11β,17β-bis(4-methoxyphenyl)-18a-homoestr-5-en-3-one cyclic (1,2-ethanediyl acetal) | 191029-96-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 11β,17β-bis(4-methoxyphenyl)-18a-homoestr-5-en-3-one cyclic (1,2-ethanediyl acetal)
• 英文别名: (8'R,9'S,10'R,11'S,13'S,14'S,17'S)-13'-ethyl-11',17'-bis(4-methoxyphenyl)spiro[1,3-dioxolane-2,3'-2,4,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene]
• CAS: 191029-96-6
• 化学式: C₃₅H₄₄O₄
• 分子量: 528.732
• InChiKey: AQVYCUQZMDDBMO-FDHYMUNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11β,17β-bis(4-methoxyphenyl)-18a-homoestr-5-en-3-one cyclic (1,2-ethanediyl acetal) 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以97%的产率得到(8R,9R,10R,11S,13S,14S,17R)-13-Ethyl-11,17-bis-(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：

  18a-methylestr-5-ene-3,11,17-trione cyclic 3-(1,2-ethanediyl acetal) 在 四(三苯基膦)钯 2,6-二叔丁基吡啶 、 氨 、 lithium 、 sodium carbonate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 11β,17β-bis(4-methoxyphenyl)-18a-homoestr-5-en-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

文献信息

• Highly diastereoselective synthesis of 11β,17β-diaryl-18a-homo-19-nor steroids
  作者：Eckhard Ottow、Arwed Cleve、Günter Neef、Wolfgang Schwede

  DOI：10.1002/prac.19973390164

  日期：——

  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.