5-amino-7-(cyclohexylamino)-2,4-dimethyl-1,6-naphthyridine-8-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-amino-7-(cyclohexylamino)-2,4-dimethyl-1,6-naphthyridine-8-carbonitrile
• 英文别名: 5-Amino-7-(cyclohexylamino)-2,4-dimethyl-1,6-naphthyridine-8-carbonitrile
• 化学式: C₁₇H₂₁N₅
• 分子量: 295.387
• InChiKey: BOFOSEKDWVJFIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环己胺 、 2-(dicyanomethylene)-1,2-dihydro-4,6-dimethylpyridine-3-carbonitrile 反应 144.0h， 以97%的产率得到5-amino-7-(cyclohexylamino)-2,4-dimethyl-1,6-naphthyridine-8-carbonitrile
  参考文献：
  名称：

  Cyclization of 2-dicyanomethylene-1,2-dihydropyridine-3-carbonitriles with amines: a mechanistic rationalization

  摘要：

  A mechanistic rationalization for the cyclization of the 1,5-dinitrile system present in pyridines 4{1-3} with amines to lead to 1,6-naphthyridines is proposed. Three factors play an important role on the direction of cyclization: (1) the cyclization involves nucleophilic attack of an amidine onto a nitrile or amidine; (2) the attack has to fulfill strict geometrical constraints to allow the cyclization to proceed; (3) the cyclization step should involve the nucleophilic attack combined with a tautomerism to achieve the high levels of regioselectivity observed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.025