17β-acetoxy-5β-estran-3-one | 2302-77-4

• 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-5β-estran-3-one
• 英文别名: 17β-Acetoxy-19-nor-5β,10β-androstan-3-on；17β-Acetoxy-5β-oestran-3-on；[(5R,8R,9R,10S,13S,14S,17S)-13-methyl-3-oxo-2,4,5,6,7,8,9,10,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
• CAS: 2302-77-4
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: QZPGVFRDAIWANC-UIUSIFNCSA-N

物化性质

• 熔点：
  130-131.5 °C
• 沸点：
  422.7±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  19-去甲睾酮乙酸酯 在 二氢吡啶 、 C₉H₁₈N₂*C₁₀H₁₆O₄S 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以90%的产率得到17β-acetoxy-5β-estran-3-one
  参考文献：
  名称：

  类固醇的共轭烯烃的直接有机催化立体选择性转移氢化† ‡

  摘要：

  通过动力学控制和有机催化的顺-选择性转移氢化已成功地证明了各种类固醇的烯酮官能团的还原。在此，已经报道了通过有机催化的许多5β-类固醇的非对映选择性合成，其具有广泛的医学和药学应用。机理研究和产物的选择性清楚地表明，催化剂1b · D -CSA足够温和，可以在以汉茨sch酸酯2a为氢源的有机催化转移加氢过程中通过亚胺离子的形成来活化各种手性环状烯酮。此外，有明确的证据表明可以选择性地形成中间亚胺鎓类物质[ I] +通过NMR和ESI-HRMS分析对受控实验进行在线监测来表征。

  DOI：

  10.1039/c3ra41519h

文献信息

• Stereochemistry of the Palladium-catalyzed Hydrogenation of 3-Oxo-4-ene Steroids. V. A Kinetic Study in Basic and Acidic Media
  作者：Shigeo Nishimura、Yasuhiro Momma、Hideo Kawamura、Michio Shiota

  DOI：10.1246/bcsj.56.780

  日期：1983.3

  Effects of the β-methyl group at C-10 and some oxygen functions (=O, OH, OAc) at C-11, C-17, and C-20 on the rates of hydrogenation of 3-oxo-4-ene steroids have been studied with palladium catalyst in pyridine or THF/HBr as solvent. In contrast to the hydrogenation in pyridine, the rate in THF/HBr was greatly depressed by the presence of 10β-methyl group. The reactivity of the steroids was enhanced

  C-10 处的 β-甲基和 C-11、C-17 和 C-20 处的一些氧官能团（=O、OH、OAc）对 3-oxo-4-ene 类固醇加氢速率的影响已经在吡啶或 THF/HBr 作为溶剂中用钯催化剂进行了研究。与吡啶中的氢化相反，10β-甲基的存在大大降低了 THF/HBr 中的氢化率。类固醇的反应性通过氧官能团增强，特别是通过 11, 17-二氧代基团。基于获得的结果，从机理考虑讨论了取代基的影响。
• Isomeric estrane derivatives
  作者：R.E. Counsell

  DOI：10.1016/0040-4020(61)80027-6

  日期：1961.1

  Various 3,17-oxygenated isomeric estrane derivatives have been synthesized as possible metabolites of 19-norsteroids. Methods employed to establish configurations are described and biological data on some of the more pertinent compounds is presented.

  已合成了各种3,17-氧化异构雌激素衍生物，作为19-降糖甾体的可能代谢产物。描述了用于建立构型的方法，并提供了一些更相关化合物的生物学数据。
• Estrane derivatives—I
  作者：Chiadao Chen

  DOI：10.1016/s0040-4020(01)82609-0

  日期：1958.1

  Three of the four possible ring A/B isomeric estrane-17-ol-3-ones and their corresponding acetates, benzoates and diones were prepared for the purpose of biochemical studies. The positions of the hydrogens on C5 and C10 of these compounds have been assigned.

  为了生化研究的目的，制备了四种可能的环A / B异构体雌激素17-醇-3-酮中的三种及其相应的乙酸酯，苯甲酸酯和二酮。已经确定了这些化合物的C5和C10上的氢的位置。
• Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging
  作者：Yearn Seong Choe、John A. Katzenellenbogen

  DOI：10.1016/0039-128x(95)00009-f

  日期：1995.5

  Seven androgens, substituted with fluorine at C-6, were prepared as potential imaging agents for androgen receptor-positive prostate tumors and were evaluated in vitro in terms of their lipophilicity and their relative binding affinities (RBA, relative to R 1881 = 100) for the androgen receptor and for sex steroid binding protein. Introduction of a fluorine atom into the C-6 position of an androgen generally decreases binding affinity to the androgen receptor, except in the two cases: 6 alpha-fluoro-19-nor-testosterone (RBA = 41.6 versus 30.6 for the unsubstituted steroid) and 6 alpha-fluoro-19-nor-testosterone (RBA = 8.9 versus 6.6). Receptor binding of the C-6 fluoro-androgens is also stereospecific, showing higher binding affinities for the alpha-epimers compared to the corresponding beta-epimers (4:1-15:1). Binding affinity to sex steroid binding protein is the lowest with 19-nor-testosterone, which is also the least lipophilic androgen studied. Based on the binding properties of compounds in this series, 6 alpha-fluoro-19-nor-testosterone appears to have the most promise as a turner imaging agent.
• Neudert,W.; Roepke,H., Steroid-Sperktrenatlas <Berlin 1965>Nr.671
  作者：Neudert,W.、Roepke,H.

  DOI：——

  日期：——