11α,17β-dihydroxy-5α-androstan-3-one | 25788-56-1

• 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: 11α,17β-dihydroxy-5α-androstan-3-one
• 英文别名: 11α,17β-Dihydroxy-5α-androstan-3-on；5alpha-Androstan-3-one, 11alpha,17beta-dihydroxy-；(5S,8S,9S,10S,11R,13S,14S,17S)-11,17-dihydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 25788-56-1
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: WARJRVLSUJRZKT-MBLYQLFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11α,17β-dihydroxy-5α-androstan-3-one 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 为溶剂， 生成 1-((3S,5S,8S,9S,10S,11R,13S,14S,17S)-11,17-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-ethanone
  参考文献：
  名称：

  Water Soluble Steroids with Catalytic Substituents II. Synthesis of 3β-(4(5)-Imidazolyl)-5α-androstane-11β, 17β,-diamine and Comparison of its Catalytic Properties with Those of 17β-(4(5)-Imidazolyl)-5α-androstane-3β, 11β-diamine

  摘要：

  3β-(4(5)-咪唑基)-5α-雄烷-11β,17β-二胺，15，是从腺酮，2，经过多步合成的，首先进行锂氨还原得到11α,17β-二羟基-5α-雄甾-3-酮，3，然后转化为其二乙酸酯，4。在3酮基上进行乙炔基化得到乙炔三醇5，纯化为其11,17-二乙酸酯6。酸催化6的重排得到3-乙酰基-5α-雄烷-2-烯-11α,17β-二醇二乙酸酯，7。这经过氢化，然后经过碱催化水解和平衡得到结晶的3β-乙酰基-5α-雄烷-11α,17β-二醇，9，它被转化为3β-乙酰氧乙酰-5α-雄烷-11α,17β-二醇，10，使用四乙酸铅。水解为三醇后，11，魏登哈根反应导致形成3β-咪唑基-5α-雄烷-11α,17β-二醇，12。最后氧化为二酮，13，形成二肟，14，和氢化得到15。如预期的那样，15比17β-(4(5)-咪唑基-5α-雄烷-3β,11β-二胺，1，更好地催化含疏水取代基的芳基酯的水解，但效果很小。对于1，当芳基酯上存在带电基团时，会出现明显的静电速率增强或减缓；而对于15，这种效应要小得多。

  DOI：

  10.1139/v73-586
• 作为产物：
  描述：

  雄诺龙 生成 11α,17β-dihydroxy-5α-androstan-3-one
  参考文献：
  名称：

  Bell,A.M. et al., Journal of the Chemical Society. Perkin transactions I, 1973, p. 2131 - 2136

  摘要：

  DOI：

文献信息

• Microbial hydroxylation of epiandrosterone by <i>Aspergillus candidus</i>
  作者：Kudret Yildirim、Ali Kuru

  DOI：10.1080/10242422.2017.1289184

  日期：2017.3.4

  work, Aspergillus candidus MRC 22634 converted epiandosterone 1 into 10 hydroxylated metabolites. A. candidus has been shown to hydroxylate 1 predominantly at C-11α, C-1α, and C-15β with minor hydroxylations occurring at C-14α and C-7α. Oxidation at C-3, reduction at C-17, and C-3 epimerization of some of the remaining substrate have also been shown. 15β-Hydroxylation and C-3 epimerization of 1 by

  摘要 在这项工作中，念珠菌 MRC 22634 将表雄酮 1 转化为 10 种羟基化代谢物。A. candidus 已显示主要在 C-11α、C-1α 和 C-15β 处羟基化 1，在 C-14α 和 C-7α 处发生少量羟基化。还显示了 C-3 处的氧化、C-17 处的还原和一些剩余底物的 C-3 差向异构化。首次报道了真菌对 1 的 15β-羟基化和 C-3 差向异构化。其中两种代谢物 1α,3α-dihydroxy-5α-androstan-17-one 4 和 15β,17β-dihydroxy-5α-androstan-3-one 7 被鉴定为新化合物。
• Steroids and related products. LII.11-Aza steroids. Part IV. The synthesis of 11-aza 9α-steroids. II. The synthesis of 11-aza-4,5α-dihydrotestosterone
  作者：Maria Gumulka、Ibrahim Halim Ibrahim、Zbigniew Bończa-Tomaszewski、Ch. R. Engel

  DOI：10.1139/v85-126

  日期：1985.3.1

  An efficient synthesis from adrenosterone or 11α-hydroxytestosterone of 17β-hydroxy-11-aza-5α-androstan-3-one, the 11-aza analogue of dihydrotestosterone, is described. For the elaboration of the 1...

  描述了从肾上腺素或 11α-羟基睾酮的 17β-羟基-11-氮杂-5α-androstan-3-one（二氢睾酮的 11-氮杂类似物）的有效合成。为了详细说明 1...
• Microbial Baeyer–Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway
  作者：Alina Świzdor、Anna Panek、Natalia Milecka-Tronina

  DOI：10.1016/j.steroids.2014.01.006

  日期：2014.4

  Beauveria bassiana KCH 1065, as was recently demonstrated, is unusual amongst fungal biocatalysts in that it converts C-19 3-oxo-4-ene and 3 beta-hydroxy-5-ene as well as 3 beta-hydroxy-5 alpha-saturated steroids to 11 alpha-hydroxy ring-D lactones. The Baeyer-Villiger monooxygenase (BVMO) of this strain is distinguished from other enzymes catalyzing BVO of steroidal ketones by the fact that it oxidizes solely substrates with 11 alpha-hydroxyl group. The current study using a series of 5 alpha-saturated steroids (androsterone, 3 alpha-androstanediol and androstanedione) has highlighted that a small change of the steroid structure can result in significant differences of the metabolic fate. It was found that the 3 alpha-stereochemistry of hydroxyl group restricted "normal" binding orientation of the substrate within 11 alpha-hydroxylase and, as a result, androsterone and 3 alpha-androstanediol were converted into a mixture of 7 beta-, 11 alpha- and 7 alpha-hydroxy derivatives. Hydroxylation of androstanedione occurred only at the 11 alpha-position, indicating that the 3-oxo group limits the alternative binding orientation of the substrate within the hydroxylase. Only androstanedione and 3 alpha-androstanediol were metabolized to hydroxylactones. The study uniquely demonstrated preference for oxidation of equatorial (11 alpha-, 7 beta-) hydroxyketones by BVMO from B. bassiana. The time course experiments suggested that the activity of 17 beta-HSD is a factor determining the amount of produced ring-D lactones. The obtained 11 alpha-hydroxylactones underwent further transformations (oxy-red reactions) at C-3. During conversion of androstanedione, a minor dehydrogenation pathway was observed with generation of 11 alpha,17 beta-dihydroxy-5 alpha-androst-1-en-3-one. The introduction of C1-C2 double bond has been recorded in B. bassiana for the first time. (C) 2014 Elsevier Inc. All rights reserved.
• Crabb, Trevor A.; Ratcliffe, Norman M., Journal of Chemical Research, Miniprint, 1989, # 9, p. 2162 - 2174
  作者：Crabb, Trevor A.、Ratcliffe, Norman M.

  DOI：——

  日期：——
• US4013688A
  申请人：——

  公开号：US4013688A

  公开（公告）日：1977-03-22