(8R,9S,13S,14S,17R)-17-ethynyl-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde | 85707-13-7

• 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: (8R,9S,13S,14S,17R)-17-ethynyl-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde
• 英文别名: 2-formyl-19-nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17β-diol；(8R,9S,13S,14S,17R)-17-ethynyl-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde
• CAS: 85707-13-7
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: DXDMAUGTMAFAGW-OKSLILNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,17R)-17-ethynyl-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde 、 一氯丙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 (17alpha-17-Hydroxy-19-norpregna-1,3,5(10)-trien-20-yno[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：

  (2Z,8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-2-(hydroxymethylidene)-13-methyl-6,7,8,9,10,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (8R,9S,13S,14S,17R)-17-ethynyl-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2-carbaldehyde
  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

文献信息

• ortho-Formylation of estrogens. Synthesis of the anti-cancer agent 2-methoxyestradiol
  作者：Øyvind W. Akselsen、Trond Vidar Hansen

  DOI：10.1016/j.tet.2011.08.005

  日期：2011.10

  Several estrogens were mono-formylated using a mixture of paraformaldehyde. MgCl2, and Et3N in refluxing THF. In all cases, the 2-isomer was formed as the major product with high regioselectivity compared to the 4-isomer. Excellent to high yields were obtained in all examples except one. The method was applied for an efficient synthesis of the anti-cancer agent 2-methoxyestradiol. (C) 2011 Elsevier Ltd. All rights reserved.
• A new efficient synthetic method for 2- and 4-hydroxy-17α-ethynyIestradiol
  作者：Xie Rugang、Chen Qiuyun、Xie Jin、Zhao Huaming

  DOI：10.1016/0039-128x(90)90085-p

  日期：1990.11

  The reaction of ethyl magnesium bromide and 17 alpha-ethynylestradiol with formaldehyde in the presence of triethyl phosphate or hexamethylphosphoramide gave the 2- and 4-formyl-17 alpha-ethynylestradiol in high yield. Treatment of the formyl derivatives with an alkaline solution of hydrogen peroxide in tetrahydrofuran afforded the corresponding catechols in almost quantitative yield. This new synthetic method was far superior to other methods, especially concerning simplicity, selectivity, and high yields.