1-methyl-6-nitro-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3,3-dicarbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-methyl-6-nitro-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3,3-dicarbonitrile
• 英文别名: 1-methyl-6-nitrospiro[4H-quinoline-2,1'-cyclohexane]-3,3-dicarbonitrile
• 化学式: C₁₇H₁₈N₄O₂
• 分子量: 310.356
• InChiKey: HZPVSXYEBWEVTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  96.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基环己胺 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-methyl-6-nitro-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3,3-dicarbonitrile
  参考文献：
  名称：

  A novel tert-amino effect based approach to 1,2,3,4-tetrahydroquinoline-2-spirocycloalkanes

  摘要：

  An interaction of 2-[cyclohexyl(methyl)amino]benzaldehydes with substituted acetonitriles X-CH2CN (X=CN, Tos, hetaryl) was found to yield 1-methyl-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3-carbonitriles. The corresponding spiroquinoline-2,1'-cyclopentane analogues were obtained similarly starting from 2-[cyclopentyl(methyl)amino]benzaldehydes. The reaction was assumed to proceed via initial Knoevenagel condensation and further ring closure of the formed adduct according to the tert-amino effect mechanism. The structure of the prepared compounds was confirmed unambiguously by X-ray crystallographic study. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.042

文献信息

• A novel tert-amino effect based approach to 1,2,3,4-tetrahydroquinoline-2-spirocycloalkanes
  作者：Anton V. Tverdokhlebov、Alexander P. Gorulya、Andrey A. Tolmachev、Alexander N. Kostyuk、Alexander N. Chernega、Eduard B. Rusanov

  DOI：10.1016/j.tet.2006.07.042

  日期：2006.9

  An interaction of 2-[cyclohexyl(methyl)amino]benzaldehydes with substituted acetonitriles X-CH2CN (X=CN, Tos, hetaryl) was found to yield 1-methyl-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclohexane)-3-carbonitriles. The corresponding spiroquinoline-2,1'-cyclopentane analogues were obtained similarly starting from 2-[cyclopentyl(methyl)amino]benzaldehydes. The reaction was assumed to proceed via initial Knoevenagel condensation and further ring closure of the formed adduct according to the tert-amino effect mechanism. The structure of the prepared compounds was confirmed unambiguously by X-ray crystallographic study. (c) 2006 Elsevier Ltd. All rights reserved.