚基）胺（TDA-1）是一种有效的相转移催化剂，可与钠-钾合金在四氢呋喃中反应。乙酸酯的脱氧，脱卤代以及甲苯磺酸酯和甲磺酸酯的水解以高收率进行。在脱氧反应中使用氘代酒精会导致特定位置的氘代。
• 17-Epimerization of 17α-methyl anabolic steroids in humans: metabolism and synthesis of 17α-hydroxy-17β-methyl steroids
  作者：Willi Schänzer、Georg Opfermann、Manfred Donike

  DOI：10.1016/0039-128x(92)90023-3

  日期：1992.11

  chromatography as trimethylsilyl derivatives from a capillary SE-54 or OV-1 column 70-170 methylen units before the corresponding 17 alpha-methyl epimer. The electron impact mass spectra of the underivatized and trimethylsilylated epimers are in most cases identical and only for I, II, and V was a differentiation between the 17-epimers possible. 1H nuclear magnetic resonance (NMR) spectra show for the 17 beta-methyl

  17个β-二醇（XIX）（也是VI，VII和XI的代谢物），17个α-甲基-5α-雄甾烷3β，17个β-二醇（XX），17个α-甲基-5β-雄烷醇-3 alpha，17 beta-diol（XXI）（也是V，VII和VIII的代谢物），17 alpha-methyl-5 beta-androstane-3 beta，17 beta-diol（XXII）和17 beta-hydroxy -7α，17α-二甲基-5β-雄烷-3-酮（XXIII）是通过17β-硫酸盐合成的，该硫酸盐在水中自发水解成几种脱水产物，再合成为17α-羟基-17β-甲基差向异构体。通过使17β-羟基-17α-甲基甾族化合物与三氧化硫吡啶配合物反应来制备17β-硫酸盐。在相应的17个α-甲基差向异构体之前，从毛细管SE-54或OV-1色谱柱的70-170个亚甲基单元中，将17种β-甲基差向异构体作为三甲基甲硅烷基衍生物从气
• 10.1016/j.jsbmb.2024.106527
  作者：Sun, Yanan、Giacomello, Ginevra、Girreser, Ulrich、Steff, Jakob、Bureik, Matthias、de la Torre, Xavier、Botrè, Francesco、Parr, Maria Kristina

  DOI：10.1016/j.jsbmb.2024.106527

  日期：——

  in humans leads to several phase І metabolites and their corresponding phase Ⅱ conjugates. Previous studies have postulated the 3α-sulfoconjugate of 17α-methyl-5β-androstane-3α,17β-diol (S2) as principal sulfate metabolite of MT, with a detection window exceeding 10 days. However, a final direct and unambiguous confirmation of the structure of this metabolite is missing until now. In this study, we

  甲基睾酮（MT）是兴奋剂控制分析中发现的最常被滥用的合成代谢雄激素类固醇之一。 MT 在人体中的代谢产生多种 І 相代谢物及其相应的 Ⅱ 相结合物。先前的研究假设17α-甲基-5β-雄甾烷-3α,17β-二醇(S2)的3α-磺基缀合物是MT的主要硫酸盐代谢物，检测窗口超过10天。然而，迄今为止，尚未对该代谢物的结构进行最终直接且明确的确认。在本研究中，我们建立了一种检测和识别 S2 的方法，使用液相色谱联用串联质谱 (LC-MS/MS) 进行完整分析，无需复杂的样品预处理。一项体外研究得出了所有 3-硫酸化 17-甲基雄甾烷-3,17-二醇非对映异构体的 LC-MS/MS 参考保留时间，从而可以对潜在检测到的代谢物进行准确的结构分配。在对一名健康男性志愿者进行的体内排泄研究中，单次口服 10 mg MT 后证实了代谢物 S2 的存在。参考标准是化学合成的，通过精确质谱 (MS) 和核磁共振
• Facilitating Children's Understanding of Misinterpretation: Explanatory Efforts and Improvements in Perspective Taking
  作者：Bradford H. Pillow、Clay Mash、Samuel Aloian、Valerie Hill

  DOI：10.1080/00221320209598673

  日期：2002.6

  The authors investigated children's understanding of how mistaken beliefs can arise through misinterpretation of ambiguous information. Children (N = 91), aged 4 to 5 years, were given pre- and posttests on their ability to infer a puppet's interpretation of a restricted-view drawing after the puppet had been led to an erroneous expectation about the drawing's identity. Before the posttest, the children received either self-explanation training or other-explanation training in which they explained the source of their own or a puppet's misinterpretations of drawings; a control group received no training. The children who received training improved from pre- to posttest, and those who had practiced explaining misinterpretations by referring to previously viewed pictures or to features of a target picture showed the greatest improvement. These results indicate that learning to explain misinterpretations can help children recognize situations in which misinterpretations are likely to occur.
• DE643978
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  公开号：——

  公开（公告）日：——