(E)-4-methoxy-2-((phenylimino)methyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-4-methoxy-2-((phenylimino)methyl)phenol
• 英文别名: N-(2-Hydroxy-5-methoxybenzylidene)aniline；N-Phenyl-5-methoxy-salicylaldehydimin
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: OZUBFLPYRPJKQL-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 苯胺 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 (E)-4-methoxy-2-((phenylimino)methyl)phenol
  参考文献：
  名称：

  分子内氢键化合物的NMR谱-II：β-二酮和邻羟基羰基化合物的席夫碱

  摘要：

  使用NMR光谱法已显示芳香胺和β-二酮的席夫碱（包括含Ph端基的席夫碱）作为酮胺互变异构体存在。衍生自芳族胺和2-羟基-1-萘醛的席夫碱被认为是酮烯胺和烯醇胺形式的平衡混合物。还研究了芳族胺中电子效应对氢键强度的影响。

  DOI：

  10.1016/0040-4020(68)88164-5

文献信息

• Spectroscopic and semi-empirical MO study of substituent effects on the intramolecular proton transfer in anils of 2-hydroxybenzaldehydes
  作者：SergioH. Alarcón、Daniela Pagani、Jose Bacigalupo、AlejandroC. Olivieri

  DOI：10.1016/s0022-2860(98)00522-5

  日期：1999.2

  2-hydroxybenzaldehyde showing strong intramolecular hydrogen bonding are studied on the basis of solution 13 C NMR spectroscopic data and semiempirical MO (AM1) calculations of the relative stability of tautomers. Excited state proton transfer is also investigated using electronic absorption and fluorescence spectroscopies, and calculation of vertical excitation energies (INDO/S). The theoretical predictions

  摘要 基于溶液 13 C NMR 光谱数据和互变异构体相对稳定性的半经验 MO (AM1) 计算，研究了显示强分子内氢键的 2-羟基苯甲醛的单取代和双取代苯胺中的取代基效应。还使用电子吸收和荧光光谱以及垂直激发能 (INDO/S) 的计算来研究激发态质子转移。理论预测与实验观察一致。
• Design, synthesis and biological evaluation of imine resveratrol derivatives as multi-targeted agents against Alzheimer's disease
  作者：Su-Yi Li、Xiao-Bing Wang、Ling-Yi Kong

  DOI：10.1016/j.ejmech.2013.10.068

  日期：2014.1

  A series of imine resveratrol derivatives (1-20) have been designed, synthesized, and evaluated as multi-targeted compounds for the treatment of Alzheimer's disease (AD).In vitro studies show that most of the molecules exhibit a significant ability to inhibit self-induced and Cu2+-induced beta-amyloid (A beta(1-42)) aggregation, and to function as potential antioxidants and biometal chelators. In particular, compound 9 is a potential lead compound for AD treatment (for compound 9, IC50 = 14.1 mu M for the antioxidant activity using DPPH free radical method; 64.6% at 20 mu M for self-induced A beta aggregation). Moreover, it is capable of decreasing reactive oxygen species (ROS) induced by Cu-A beta and shows good neuroprotective effects in human SH-SY5Y neuroblastoma cells. Taken together, these results suggest that 9 might be a promising lead compound for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.
• US7312284B2
  申请人：——

  公开号：US7312284B2

  公开（公告）日：2007-12-25