N-(2,2-dimethylpent-4-enyl)-N'-o-toluenesulfonylurea | 1200242-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,2-dimethylpent-4-enyl)-N'-o-toluenesulfonylurea
• CAS: 1200242-02-9
• 化学式: C₁₅H₂₂N₂O₃S
• 分子量: 310.417
• InChiKey: KTRBJJVSRLBUJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 N-(2,2-dimethylpent-4-enyl)-N'-o-toluenesulfonylurea 在 (M,3aS,3a'S)-3,3',3a',4,4',5,5'-octahydro-3,3,3',3'-tetraisopropyl-6,6'-spirobi[6H-cyclopent[c]isoxazole] 、 tetrakis(acetonitrile)palladium(II) tetrafluoroborate 、 对苯醌 作用下， 以 甲醇 为溶剂， -40.0 ℃ 、101.33 kPa 条件下， 生成 (R)-6,6-dimethyl-2-(toluene-2-sulfonyl)tetrahydropyrrolo[1,2-c]pyrimidine-1,3(2H,4H)-dione 、 (S)-6,6-dimethyl-2-(toluene-2-sulfonyl)tetrahydropyrrolo[1,2-c]pyrimidine-1,3(2H,4H)-dione
  参考文献：
  名称：

  Enantioselective Intramolecular Oxidative Aminocarbonylation of Alkenylureas Catalyzed by Palladium−Spiro Bis(isoxazoline) Complexes

  摘要：

  An enantioselective synthesis of tetrhydropyrrolo[1,2-c]pyrimidine-1,3-diones via a palladium-catalyzed intramolecular oxidative aminocarbonylation is described. The carbon-carbon double bond of alkenylurea substrates has been shown to react intramolecularly with a nitrogen nucleophile in the presence of a palladium catalyst under a carbon monoxide atmosphere. The use of a chiral Spiro bis(isoxazoline) ligand (SPRIX) is essential to obtain the desired products in optically active forms. In comparison with the coordination ability of other known ligands, this peculiar character of SPRIX originates from two structural characteristics: low sigma-donor ability of the isoxazoline coordination site and rigidity of the spiro skeleton.

  DOI：

  10.1021/jo901778a
• 作为产物：
  描述：

  2,2-dimethyl-1-amino-pent-4-ene 、 邻甲苯磺酰异氰酸酯 以 四氢呋喃 为溶剂， 以79%的产率得到N-(2,2-dimethylpent-4-enyl)-N'-o-toluenesulfonylurea
  参考文献：
  名称：

  Enantioselective Intramolecular Oxidative Aminocarbonylation of Alkenylureas Catalyzed by Palladium−Spiro Bis(isoxazoline) Complexes

  摘要：

  An enantioselective synthesis of tetrhydropyrrolo[1,2-c]pyrimidine-1,3-diones via a palladium-catalyzed intramolecular oxidative aminocarbonylation is described. The carbon-carbon double bond of alkenylurea substrates has been shown to react intramolecularly with a nitrogen nucleophile in the presence of a palladium catalyst under a carbon monoxide atmosphere. The use of a chiral Spiro bis(isoxazoline) ligand (SPRIX) is essential to obtain the desired products in optically active forms. In comparison with the coordination ability of other known ligands, this peculiar character of SPRIX originates from two structural characteristics: low sigma-donor ability of the isoxazoline coordination site and rigidity of the spiro skeleton.

  DOI：

  10.1021/jo901778a