1-carbamoylmethylide-3-cyanopyridinium | 133828-85-0

• 英文名称: 1-carbamoylmethylide-3-cyanopyridinium
• CAS: 133828-85-0
• 化学式: C₈H₇N₃O
• 分子量: 161.163
• InChiKey: AZLDZWUDBPCIAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  2-(4-氟亚苄基)-丙二腈 、 1-carbamoylmethylide-3-cyanopyridinium 以 乙醇 为溶剂， 生成 (2S,3S,8aR)-1,1,6-Tricyano-2-(4-fluoro-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
• 作为产物：
  描述：

  1-Carbamoylmethyl-3-cyano-pyridinium; chloride 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 1-carbamoylmethylide-3-cyanopyridinium
  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