17-chloro-3,3-<1,2-ethanediylbis(oxy)>-17aα-(1-propynyl)-11β-<4-<<(trifluoromethyl)sulfonyl>oxy>phenyl>-17a-homo-5α-estr-16-en-5,17aβ-diol | 143611-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 17-chloro-3,3-<1,2-ethanediylbis(oxy)>-17aα-(1-propynyl)-11β-<4-<<(trifluoromethyl)sulfonyl>oxy>phenyl>-17a-homo-5α-estr-16-en-5,17aβ-diol
• 英文别名: [4-[(4aR,4bR,5S,6aS,7S,10aS,10bR,12aR)-8-chloro-7,12a-dihydroxy-6a-methyl-7-prop-1-ynylspiro[1,3,4,4a,4b,5,6,10,10a,10b,11,12-dodecahydrochrysene-2,2'-1,3-dioxolane]-5-yl]phenyl] trifluoromethanesulfonate
• CAS: 143611-09-0
• 化学式: C₃₁H₃₆ClF₃O₇S
• 分子量: 645.137
• InChiKey: TXOIPGPWILGBEC-OBHSISSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  43
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  17-chloro-3,3-<1,2-ethanediylbis(oxy)>-17aα-(1-propynyl)-11β-<4-<<(trifluoromethyl)sulfonyl>oxy>phenyl>-17a-homo-5α-estr-16-en-5,17aβ-diol 在 吡啶 、 盐酸 、 四(三苯基膦)钯 、 lithium chloride 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 2.33h， 生成 11β-(4-acetylphenyl)-17-chloro-17aβ-hydroxy-17aα-(1-propynyl)-17a-homoestra-4,16-dien-3-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
• 作为产物：
  描述：

  三氟甲磺酸酐 、 丙炔 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以73%的产率得到17-chloro-3,3-<1,2-ethanediylbis(oxy)>-17aα-(1-propynyl)-11β-<4-<<(trifluoromethyl)sulfonyl>oxy>phenyl>-17a-homo-5α-estr-16-en-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