(8R,9S,10R,13S,14S)-10,13-Dimethyl-17-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid methyl ester | 96837-80-8

• 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,10R,13S,14S)-10,13-Dimethyl-17-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid methyl ester
• CAS: 96837-80-8
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: WSVRVSGHOJSKHP-RNEDXHKXSA-N

物化性质

• 沸点：
  457.5±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S)-10,13-Dimethyl-17-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid methyl ester 在 盐酸羟胺 作用下， 以 吡啶 、 乙醇 为溶剂， 以91%的产率得到C₂₁H₂₉NO₃
  参考文献：
  名称：

  Discovery of a novel hybrid from finasteride and epristeride as 5α-reductase inhibitor

  摘要：

  Finasteride and epristeride both inhibit 5 alpha-reductase with high potency via competitive and non-competitive mechanism, respectively. A new hybrid of finasteride and epristeride was designed as a new 5a-reductase inhibitor based on combination principles in medicinal chemistry. Human 5 beta-reductase was chosen as a plausible surrogate of 5 alpha-reductase type II and the results indicate that although the hybrid compound possesses the main bulk of epristeride, its inhibitory mechanism is same as of finasteride. The hybrid turned out to be a potent 5 alpha-reductase inhibitor in low IC50 ranges. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.10.112
• 作为产物：
  描述：

  雄烯二酮 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (8R,9S,10R,13S,14S)-10,13-Dimethyl-17-oxo-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 17-oxoandrosta-3,5-dien-3-methyl Sulfonate as Stable Analog of Dehydroepiandrosterone Sulfate

  摘要：

  The synthesis of 17-oxoandrosta-3,5-dien-3-methyl sulfonate 3, a stable analog of memory-enhancing neurosteroid dehydroepiandrosterone sulfate, is described. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00006-3

文献信息

• Palladium-catalyzed carbonylation of enol triflates. A novel method for one-carbon homologation of ketones to α,β-unsaturated carboxylic acid derivatives
  作者：Sandro Cacchi、Enrico Morera、Giorgio Ortar

  DOI：10.1016/s0040-4039(00)98525-3

  日期：1985.1

  Ketones can be homologated to α,gb-unsaturated esters or amides via their enol triflates by a palladium-catalyzed reaction with carbon monoxide and alcohols or amines.

  酮可通过钯与一氧化碳，醇或胺的催化反应，通过烯醇三氟甲磺酸酯与α，gb-不饱和酯或酰胺同源。