2-[cyclopentyl(methyl)amino]-5-nitrobenzaldehyde | 912840-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[cyclopentyl(methyl)amino]-5-nitrobenzaldehyde
• CAS: 912840-69-8
• 化学式: C₁₃H₁₆N₂O₃
• mdl: MFCD11524672
• 分子量: 248.282
• InChiKey: QSYAMWJZALJAFF-UHFFFAOYSA-N

物化性质

• 熔点：
  79 °C(Solv: isopropanol (67-63-0))
• 沸点：
  411.2±35.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[cyclopentyl(methyl)amino]-5-nitrobenzaldehyde 、 4-甲苯磺酰乙腈 在 三乙胺 作用下， 以 乙醇 为溶剂， 以91%的产率得到1-methyl-3-[(4-methylphenyl)sulfonyl]-6-nitro-1,2,3,4-tetrahydrospiro(quinoline-2,1'-cyclopentane)-3-carbonitrile
  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
• 作为产物：
  描述：

  环戊基甲基胺 、 2-氯-5-硝基苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以57%的产率得到2-[cyclopentyl(methyl)amino]-5-nitrobenzaldehyde
  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