(E)-2-hydroxy-3-methoxy-5-(4-fluorophenyldiazenyl)benzaldehyde | 1379512-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: (E)-2-hydroxy-3-methoxy-5-(4-fluorophenyldiazenyl)benzaldehyde
• CAS: 1379512-91-0
• 化学式: C₁₄H₁₁FN₂O₃
• 分子量: 274.251
• InChiKey: WTQMQBJYGLKFLC-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.25
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-2-hydroxy-3-methoxy-5-(4-fluorophenyldiazenyl)benzaldehyde 、 3-氨基-1-丙醇 以 乙醇 为溶剂， 反应 2.0h， 以85%的产率得到(Z)-4-[(E)-(4-fluorophenyl)diazenyl]-6-[(3-hydroxypropylamino)methylene]-2-methoxycyclohexa-2,4-dienone
  参考文献：
  名称：

  Synthesis, spectroscopic characterizations and quantum chemical computational studies of (Z)-4-[(E)-(4-fluorophenyl)diazenyl]-6-[(3-hydroxypropylamino)methylene]-2-methoxycyclohexa-2,4-dienone

  摘要：

  In this study, the molecular structure and spectroscopic properties of the title compound were characterized by X-ray diffraction, FT-IR and UV-vis spectroscopies. These properties were also investigated using DFT method. The most convenient conformation of title compound was firstly determined. The geometry optimizations in gas phase and solvent media were performed by DFT methods with B3LYP adding 6-31G(d) basis set. The differences between crystal and computational structures are due to crystal packing in which hydrogen bonds play an important role. UV-vis spectra were recorded in different organic solvents. The results show that title compound exists in both keto and enol forms in DMSO, EtOH but it tends to shift towards enol form in benzene. The polar solvents facilitate the proton transfer by decreasing the activation energy needed for Transition State. The formation of both keto and enol forms in DMSO and EtOH is due to decrease in the activation energy. TD-DFT calculations starting from optimized geometry were carried out in both gas and solution phases to calculate excitation energies of the title compound. The non-linear optical properties were computed at the theory level and the title compound showed a good second order non-linear optical property. In addition, thermodynamic properties were obtained in the range of 100-500K.

  DOI：

  10.1016/j.saa.2011.09.020
• 作为产物：
  描述：

  邻香草醛 、 4-氟苯胺 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (E)-2-hydroxy-3-methoxy-5-(4-fluorophenyldiazenyl)benzaldehyde
  参考文献：
  名称：

  Synthesis, spectroscopic characterizations and quantum chemical computational studies of (Z)-4-[(E)-(4-fluorophenyl)diazenyl]-6-[(3-hydroxypropylamino)methylene]-2-methoxycyclohexa-2,4-dienone

  摘要：

  In this study, the molecular structure and spectroscopic properties of the title compound were characterized by X-ray diffraction, FT-IR and UV-vis spectroscopies. These properties were also investigated using DFT method. The most convenient conformation of title compound was firstly determined. The geometry optimizations in gas phase and solvent media were performed by DFT methods with B3LYP adding 6-31G(d) basis set. The differences between crystal and computational structures are due to crystal packing in which hydrogen bonds play an important role. UV-vis spectra were recorded in different organic solvents. The results show that title compound exists in both keto and enol forms in DMSO, EtOH but it tends to shift towards enol form in benzene. The polar solvents facilitate the proton transfer by decreasing the activation energy needed for Transition State. The formation of both keto and enol forms in DMSO and EtOH is due to decrease in the activation energy. TD-DFT calculations starting from optimized geometry were carried out in both gas and solution phases to calculate excitation energies of the title compound. The non-linear optical properties were computed at the theory level and the title compound showed a good second order non-linear optical property. In addition, thermodynamic properties were obtained in the range of 100-500K.

  DOI：

  10.1016/j.saa.2011.09.020

文献信息

• Investigation of solvatochromic, optical, organic field effect transistor (OFET), antibacterial, and molecular bonding of some azothiazolidine-2,4-dione (AZO-TZD) dyes
  作者：Hadiseh Yazdani Nyaki、Nosrat O. Mahmoodi、Hossein Taherpour Nahzomi

  DOI：10.1016/j.jphotochem.2024.115476

  日期：2024.5

  another attempt, solvatochromic absorption was studied using different solvents. Also, the effects of substituent with electron-withdrawing and electron-donating groups at their o-, m-, and p-position were investigated. To access a deeper understanding of molecular properties, computational analysis of molecular geometry, optoelectronic properties, and ionization potential was performed. The purpose of

  在这里，使用硫酸纤维素（CSA）作为催化剂合成了新的AZO-TZD衍生物（1−11），制备重氮盐并进行Knoevenagel缩合以生产最终产品。所制备的染料通过多种方法进行表征，包括紫外可见分光光度计、傅立叶变换红外光谱、质谱、核磁共振波谱技术、X射线衍射分析（XRD）和元素分析，以进行详细的结构解析。然后，在另一项尝试中，使用不同的溶剂研究了溶剂化显色吸收。此外，还研究了邻位、间位和对位上具有吸电子基团和给电子基团的取代基的影响。为了更深入地了解分子特性，对分子几何、光电特性和电离势进行了计算分析。计算的目的是阐明合成化合物中不同溶剂、取代基以及连接环的供体和受体特征的作用。紫外-可见光谱分析证实这些分子具有类似于有机场效应晶体管（OFET）的受体-供体-受体特性。 在其他努力中，评估了它们作为抗菌、抗癌和抗阿尔茨海默病药物的用途以及它们与四种不同类型的酶的相互作用，例如类胡萝卜素脱氢角鲨烯合酶（PDB