17-(N-methoxycarbonylmethylcarboxamido)androst-5,16-diene-3-one | 1268610-25-8

• 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: 17-(N-methoxycarbonylmethylcarboxamido)androst-5,16-diene-3-one
• 英文别名: methyl 2-[[(8R,9S,10R,13S,14S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-17-carbonyl]amino]acetate
• CAS: 1268610-25-8
• 化学式: C₂₃H₃₁NO₄
• 分子量: 385.503
• InChiKey: FBEPTCJRGKLRII-BQBMVXNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  雄烯二酮 在 盐酸 、 hydrazine hydrate 、 水 、 碘 、 palladium diacetate 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 、 barium(II) oxide 、 四甲基胍 作用下， 以 甲乙醚 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0~160.0 ℃ 、100.0 kPa 条件下， 反应 92.0h， 生成 17-(N-methoxycarbonylmethylcarboxamido)androst-5,16-diene-3-one
  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