14-Hydroxy-3β-acetoxyandrost-5-en-17-on | 1443-89-6

• 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: 14-Hydroxy-3β-acetoxyandrost-5-en-17-on
• 英文别名: Androst-5-en-17-one, 3-(acetyloxy)-14-hydroxy-, (3beta)-；[(3S,8R,9S,10R,13S,14R)-14-hydroxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,11,12,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1443-89-6
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: CILYEVDVHHCNDN-XCPHWNSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  14-Hydroxy-3β-acetoxyandrost-5-en-17-on 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 5α-Androstan-14α-ol-3,7,17-trion
  参考文献：
  名称：

  Valcavi; Martelli; Sironi, Farmaco, Edizione Scientifica, 1975, vol. 30, # 6, p. 464 - 478

  摘要：

  DOI：
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 chromium(VI) oxide 作用下， 生成 14-Hydroxy-3β-acetoxyandrost-5-en-17-on
  参考文献：
  名称：

  Direct Introduction of Oxygen into the Steroid Nucleus. I. Studies on the Chromic Anhydride Oxidation of Dehydroisoandrosterone Acetate Dibromide¹

  摘要：

  DOI：

  10.1021/ja01141a084

文献信息

• C−H Acetoxylation-Based Chemical Synthesis of 17 β-Hydroxymethyl-17 α-methyl-18-norandrost-13-ene Steroids
  作者：Alaksiej L. Hurski、Maryia V. Barysevich、Tatsiana S. Dalidovich、Marharyta V. Iskryk、Nastassia U. Kolasava、Vladimir N. Zhabinskii、Vladimir A. Khripach

  DOI：10.1002/chem.201602957

  日期：2016.9.26

  Palladium‐catalyzed C−H acetoxylation has been proposed as a key transformation in the first chemical synthesis of steroids bearing a unique 17β‐hydroxymethyl‐17α‐methyl‐18‐nor‐13‐ene D‐fragment. This C−H functionalization step was crucial for inverting the configuration at the quaternary stereocenter of a readily available synthetic intermediate. The developed approach was applied to prepare the metandienone

  在具有独特的17β-羟甲基-17a-甲基-18-nor-13-烯D片段的类固醇的第一个化学合成中，钯催化的CH乙酰氧基化已被提议作为关键转化。此CH功能化步骤对于反转易于获得的合成中间体的四级立体中心的构型至关重要。所开发的方法被用于制备抗兴奋剂分析中作为参考物质所需的甲氧萘醌代谢物，以控制这种雄激素合成代谢类固醇的滥用。
• Radical Oxidation of 17-Functionalized 14α-Hydroxy Steroids
  作者：Vladimir A. Khripach、Vladimir N. Zhabinskii、Anna I. Kotyatkina、Galina P. Fando、Yuliya Y. Zhiburtovich、Alexander S. Lyakhov、Alla A. Govorova、Marinus B. Groen、Jaap van der Louw、Aede de Groot

  DOI：10.1135/cccc20011764

  日期：——

  The radical oxidation of 14α-hydroxy steroids with various functional groups at C-17 was studied. Lead tetraacetate and ceric ammonium nitrate were used as oxidizing agents. It was shown that reactions of this type afforded complex mixtures of compounds. However, the radical oxidation of 14α-hydroxy-17-oxo steroid (lead tetraacetate version of the hypoiodite reaction) proceeded smoothly with formation of the 13,14-secosteroid in up to 85% yield. The structure and conformation of the formed 13α-iodo-3α,5-cyclo-13,14-seco-5α-androst-5-ene-14,17-dione was determined by X-ray analysis.

  14α-羟基类固醇在C-17位置带有各种官能团的激进氧化进行了研究。铅四乙酸盐和铈铵硝酸盐被用作氧化剂。结果表明，这类反应产生了复杂的化合物混合物。然而，14α-羟基-17-酮类固醇的激进氧化（铅四乙酸盐版本的次碘酸盐反应）顺利进行，产率高达85％，形成了13,14-环类固醇。通过X射线分析确定了形成的13α-碘代-3α,5-环-13,14-环-5α-雄烷-5-烯-14,17-二酮的结构和构象。
• A cycloaddition route to 14-hydroxysteroids
  作者：Gerald Kirsch、Roland Golde、Günter Neef

  DOI：10.1016/s0040-4039(01)80727-9

  日期：1989.1

  Steroidal 14,16-dienolacetates are stereoselectively converted to either 14β- or 14α-hydroxy steroids by a reaction sequence based on [4+2] cycloaddition with benzyl nitrosoformate.

  通过基于与亚硝基甲酸苄酯的[4 + 2]环加成的反应序列，将甾类14，16-二烯基乙酸酯立体选择性地转化为14β-或14α-羟基甾族化合物。
• New process for the preparation of certain steroids, especially intermediates for the preparation of proligestone and related compounds, and new intermediates formed in this process
  申请人：AKZO N.V.

  公开号：EP0189951A1

  公开（公告）日：1986-08-06

  The invention relates to a new process for the preparation of 14-alpha-17-alpha-dihydroxy-17-beta-substituted steriods by reaction of 14-alpha-hydroxy-17-oxo-steroids with metal organic compounds. Furthermore, the invention relates to the 14-alpha-17-alpha-dihydroxy-17-beta- substituted steroids prepared by the new process and their use in the production of 14-alpha-17-alpha- methylenedioxypregnane derivatives.

  本发明涉及一种通过 14-α-羟基-17-氧代类固醇与金属有机化合物反应制备 14-α-17-α-二羟基-17-β-取代类固醇的新工艺。 此外，本发明还涉及通过新工艺制备的 14-α-17-α-二羟基-17-β-取代类固醇及其在生产 14-α-17-α-亚甲基二氧孕甾烷衍生物中的用途。
• Mamlok,L., Bulletin de la Societe Chimique de France, 1967, p. 3827 - 3836
  作者：Mamlok,L.

  DOI：——

  日期：——