2-(2,3-dihydroxybenzylideneamino)phenol | 1761-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2,3-dihydroxybenzylideneamino)phenol
• 英文别名: 3-[(E)-(2-hydroxyphenyl)iminomethyl]benzene-1,2-diol；3-[(2-hydroxyphenyl)iminomethyl]benzene-1,2-diol
• CAS: 1761-58-6
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: KOEKVAZQCLBLQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,3-dihydroxybenzylideneamino)phenol 、 nickel(II) acetate tetrahydrate 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  一种氨基苯酚席夫碱衍生物及其制备方法和应用

  摘要：

  本发明公开了一种氨基苯酚席夫碱衍生物及其制备方法和应用，其结构式为其结构式为其中，R为H、OH、烷氧基、1‑4个碳原子的未取代的烷基或1‑4个碳原子的取代烷基。本发明的氨基苯酚席夫碱衍生物具有完全不同于现有抗真菌药物的分子结构，为抗真菌药物研发提供了新的思路，同时显示出良好的抗癌活性，这对于有效开发和利用系列抗真菌及抗癌药物具有重要意义。

  公开号：

  CN113511985B
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 、 2-氨基苯酚 以 乙醇 为溶剂， 反应 5.0h， 以89%的产率得到2-(2,3-dihydroxybenzylideneamino)phenol
  参考文献：
  名称：

  两种新型钳型钯（II）-席夫碱配合物的合成，晶体结构及其在CC交叉偶联反应中的应用

  摘要：

  摘要两种新的钳型Pd（II）-Schiff碱配合物，其通式为[PdL 1（PPh 3）] 1和[PdL 2（PPh 3）] 2，其中L 1 = 2-（2,3-二羟基苄叉亚氨基通过乙酸钯与相应的配体在甲醇中以黄色结晶固体的高产率反应，合成了苯酚盐和L 2 ＝ 2-（2,3-二羟基亚苄基）肼基氨基甲硫基氨基甲酸）。两种配合物均通过FT-IR，1 H NMR，13 C NMR，31 P NMR，元素分析和单晶X射线衍射研究得到充分表征。两种情况下，晶体结构均证实了钳型席夫碱配体的三齿性质和金属中心周围扭曲的正方形平面几何形状。三苯基膦充当辅助配体并占据了钯的第四个配位位点。发现该络合物在低催化剂负载量（0.08mol％）下且不使用任何添加剂的情况下是用于一系列Suzuki-Miyaura，Heck-Mizoroki和Sonogashira反应的有效均相催化剂。通过1 H和13 C NMR研究充分表征了所有有机产物。

  DOI：

  10.1016/j.ica.2017.11.018

文献信息

• Synthesis, characterization and single crystal X-ray studies of pincer type Ni(II)-Schiff base complexes: Application in synthesis of 2-substituted benzimidazoles
  作者：Bhumika Agrahari、Samaresh Layek、Rakesh Ganguly、Necmi Dege、Devendra D. Pathak

  DOI：10.1016/j.jorganchem.2019.03.018

  日期：2019.7

  were synthesized by the reaction of the Ni(OAc)2.4H2O with the corresponding Schiff base ligand in methanol as coloured crystalline solids in high yields. All the five complexes were fully characterized by FT-IR, UV–Vis, 1H NMR, 13C1H} NMR, 31P1H} NMR, mass spectrometry and single crystal X-ray diffraction studies. The crystal structures of all five new complexes confirmed the tridentate nature of the

  五个新的通式为[NiL 1（PPh 3）] 1，[NiL 2（PPh 3）] 2，[NiL 3（PPh 3）] 3，[NiL 4（ PPh 3）] 4和[NiL 4（4-MePy）] 5 [其中H 2 L 1  = 2-（2,3-二羟基亚苄基氨基）苯酚，H 2 L 2  = N-（2,3-二羟基亚苄基）苯并肼， H 2 L 3  = 2-（2,3-二羟基亚苄基）肼碳硫磺酰胺，H2大号4  = 5-（二乙基氨基）-2-（2-羟基亚）苯酚，4- MePy = 4-甲基吡啶]由Ni的反应（OAC）的合成2 ·4H 2 O，其相应的席夫碱配体中甲醇作为有色结晶固体，产率很高。通过FT-IR，UV-Vis，1 H NMR，13 C 1 H} NMR，31 P 11 H NMR，质谱和单晶X射线衍射研究。所有这五个新配合物的晶体结构均证实了钳型席夫碱配体（ONO和ONS）的三齿性质，并且在所有
• Anion selective chromogenic and fluorogenic chemosensor and its application in breast cancer live cell imaging
  作者：Darshna Sharma、Anuradha Moirangthem、Suban K. Sahoo、Anupam Basu、Sutapa M. Roy、Ranjan K. Pati、Ashok Kumar SK、Jitendra P. Nandre、Umesh D. Patil

  DOI：10.1039/c4ra04453c

  日期：——

  A novel anion selective chromogenic and fluorogenic chemosensor (L) bearing catechol and phenol groups was developed. The sensorLwas tested for live breast cancer cell imaging and can be applied to the breast tumour diagnosis.

