2-(2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-4-oxo-4,5-dihydrothiazol-5-yl)acetic acid | 400749-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-4-oxo-4,5-dihydrothiazol-5-yl)acetic acid
• 英文别名: 3-(2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-4-oxo-4,5-dihydrothiazol-5-yl)acetic acid；2-[(2Z)-2-[(2,6-dichlorophenyl)methylidenehydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl]acetic acid
• CAS: 400749-88-4
• 化学式: C₁₂H₉Cl₂N₃O₃S
• 分子量: 346.194
• InChiKey: AFVPZSNVBOVOOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  nickel(II) chloride hexahydrate 、 2-(2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-4-oxo-4,5-dihydrothiazol-5-yl)acetic acid 以 乙醇 为溶剂， 以63%的产率得到bis[3-(2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-4-oxo-4,5-dihydrothiazol-5-yl)acetic acid]dichloridonickel(II) tetrahydrate
  参考文献：
  名称：

  Synthesis, Spectroscopic, and Thermal Characterization of Thiazole Metal Complexes: Biological Activity Studies

  摘要：

  Metal complexes of the organic ligand with N azomethine and N thiazole donation sites, derived from 3-(2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-4-oxo-4,5-dihydrothiazol-5-yl) acetic acid (H2L), with some transition metal ions, namely Mn(II), Fe(III), Co(II), Ni(II), Cu(II), and Zn(II), are reported. They are characterized based on elemental analyses, IR, 1H NMR, solid reflectance, magnetic moment, and molar conductance. The ionization constants are found to be 5.57 and 11.50, which can be attributed to loss of the hydrazo and the carboxylic acid protons, respectively. The stability constants of metal chelates, is calculated spectrophotometrically at 25 degrees C, and the order of stability follows the Irving and Williams order. The chelates are found to have octahedral geometrical structures. The ligand (H2L) and its binary chelates are subjected to thermal analyses, and the different activation thermodynamic parameters are calculated using Coats-Redfern equation. The ligand and its metal complexes show a remarkable biological activity against the desert locust Schistocerca gregaria (Forsk) (Orthoptera - Acrididae) and its adult longevities.

  DOI：

  10.1080/15533174.2010.509300
• 作为产物：
  描述：

  马来酸酐 、 2,6-二氯苯甲醛 、 氨基硫脲 在 montmorillonite KSF(at)Ni 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 70.0 ℃ 、344.75 kPa 条件下， 反应 0.07h， 以80%的产率得到2-(2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-4-oxo-4,5-dihydrothiazol-5-yl)acetic acid
  参考文献：
  名称：

  使用KSF@Ni作为高效多相催化剂微波辅助一锅三组分合成噻唑烷酮

  摘要：

  摘要 开发了一种方便的一锅三组分反应，用于在微波辐射下，在 KSF@Ni 作为多相催化剂存在下，由醛、氨基硫脲和马来酸酐合成噻唑烷酮。在较短的反应时间内以合理的收率获得产物。图形概要

  DOI：

  10.1080/17415993.2017.1343334

文献信息

• Microwave-assisted one-pot three-component synthesis of thiazolidinones using KSF@Ni as an efficient heterogeneous catalyst
  作者：Nosrat O. Mahmoodi、Samane Mohammadgholipour、Fateme Ghanbari Pirbasti

  DOI：10.1080/17415993.2017.1343334

  日期：2017.11.2

  ABSTRACT Convenient, one-pot three-component reaction for the synthesis of thiazolidinones from aldehydes, thiosemicarbazide, and maleic anhydride in the presence of KSF@Ni as heterogeneous catalyst under microwave irradiation was developed. Products were obtained in reasonable yield in short reaction time. GRAPHICAL ABSTRACT

  摘要 开发了一种方便的一锅三组分反应，用于在微波辐射下，在 KSF@Ni 作为多相催化剂存在下，由醛、氨基硫脲和马来酸酐合成噻唑烷酮。在较短的反应时间内以合理的收率获得产物。图形概要
• Synthesis, Spectroscopic, and Thermal Characterization of Thiazole Metal Complexes: Biological Activity Studies
  作者：M. M. Omar、G. G. Mohamed、M. A. Badawy、M. M. Nassar、A. B. Kamel

  DOI：10.1080/15533174.2010.509300

  日期：2010.10.15

  Metal complexes of the organic ligand with N azomethine and N thiazole donation sites, derived from 3-(2-(2-(2,6-dichlorobenzylidene)hydrazinyl)-4-oxo-4,5-dihydrothiazol-5-yl) acetic acid (H2L), with some transition metal ions, namely Mn(II), Fe(III), Co(II), Ni(II), Cu(II), and Zn(II), are reported. They are characterized based on elemental analyses, IR, 1H NMR, solid reflectance, magnetic moment, and molar conductance. The ionization constants are found to be 5.57 and 11.50, which can be attributed to loss of the hydrazo and the carboxylic acid protons, respectively. The stability constants of metal chelates, is calculated spectrophotometrically at 25 degrees C, and the order of stability follows the Irving and Williams order. The chelates are found to have octahedral geometrical structures. The ligand (H2L) and its binary chelates are subjected to thermal analyses, and the different activation thermodynamic parameters are calculated using Coats-Redfern equation. The ligand and its metal complexes show a remarkable biological activity against the desert locust Schistocerca gregaria (Forsk) (Orthoptera - Acrididae) and its adult longevities.