4-methyl-4-aza-androst-16-en-3-one

• 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-4-aza-androst-16-en-3-one
• 英文别名: (3aS,3bS,9aR,9bS,11aR)-6,9a,11a-trimethyl-3a,3b,4,5,5a,8,9,9b,10,11-decahydro-3H-indeno[5,4-f]quinolin-7-one
• 化学式: C₁₉H₂₉NO
• 分子量: 287.445
• InChiKey: ZRKPNCPNVMCFFE-XYXPWHQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  17-iodo-4-aza-androst-16-en-3-one 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三乙胺 作用下， 反应 25.0h， 生成 4-methyl-4-aza-androst-16-en-3-one
  参考文献：
  名称：

  Steroidal alkenylphosphonates via palladium-catalyzed coupling reactions

  摘要：

  The palladium-catalyzed coupling of various 17-iodo-Delta(16) steroids (17-iodo-androst-16-ene, 17-iodo-4-methyl-4-aza-androst-16-en-3-one, and 17-iodo-4-aza-androst-16-en-3-one) with dialkyl phosphites (dimethyl phosphite, diethyl phosphite, and diisopropyl phosphite) was examined in detail. The only successful condition for homogeneous coupling involved carrying out the reaction in the absence of any solvents. A large excess of dialkyl phosphite was used, which means that the phosphite itself acted as a solvent. Eight new androst-16-ene derivatives with phosphonate groups at C-17 were synthesized and characterized. These steroids are of pharmacological interest as potential Sol-reductase inhibitors. Under the same conditions, methylation of lactam NH was observed using dimethyl phosphite.

  DOI：

  10.1016/0039-128x(95)00121-6

文献信息

• Homogeneous catalytic dehalodimerization of 17-iodo-Δ16 steroids
  作者：Rita Skoda-Földes、Zita Csákai、László Kollár、Gábor Szalontai、Judit Horváth、Zoltán Tuba

  DOI：10.1016/0039-128x(95)00120-f

  日期：1995.12

  17-Iodo-Delta(16) steroids undergo selective dimerization and carbonylative dimerization in the presence of palladium catalysts in dimethylformamide which result in 16-17'-coupled dienes and 17-carboxylic anhydrides, respectively. Moderate to good yields have been obtained for both types of dimers.
• Steroidal alkenylphosphonates via palladium-catalyzed coupling reactions
  作者：Rita Skoda-Földes、László Kollár、Judit Horváth、Zoltán Tuba

  DOI：10.1016/0039-128x(95)00121-6

  日期：1995.12

  The palladium-catalyzed coupling of various 17-iodo-Delta(16) steroids (17-iodo-androst-16-ene, 17-iodo-4-methyl-4-aza-androst-16-en-3-one, and 17-iodo-4-aza-androst-16-en-3-one) with dialkyl phosphites (dimethyl phosphite, diethyl phosphite, and diisopropyl phosphite) was examined in detail. The only successful condition for homogeneous coupling involved carrying out the reaction in the absence of any solvents. A large excess of dialkyl phosphite was used, which means that the phosphite itself acted as a solvent. Eight new androst-16-ene derivatives with phosphonate groups at C-17 were synthesized and characterized. These steroids are of pharmacological interest as potential Sol-reductase inhibitors. Under the same conditions, methylation of lactam NH was observed using dimethyl phosphite.