17β-(4-methoxyphenyl)-11-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,9(11)-dien-3-one cyclic (1,2-ethanediyl acetal) | 191029-98-8

• 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: 17β-(4-methoxyphenyl)-11-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,9(11)-dien-3-one cyclic (1,2-ethanediyl acetal)
• CAS: 191029-98-8
• 化学式: C₂₉H₃₅F₃O₆S
• 分子量: 568.655
• InChiKey: OMYXDYLPUPUGRD-RTCYWULBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  17β-(4-methoxyphenyl)-11-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,9(11)-dien-3-one cyclic (1,2-ethanediyl acetal) 在 四(三苯基膦)钯 盐酸 、 氨 、 lithium 、 sodium carbonate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 、 甲苯 为溶剂， 生成 (8R,9R,10R,11S,13S,14S,17R)-11-(4-Dimethylamino-phenyl)-13-ethyl-17-(4-methoxy-phenyl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Highly diastereoselective synthesis of 11β,17β-diaryl-18a-homo-19-nor steroids

  摘要：

  In a highly diastereoselective fashion novel 11 beta, 17 beta-diaryl steroids 17 and 18 were synthesized via Birch-type reduction [1] of styrylic precursors 11 and 15. Both precursors were readily available by Suzuki-type coupling reactions [2] of aromatic boronic acids [3] and the corresponding enol triflates 6, 10, and 14. Regioselective 17-enol triflate formation in presence of a 11-keto function could be demonstrated in case of steroid 5. The remarkably high degree of stereoselectivity observed parallels results from the natural series [4] and demonstrated a broader applicability of such single electron transfer reductions in stereoselective transformations on the steroid skeleton.

  DOI：

  10.1002/prac.19973390164
• 作为产物：
  描述：

  11β-hydroxy-17β-(4-methoxyphenyl)-18a-homoestr-5-en-3-one cyclic 3-(1,2-ethanediyl acetal) 在 吡啶 、 chromium(VI) oxide 、 2,6-二叔丁基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 17β-(4-methoxyphenyl)-11-{[(trifluoromethyl)sulfonyl]oxy}-18a-homoestra-5,9(11)-dien-3-one cyclic (1,2-ethanediyl acetal)
  参考文献：
  名称：

  Highly diastereoselective synthesis of 11β,17β-diaryl-18a-homo-19-nor steroids

  摘要：

  In a highly diastereoselective fashion novel 11 beta, 17 beta-diaryl steroids 17 and 18 were synthesized via Birch-type reduction [1] of styrylic precursors 11 and 15. Both precursors were readily available by Suzuki-type coupling reactions [2] of aromatic boronic acids [3] and the corresponding enol triflates 6, 10, and 14. Regioselective 17-enol triflate formation in presence of a 11-keto function could be demonstrated in case of steroid 5. The remarkably high degree of stereoselectivity observed parallels results from the natural series [4] and demonstrated a broader applicability of such single electron transfer reductions in stereoselective transformations on the steroid skeleton.

  DOI：

  10.1002/prac.19973390164