(8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate

• 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: (8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate
• 英文别名: (3S,8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate；[(3S,8R,9S,10R,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate
• 化学式: C₂₆H₄₁F₃O₄SSi
• 分子量: 534.756
• InChiKey: XXAWARXRWOSXSC-FYVXYBBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate 在 盐酸 、 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 1.67h， 生成 乙酸阿比特龙酯
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF ABIRATERONE AND INTERMEDIATES THEREOF

  摘要：

  本发明提供了用于制备阿比特隆的中间体，以及用于制备阿比特隆及其中间体的方法。中间体包括式（IV）的化合物： 其中R代表一个羟基保护基团。

  公开号：

  US20150005489A1
• 作为产物：
  描述：

  去氢表雄酮 在 咪唑 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 (8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate
  参考文献：
  名称：

  双脱氢表雄酮类似物作为潜在的新型抗癌剂的合成和生物学评价

  摘要：

  报告了 13 种皮质抑素 A 类似物对 CDK8 的合成、细胞毒性和抑制作用。这些努力表明，在 17 位具有 6-或 7-异喹啉或 5-吲哚侧链的类似物是最有前途的抗增殖剂。这些化合物在 CEM、HeLa 和 HMEC-1 细胞中显示出有效的细胞毒性作用。所有三种化合物的 IC50 值均小于 10µM。最有趣的 10l 类似物对人真皮微血管内皮细胞系 (HMEC-1) 的 IC50 值为 0.59 µM，明显低于参考标准 2-甲氧基雌二醇。在 50 nM 的浓度下，最有效的 10 小时化合物将 CDK8 的活性降低到 35%。

  DOI：

  10.3390/molecules25133052

文献信息

• Electro‐Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes
  作者：Andreas N. Baumann、Arif Music、Jonas Dechent、Nicolas Müller、Thomas C. Jagau、Dorian Didier

  DOI：10.1002/chem.202001394

  日期：2020.7.8

  Conventional methods carrying out C(sp2)−C(sp2) bond formations are typically mediated by transition‐metal‐based catalysts. Herein, we conceptualize a complementary avenue to access such bonds by exploiting the potential of electrochemistry in combination with organoboron chemistry. We demonstrate a transition metal catalyst‐free electrocoupling between (hetero)aryls and alkenes through readily available

  进行 C(sp 2 )−C(sp 2 ) 键形成的传统方法通常是由过渡金属基催化剂介导的。在此，我们通过利用电化学与有机硼化学相结合的潜力，概念化了一种获取此类键的补充途径。我们通过容易获得的烯基三（杂）芳基硼酸盐（ATB）以立体会聚的方式展示了（杂）芳基和烯烃之间的无过渡金属催化剂电偶合。这种前所未有的转变通过理论和实验进行了研究，并产生了功能化烯烃库。随后这一概念被进一步推广并应用于天然产物松酚的合成和甾体脱氢表雄酮（DHEA）支架的衍生化。
• A facile generation of enolates from silyl enol ethers by potassium ethoxide
  作者：Wensheng Yu、Zhendong Jin

  DOI：10.1016/s0040-4039(00)01970-5

  日期：2001.1

  Cyclic silyl enol ethers were successfully cleaved by EtOK to generate the corresponding enolates. Reactions with EtOK; were faster and the corresponding enolates could be trapped by electrophiles and oxidants to give the kinetic products exclusively. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Selective inhibition of the cellular sodium pump by emicymarin and 14ß anhydroxy bufadienolides
  作者：Philip J. Hilton、William McKinnon、Edward C. Gravett、Jean-Marie R. Peron、Christopher M. Frampton、M. Gary Nicholls、Gwyn Lord

  DOI：10.1016/j.steroids.2010.07.010

  日期：2010.12

  Partial inhibition of the sodium pump (Na/K-ATP-ase) by a circulating inhibitor is known to occur in humans. The objectives of this study were to determine the effects of novel bufadienolides lacking an oxygen at C14 on sodium pumps in human erythrocytes and leucocytes, dog kidney and pig brain and to document the importance of the stereochemistry at C17 on the ability to inhibit these sodium pumps. 14 alpha bufadienolides were weak inhibitors of all preparations studied. 3 beta-OH,5 beta,14 beta bufadienolide produced near-total inhibition of dog kidney and pig brain Na/K-ATP-ase. Over the same concentration range, it maximally inhibited the sodium pump of erythrocytes by 70% and leucocytes by 47%. The inhibition profile induced in the leucocyte sodium pump deviated significantly from the simple sigmoidal relationship present in the other preparations over the 3 x 10(-5) to 1 x 10(-7) mol/1 concentration range. Allo-emicymarin (17 alpha) was confirmed to be a weak inhibitor of the sodium pump/ATP-ase compared with emicymarin (17 beta) but both were weaker inhibitors of the leucocyte sodium pump than that of the other preparations. Molecules with the C14 in the beta configuration are more efficacious than in the a configuration. In the case of emicymarin, the attachment of the furone at C17 in the a configuration results in substantially weaker inhibitory activity than in the beta configuration, seen in most cardenolides and bufadienolides. Unlike ouabain and bufalin that show no specificity of action in these preparations, 3 beta-OH,5 beta,14 beta bufadienolide selectively inhibits the activity of at least one low-prevalence subset of the leucocyte Na/K-ATP-ase. (C) 2010 Elsevier Inc. All rights reserved.
• A Suzuki coupling approach to bufadienolides
  作者：Edward C Gravett、Philip J Hilton、Keith Jones、Fernando Romero

  DOI：10.1016/s0040-4039(01)01980-3

  日期：2001.12

  A high yielding route to bufadienolide type steroids using a novel Suzuki Coupling reaction between a range of steroid vinyl triflates and 2-pyrone-5-boronate 11 is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.