5-[(8S,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one | 181866-21-7

• 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: 5-[(8S,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
• CAS: 181866-21-7
• 化学式: C₂₃H₂₄O₃
• 分子量: 348.442
• InChiKey: ZMGITQAJLQQYNA-AMEVOLBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  5-[(8S,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one 在 Lindlar's catalyst 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以80%的产率得到
  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 四(三苯基膦)钯 、 正丁基锂 、 四丁基氟化铵 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 5-[(8S,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[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

文献信息

• 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.
• 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.