1,1-dicyano-3-carbamoyl-3-(1-pyridinio)-2-phenyl-1-propenide | 127458-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,1-dicyano-3-carbamoyl-3-(1-pyridinio)-2-phenyl-1-propenide
• 英文别名: 1,1-dicyano-3-carbamoyl-3-(1-pyridino)-2-phenyl-1-propanide；(5-Amino-2-cyano-5-oxo-3-phenyl-4-pyridin-1-ium-1-ylpent-1-enylidene)azanide
• CAS: 127458-39-3
• 化学式: C₁₇H₁₄N₄O
• 分子量: 290.324
• InChiKey: NXBXFMPKHVJEPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dicyano-3-carbamoyl-3-(1-pyridinio)-2-phenyl-1-propenide 以 二甲基亚砜 为溶剂， 以85%的产率得到trans-1,1-dicyano-2-carbamoyl-3-phenylcyclopropane
  参考文献：
  名称：

  Litvinov, V. P.; Shestopalov, A. M.; Sharanin, Yu. A., Doklady Chemistry, 1989, vol. 309, # 1-3, p. 315 - 318

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(氨甲酰甲基)吡啶氯 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 1,1-dicyano-3-carbamoyl-3-(1-pyridinio)-2-phenyl-1-propenide
  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

文献信息

• Electronic regioselectivity in the reactions of pyridinium ylides with tetracyanoethylene
  作者：A. M. Shestopalov、Yu. A. Sharanin、I. A. Aitov、V. N. Nesterov、Yu. T. Struchkov、V. P. Litvinov

  DOI：10.1007/bf00472289

  日期：1991.8
• Litvinov, V. P.; Shestopalov, A. M.; Sharanin, Yu. A., Doklady Chemistry, 1989, vol. 309, # 1-3, p. 315 - 318
  作者：Litvinov, V. P.、Shestopalov, A. M.、Sharanin, Yu. A.、Mortikov, V. Yu.

  DOI：——

  日期：——
• LITVINOV, V. P.;SHESTOPALOV, A. M.;SHARANIN, YU. A.;MORTIKOV, V. YU., DOKL. AN CCCP, 309,(1989) N, S. 115-119
  作者：LITVINOV, V. P.、SHESTOPALOV, A. M.、SHARANIN, YU. A.、MORTIKOV, V. YU.

  DOI：——

  日期：——
• SHESTOPALOV, A. M.;LITVINOV, V. I.;RODINOVSKAYA, L. A.;SHARANIN, YU. A., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 146-155
  作者：SHESTOPALOV, A. M.、LITVINOV, V. I.、RODINOVSKAYA, L. A.、SHARANIN, YU. A.

  DOI：——

  日期：——
• Regio- and stereoselective synthesis of tetrahydroindolysines, tetrahydropyridin-6-olates, and cyclopropanes from pyridinium ylides and unsaturated nitriles
  作者：A. M. Shestopalov、V. P. Litvinov、L. A. Rodinovskaya、Yu. A. Sharanin

  DOI：10.1007/bf00959644

  日期：1991.1

  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.