(1R,2S,10S,13R,14S,17S,18S)-17-hydroxy-18-methyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-diene-6-carboxylic acid | 160458-66-2

• 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: (1R,2S,10S,13R,14S,17S,18S)-17-hydroxy-18-methyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-diene-6-carboxylic acid
• CAS: 160458-66-2
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: DIYFUVNGKIKNAX-NOTDXJRISA-N

物化性质

• 沸点：
  528.9±50.0 °C(predicted)
• 密度：
  1.223±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,10S,13R,14S,17S,18S)-17-hydroxy-18-methyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-diene-6-carboxylic acid 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以47%的产率得到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 盐酸 、 正丁基锂 、 二异丁基氢化铝 、 sodium t-butanolate 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (1R,2S,10S,13R,14S,17S,18S)-17-hydroxy-18-methyl-7-oxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-diene-6-carboxylic acid
  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