(E)-2-((1H-indol-3-yl)methyleneamino)phenol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-2-((1H-indol-3-yl)methyleneamino)phenol
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: ILOLDUBZKMFYIZ-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.38
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-((1H-indol-3-yl)methyleneamino)phenol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以80%的产率得到2-(1H-indol-3-ylmethylamino)phenol
  参考文献：
  名称：

  Mruthyunjayaswamy; Shanthaveerappa; Rajshekhar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 453 - 460

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium nitrite 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (E)-2-((1H-indol-3-yl)methyleneamino)phenol
  参考文献：
  名称：

  Synthesis and Evaluation of Schiff’s Base Indole Derivatives Against Inflammation Induced by Carrageenan in Rats

  摘要：

  Inflammation is a complex physiological response that can lead to various health issues. The development of effective anti-inflammatory agents is crucial for managing inflammatory conditions. This study focused on synthesizing and evaluating Schiff's base Indole derivatives for their anti-inflammatory potential. Among several synthesized compounds, C1IN, C2IN, C3IN, C7IN, C8IN, and C11IN demonstrated substantial reductions in paw edema and levels of cytokines of inflammation such as IL-1β and TNF-α. In-silico analysis and molecular docking studies further supported the observed effects, indicating potential interactions with TNF-α. The study highlights the therapeutic potential of Schiff's base Indole derivatives in mitigating inflammatory responses. Hence, Schiff's base Indole derivatives present a novel avenue for future research and the potential development of anti-inflammatory drugs.

  DOI：

  10.13005/ojc/400113

文献信息

• Electronic spectral studies of some fluorescent probes: A comparison of two approaches
  作者：C. Anbuselvan、J. Jayabharathi、V. Thanikachalam、K. Jayamoorthy

  DOI：10.1016/j.saa.2012.07.119

  日期：2012.10

  fluorescence properties of these dyes are strongly solvent dependent and the wavelength of maximum fluorescence emission shifts to red. The Kamlet-Taft and Catalan's solvent scales were found to be the most suitable for describing the solvatochromic shifts of the absorption and fluorescence emission. From the NMR chemical shifts and DFT studies, it was found that the azomethine hydrogen is anti to the amine

  合成了席夫碱衍生物，并通过NMR光谱，质量和CHN分析对其进行了表征。这些染料的荧光特性强烈依赖于溶剂，最大荧光发射的波长变为红色。发现Kamlet-Taft和Catalan的溶剂规模最适合描述吸收和荧光发射的溶剂化变色。从NMR化学位移和DFT研究，发现偶氮甲碱氢对胺芳基环是抗性的，即，这些染料以反构象存在。还进行了DFT计算，以确定更稳定的最小能量构象中羟基的取向。
• Physico-chemical studies on some fluorescence sensors: DFT based ESIPT process
  作者：C. Anbuselvan、J. Jayabharathi、V. Thanikachalam、G. Tamilselvi

  DOI：10.1016/j.saa.2012.05.084

  日期：2012.11

  of novel heterocyclic Schiff base derivatives were synthesized and characterized by NMR spectra, mass and CHN analysis. Excited state intramolecular proton transfer (ESIPT) processes in o-hydroxy Schiff base have been studied using electronic spectral studies. Experimental and FT studies support that trans enol form predominates over the cis enol form. The fluorescence of Schiff bases quenched markedly

  合成了一组新型的席夫碱杂环衍生物，并通过NMR光谱，质量和CHN分析对其进行了表征。使用电子光谱研究了在邻羟基席夫碱中的兴奋态分子内质子转移（ESIPT）过程。实验和FT研究支持反式烯醇形式比顺式烯醇形式占主导地位。席夫碱的荧光猝灭与逐渐添加Cu（2+）。对能量，偶极矩，旋转异构体在基态中的电荷分布以及席夫碱衍生物的激发态进行了DFT计算，并进行了讨论。PES计算表明，两个旋转异构体互变的能垒在激发态比基态高。通过非线性光学（NLO）和自然键轨道（NBO）分析从原子电荷计算出电荷分布。最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）能级的能量以及分子静电势（MEP）能量表面研究证明了分子内存在分子内电荷转移（ICT）。