4-methyl-17-(N-(prop-2-ynyl)-carbamoyl)-4-aza-5α-androst-16-en-3-one | 1337993-02-8

• 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: 4-methyl-17-(N-(prop-2-ynyl)-carbamoyl)-4-aza-5α-androst-16-en-3-one
• 英文别名: (3aS,3bS,5aR,9aR,9bS,11aS)-6,9a,11a-trimethyl-7-oxo-N-prop-2-ynyl-3a,3b,4,5,5a,8,9,9b,10,11-decahydro-3H-indeno[5,4-f]quinoline-1-carboxamide
• CAS: 1337993-02-8
• 化学式: C₂₃H₃₂N₂O₂
• 分子量: 368.519
• InChiKey: AAPVDRJVOPMEPE-DZYDHYRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  一氧化碳 、 炔丙胺 、 17-iodo-4-aza-4-methyl-androst-16-en-3-one 在 palladium diacetate 、 caesium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以70%的产率得到4-methyl-17-(N-(prop-2-ynyl)-carbamoyl)-4-aza-5α-androst-16-en-3-one
  参考文献：
  名称：

  Synthesis of steroid–ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation – Copper-catalyzed azide–alkyne cycloaddition reaction sequence

  摘要：

  Steroids with the 17-iodo-16-ene functionality were converted to ferrocene labeled steroidal 17-carboxamides via a two step reaction sequence. The first step involved the palladium-catalyzed aminocarbonylation of the alkenyl iodides with prop-2-yn-1-amine as the nucleophile in the presence of the Pd(OAc)(2)/ PPh(3) catalyst system. In the second step, the product N-(prop-2-ynyl)-carboxamides underwent a facile azide-alkyne cycloaddition with ferrocenyl azides in the presence of CuSO(4)/sodium ascorbate to produce the steroid ferrocene conjugates. The new compounds were obtained in good yield and were characterized by (1)H and (13)C NMR, IR. MS and elemental analysis. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.07.006