  开发了一种新型阴离子选择性显色和荧光化学传感器（L），具有邻二酚和酚基团。传感器L已经用于活体乳腺癌细胞成像，并可应用于乳腺肿瘤诊断。
• OH-substituted tridentate ONO Schiff base ligands and related molybdenum(VI) complexes for solvent-free (ep)oxidation catalysis with TBHP as oxidant
  作者：Weili Wang、Jean-Claude Daran、Rinaldo Poli、Dominique Agustin

  DOI：10.1016/j.molcata.2016.02.021

  日期：2016.5

  Molybdenum complexes with ONO tridentate Schiff base ligands based on salicylideneaminophenolato (SAP) backbone with OH substitution on the salicyl arene ring have been synthesized and characterized. The molecular structures of the full series of OH substituted molybdenum complexes were determined by X-ray crystallography as monomers stabilized by one solvent molecule, [MoO2L(D)]. All dimeric complexes [MoO2L](2) were tested for the epoxidation of cyclooctene and cyclohexene under organic solvent-free conditions using aqueous TBHP as oxidant. The position of the OH on the SAP-modified ligand influenced the catalytic activity of the respective complexes. DFT calculations for the catalytic cycle yield energy spans in agreement with the experimentally observed activity trend. (C) 2016 Elsevier B.V. All rights reserved.
• A Simple and Highly Sensitive Turn-on Schiff Base Type Naked-eye Fluorescent Sensor for Aluminum Ion in Living Cells
  作者：Sedat Keskin、Mevlut Bayrakci

  DOI：10.17344/acsi.2018.4755

  日期：——

  Six different Schiff bases to be used as turn-on fluorescent probes based on photoinduced electron transfer (PET) mechanism for the recognition of aluminum ions were successfully synthesized and characterized. The binding abilities of synthesized compounds with different metal cations were investigated by absorption and emission spectra. From the spectrophotometric experiments, it were seen that compound SK-1 displayed an excellent fluorescence response towards targeted aluminum ions probably due to its suitable chelating structure. Furthermore, such compound SK-1 also showed high sensitivity and selectivity response towards aluminum ions over other competing ions. In addition, the potential biological applications of SK-1 to detect aluminum ions in living cells were also investigated and results showed that fluorescence sensor SK-1 could be a promising probe for determining and/or monitoring aluminum ions in both biological and/or chemical samples.
• Synthesis, crystal structures, and application of two new pincer type palladium(II)-Schiff base complexes in C-C cross-coupling reactions
  作者：Bhumika Agrahari、Samaresh Layek、Anuradha、Rakesh Ganguly、Devendra D. Pathak

  DOI：10.1016/j.ica.2017.11.018

  日期：2018.2

  Abstract Two new pincer type Pd(II)-Schiff base complexes of the general formula [PdL 1 (PPh 3 )] 1 and [PdL 2 (PPh 3 )] 2, (where L 1 = 2-(2,3-Dihydroxybenzylideneamino)phenolate and L 2 = 2-(2,3-dihydroxybenzylidene)hydrazinecarbothioamidate) were synthesised by the reaction of the palladium acetate with the corresponding ligand in methanol as yellow crystalline solids in high yields. Both complexes

  摘要两种新的钳型Pd（II）-Schiff碱配合物，其通式为[PdL 1（PPh 3）] 1和[PdL 2（PPh 3）] 2，其中L 1 = 2-（2,3-二羟基苄叉亚氨基通过乙酸钯与相应的配体在甲醇中以黄色结晶固体的高产率反应，合成了苯酚盐和L 2 ＝ 2-（2,3-二羟基亚苄基）肼基氨基甲硫基氨基甲酸）。两种配合物均通过FT-IR，1 H NMR，13 C NMR，31 P NMR，元素分析和单晶X射线衍射研究得到充分表征。两种情况下，晶体结构均证实了钳型席夫碱配体的三齿性质和金属中心周围扭曲的正方形平面几何形状。三苯基膦充当辅助配体并占据了钯的第四个配位位点。发现该络合物在低催化剂负载量（0.08mol％）下且不使用任何添加剂的情况下是用于一系列Suzuki-Miyaura，Heck-Mizoroki和Sonogashira反应的有效均相催化剂。通过1 H和13 C NMR研究充分表征了所有有机产物。