androst-16-en-17-carboxamide | 935764-08-2

• 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: androst-16-en-17-carboxamide
• 英文别名: 5α-androst-16-en-17-carboxamide；(5R,8R,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
• CAS: 935764-08-2
• 化学式: C₂₀H₃₁NO
• 分子量: 301.472
• InChiKey: CBGCCVQZIJKBEF-NIDXHAAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  17-iodo-androst-16-ene 在 一氧化碳 、 palladium diacetate 、 caesium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 80.0 ℃ 、100.0 kPa 条件下， 反应 12.0h， 生成 androst-16-en-17-carboxamide
  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

文献信息

• Amino- and azidocarbonylation of iodoalkenes
  作者：Gábor Mikle、Rita Skoda-Földes、László Kollár

  DOI：10.1016/j.tet.2021.132495

  日期：2021.11

  on the structure of the acyl azides, consecutive hydrolysis toward corresponding primary amides was observed. ‘Direct’ aminocarbonylation of the same iodoalkenes was also carried out by using ammonium carbamate as ammonia source under mild conditions. The α,β-unsaturated primary amides, formed in a chemoselective reaction, were isolated in good to excellent yields.

  碘代烯烃可通过其腙从酮中获得，经过钯催化的叠氮羰基化。根据酰基叠氮化物的结构，观察到连续水解为相应的伯酰胺。在温和条件下，使用氨基甲酸铵作为氨源也可以进行相同碘代烯烃的“直接”氨基羰基化。在化学选择性反应中形成的 α,β-不饱和伯酰胺以良好至极好的产率分离。
• Facile Synthesis of Steroidal Primary Amides via Palladium-Catalyzed Aminocarbonylation of Steroidal Alkenyl Halides
  作者：Rita Skoda-Földes、János Balogh、Sándor Mahó、Viktor Háda、László Kollár

  DOI：10.1055/s-2008-1067265

  日期：2008.10

  A new method for the synthesis of primary amides from alkenyl iodides in one carbonylation step using ammonium carbamate as ammonia synthon is reported. The products were obtained in good yields under mild reaction conditions using CO (1-6 bar). Steroidal substrates with various moieties (e.g., 6-OH group, lactams, or aromatic A-ring) could be converted selectively into the products.

  报道了一种使用氨基甲酸铵作为氨合成子在羰基化步骤中由链烯基碘合成伯酰胺的新方法。使用 CO (1-6 bar) 在温和的反应条件下以良好的收率获得产物。具有各种部分（例如，6-OH 基团、内酰胺或芳族 A 环）的甾体底物可以选择性地转化为产物。
• Synthesis of steroid–ferrocene conjugates of steroidal 17-carboxamides via a palladium-catalyzed aminocarbonylation – Copper-catalyzed azide–alkyne cycloaddition reaction sequence
  作者：Eszter Szánti-Pintér、János Balogh、Zsolt Csók、László Kollár、Ágnes Gömöry、Rita Skoda-Földes

  DOI：10.1016/j.steroids.2011.07.006

  日期：2011.11

  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.