3,5-dibromo-2-hydroxy-6-methoxybenzaldehyde | 65162-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-dibromo-2-hydroxy-6-methoxybenzaldehyde
• CAS: 65162-33-6
• 化学式: C₈H₆Br₂O₃
• 分子量: 309.942
• InChiKey: HMUKNTZUEOECEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  316.4±37.0 °C(Predicted)
• 密度：
  1.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dibromo-2-hydroxy-6-methoxybenzaldehyde 、 2,6-二甲基苯胺 以 乙醇 为溶剂， 反应 2.0h， 以87%的产率得到(E)-4,6-dibromo-2-[(2,6-dimethylphenylimino)methyl]-3-methoxyphenol
  参考文献：
  名称：

  Molecular structure, quantum mechanical calculation and radical scavenging activities of (E)-4,6-dibromo-2-[(3,5-dimethylphenylimino)methyl]-3-methoxyphenol and (E)-4,6-dibromo-2-[(2,6-dimethylphenylimino)methyl]-3-methoxyphenol compounds

  摘要：

  In this study, (E)-4,6-dibromo-2-[(3,5-dimethylphenylimino)methyl]-3-methoxyphenol and (E)-4,6-dibromo-2-[(2,6-dimethylphenylimino)methyl]-3-methoxyphenol compounds have been.synthesized and characterized by using X-ray crystallographic method, FT-IR and Density functional method. The molecular geometry, vibrational frequencies of, the title compounds in the ground state have been calculated by using B3LYP with the 6-31G(d,p) basis set. The tautomeric form of the compounds has been demonstrated by using single crystal X-ray method, FT-IR spectrometer and DFT method. In addition, HOMO-LUMO energy gap, molecular electrostatic potential map and NBO analysis of the compounds are performed at B3LYP/6-31G(d,p) level. It may be remarked that the free radical scavenging activities of the title compounds were assessed using DPPH., DMPD.+, and ABTS(.+) assays. The obtained results show that especially compound 2 has effective DPPH. (SC50 1.52 +/- 0.14 mu g/mL), DMPD.+ (SC50 1.22 +/- 0.21 mu g/mL), and ABTS' (SC50 3.32 +/- 0.17 mu g/mL) scavenging activities compared with standards (BHA, rutin, and trolox). (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.03.069
• 作为产物：
  描述：

  2,6-二甲氧基苯甲醛 在 溴 、 溶剂黄146 作用下， 生成 3,5-dibromo-2-hydroxy-6-methoxybenzaldehyde
  参考文献：
  名称：

  Akermark,B., Acta Chemica Scandinavica (1947), 1970, vol. 24, # 4, p. 1459 - 1460

  摘要：

  DOI：

文献信息

• Synthesis, spectroscopic characterization and in-silico bio-activity studies of (E)-4,6-dibromo-2-[(2-bromo-4-methylphenylimino)methyl]-3-methoxyphenol
  作者：M. Hakkı Yıldırım

  DOI：10.1016/j.molstruc.2021.131141

  日期：2021.12

  computational Potential Energy Distribution analysis. Experimental and calculated UV-Vis. spectra of the compound in ethanol (polar-protic), DMSO (polar-aprotic) and chloroform (apolar) solvents were analysed to obtain information about the keto-enol tautomeric equilibrium. 1H and 13C interpretations of the compound were done with the help of the calculated spectra. Natural Orbital Fukui Functions, which

  (E)-4,6-二溴-2-[(2-溴-4-甲基苯基亚氨基)甲基]-3-甲氧基苯酚是首次合成，并通过实验和计算方法对其进行表征。分子结构、分子内和分子间相互作用是从单晶 X 射线衍射研究中获得的。标题分子的芳环几乎位于一个平面上，C−H•••Br 氢键和 π•••π 堆积相互作用在晶体稳定和堆积中起着重要作用。通过使用计算势能分布分析将实验 FT-IR 光谱带分配到法线坐标。实验和计算 UV-Vis。分析了该化合物在乙醇（极性质子）、DMSO（极性非质子）和氯仿（非极性）溶剂中的光谱，以获得有关酮 - 烯醇互变异构平衡的信息。1化合物的H 和13 C 解释是在计算光谱的帮助下完成的。自然轨道福井函数是基于自然键轨道的化学反应性描述符，被定义为获得化学有利位点。进行了计算机内 ADMET 和 α-葡萄糖苷酶对接研究，以估计化合物的生物活性。计算 NLO 分析表明，该化合物的极化率是尿素的 9 倍，超极化率是尿素的
• Scrutinizing the two new o-hydroxy Schiff bases from the point of tautomeric behavior and non-covalent interactions (H-bond, Br⋯Br, π⋯π and C H⋯π) in their supramolecular architectures
  作者：Gökhan Kaştaş、Çiğdem Albayrak Kaştaş

  DOI：10.1016/j.molstruc.2019.02.058

  日期：2019.5

  Abstract Two new Schiff bases, (E)-4,6-dibromo-2-[(5-chloro-2-methylphenylimino)methyl]-3-methoxyphenol (1) and (E)-4-bromo-2-[(4-bromophenylimino)methyl]-5-methoxyphenol (2), have been investigated by focusing on the prototropy-related-changes in the geometric parameters, the molecular planarity and the way of crystal packing. X-ray diffraction (XRD), density functional theory (DFT), Hartree-Fock

