11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-5-hydroxy-5α-estran-17-one | 156352-61-3

• 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: 11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-5-hydroxy-5α-estran-17-one
• 英文别名: 11β-[4-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]phenyl]-3,3 [1,2-ethanediylbis(oxy)]5-hydroxy-5α-estran-17-one；(5'R,8'R,9'R,10'R,11'S,13'S,14'S)-11'-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-5'-hydroxy-13'-methylspiro[1,3-dioxolane-2,3'-2,4,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene]-17'-one
• CAS: 156352-61-3
• 化学式: C₃₂H₄₈O₅Si
• 分子量: 540.816
• InChiKey: OYZNDVBKSRMUEL-UXYZQLHTSA-N

物化性质

• 沸点：
  614.2±55.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-5-hydroxy-5α-estran-17-one 在 正丁基锂 、 苄基三乙基氯化铵 、 lithium diisopropyl amide 作用下， 以 氯仿 为溶剂， 反应 6.5h， 生成 17-chloro-11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediyl-bis(oxy)>-17aα-(1-propynyl)-17a-homo-5α-estr-16-ene-5,17aβ-diol
  参考文献：
  名称：

  Synthesis and biological activity of 17-chloro-16(17) unsaturated D-homo antiprogestins

  摘要：

  An efficient approach to 17-chloro-16(17) unsaturated D-homo antiprogestins is described. The key steps of the synthesis are a ring-expansion via dichlorocarbene addition to a 17-silyl enol ether and a palladium catalyzed coupling of an 11 beta-(4-aryltriflate) with tributyl(1-ethoxyethenyl)stannane or diethyl(3-pyridinyl)borane. The new progestelone antagonists were tested for their biological activities and compared to those of known antiprogestins.

  DOI：

  10.1016/0039-128x(94)90024-8
• 作为产物：
  描述：

  3,3-<1,2-ethanediylbis(oxy)>-11β-(4-methoxyphenyl)estr-4-en-17-one 在 吡啶 、 咪唑 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 3-硝基-2,2,2-三氟苯乙酮 、 双氧水 、 mesna 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 125.0h， 生成 11β-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>phenyl>-3,3-<1,2-ethanediylbis(oxy)>-5-hydroxy-5α-estran-17-one
  参考文献：
  名称：

  Synthesis and biological activity of 17-chloro-16(17) unsaturated D-homo antiprogestins

  摘要：

  An efficient approach to 17-chloro-16(17) unsaturated D-homo antiprogestins is described. The key steps of the synthesis are a ring-expansion via dichlorocarbene addition to a 17-silyl enol ether and a palladium catalyzed coupling of an 11 beta-(4-aryltriflate) with tributyl(1-ethoxyethenyl)stannane or diethyl(3-pyridinyl)borane. The new progestelone antagonists were tested for their biological activities and compared to those of known antiprogestins.

  DOI：

  10.1016/0039-128x(94)90024-8