2,2,2-trichloro-1-(5α,17β-17-acetoxyestr-2-eno<3,2-b>furan-5'-yl)ethanone | 160458-52-6

• 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: 2,2,2-trichloro-1-(5α,17β-17-acetoxyestr-2-eno<3,2-b>furan-5'-yl)ethanone
• 英文别名: [(1R,2S,10S,13R,14S,17S,18S)-18-methyl-6-(2,2,2-trichloroacetyl)-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-yl] acetate
• CAS: 160458-52-6
• 化学式: C₂₄H₂₉Cl₃O₄
• 分子量: 487.851
• InChiKey: SZQNWIHAAQEKDW-LYBSAGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloro-1-(5α,17β-17-acetoxyestr-2-eno<3,2-b>furan-5'-yl)ethanone 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 3.25h， 生成 1-(5α,17β-17-hydroxyestr-2-eno<3,2-b>furan-5'-yl)ethanone
  参考文献：
  名称：

  Androgen Receptor Affinity of 5'-Acyl Furanosteroids

  摘要：

  Syntheses of 5'-acyl furanosteroids are described from the corresponding unsubstituted [3,2-b]furanosteroids using acid anhydrides and acid chlorides in the presence or absence of Lewis acids. New methods have been developed to prepare 5'-acetyl derivatives: reduction of a 5'-trichloroacetyl intermediate either by sodium formaldehyde sulfoxylate or with 10% Pd/C. Most of these 5'-acyl derivatives bind to the rat ventral prostate androgen receptor. However the antiandrogenic activity was diminished when compared with 4, 5'-methylsulfonyl furanosteroid. Biological studies revealed that 5'-acyl furanosteroids were either androgens or modest antiandrogens. The electrostatic potential maps of the substructures of 3, 4, and 5'-acetyl syn- and anti-furanosteroids showed striking differences which may explain, to some extent, the lack of significant antiandrogenic activity of 5'-acyl furanosteroids.

  DOI：

  10.1021/jm00050a019
• 作为产物：
  描述：

  2-((四氢-2H-吡喃-2-基)氧基)乙酸甲酯 在 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 二异丁基氢化铝 、 sodium t-butanolate 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 生成 2,2,2-trichloro-1-(5α,17β-17-acetoxyestr-2-eno<3,2-b>furan-5'-yl)ethanone
  参考文献：
  名称：

  Androgen Receptor Affinity of 5'-Acyl Furanosteroids

  摘要：

  Syntheses of 5'-acyl furanosteroids are described from the corresponding unsubstituted [3,2-b]furanosteroids using acid anhydrides and acid chlorides in the presence or absence of Lewis acids. New methods have been developed to prepare 5'-acetyl derivatives: reduction of a 5'-trichloroacetyl intermediate either by sodium formaldehyde sulfoxylate or with 10% Pd/C. Most of these 5'-acyl derivatives bind to the rat ventral prostate androgen receptor. However the antiandrogenic activity was diminished when compared with 4, 5'-methylsulfonyl furanosteroid. Biological studies revealed that 5'-acyl furanosteroids were either androgens or modest antiandrogens. The electrostatic potential maps of the substructures of 3, 4, and 5'-acetyl syn- and anti-furanosteroids showed striking differences which may explain, to some extent, the lack of significant antiandrogenic activity of 5'-acyl furanosteroids.

  DOI：

  10.1021/jm00050a019