2-(N-aminoformimidoyl)-6-methoxyphenol | 51084-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(N-aminoformimidoyl)-6-methoxyphenol
• 英文别名: 2-hydroxy-3-benzaldehyde hydrazone；o-vanillin hydrazone；6-(Hydrazinylmethylidene)-2-methoxycyclohexa-2,4-dien-1-one；2-methanehydrazonoyl-6-methoxyphenol
• CAS: 51084-72-1
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: KPPHXJSROYFNRC-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  326.4±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(N,N-dimethylaminomethylferrocene)carboxaldehyde 、 2-(N-aminoformimidoyl)-6-methoxyphenol 以 乙醇 为溶剂， 反应 16.0h， 以66%的产率得到
  参考文献：
  名称：

  Synthesis, characterization and pharmacological evaluation of ferrocenyl azines and their rhodium(I) complexes

  摘要：

  Ferrocenyl azines containing salicylaldimine motifs were prepared by Schiff-base condensation of salicylaldehyde hydrazones and (dimethylamino) methyl ferrocenecarboxaldehyde. Their corresponding Rh(I) complexes were prepared by reaction of the various ferrocenyl azines with [RhCl(COD)](2) (where COD = 1,5-cyclooctadiene) to yield heterobimetallic complexes. The compounds were characterized using standard spectroscopic and analytical techniques. The characterization data suggests that the ferrocenyl azine acts as a bidentate donor. The rhodium(I) centre binds to the imine nitrogen and phenolic oxygen of the salicylaldimine, forming a neutral complex. The compounds were screened against the NF54 chloroquine-sensitive (CQS) and K1 chloroquine-resistant (CQR) strains of Plasmodium falciparum. The ferrocene-containing salicylaldimines exhibited weak to moderate activity across both parasite strains. The heterometallic complexes exhibited enhanced activity compared to the ferrocenyl azines in both strains. Most of the compounds exhibited enhanced activity in the resistant strain compared to the sensitive strain. Inhibition of haemozoin formation was considered as a possible mechanism of action of these compounds and indeed they exhibited beta-haematin inhibition activity, albeit weaker than chloroquine. All compounds were also screened against the G3 strain of Trichomonas vaginalis. The compounds inhibited no more than 50% parasite growth at the tested concentration. One complex exhibited moderate cytotoxicity against WHCO1 oesophageal cancer cells. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.04.009
• 作为产物：
  描述：

  邻香草醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以66.2%的产率得到2-(N-aminoformimidoyl)-6-methoxyphenol
  参考文献：
  名称：

  Synthesis and Characterization of Benzo-15-Crown-5 Ethers with Appended N2O Schiff Bases

  摘要：

  本研究采用两步法制备了苯并-15-冠醚-5 的新衍生物，这些衍生物具有灵活的 N2O 不对称席夫碱，包括：(i) 通过肼与水杨醛、3-甲氧基水杨醛或 2-羟基-1-萘甲醛缩合制备 N2O 席夫碱；(ii) 将生成的 NH2 功能化化合物与 4-甲酰基苯并-15-冠醚-5 反应。

  DOI：

  10.3390/81200894

文献信息

• Calix[4]arene Schiff bases—potential ligands for fluorescent studies
  作者：Mary F. Mahon、John McGinley、A. Denise Rooney、John M.D. Walsh

  DOI：10.1016/j.tet.2008.09.091

  日期：2008.12

  derivatives incorporating imine substituents were synthesised from the Schiff-base reaction of 25,27-bis[2-[(1-formyl-2-phenyl)oxy]ethyl]-p-tert-butylcalix[4]arene (1) with the appropriate amine or hydrazone. All compounds were characterised by various spectroscopic and analytical techniques, and in three cases, by X-ray crystallographic studies. In the case of compound 2, inclusion compounds were synthesised

  从25,27-双[2-[（[1-甲酰基-2-苯基）氧基]乙基] -p-的席夫碱反应合成了一系列新的掺有亚胺取代基的双臂杯[4]芳烃衍生物。叔丁基杯[4]芳烃（1）与适当的胺或。所有化合物均通过各种光谱学和分析技术进行了表征，在三种情况下，通过X射线晶体学研究对其进行了表征。在化合物的情况下2，用两个合成的包接化合物米-二甲苯和二甲基甲酰胺及其X射线结构揭示了这些包含位点-分别位于悬臂之间和上腔中。在所有情况下，悬吊臂都弯曲成彼此远离，而不是采用面对面的构造。