11,17-bis(4-methoxyphenyl)-18a-homoestra-5,9(11),16-trien-3-one cyclic (1,2-ethanediyl acetal) | 191029-95-5

• 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: 11,17-bis(4-methoxyphenyl)-18a-homoestra-5,9(11),16-trien-3-one cyclic (1,2-ethanediyl acetal)
• 英文别名: (8'S,10'S,13'S,14'S)-13'-ethyl-11',17'-bis(4-methoxyphenyl)spiro[1,3-dioxolane-2,3'-2,4,7,8,10,12,14,15-octahydro-1H-cyclopenta[a]phenanthrene]
• CAS: 191029-95-5
• 化学式: C₃₅H₄₀O₄
• 分子量: 524.7
• InChiKey: FBYYRRLBIIGWLW-DGCCARMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 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：

  11,17-bis(4-methoxyphenyl)-18a-homoestra-5,9(11),16-trien-3-one cyclic (1,2-ethanediyl acetal) 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到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
• 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 、 sodium carbonate 、 lithium chloride 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 11,17-bis(4-methoxyphenyl)-18a-homoestra-5,9(11),16-trien-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.