(2S,10aR)-1-(t-butoxycarbonylamino)-2-isopropyl-10-methylene-1,5,10,10a-tetrahydro-1H-imidazo[1,2-b]isoquinolin-3(2H)-one | 1133721-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (2S,10aR)-1-(t-butoxycarbonylamino)-2-isopropyl-10-methylene-1,5,10,10a-tetrahydro-1H-imidazo[1,2-b]isoquinolin-3(2H)-one
• 英文别名: tert-butyl (2S,10aR)-10-methylidene-3-oxo-2-propan-2-yl-5,10a-dihydro-2H-imidazo[1,2-b]isoquinoline-1-carboxylate
• CAS: 1133721-85-3
• 化学式: C₂₀H₂₆N₂O₃
• 分子量: 342.438
• InChiKey: YFUMSJKRHPCGCN-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-2-(t-butoxycarbonylamino)-N-(2-iodobenzyl)-3-methyl-N-(1,2-propadienyl)butanamide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2S,10aR)-1-(t-butoxycarbonylamino)-2-isopropyl-10-methylene-1,5,10,10a-tetrahydro-1H-imidazo[1,2-b]isoquinolin-3(2H)-one 、 (2S,10aS)-1-(t-butoxycarbonylamino)-2-isopropyl-10-methylene-1,5,10,10a-tetrahydro-1H-imidazo[1,2-b]isoquinolin-3(2H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Domino Carbopalladation/5-exo-Allylic Amination of α-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones

  摘要：

  Allenamides of alpha-amino acids were converted into enantiopure 2-vinylimidazolidin-4-ones by a carbopalladation/exo-cyclization process. The products were obtained in 2.5:1-5.5:1 dr, with 94-99% ee. The palladium-catalyzed carbonylative cyclization of the same substrates afforded enone structures. Starting from properly substituted allenamides, an intramolecular carbopalladation followed by intramolecular amination gave rise to tricyclic fused-ring imidazolidinones.

  DOI：

  10.1021/ol900171g

文献信息

• Palladium-Catalyzed Domino Carbopalladation/5-<i>exo</i>-Allylic Amination of α-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones
  作者：Egle M. Beccalli、Gianluigi Broggini、Francesca Clerici、Simona Galli、Claire Kammerer、Micol Rigamonti、Silvia Sottocornola

  DOI：10.1021/ol900171g

  日期：2009.4.2

  Allenamides of alpha-amino acids were converted into enantiopure 2-vinylimidazolidin-4-ones by a carbopalladation/exo-cyclization process. The products were obtained in 2.5:1-5.5:1 dr, with 94-99% ee. The palladium-catalyzed carbonylative cyclization of the same substrates afforded enone structures. Starting from properly substituted allenamides, an intramolecular carbopalladation followed by intramolecular amination gave rise to tricyclic fused-ring imidazolidinones.