ethyl-2-(2-(4-bromobenzylidene)hydrazinyl)thiazole-4-carboxylate | 136265-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl-2-(2-(4-bromobenzylidene)hydrazinyl)thiazole-4-carboxylate
• 英文别名: ethyl 2-[2-[(4-bromophenyl)methylidene]hydrazinyl]-1,3-thiazole-4-carboxylate
• CAS: 136265-60-6
• 化学式: C₁₃H₁₂BrN₃O₂S
• 分子量: 354.227
• InChiKey: UMOLGTGACBKQPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.58
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-氯己烷 、 ethyl-2-(2-(4-bromobenzylidene)hydrazinyl)thiazole-4-carboxylate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  2-(2-Arylidene-1-烷基肼基)噻唑-4-羧酸乙酯作为抗糖化剂的合成和计算机对接研究

  摘要：

  2-(2-亚芳基-1-烷基肼基)噻唑-4-甲酸乙酯 ( 1a – k ) 是通过 2-(2-亚芳基肼基)噻唑-4-甲酸乙酯的 HN- 烷基化合成的。所提出的结构 ( 1a – k ) 已通过光谱分析技术（如 UV、FT-IR、1 H-、13 C-NMR 和 HR-MS）得到证实。筛选所有合成的化合物的抗糖化和抗氧化测定。体外抗糖化结果显示化合物1a、1b、1d、1e、1f、1g、1j和1k ，与标准氨基胍相比，IC 50值为 0.0004±1.097-17.22±0.538 μM (IC 50 =25.50±0.337 μM)。在所有测试的化合物中， 1j和1k是最好的抗糖化剂，IC 50值分别为 1.848±0.646 和 0.0004±1.097 μM。计算机研究也与这些结果一致，其中1j和1k的结合能为-9.25 和 -8.42 kcal/mol，计算的解离常数分别为 0.16 和 0

  DOI：

  10.1002/cbdv.202100581
• 作为产物：
  描述：

  (E)-2-(4-bromobenzylidene)hydrazinecarbothioamide 、 乙基3-氯-2-氧代丙酸酯 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以60%的产率得到ethyl-2-(2-(4-bromobenzylidene)hydrazinyl)thiazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and some reactions of 4-carboxy-2-thiazolylhydrazones

  摘要：

  DOI：

  10.1007/bf00480845

文献信息

• Synthesis, spectroscopic, SC-XRD characterizations and DFT based studies of ethyl2-(substituted-(2-benzylidenehydrazinyl))thiazole-4-carboxylate derivatives
  作者：Muhammad Haroon、Muhammad Khalid、Tashfeen Akhtar、Muhammad Nawaz Tahir、Muhammad Usman Khan、Muhammad Saleem、Rifat Jawaria

  DOI：10.1016/j.molstruc.2019.03.075

  日期：2019.7

  In the present study, ethyl-2-(2-(2 methylbenzylidene)hydrazinyl)thiazole-4-carboxylate (1) and ethyl2-(2-(4-bromobenzylidene )hydrazinyl)thiazole-4-carboxylate (2) were synthesized. The characterization of synthesized compounds was accomplished by employing analytical techniques of spectroscopy as H-1 NMR, C-13 NMR, FT-IR, UV-Vis and final confirmation was furnished using single crystal X-ray diffraction (SC-XRD) technique. The informations regarding optimized geometry, nonlinear optical (NLO) properties and frontier molecular orbitals (FMOs) were obtained by applying B3LYP level of DFT and 6-311 + G(d,p) basis set. As a whole, the computed results from DFT were found in close agreement to that of experimental results. The combination of B3LYP level of time dependent DFT (TDDFT) and 6-311 + G (d,p) basis set were employed for computational calculations of vertical electronic transition states. The stability on account of hyperconjugation and charge delocalization factors was evaluated through the study of natural bond orbitals (NBO). The capabilities of the title compounds with respect to charge transfer and involvement of various sites in chemical activities were evaluated quantitatively by employing the analysis involving frontier molecular orbitals (FMOs). The studies revealed that the compounds possess sizable NLO character as the NLO properties of urea molecule were found smaller as compared to the compounds under investigation which means that such compounds are significant in perspective of technology applications. (C) 2019 Elsevier B.V. All rights reserved.