2-amino-3-cyano-5-(3,3-dicyanopropyl)-6-cyclopropyl-4-ethylpyridine

• 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-amino-3-cyano-5-(3,3-dicyanopropyl)-6-cyclopropyl-4-ethylpyridine
• 英文别名: 2-[2-(6-amino-5-cyano-2-cyclopropyl-4-ethylpyridin-3-yl)ethyl]propanedinitrile
• 化学式: C₁₆H₁₇N₅
• 分子量: 279.344
• InChiKey: FBZBXFQGRFVOES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110.28
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  乙基氯化镁 、 环丙基腈 、 丙二腈 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到2-amino-5-chloroethyl-3-cyano-6-cyclopropyl-4-ethylpyridine
  参考文献：
  名称：

  Dimerization of Cyclopropanecarbonitrile Mediated by Grignard Reagents. Formation of Highly Substituted Pyridines.

  摘要：

  The reaction of cyclopropanecarbonitrile with ethylmagnesium bromide in diethyl ether followed by quenching with malononitrile gave the expected 2-cyano-3-cyclopropylpent-2-enonitrile (1a) in high yields. When the solvent was changed to tetrahydrofuran (THF) using ethylmagnesium chloride, low yields of 1a (12%) were obtained; the main products were two pentasubstituted pyridines, 2-amino-5-(2-chloroethyl)-3-cyano-6-cyclopropyl-4-ethylpyridine (2a, 70%) and 2-amino-3-cyano-5-(3,3-dicyanopropyl)-6-cyclopropyl-4-ethylpyridine (2c, 10%). In addition, their isomers, 2-amino-5-(2-chloroethyl)-3-cyano-4-cyclopropyl-6-ethylpyridine (3a, 7%) and 2-amino-3-cyano-5-(3,3-dicyanopropyl)-4-cyclopropyl-6-ethylpyridine (3c, 1%), were observed and identified by combined gas chromatography-mass spectrometry (GC-MS). When methylmagnesium chloride was used (solvent THF), in addition to 1b and the isomers 2d, 2e, 3d and 3e, a tetrasubstituted pyridine, 2-amino-3-cyano-4,6-dicyclopropylpyridine (11), was formed. Similar reaction between cyclopropyl-magnesium bromide and cyclopropanecarbonitrile gave after hydrolysis about equal yields of dicyclopropyl ketone and a diketone, 1,1-di(cyclopropanecarbonyl)cyclopropane (8b). The structures of 2c and 2d were established by X-ray crystallography.

  DOI：

  10.3891/acta.chem.scand.51-1104

文献信息

• Dimerization of Cyclopropanecarbonitrile Mediated by Grignard Reagents. Formation of Highly Substituted Pyridines.
  作者：Per Kolsaker、Pål Songe、Christian Rømming、Frode Rise、Michael P. Hartshorn、Manuela Merchán、Ward T. Robinson、Björn O. Roos、Claire Vallance、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-1104

  日期：——

  The reaction of cyclopropanecarbonitrile with ethylmagnesium bromide in diethyl ether followed by quenching with malononitrile gave the expected 2-cyano-3-cyclopropylpent-2-enonitrile (1a) in high yields. When the solvent was changed to tetrahydrofuran (THF) using ethylmagnesium chloride, low yields of 1a (12%) were obtained; the main products were two pentasubstituted pyridines, 2-amino-5-(2-chloroethyl)-3-cyano-6-cyclopropyl-4-ethylpyridine (2a, 70%) and 2-amino-3-cyano-5-(3,3-dicyanopropyl)-6-cyclopropyl-4-ethylpyridine (2c, 10%). In addition, their isomers, 2-amino-5-(2-chloroethyl)-3-cyano-4-cyclopropyl-6-ethylpyridine (3a, 7%) and 2-amino-3-cyano-5-(3,3-dicyanopropyl)-4-cyclopropyl-6-ethylpyridine (3c, 1%), were observed and identified by combined gas chromatography-mass spectrometry (GC-MS). When methylmagnesium chloride was used (solvent THF), in addition to 1b and the isomers 2d, 2e, 3d and 3e, a tetrasubstituted pyridine, 2-amino-3-cyano-4,6-dicyclopropylpyridine (11), was formed. Similar reaction between cyclopropyl-magnesium bromide and cyclopropanecarbonitrile gave after hydrolysis about equal yields of dicyclopropyl ketone and a diketone, 1,1-di(cyclopropanecarbonyl)cyclopropane (8b). The structures of 2c and 2d were established by X-ray crystallography.