[allyl-(4-methoxyphenyl)amino]-acetonitrile | 1204614-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [allyl-(4-methoxyphenyl)amino]-acetonitrile
• 英文别名: 2-(4-methoxy-N-prop-2-enylanilino)acetonitrile
• CAS: 1204614-51-6
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: PQYBWUYDYPOXFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [allyl-(4-methoxyphenyl)amino]-acetonitrile 600.0 ℃ 、0.2 Pa 条件下， 以25%的产率得到(p-methoxyphenyl)iminoacetonitrile
  参考文献：
  名称：

  Synthesis of aryliminoacetonitriles under FVT conditions or by dehydrogenation of arylaminoacetonitriles: an NMR and UV-photoelectron spectroscopy study

  摘要：

  The synthesis of [(E)-arylimino]-acetonitriles 3 has been described. It was found that the title compounds can be obtained on the three ways, namely by: (i) dehydrogenation of arylaminoacetonitriles 1, (ii) thermal fragmentation of 1-aryl-4-cyano-beta-lactams 4 and (iii) retro-ene reaction of (allyl-p-methoxyphenyl-amino)-acetonitrile (7a) under FVT conditions. H-1 and C-13 NMR spectra of compounds 3, 5 and 6, and all their precursors 1 and 4, were recorded and analysed in detail using chemical Shifts delta(H) and delta(C) [from GIAO DFT B3LYP/6-31(d) calculations] and J-couplings predicted at the DFT B3LYP/IGLO-II level. Also, UV-photoelectron spectra of 4a,d and 3a,d were measured and analysed considering the theoretical evaluation of their ionisation potentials. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.080

文献信息

• Synthesis of aryliminoacetonitriles under FVT conditions or by dehydrogenation of arylaminoacetonitriles: an NMR and UV-photoelectron spectroscopy study
  作者：Stanisław Leśniak、Anna Chrostowska、Dawid Kuc、Małgorzata Maciejczyk、Saïd Khayar、Ryszard B. Nazarski、Łukasz Urbaniak

  DOI：10.1016/j.tet.2009.10.080

  日期：2009.12

  The synthesis of [(E)-arylimino]-acetonitriles 3 has been described. It was found that the title compounds can be obtained on the three ways, namely by: (i) dehydrogenation of arylaminoacetonitriles 1, (ii) thermal fragmentation of 1-aryl-4-cyano-beta-lactams 4 and (iii) retro-ene reaction of (allyl-p-methoxyphenyl-amino)-acetonitrile (7a) under FVT conditions. H-1 and C-13 NMR spectra of compounds 3, 5 and 6, and all their precursors 1 and 4, were recorded and analysed in detail using chemical Shifts delta(H) and delta(C) [from GIAO DFT B3LYP/6-31(d) calculations] and J-couplings predicted at the DFT B3LYP/IGLO-II level. Also, UV-photoelectron spectra of 4a,d and 3a,d were measured and analysed considering the theoretical evaluation of their ionisation potentials. (C) 2009 Elsevier Ltd. All rights reserved.