D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-triene-6,17-dione

• 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: D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-triene-6,17-dione
• 英文别名: 13β-ethyl-3-methoxygona-1,3,5(10)-trien-6,17-dione；(8R,9S,13S,14S)-13-ethyl-3-methoxy-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-6,17-dione
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: TVSKYHQAOUHNPU-UOSKARGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  左炔诺孕酮 在 ammonium cerium(IV) nitrate 、 Celite 、 碘 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-triene-6,17-dione
  参考文献：
  名称：

  Preparative chemical methods for aromatization of 19-nor-Δ4-3-oxosteroids

  摘要：

  Two preparative chemical methods for aromatization of 19-nor-Delta(4)-3-oxosteroids are described. The first method consists of an oxidative aromatization of 19-nor-Delta(4)-3-oxosteroids with iodine-eerie ammonium nitrate in methanol to give a mixture of 3-methoxy ring-A aromatized derivatives consisting of the desired product, the Delta(9,11) derivative, the 6-oxo derivative as well as some ring-A iodinated material. Conversion of this material to a mixture of the 3-methoxy ring-A aromatized derivative and its 6-oxo derivative was achieved by catalytic hydrogenation. Finally, reduction of the 6-oxo function with triethylsilane in trifluoroacetic acid gave the 3-methoxy-17-trifluoroacetate ring-A aromatized derivative as a single product. In the second method, reaction of 19-nor-Delta(4)-3-oxosteroids with copper(II) bromide in acetonitrile at room temperature resulted in aromatic steroids in a single step in excellent yields. The second method was used in the first practical chemical synthesis of a 6-dehydroestrogen from a 19-nor-Delta(4,6)-3-oxosteroid.

  DOI：

  10.1016/0039-128x(94)90017-5

文献信息

• Copper Bromide Mediated A-Ring Dehydrogenation of 19-Norsteroids
  作者：Marco Brito、Elena Campos、Héctor Salgado Zamora、Palmira del Fabbro

  DOI：10.1080/00397919608003657

  日期：1996.2

  dehydrogenation reaction applied to 19-norsteroids 1a or 1b, with copper(II) bromide in different alcohols yielded estrone alkyl ethers or 13β-ethyl-3-alkoxy gonanes along with products in which the steroid 6-position has been oxidized as well. Use of small amounts of trialkyl orthoformates in the reaction considerably diminished the overoxidized products.

  摘要 19-去甲甾体 1a 或 1b 与溴化铜（II）在不同醇中的脱氢反应产生雌酮烷基醚或 13β-乙基-3-烷氧基 gonanes 以及类固醇 6-位也被氧化的产物。 . 在反应中使用少量原甲酸三烷基酯大大减少了过氧化产物。
• Preparative chemical methods for aromatization of 19-nor-Δ4-3-oxosteroids
  作者：Pemmaraju N. Rao、James W. Cessac、Hyun K. Kim

  DOI：10.1016/0039-128x(94)90017-5

  日期：1994.11

  Two preparative chemical methods for aromatization of 19-nor-Delta(4)-3-oxosteroids are described. The first method consists of an oxidative aromatization of 19-nor-Delta(4)-3-oxosteroids with iodine-eerie ammonium nitrate in methanol to give a mixture of 3-methoxy ring-A aromatized derivatives consisting of the desired product, the Delta(9,11) derivative, the 6-oxo derivative as well as some ring-A iodinated material. Conversion of this material to a mixture of the 3-methoxy ring-A aromatized derivative and its 6-oxo derivative was achieved by catalytic hydrogenation. Finally, reduction of the 6-oxo function with triethylsilane in trifluoroacetic acid gave the 3-methoxy-17-trifluoroacetate ring-A aromatized derivative as a single product. In the second method, reaction of 19-nor-Delta(4)-3-oxosteroids with copper(II) bromide in acetonitrile at room temperature resulted in aromatic steroids in a single step in excellent yields. The second method was used in the first practical chemical synthesis of a 6-dehydroestrogen from a 19-nor-Delta(4,6)-3-oxosteroid.