N-(5-甲基-2-羟基苯基)水杨醛亚胺 | 111200-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: N-(5-甲基-2-羟基苯基)水杨醛亚胺
• 英文名称: N-(5-methyl-2-hydroxyphenyl)salicylaldimine
• 英文别名: N-(2-hydroxy-5-methylphenyl), 2-hydroxybenzaldehydeimine；2-[(2-hydroxybenzyliden)amino]-4-methylphenol
• CAS: 111200-02-3
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: FHQCBKGDZMFQNZ-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.82
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(5-甲基-2-羟基苯基)水杨醛亚胺 在 magnesium chloride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  一种新型的双酚配体，用于选择性检测Mg 2+和Zn 2+离子，然后进行比色，光谱和细胞成像方法

  摘要：

  合成了（E）-2-（（（2-氢氢-5-甲基苯基亚氨基）甲基）苯酚配体。该受体通过IR，1 H和13 C NMR以及CHN分析来表征。配体在半水介质（DMSO-H2O）中显示Zn 2+和Mg 2+离子的比色和荧光检测。用一系列过渡金属离子（Cr 2 +，Fe 2 +，Ni 2 +，Co 2 +，Cu 2 +，Zn 2+）和重金属离子（Sn 2 +，Pd 2 +，Ce 2）测试了该受体+，汞2+，镉2+）和人体必需的元素，例如Ca 2 +，Mg 2 +，Na +和K +离子。肉眼比色传感仅吸收Zn 2+和Mg 2+。当两种离子（H 2 O中的ZnCl 2和MgCl 2）以逐步添加的方式添加到约1当量的受体的无色溶液中时，都会将该溶液变成亮黄姜黄。在比色检测中，所有其他离子保持非活性状态。Zn 2+和Mg 2+离子通过吸收和发射光谱法通过逐步添加相应的金属离子进行探测。在原位通过1 H NMR滴定研究证实了Mg

  DOI：

  10.1016/j.ejps.2018.01.025
• 作为产物：
  描述：

  水杨醛 、 邻氨基对甲苯酚 以 乙醇 为溶剂， 反应 6.0h， 以84%的产率得到N-(5-甲基-2-羟基苯基)水杨醛亚胺
  参考文献：
  名称：

  一种新型的双酚配体，用于选择性检测Mg 2+和Zn 2+离子，然后进行比色，光谱和细胞成像方法

  摘要：

  合成了（E）-2-（（（2-氢氢-5-甲基苯基亚氨基）甲基）苯酚配体。该受体通过IR，1 H和13 C NMR以及CHN分析来表征。配体在半水介质（DMSO-H2O）中显示Zn 2+和Mg 2+离子的比色和荧光检测。用一系列过渡金属离子（Cr 2 +，Fe 2 +，Ni 2 +，Co 2 +，Cu 2 +，Zn 2+）和重金属离子（Sn 2 +，Pd 2 +，Ce 2）测试了该受体+，汞2+，镉2+）和人体必需的元素，例如Ca 2 +，Mg 2 +，Na +和K +离子。肉眼比色传感仅吸收Zn 2+和Mg 2+。当两种离子（H 2 O中的ZnCl 2和MgCl 2）以逐步添加的方式添加到约1当量的受体的无色溶液中时，都会将该溶液变成亮黄姜黄。在比色检测中，所有其他离子保持非活性状态。Zn 2+和Mg 2+离子通过吸收和发射光谱法通过逐步添加相应的金属离子进行探测。在原位通过1 H NMR滴定研究证实了Mg

  DOI：

  10.1016/j.ejps.2018.01.025

文献信息

• Stereoselective addition of acetone to the C=N bond of [4.3.0] boron heterobicycles
  作者：Victor Barba、Damian Cuahutle、Rosa Santillan、Norberto Farfán

  DOI：10.1139/v01-107

  日期：2001.8.1

  The reaction of N-salicylidene-2-aminophenolate (SAP-H₂) derivatives with phenyl boronic acid afforded five new boron bicyclic species in moderate yields, as confirmed by an X-ray study of the boron heterocycle derived from 2-amino-4-chlorophenol. The results also showed that the boron complexes derived from Schiff bases undergo an acetolysis reaction to give the corresponding dioxazaborocines containing all substituents on the same side also in good yields. The structure of one of the addition products was established by X-ray analysis showing that, in the solid state, it exists as a dimeric structure formed by hydrogen bonds.Key words: borocines, tridentate ligands, imines, boronic acids.

