2α-bromo-17β-hydroxy-17α-methyl-5α-androstan-3-one | 74252-42-9

• 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: 2α-bromo-17β-hydroxy-17α-methyl-5α-androstan-3-one
• 英文别名: 2-α-bromo-17-α-methyl-5-α-androstan-17-β-ol-3-one；2α-Bromo-17α-methyldihydrotestosterone；2α-bromo-17β-hydroxy-17α-methyl-(5α)-androstan-3-one；2α-Brom-17β-hydroxy-17α-methyl-5α-androstanon-(3)；2α-Brom-17α-methyl-5α-androstanol-(17β)-on-(3)
• CAS: 74252-42-9；76333-34-1
• 化学式: C₂₀H₃₁BrO₂
• 分子量: 383.369
• InChiKey: OJVJQLMYHBKROI-USILWVMGSA-N

物化性质

• 沸点：
  450.7±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2α-bromo-17β-hydroxy-17α-methyl-5α-androstan-3-one 在 sodium peroxide 、 双氧水 、 lithium carbonate 、 lithium bromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 17β-hydroxy-17α-methyl-1α,2α-spirooxirane-5α-androst-3-one
  参考文献：
  名称：

  Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes

  摘要：

  Desoxymethyltestosterone (DMT; 17 beta-hydroxy-17 alpha-methyl-5 alpha-androst-2-ene) is a designer steroid present in hormonal supplements distributed illegally as such or in combination with other steroids, for self-administration. It figures on the list of substances prohibited in sports and its detection in athlete's urine samples is based upon the presence of the parent compound or the main urinary metabolite, which has not been characterized yet. Following its isolation from cultures of human fresh hepatocytes and S9 fractions of liver homogenates, we were able to identify this metabolite as being 17 alpha-methyl-2 beta,3 alpha,17 beta-trihydroxy-5 alpha-androstane. Other minor metabolites were also characterized. The production, isolation, NMR, mass spectral analyses and chemical synthesis are presented. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.02.008
• 作为产物：
  描述：

  17Alpha-甲基-5Alpha-雄甾-3Β,17Β-二醇 在 jones reagent 、 pyridinium hydrobromide perbromide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 2α-bromo-17β-hydroxy-17α-methyl-5α-androstan-3-one
  参考文献：
  名称：

  A convenient synthesis of oxandrolone through a regioselective Candida antarctica lipase-catalyzed transformation

  摘要：

  The use of a regioselective CAL-catalyzed transformation of a suitable intermediate allowed a convenient synthesis of oxandrolone, an anabolic hormone actually employed to improve the quality of life for patients with HIV-infections. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00593-7

文献信息

• Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route toward <i>contra</i>-Thermodynamic Olefins
  作者：Huaibo Zhao、Alastair J. McMillan、Timothée Constantin、Rory C. Mykura、Fabio Juliá、Daniele Leonori

  DOI：10.1021/jacs.1c06768

  日期：2021.9.15

  mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric

  我们在这里报告了一种在烷基卤化物上进行 E2 型消除的机械上不同的策略。该策略利用了 α-氨基烷基自由基介导的卤素原子转移 (XAT) 与去饱和钴催化的相互作用。该方法产量高，具有多种功能，并用于获取工业相关材料。与不对称底物产生区域异构混合物的热 E2 消除相比，这种方法能够通过微调钴催化剂的电子和空间性质，获得高烯烃位置选择性。这一史无前例的机械特性允许访问禁忌-thermodynamic烯烃，由E2淘汰难以捉摸。
• Synthesis and investigation of certain androstane derivatives of 5-fluorouracil
  作者：L. N. Volovel'skii、I. A. Rastrepina、N. V. Popova、V. N. Koryukina、A. A. Zidermane、A. Zh. Dauvarte

  DOI：10.1007/bf01148631

  日期：1986.9

  tumors [i]. Because of its high toxicity, it is presently employed in its N-substituted forms, e.g., l-(2-furanidyl)-5-fluorouracil (fluorofur) [4J. Based on the assumption that dihydrotestosterone derivatives which easily penetrate cell membranes would be good conductors of this antimetabolite, we synthesized N-derivatives of 5-fluorouracil, dihydrotestosterone, and 17=-methyl dihydrotestosterone according

  核酸拮抗剂5-氟尿嘧啶已广泛用于治疗多种恶性肿瘤[i]。由于其高毒性，它目前以其 N-取代形式使用，例如，1-(2-呋喃基)-5-氟尿嘧啶 (fluorofur) [4J. 基于容易穿透细胞膜的二氢睾酮衍生物是这种抗代谢物的良导体的假设，我们根据以下模式合成了 5-氟尿嘧啶、二氢睾酮和 17=-甲基二氢睾酮的 N-衍生物：
• Steroids IX
  作者：Norman J. Doorenbos、Conrad P. Dorn

  DOI：10.1002/jps.2600510504

  日期：1962.5

  The synthesis of thiazolo[d-3,2]-5α-cholest-2-ene, and thiazolo[d-3,2]-17α-methyl-5α-androst-2-en-17β-ol, and eight of their 2′-derivatives is reported. These derivatives include the 2′-methyl, 2′-amino, 2′-allylamino, and 2′-phenylamino substituted thiazolosteroids. Preliminary data indicate that 2′-methylthiazolo[d-3,2]-17α methyl-5α-androst-2-en-17β-ol is a good anabolic agent.

  噻唑并[d-3,2]-5α-胆甾-2-烯和噻唑并[d-3,2]-17α-甲基-5α-androst-2-en-17β-ol的合成及其八个报告了2'-衍生物。这些衍生物包括2'-甲基，2'-氨基，2'-烯丙基氨基和2'-苯基氨基取代的噻唑类固醇。初步数据表明，2′-甲基噻唑并[d-3，2]-17α甲基-5α-雄甾烷-2-en-17β-ol是良好的合成代谢剂。
• Development of a Commercial Process to Produce Oxandrolone
  作者：John E. Cabaj、David Kairys、Thomas R. Benson

  DOI：10.1021/op060231b

  日期：2007.5.1

  A manufacturing scale process for the preparation of the anabolic steroid Oxandrolone was developed. Key elements included the following: the bromination of methylandrostanolone with perbromide to give the 2-bromoketone in ca. 80% yield with minimal dehydration, subsequent elimination of the bromide with Li2CO3/LiBr to give the 2-enone in ca. 70% yield with minimal formation of methyltestosterone, and an ozonolysis procedure to give the penultimate intermediate in ca. 90% yield. The overall yield from methylandrostanolone to Oxandrolone using the described process was 45% as compared to the original Searle yield of 8%.
• Steroids. CLXXXIII.¹ New Anabolic Agents from Steroids²
  作者：John A. Zderic、H. Carpio、A. Ruiz、D. Chávez Limón、F. Kincl、H. J. Ringold

  DOI：10.1021/jm00338a024

  日期：1963.3