4'-(dimethylamino)-3-ethoxy-17α-(1-propynyl)benzo<12,12a>-11α,18-cyclo-12a,12b-dihomo-13α-estra-3,5-dien-17β-ol | 156383-14-1

• 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: 4'-(dimethylamino)-3-ethoxy-17α-(1-propynyl)benzo<12,12a>-11α,18-cyclo-12a,12b-dihomo-13α-estra-3,5-dien-17β-ol
• CAS: 156383-14-1
• 化学式: C₃₁H₃₉NO₂
• 分子量: 457.656
• InChiKey: NJACZSHHIOCSRN-JJDTWUKVSA-N

物化性质

• 沸点：
  661.5±55.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4'-(dimethylamino)-3-ethoxy-17α-(1-propynyl)benzo<12,12a>-11α,18-cyclo-12a,12b-dihomo-13α-estra-3,5-dien-17β-ol 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以47%的产率得到4'-(dimethylamino)-17β-hydroxy-17α-(1-propynyl)benzo<12,12a>-11α,18-cyclo-12a,12b-dihomo-13α-estr-4-en-3-one
  参考文献：
  名称：

  Synthesis and biological testing of 4′-(dimenthylamino)-17β-hydroxy-17α-(1-propynyl)benzo[12,12a]-11α,18-cyclo-12a,12b-dihomo-13α-estr-4-en-3-one: an interesting RU 38 486 analog

  摘要：

  A partial synthesis of the title compound, 4'-(dimethylamino)-17 beta-hydroxy-17 alpha-(1-propynyl)benzo[12,12a]11 alpha,18-cyclo-12a,12b-dihomo-13 alpha-estr-4-en-3-one 1, is reported The key step in this synthesis represents an intramolecular alkenylaryl radical cyclization. Treatment of 18-[bromo-5-(dimethylamino)phenyl]gona-5,9(11)-diene-3,17-dione-3,17-bis[cyclic acetal] 5 with tributyl tin hydride and a radical initiator introduces the desired 11 beta,18-bridge. The reduced progesterone receptor affinity of this RU 38 486 analog contributes valuable information to the empirical characterization of the steroid binding site of the receptor protein and explains the observed lack of in vivo antigestational activity.

  DOI：

  10.1016/0039-128x(94)90026-4
• 作为产物：
  描述：

  4'-(dimethylamino)benzo<12,12a>-11α,18-cyclo-12a,12b-dihomo-13α-estr-4-ene-3,17-dione 在 正丁基锂 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 4'-(dimethylamino)-3-ethoxy-17α-(1-propynyl)benzo<12,12a>-11α,18-cyclo-12a,12b-dihomo-13α-estra-3,5-dien-17β-ol
  参考文献：
  名称：

  Synthesis and biological testing of 4′-(dimenthylamino)-17β-hydroxy-17α-(1-propynyl)benzo[12,12a]-11α,18-cyclo-12a,12b-dihomo-13α-estr-4-en-3-one: an interesting RU 38 486 analog

  摘要：

  A partial synthesis of the title compound, 4'-(dimethylamino)-17 beta-hydroxy-17 alpha-(1-propynyl)benzo[12,12a]11 alpha,18-cyclo-12a,12b-dihomo-13 alpha-estr-4-en-3-one 1, is reported The key step in this synthesis represents an intramolecular alkenylaryl radical cyclization. Treatment of 18-[bromo-5-(dimethylamino)phenyl]gona-5,9(11)-diene-3,17-dione-3,17-bis[cyclic acetal] 5 with tributyl tin hydride and a radical initiator introduces the desired 11 beta,18-bridge. The reduced progesterone receptor affinity of this RU 38 486 analog contributes valuable information to the empirical characterization of the steroid binding site of the receptor protein and explains the observed lack of in vivo antigestational activity.

  DOI：

  10.1016/0039-128x(94)90026-4