Trifluoro-methanesulfonic acid (8R,9S,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl ester | 181866-52-4

• 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 (8R,9S,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl ester
• 英文别名: [(8R,9S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-14-hydroxy-13-methyl-7,8,9,11,12,15-hexahydro-6H-cyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate
• CAS: 181866-52-4
• 化学式: C₂₅H₃₅F₃O₅SSi
• 分子量: 532.697
• InChiKey: ZZSAVZHZTWIXAC-DVJXIFHOSA-N

物化性质

• 沸点：
  536.759±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.275±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(trimethylstannyl)-2H-pyran-2-one 、 Trifluoro-methanesulfonic acid (8R,9S,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl ester 在 四(三苯基膦)钯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以61%的产率得到5-[(8R,9S,13R,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-pyran-2-one
  参考文献：
  名称：

  5-(Trimethylstannyl)-2H-pyran-2-one and 3-(Trimethylstannyl)-2H-pyran-2-one:  New 2H-Pyran-2-one Synthons

  摘要：

  5-(Trimethylstannyl)-2H-pyran-2-one (11) and 3-(trimethylstannyl)-2H-pyran-2-one (30), readily prepared from the corresponding bromo-2H-pyran-2-ones, undergo Pd(0)-catalyzed coupling reactions with a variety of enol triflates to give 5- and 3- substituted 2H-pyran-2-ones, respectively, This reaction is applicable to the enol triflates of 14 beta-hydroxy-17-ketosteroids, and therefore may prove useful in convergent syntheses of lucibufagins and bufadienolides.

  DOI：

  10.1021/jo951394t
• 作为产物：
  描述：

  3-(t-butyldimethylsilyloxy)estra-1,3,5(10),15-tetraen-17-one 在 palladium on activated charcoal 甲醇 、 正丁基锂 、 氢气 、 对甲苯磺酸 、 二异丙胺 作用下， 以 甲醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 62.0h， 生成 Trifluoro-methanesulfonic acid (8R,9S,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl ester
  参考文献：
  名称：

  5-(Trimethylstannyl)-2H-pyran-2-one and 3-(Trimethylstannyl)-2H-pyran-2-one:  New 2H-Pyran-2-one Synthons

  摘要：

  5-(Trimethylstannyl)-2H-pyran-2-one (11) and 3-(trimethylstannyl)-2H-pyran-2-one (30), readily prepared from the corresponding bromo-2H-pyran-2-ones, undergo Pd(0)-catalyzed coupling reactions with a variety of enol triflates to give 5- and 3- substituted 2H-pyran-2-ones, respectively, This reaction is applicable to the enol triflates of 14 beta-hydroxy-17-ketosteroids, and therefore may prove useful in convergent syntheses of lucibufagins and bufadienolides.

  DOI：

  10.1021/jo951394t