  摘要 两种新的席夫碱，(E)-4,6-dibromo-2-[(5-chloro-2-methylphenylimino)methyl]-3-methoxyphenol (1) 和 (E)-4-bromo-2-[( 4-溴苯基亚氨基)甲基]-5-甲氧基苯酚(2)，通过几何参数、分子平面性和晶体堆积方式与原向性相关的变化进行了研究。X 射线衍射 (XRD)、密度泛函理论 (DFT)、Hartree-Fock 理论 (HF) 和 Moller-Plesset 微扰理论 (MP2) 以及芳香性谐振子模型 (HOMA) 研究表明苯酚-亚胺形式的偏好性化合物。通过注意到取代基类型和位置在调节非共价相互作用中的重要性，从而详细研究了化合物的晶体堆积，从而形成了超分子网络。
• Investigation of molecular structure and solvent/temperature effect on tautomerism in (E)-4,6-dibromo-3-methoxy-2-[(p-tolylimino)methyl]phenol, a new thermochromic Schiff base, by using XRD, FT-IR, UV–vis, NMR and DFT methods
  作者：Gökhan Kaştaş、Çiğdem Albayrak Kaştaş、Ahmet Tabak

  DOI：10.1016/j.saa.2019.117198

  日期：2019.11

  for the electronic transitions lead to the same conclusion as the absorption spectra. 1H NMR and 13C NMR studies at room and low (−60 °C) temperatures indicate that the tautomeric equilibrium occurs rapidly in the compound. Therefore, it is difficult to observe two tautomers. However, the presence of tautomeric structures is clearly seen in acetone‑d6, alternatively underlying the solvent and temperature

  新型席夫碱中的分子结构和溶剂/温度对互变异构的影响（E）-4,6-二溴-3-甲氧基-2-[[（对甲苯基氨基）甲基]苯酚，使用光谱学（NMR，UV-vis，FT-IR），晶体学（XRD），计算学（DFT和TD）进行了研究。 -DFT）方法和芳香族谐波振荡器模型（HOMA）。XRD，DFT和FT-IR结果表明该化合物以苯酚-亚胺形式固态存在。HOMA指数支持该化合物的芳族结构。进行DFT计算以了解质子转移过程，并获得互变异构体能量的相对接近的值。紫外可见研究通过揭示极性溶剂中同时存在酚亚胺和酮胺形式而在非极性溶剂中仅存在酚亚胺形式，证明了互变异构体在溶剂中的依赖性。在室温和低温（-60°C）下的1 H NMR和13 C NMR研究表明，互变异构平衡在化合物中快速发生。因此，很难观察到两个互变异构体。但是，在丙酮d 6中可以清楚地看到互变异构结构的存在，这可能是标题化合物中互变异构的溶剂和温度依赖性的基础。
• Crystal structure, DFT and HF calculations and radical scavenging activities of (E)-4,6-dibromo-3-methoxy-2-[(3-methoxyphenylimino)methyl]phenol
  作者：Can Alaşalvar、Mustafa Serkan Soylu、Aytaç Güder、Çiğdem Albayrak、Gökhan Apaydın、Nefise Dilek

  DOI：10.1016/j.saa.2014.01.104

  日期：2014.5

  In this study, (E)-4,6-dibromo-3-methoxy-2-[(3-methoxyphenylimino)methyl]phenol has been synthesized and characterized by using X-ray technique and FT-IR experimentally and using B3LYP/6-31G(d,p) and HF/6-31G(d,p) methods theoretically. The intermolecular and intramolecular interactions of the title compound have been determined according to X-ray results. The molecular geometry, vibrational frequencies of the title compound in the ground state have been calculated using the density functional B3LYP and HF method with the 6-31G(d,p) basis set and calculated bond parameters and vibrational frequencies values show good agreement with experimental values. Theoretical and experimental results show that tautomeric form of the structure is phenol-imine form. Besides HOMO-LUMO energy gap, molecular electrostatic potential map were performed at B3LYP/6-31G(d,p) level. It is worthy note of that, the free radical scavenging activities of the title compound were assessed using DPPH center dot, DMPD center dot +/-, and ABTS(center dot +/-) assays. The obtained results show that the title compound has effective DPPH center dot (SC50 2.61 +/- 0.09 mu g/mL), DMPD center dot +/- (SC50 2.82 +/- 0.14 mu g/mL), and ABTS(center dot +/-) (SC50 4.91 +/- 0.18 mu g/mL) radical scavenging activities when compared with standard antioxidants (BHA, rutin, and trolox). (C) 2014 Elsevier B.V. All rights reserved.
• Analysis of tautomeric equilibrium in (E)-4,6-dibromo-2-[(4-fluorophenylimino)methyl]-3-methoxyphenol compound
  作者：Çiğdem Albayrak Kaştaş、Gökhan Kaştaş、Mahmut Gür、Halit Muğlu、Orhan Büyükgüngör

  DOI：10.1016/j.saa.2015.07.030

  日期：2015.12

  In this study, the tautomeric equilibrium between the phenol-imine and keto-amine structural forms of (E)-4,6-dibromo-2-[(4-fluorophenylimino)methyl]-3-methoxyphenol compound has been investigated with experimental (XRD, UV-vis and NMR) and theoretical (DFT and TD-DFT) methods. The results clearly show that structural preference of the compound is definitely depended on its state. Namely, the compound exists in phenol-imine form in the solid state while one or both of these forms can be seen in solvent media. For example, the compound prefers phenol-imine form in benzene while both forms exist in EtOH and DMSO solvents. Coexistence of two forms has been quantified with NMR studies, giving a ratio of 11:9 for phenol and keto structures of the compound in acetone-d6 solvent.