  N-水杨醛基-2-氨基苯酚（SAP-H₂）衍生物与苯硼酸反应，以中等产率得到五种新的硼双环物种，通过对由2-氨基-4-氯苯酚衍生的硼杂环化合物的X射线研究确认。结果还表明，由席夫碱衍生的硼配合物经过乙醇解反应，以较高产率得到含有所有取代基的二氧杂硼环化合物。其中一种加成产物的结构经X射线分析确定，固态下它存在为由氢键形成的二聚体结构。关键词：硼环化合物、三牙配体、亚胺、硼酸。
• Stereoselective addition of allylmagnesium chloride to the CN bond of [4.3.0] boron heterobicycles
  作者：Heraclio López-Ruiz、Iván Mera-Moreno、Susana Rojas-Lima、Rosa Santillán、Norberto Farfán

  DOI：10.1016/j.tetlet.2007.12.122

  日期：2008.3

  An efficient, simple protocol for the addition of allylmagnesium chloride to the C=N bond of [4.3.0] boron heterobicycles afforded five new dioxaboracyclononenes 4a-e in moderate yields (51-61%). The boronates were characterized by (1)H, (13)C, (11)B and 2D NMR experiments, and confirmed by X-ray analogues. The stereochemistry of the N-H, -CH(2)CH=CH, and B-Ph fusion is always cis, as established through NMR, and confirmed by X-ray structure of 4d. The structure of one of the addition products was established by X-ray analysis showing that, in the solid state, it exists as a polymeric structure formed by hydrogen bonds between the amine proton and the ester oxygen of the five-membered ring. (c) 2008 Elsevier Ltd. All rights reserved.
• Keto–enol tautomerism, conformations and structure of N-(2-hydroxy-5-methylphenyl), 2-hydroxybenzaldehydeimine
  作者：M Kabak、A Elmali、Y Elerman

  DOI：10.1016/s0022-2860(98)00604-8

  日期：1999.3

  N-(2-hydroxy-5-methylphenyl), 2-hydroxybenzaldehydeimine (C14H13NO2) has been studied by X-ray analysis and AM1 semi-empirical quantum mechanical method. It crystallizes in the monoclinic space group P2(1)/c with a = 7.433(1), b = 9.185(3), c = 186(4) Angstrom, beta = 97.13(1)degrees, V = 1164.3(5) Angstrom(3), Z = 4, D-c = 1.30 gcm(-3) and mu(MoK alpha) = 0.087 mm(-1). The structure was solved by direct methods and refined to R = 0.034 for 1407 reflections [I > 2 sigma(I)]. The title compound is photochromic and the molecule is not planar. Intramolecular hydrogen bonds occur between the pairs of atoms N(1) and O(1) [2.582(1) Angstrom], and N(1) and O2) [2.655(1) Angstrom], the H atom essentially being bonded to the N atom. Adjacent molecules are linked via an intermolecular O-H ... O hydrogen bond [2.582(1) Angstrom] between neighbouring molecules. Tautomeric properties and conformations of the title compound were investigated by semi-empirical quantum mechanical AMI calculations and the results are compared with the X-ray results. (C) 1999 Elsevier Science B.V. All rights reserved.
• COMPOUNDS WITH ANTIMICROBIAL ACTIVITY
  申请人：The Hong Kong Polytechnic University

  公开号：US20200347010A1

  公开（公告）日：2020-11-05

  This invention relates to compounds of formula 1, 2 or 3 a pharmaceutically acceptable salt, or solvate thereof, wherein X 1 , Y, R 1 , R 2 , R 3 , R 4 , and R 5 are as defined herein. The compounds are antimicrobial agents that may be used to treat various bacterial and protozoal infections and disorders related to such infections. The invention also relates to pharmaceutical compositions containing the compounds and to methods of treating bacterial and protozoal infections by administering the compounds of formula 1, 2 or 3.
• A novel biphenolic ligand for selective Mg 2+ and Zn 2+ ions sensing followed by colorimetric, spectroscopic and cell imaging methods
  作者：Palanisamy Uma Maheswari、Duraisamy Renuga、Linda Jeeva Kumari Henry、Kandasamy Ruckmani

  DOI：10.1016/j.ejps.2018.01.025

  日期：2018.4

  NMR titration studies. The imino nitrogen of the receptor is not coordinated to the metal ions. The Job's plot studies reveal the 1:2 binding ratio of metal ions to the receptor. The high fold fluorescence output on metal ions binding was positively used to sense the Zn2+ and Mg2+ ions, separately and together in HeLa cancer cells through cell imaging.

  合成了（E）-2-（（（2-氢氢-5-甲基苯基亚氨基）甲基）苯酚配体。该受体通过IR，1 H和13 C NMR以及CHN分析来表征。配体在半水介质（DMSO-H2O）中显示Zn 2+和Mg 2+离子的比色和荧光检测。用一系列过渡金属离子（Cr 2 +，Fe 2 +，Ni 2 +，Co 2 +，Cu 2 +，Zn 2+）和重金属离子（Sn 2 +，Pd 2 +，Ce 2）测试了该受体+，汞2+，镉2+）和人体必需的元素，例如Ca 2 +，Mg 2 +，Na +和K +离子。肉眼比色传感仅吸收Zn 2+和Mg 2+。当两种离子（H 2 O中的ZnCl 2和MgCl 2）以逐步添加的方式添加到约1当量的受体的无色溶液中时，都会将该溶液变成亮黄姜黄。在比色检测中，所有其他离子保持非活性状态。Zn 2+和Mg 2+离子通过吸收和发射光谱法通过逐步添加相应的金属离子进行探测。在原位通过1 H NMR滴定研究证实了Mg