Trifluoro-methanesulfonic acid (8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester | 126745-68-4

• 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: Trifluoro-methanesulfonic acid (8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
• 英文别名: (10R,13R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate
• CAS: 126745-68-4
• 化学式: C₂₈H₄₃F₃O₃S
• 分子量: 516.709
• InChiKey: IDWZAUUTNSFIDN-GYKMGIIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.39
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(1-甲基乙氧基)-4-(三丁基锡烷基)-3-环丁烯-1,2-二酮 、 Trifluoro-methanesulfonic acid (8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 三(2-呋喃基)膦 、 zinc(II) chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 various solvent(s) 为溶剂， 反应 0.75h， 以95%的产率得到3-[(8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]-4-isopropoxy-cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  3-Stannylcyclobutenediones as nucleophilic cyclobutenedione equivalents. Synthesis of substituted cyclobutenediones and cyclobutenedione monoacetals and the beneficial effect of catalytic copper iodide on the Stille reaction

  摘要：

  DOI：

  10.1021/jo00306a012
• 作为产物：
  描述：

  三氟甲烷磺基苯胺 、 4-胆甾烯-3-酮 在 正丁基锂 作用下， 生成 Trifluoro-methanesulfonic acid (8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  3-Stannylcyclobutenediones as nucleophilic cyclobutenedione equivalents. Synthesis of substituted cyclobutenediones and cyclobutenedione monoacetals and the beneficial effect of catalytic copper iodide on the Stille reaction

  摘要：

  DOI：

  10.1021/jo00306a012

文献信息

• Nickel‐Catalyzed Regioselective Alkenylarylation of γ,δ‐Alkenyl Ketones via Carbonyl Coordination
  作者：Roshan K. Dhungana、Vivek Aryal、Doleshwar Niroula、Rishi R. Sapkota、Margaret G. Lakomy、Ramesh Giri

  DOI：10.1002/anie.202104871

  日期：2021.8.23

  which enabled us to difunctionalize unactivated γ,δ-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction was made feasible by the use of 5-chloro-8-hydroxyquinoline as a ligand along with NiBr2⋅DME as a catalyst and LiOtBu as base. The reaction proceeded with a wide range of cyclic, acyclic, endocyclic and exocyclic alkenyl ketones, and electron-rich and electron-deficient arylboronate

  我们公开了镍催化的反应，该反应使我们能够用三氟甲磺酸烯基酯和芳基硼酸酯对酮中未活化的γ,δ-烯烃进行双官能化。通过使用 5-氯-8-羟基喹啉作为配体以及 NiBr 2· DME 作为催化剂和 LiO t Bu 作为碱，使该反应变得可行。该反应适用于各种环状、无环、环内和环外烯基酮，以及富电子和缺电子芳基硼酸酯。该反应也适用于环状和无环烯基三氟甲磺酸酯。对照实验表明反应的进行需要羰基配位。
• Palladium-catalyzed phosphorylation of alkenyl triflates
  作者：Dennis A. Holt、Jill M. Erb

  DOI：10.1016/s0040-4039(01)80576-1

  日期：1989.1

  A method is described for the efficient preparation of α,β-unsaturated phosphonates and phosphinates from alkenyl triflates via palladium(0)-catalyzed coupling with dialkylphosphites or hypophosphorous acid.

  描述了通过钯（0）催化的与二烷基亚磷酸酯或次磷酸从烯基三氟甲磺酸酯高效制备α，β-不饱和膦酸酯和次膦酸酯的方法。
• Nickel‐Catalyzed Reductive C(sp ² )−Si Coupling of Chlorohydrosilanes via Si−Cl Cleavage
  作者：Zhen‐Zhen Zhao、Xiaobo Pang、Xiao‐Xue Wei、Xue‐Yuan Liu、Xing‐Zhong Shu

  DOI：10.1002/anie.202200215

  日期：2022.5.16

  C−Si bond-forming reaction between R−X and Cl−Si(H)R2 was achieved using reductive nickel catalysis. This method offers access to structurally diverse aryl- and alkenylhydrosilanes from phenol and ketone derivatives. The reaction can be conducted on gram scale and allows for incorporating a hydrosilane moiety into biologically active molecules.

  使用还原性镍催化，在 R-X 和 Cl-Si(H)R 2之间实现了新的 C-Si 键形成反应。该方法提供了从苯酚和酮衍生物中获得结构多样的芳基和烯基氢硅烷的途径。该反应可以以克级进行并且允许将氢硅烷部分结合到生物活性分子中。