11-(N,N-pentan-1,5-diylcarboxamido)androst-5,11-diene-3,17-dione | 1268610-36-1

• 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: 11-(N,N-pentan-1,5-diylcarboxamido)androst-5,11-diene-3,17-dione
• 英文别名: (8S,9S,10R,13R,14S)-10,13-dimethyl-11-(piperidine-1-carbonyl)-2,6,7,8,9,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 1268610-36-1
• 化学式: C₂₅H₃₃NO₃
• 分子量: 395.542
• InChiKey: OMLFJZGDUXEPAA-PZLPAFFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-androstene-3,11,17-trione 3,17-bisethyleneketal 在 hydrazine hydrate 、 碘 、 barium(II) oxide 、 四甲基胍 作用下， 以 anhydrous diethylene glycol dimethyl ether 、 二氯甲烷 为溶剂， 20.0~195.0 ℃ 、100.0 kPa 条件下， 反应 120.0h， 生成 11-(N,N-pentan-1,5-diylcarboxamido)androst-5,11-diene-3,17-dione 、 11-(N,N-pentan-1,5-diylcarboxamido)androst-5,9(11)-diene-3,17-dione
  参考文献：
  名称：

  Systematic investigation on the synthesis of androstane-based 3-, 11- and 17-carboxamides via palladium-catalyzed aminocarbonylation

  摘要：

  3,17-Dicarboxamido-androst-3,5,16-triene, 3-carboxamido-androst-3,5-dien-17-one, 17-carboxamidoandrost-4,16-dien-3-one and 11-carboxamido-androst-5,9(11)-dien-3,17-dione derivatives were synthesized in homogeneous carbonylation reactions from the corresponding 3,17-diiodo-androst-3,5,16-triene, 3-iodo-androst-3,5-diene-17-ethylene ketal, 17-iodo-androst-5,16-dien-3-ethylene ketal, 11-iodo-androst-5,9(11)-diene-3,17-bis(ethylene ketal) derivatives, respectively. A highly chemoselective palladium-catalyzed aminocarbonylation of the corresponding iodo-alkene, carried out under mild reaction conditions, can be considered as the key-step for the introduction of the carboxamide functionalities. The synthesis of the iodo-alkene substrate is based on the transformation of the corresponding keto derivative to hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethyl guanidine). The aminocarbonylation reaction is highly tolerant towards the N-nucleophiles, i.e. various primary and secondary amines including amino acid methyl esters can also be used. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.11.008

文献信息

• Systematic investigation on the synthesis of androstane-based 3-, 11- and 17-carboxamides via palladium-catalyzed aminocarbonylation
  作者：Péter Ács、Attila Takács、Mercédesz Kiss、Noémi Pálinkás、Sándor Mahó、László Kollár

  DOI：10.1016/j.steroids.2010.11.008

  日期：2011.2

  3,17-Dicarboxamido-androst-3,5,16-triene, 3-carboxamido-androst-3,5-dien-17-one, 17-carboxamidoandrost-4,16-dien-3-one and 11-carboxamido-androst-5,9(11)-dien-3,17-dione derivatives were synthesized in homogeneous carbonylation reactions from the corresponding 3,17-diiodo-androst-3,5,16-triene, 3-iodo-androst-3,5-diene-17-ethylene ketal, 17-iodo-androst-5,16-dien-3-ethylene ketal, 11-iodo-androst-5,9(11)-diene-3,17-bis(ethylene ketal) derivatives, respectively. A highly chemoselective palladium-catalyzed aminocarbonylation of the corresponding iodo-alkene, carried out under mild reaction conditions, can be considered as the key-step for the introduction of the carboxamide functionalities. The synthesis of the iodo-alkene substrate is based on the transformation of the corresponding keto derivative to hydrazone, which was treated with iodine in the presence of a base (1,1,3,3-tetramethyl guanidine). The aminocarbonylation reaction is highly tolerant towards the N-nucleophiles, i.e. various primary and secondary amines including amino acid methyl esters can also be used. (C) 2010 Elsevier Inc. All rights reserved.