3β,5α,6β-trihydroxy-5α-androstan-17-one | 10161-36-1

• 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: 3β,5α,6β-trihydroxy-5α-androstan-17-one
• 英文别名: 3β,5α,6β-trihydroxy-androstan-17-one；3β,5α,6β-trihydroxyandrostan-17-one；3β.5.6β-trihydroxy-5α-androstanone-(17)；3β.5.6β-Trihydroxy-5α-androstanon-(17)；3β,5α,6β-trihydroxy-17-oxo-androstane；3beta,5alpha,6beta-Trihydroxyandrostan-17-one；(3S,5R,6R,8R,9S,10R,13S,14S)-3,5,6-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 10161-36-1
• 化学式: C₁₉H₃₀O₄
• 分子量: 322.445
• InChiKey: FRPCYGNWEDESDG-LYVQZGCSSA-N

物化性质

• 熔点：
  297-300 °C
• 沸点：
  469.7±45.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β,5α,6β-trihydroxy-5α-androstan-17-one 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以95%的产率得到5α-hydroxyandrostane-3,6,17-trione
  参考文献：
  名称：

  Dawidar, A. M.; Saleh, A. A.; Abdel-Malek, M. M., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1980, vol. 35, # 1, p. 102 - 106

  摘要：

  DOI：
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 双氧水 、 溶剂黄146 作用下， 生成 3β,5α,6β-trihydroxy-5α-androstan-17-one
  参考文献：
  名称：

  葡糖苷der Sterin-und Sexualhormonreihe。Ein Beitrag zur立体化学差向异构体Alkohole

  摘要：

  DOI：

  10.1002/hlca.19380210147

文献信息

• The microbiological hydroxylation of 3α,5-cycloandrostanes by Cephalosporium aphidicola
  作者：Caroline S. Bensasson、James R. Hanson、Yvan Le Huerou

  DOI：10.1016/s0031-9422(99)00415-x

  日期：1999.12

  The microbiological hydroxylation of some 3α,5-cycloandrostanes by the fungus, Cephalosporium aphidicola has been shown to take place at C-2α and C-14α and a 6β-alcohol was oxidized to the 6-ketone.

  真菌 Cephalosporium aphidicola 对某些 3α,5-环雄甾烷的微生物羟基化作用已显示在 C-2α 和 C-14α 处发生，并且 6β-醇被氧化为 6-酮。
• Synthesis of Heterocyclic-Substituted Novel Hydroxysteroids with Regioselective and Stereoselective Reactions
  作者：Abubakar Mohammed Kolo、Emine İpek、İrfan Çapan、Süleyman Servi

  DOI：10.1002/jhet.3070

  日期：2018.2

  Polyhydroxy steroids bearing the 3β,5α,6β‐trihydroxy pattern were synthesized from different heterocyclic‐substituted unsaturated steroid by an easy and simple method with high yields. The endocyclic double bond of thiophene‐substituted and quinoline‐substituted steroids were converted to the trans‐diaxial diol by the regioselective and stereoselective reactions with m‐chloroperoxybenzoic acid in the

  通过简单易行的高收率方法，由不同的杂环取代的不饱和类固醇合成了具有3β，5α，6β-三羟基模式的多羟基类固醇。的噻吩基取代的喹啉和取代的甾族化合物被转化为环内双键的反式-diaxial二醇由区域选择性和立体选择性的反应与米在碱性介质中氯过氧酸。
• Thiosteroid—XXVIII
  作者：T. Komeno、M. Kishi

  DOI：10.1016/s0040-4020(01)98017-2

  日期：1971.1

  to that described in the preceding paper. In the course of the synthesis, the reaction of 3-oxo-2α,5α-episulphides with alkali was found to give rise to CβS bond cleavage. In a model experiment with 3-oxo-5α-cholestan-2α,5-episulphide, 3-oxocholest-4-ene-2α-thiol was formed under nitrogen and bis 3-oxocholesta-1,4-dien-2-yl disulphide in the air.

  17β-羟基-3-氧代-5α-雄烷-2α，5-异硫醚及其19-nor衍生物的合成方法与前文所述相似。在合成过程中，发现3-氧代-2α，5α-环硫化物与碱的反应引起CβS键的裂解。在3-oxo-5α-胆甾烷-2α，5-异硫醚的模型实验中，在氮和双3-oxocholesta-1,4-dien-2-yl二硫化物下形成3-oxocholest-4-ene-2α-硫醇。在空中。
• Sterols as Anticancer Agents: Synthesis of Ring-B Oxygenated Steroids, Cytotoxic Profile, and Comprehensive SAR Analysis
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm1007769

  日期：2010.11.11

  The cytotoxicity of oxysterols was systematically studied in tumor and normal cells. Synthetic strategies to prepare this library included oxidations at ring B and a new method to yield 6 beta-hemiphthalates directly from Delta(5)-steroids. Most oxysterols were cytotoxic and showed selectivity toward cancer cells, LAMA-84 cells (leukemia) being particularly sensitive to 4, 8, 22, and 27 (IC50 < 5.6 mu M). The structural requirements to induce selective toxicity are discussed to shed light on the development of new anticancer drugs.
• Efficient trans-diaxial hydroxylation of Δ5-steroids
  作者：João F.S. Carvalho、M. Manuel Cruz Silva、M. Luisa Sá e Melo

  DOI：10.1016/j.tet.2010.01.089

  日期：2010.3

  A convenient, fast, and high-yielding process to synthesize 5 alpha,6 beta-dihydroxysteroids directly from the correspondent Delta(5)-steroids is reported. The reaction protocol consists in the conjugation of a readily available and stable oxidant, magnesium bis(monoperoxyphthalate) hexahydrate, with the non-toxic bismuth(III) triflate in acetone to afford the trans-diaxial hydroxylation product in a stepwise manner and in excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.