17β-acetoxy-5α-androst-2-ene | 2324-10-9

• 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: 17β-acetoxy-5α-androst-2-ene
• 英文别名: 5α-androst-2-en-17β-ol 17-acetate；5α-androst-2-en-17β-ol-acetate；17β-Acetoxy-5α-androst-2-en；(10S)-17c-Acetoxy-10r.13c-dimethyl-(5tH.8cH.9tH.14tH)-Δ²-tetradecahydro-1H-cyclopenta[a]phenanthren；Essigsaeure-(5α-androsten-(2)-yl-(17β)-ester)；5α-Androsten-(2)-yl-(17β)-acetat；17beta-Acetoxy-5alpha-androst-2-ene；[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
• CAS: 2324-10-9
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: CIBOOPKLBBFHSW-MQWPULPWSA-N

物化性质

• 熔点：
  101-101.5 °C(Solv: methanol (67-56-1))
• 沸点：
  388.9±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17β-acetoxy-5α-androst-2-ene 在 氯仿 、 乙酸酐 、 臭氧 作用下， 生成 17β-hydroxy-A-nor-5α-androstan-2-one
  参考文献：
  名称：

  Sterols. XIV. Pyroandrosterone and Derivatives

  摘要：

  DOI：

  10.1021/ja01286a059
• 作为产物：
  描述：

  (10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基)乙酸酯 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 氯 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 1.92h， 生成 17β-acetoxy-5α-androst-2-ene
  参考文献：
  名称：

  Kumar, Sashi; Templeton, John F.; Zeglam, Talal Hasan, Synthetic Communications, 1984, vol. 14, # 14, p. 1333 - 1340

  摘要：

  DOI：

文献信息

• Reductive desulfonylation of phenyl sulfones by samarium(II) iodide-hexamethylphosphoric triamide
  作者：H. Künzer、M. Stahnke、G. Sauer、R. Wiechert

  DOI：10.1016/0040-4039(91)85009-t

  日期：1991.4

  Samarium(II) iodide in tetrahydrofuran reductively desulfonylates phenyl sulfones in the presence of hexamethylphosphoric triamide. This transformation is illustrated here for ten substrates, which include secondary alicyclic, β-hydroxy, vicinal bis-, and α,β-unsaturated sulfones.

  在六甲基磷酸三酰胺存在下，四氢呋喃中的碘化mar（II）还原性还原苯砜。这里说明了十种底物的这种转化，其中包括仲脂环族，β-羟基，邻位双-和α，β-不饱和砜。
• Reaction of phosphoryl chloride in pyridine with halogenohydrins
  作者：A. Guzmán、P. Ortiz de Montellano、Pierre Crabbé

  DOI：10.1039/p19730000091

  日期：——

  The reaction of iodohydrins with a solution of phosphoryl chloride in pyridine constitutes a useful modification of the Cornforth method for the stereospecific preparation of olefins.

  碘代醇与磷酰氯在吡啶中的溶液反应构成了用于烯烃立体定向制备的Cornforth方法的有用改进。
• Photocatalytic Generation of Trifluoromethyl Nitrene for Alkene Aziridination
  作者：Norbert Baris、Martin Dračínský、Ján Tarábek、Josef Filgas、Petr Slavíček、Lucie Ludvíková、Soňa Boháčová、Tomáš Slanina、Blanka Klepetářová、Petr Beier

  DOI：10.1002/anie.202315162

  日期：2024.1.8

  N‐Trifluoromethylated organics may be applied in drug design, agrochemical synthesis, and materials science, among other areas. Yet, despite recent advances in the synthesis of aliphatic, cyclic and heterocyclic N‐trifluoromethyl compounds, no strategy based on trifluoromethyl nitrene has hitherto been explored. Here we describe the formation of triplet trifluoromethyl nitrene from azidotrifluoromethane, a stable and safe‐to‐use precursor, by visible light photocatalysis. The addition of CF₃N to alkenes via biradical intermediates afforded previously unknown aziridines substituted with trifluoromethyl group on the nitrogen atom. The obtained aziridines were converted into either N‐trifluoromethylimidazolines, via formal [3+2] cycloaddition with nitriles, mediated by a Lewis acid, or into N‐trifluoromethylaldimines, via ring opening and aryl group migration mediated by a strong Brønsted acid. Our findings open new opportunities for the development of novel classes of N‐CF₃ compounds with possible applications in the life sciences.

  摘要N-三氟甲基有机物可应用于药物设计、农用化学品合成和材料科学等领域。然而，尽管最近在合成脂肪族、环状和杂环 N-三氟甲基化合物方面取得了进展，但迄今为止还没有人探索过基于三氟甲基芘的策略。在此，我们介绍了利用可见光光催化技术从叠氮三氟甲烷（一种稳定且可安全使用的前体）中生成三氟甲基腈的过程。通过双辐射中间体将 CF3N 加到烯烃中，可以得到氮原子上被三氟甲基取代的、之前未知的氮杂环丁烷。在路易斯酸的介导下，获得的氮丙啶通过与腈的正式 [3+2] 环加成转化为 N-三氟甲基咪唑啉；或在强布氏酸的介导下，通过开环和芳基迁移转化为 N-三氟甲基甲醛亚胺。我们的发现为开发可能应用于生命科学领域的新型 N-CF3 化合物提供了新的机遇。
• Chemical synthesis of 2β-amino-5α-androstane-3α,17β-diol N-derivatives and their antiproliferative effect on HL-60 human leukemia cells
  作者：Dominic Thibeault、Jenny Roy、Patrick DeRoy、Donald Poirier

  DOI：10.1016/j.bmc.2008.03.031

  日期：2008.5

  Even though few steroids are used for the treatment of leukemia, 2 beta-(4-methylpiperazinyl)-5 alpha-androstane-3 alpha,17 beta-diol (1) was recently reported for its ability to inhibit the proliferation of human leukemia HL-60 cells. With an efficient procedure that we had developed for the aminolysis of hindered steroidal epoxides, we synthesized a series of 2 beta-amino-5 alpha-androstane-3 alpha,17 beta-diol N-derivatives structurally similar to 1. Hence, the opening of 2,3 alpha-epoxy-5 alpha-androstan-17 beta-diol with primary and secondary amines allowed the synthesis of aminosteroids with diverse length, rami. cation, and functionalization of the 2 beta-side chain. Sixty-four steroid derivatives were tested for their capacity to inhibit the proliferation of HL-60 cells; thus obtaining first structure - activity relationship results. Ten aminosteroids with long alkyl chains (7 - 16 carbons) or bulky groups (diphenyl or adamantyl) have shown antiproliferative activity over 78% at 10 mu M and superior to that of the lead compound. The 3,3-diphenylpropylamino, 4-nonylpiperazinyl and octylamino derivatives of 5 alpha-androstane-3 alpha,17 beta-diol inhibited the HL-60 cell growth with IC(50) of 3.1, 4.2 and 6.4 mu M, respectively. They were also found to induce the HL-60 cell differentiation. (c) 2008 Elsevier Ltd. All rights reserved.
• Regio- and stereoselective remote hydroxylations of the A ring of steroids. A novel route to 5-.alpha. steroids with cis-coupled A and B rings
  作者：Jean Pierre Begue

  DOI：10.1021/jo00143a019

  日期：1982.10