(8R,9S,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one | 181866-48-8

• 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,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one
• 英文别名: (8R,9S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-14-hydroxy-13-methyl-6,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-one
• CAS: 181866-48-8
• 化学式: C₂₄H₃₆O₃Si
• 分子量: 400.634
• InChiKey: QXPDQWMQGLISSY-DVJXIFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one 在 四(三苯基膦)钯 、 正丁基锂 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 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-(O-tert-butyl(dimethyl)silyl)estrone 在 palladium on activated charcoal 甲醇 、 palladium diacetate 、 正丁基锂 、 氢气 、 对甲苯磺酸 、 二异丙胺 作用下， 以 甲醇 、 苯甲腈 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 82.83h， 生成 (8R,9S,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-14-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-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

文献信息

• 5-(Trimethylstannyl)-2<i>H</i>-pyran-2-one and 3-(Trimethylstannyl)-2<i>H</i>-pyran-2-one:  New 2<i>H</i>-Pyran-2-one Synthons
  作者：Zhi Liu、Jerrold Meinwald

  DOI：10.1021/jo951394t

  日期：1996.1.1

  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.