2-methylamino-3-cyano-4-phenyl-6-tert-butylpyridine

• 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: 2-methylamino-3-cyano-4-phenyl-6-tert-butylpyridine
• 英文别名: 6-tert-butyl-2-(methylamino)-4-phenylpyridine-3-carbonitrile
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.358
• InChiKey: UYMXOVCUWMXHSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.71
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-(1-苯基亚乙基)丙二腈 在 potassium tert-butylate 作用下， 以 乙醚 、 乙腈 、 叔丁醇 为溶剂， 反应 4.0h， 生成 2-methylamino-3-cyano-4-phenyl-6-tert-butylpyridine
  参考文献：
  名称：

  Reaction between 2-Phenyl-1,1-dicyanoallyl Anion and N-Methyl-2,2-dimethylpropionitrilium and N1,N2,N2-Trimethyl-2,2-dimethylpropionylamidinium Trifluoromethanesulfonates.

  摘要：

  The reaction of 2-phenyl-1,1-dicyanoallyl anion with N-methyl-2,2-dimethyl-propionitrilium ion (2) in acetonitrile solution resulted in formation of [3-(N-methylamino)-4,4-dimethyl-1-phenyl-2-pentenylidene]propanedinitrile (6), which at elevated temperature (25-50 degrees C, depending on the solvent) undergoes a ring closure to 2-(N-methylamino)-3-cyano-4-phenyl-6-tert-butylpyridine (7) or in the presence of aqueous acid to 3-cyano-4-phenyl-6-tert-butyl-2-pyrone (8). Using N,N-dimethylformamide as solvent, in addition to 7, two other compounds are formed, viz. (3-(N,N-dimethylamino)-1-phenyl-2-propenylidene)propanedinitrile (9) and N-(4,4-dicyano-3-phenyl-1, 3-butadienyl)-N,2,2-trimethylpropanamide (10). The latter two compounds are results of a primary reaction of the title nitrilium ion with the solvent to give N-1,N-2,N-2-trimethyl-N-1-2,2-dimethyl-propionylamidinium trifluoromethanesulfonate (11) which in turn reacted with the title allyl anion 2 to give 9 and 10, for which X-ray crystal structures were determined. Strong indications of a tetrahedral mechanism in the reaction of 2 with 11 are presented.

  DOI：

  10.3891/acta.chem.scand.50-0623

文献信息

• Reaction between 2-Phenyl-1,1-dicyanoallyl Anion and N-Methyl-2,2-dimethylpropionitrilium and N1,N2,N2-Trimethyl-2,2-dimethylpropionylamidinium Trifluoromethanesulfonates.
  作者：Per Kolsaker、Hege Karlsen、Christian Rømming、Joseph Arukwe、Jo Klaveness、Frode Rise、Kjell Undheim、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0623

  日期：——

  The reaction of 2-phenyl-1,1-dicyanoallyl anion with N-methyl-2,2-dimethyl-propionitrilium ion (2) in acetonitrile solution resulted in formation of [3-(N-methylamino)-4,4-dimethyl-1-phenyl-2-pentenylidene]propanedinitrile (6), which at elevated temperature (25-50 degrees C, depending on the solvent) undergoes a ring closure to 2-(N-methylamino)-3-cyano-4-phenyl-6-tert-butylpyridine (7) or in the presence of aqueous acid to 3-cyano-4-phenyl-6-tert-butyl-2-pyrone (8). Using N,N-dimethylformamide as solvent, in addition to 7, two other compounds are formed, viz. (3-(N,N-dimethylamino)-1-phenyl-2-propenylidene)propanedinitrile (9) and N-(4,4-dicyano-3-phenyl-1, 3-butadienyl)-N,2,2-trimethylpropanamide (10). The latter two compounds are results of a primary reaction of the title nitrilium ion with the solvent to give N-1,N-2,N-2-trimethyl-N-1-2,2-dimethyl-propionylamidinium trifluoromethanesulfonate (11) which in turn reacted with the title allyl anion 2 to give 9 and 10, for which X-ray crystal structures were determined. Strong indications of a tetrahedral mechanism in the reaction of 2 with 11 are presented.