(2S,3R,8aS)-1,1,6-Tricyano-2-(2-nitro-phenyl)-1,2,3,8a-tetrahydro-indolizine-3-carboxylic acid amide | 133828-88-3

• 英文名称: (2S,3R,8aS)-1,1,6-Tricyano-2-(2-nitro-phenyl)-1,2,3,8a-tetrahydro-indolizine-3-carboxylic acid amide
• CAS: 133828-88-3
• 化学式: C₁₈H₁₂N₆O₃
• 分子量: 360.332
• InChiKey: ONJPCURUHOMINI-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  160.84
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-(2-nitrobenzylidene)malononitrile 、 1-carbamoylmethylide-3-cyanopyridinium 以 乙醇 为溶剂， 生成 (2S,3R,8aS)-1,1,6-Tricyano-2-(2-nitro-phenyl)-1,2,3,8a-tetrahydro-indolizine-3-carboxylic acid amide
  参考文献：
  名称：

  Regio- and stereoselective synthesis of tetrahydroindolysines, tetrahydropyridin-6-olates, and cyclopropanes from pyridinium ylides and unsaturated nitriles

  摘要：

  The regio- and stereoselectivity of the reactions of pyridinium ylides with unsaturated nitriles are dependent on the electronic nature of the substituent in position 3 of the pyridine ring. The reaction of 1-carbamoylmethylide-3-cyanopyridinium with arylmethylenemalononitriles or arylmethylcyanoacetic esters proceeds regio- and stereoselectively with the formation of substituted 2-aryl-3-carbamoyl-6-cyano-2,3-trans- or 2,3-cis-1,2,3,8a-tetrahydroindolysines. The condensation of pyridinium 1-carbamoylmethylide with arylmethylenecyanoacetic ether leads to 4-aryl-2-oxo-3-(1-pyridinio)-5-cyano-3,4-trans-1,2,3,4-tetrahydropyridin-6-olates. The reaction of pyridinium (3-methylpyridinium) 1-carbamoylmethylide with arylmethylenemalononitriles results in the formation of 2-aryl-1,1-dicyano-3-carbamoyl-3-(1-pyridinio)- or (3-methyl-1-pyridinio)-1-propanides, which undergo stereoselective 1,3-transelimination with the formation of 3-aryl-1,1-dicyano-2-carbamoylcyclopropanes.

  DOI：

  10.1007/bf00959644