1-(3-methylphenyl)-4-carboxy-5-methyl-1,2,3-triazole | 210159-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-methylphenyl)-4-carboxy-5-methyl-1,2,3-triazole
• 英文别名: 5-methyl-1-(m-tolyl)-1H-1,2,3-triazole-4-carboxylic acid；5-methyl-1-(3-methylphenyl)-1H-1,2,3-triazole-4-carboxylic acid；5-methyl-1-(3-methylphenyl)triazole-4-carboxylic acid
• CAS: 210159-14-1
• 化学式: C₁₁H₁₁N₃O₂
• mdl: MFCD02168479
• 分子量: 217.227
• InChiKey: CFWWWVDWLUAXPU-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159 °C(Solv: ethanol (64-17-5))
• 沸点：
  448.7±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-methylphenyl)-4-carboxy-5-methyl-1,2,3-triazole 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 5-methyl-N-(4-sulfamoylphenyl)-1-m-tolyl-1H-1,2,3-triazole-4-carboxamide
  参考文献：
  名称：

  Primary discovery of 1-aryl-5-substituted-1H-1,2,3-triazole-4-carboxamides as promising antimicrobial agents

  摘要：

  DOI：

  10.1016/j.molstruc.2021.131146
• 作为产物：
  描述：

  Ethyl 5-methyl-1-(m-tolyl)-1H-1,2,3-triazole-4-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 1-(3-methylphenyl)-4-carboxy-5-methyl-1,2,3-triazole
  参考文献：
  名称：

  取代的 1,2,3-三唑的 1H 和 13C NMR 光谱

  摘要：

  1-芳基-4-羧基-5-甲基-1,2,3-三唑是通过芳基叠氮化物与乙酰乙酸乙酯缩合制备的。这些化合物的结构通过 MS、IR 和 1H 和 13C NMR 光谱表征。比较测量和计算的芳族碳的 13C 化学位移。©1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1097-458x(199806)36:6<459::aid-omr297>3.0.co;2-h

文献信息

• Triazole-Based Inhibitors of the Wnt/β-Catenin Signaling Pathway Improve Glucose and Lipid Metabolisms in Diet-Induced Obese Mice
  作者：Obinna N. Obianom、Yong Ai、Yingjun Li、Wei Yang、Dong Guo、Hong Yang、Srilatha Sakamuru、Menghang Xia、Fengtian Xue、Yan Shu

  DOI：10.1021/acs.jmedchem.8b01408

  日期：2019.1.24

  implicated in the etiology and progression of metabolic disorders. Although lines of genetic evidence suggest that blockage of this pathway yields favorable outcomes in treating such ailments, few inhibitors have been used to validate the promising genetic findings. Here, we synthesized and characterized a novel class of triazole-based Wnt/β-catenin signaling inhibitors and assessed their effects on energy

  Wnt /β-catenin信号传导途径与代谢紊乱的病因和进展有关。尽管遗传证据表明该途径的阻断在治疗此类疾病方面产生了有利的结果，但很少有抑制剂被用于验证有前途的遗传发现。在这里，我们合成和表征了一类新型的基于三唑的Wnt /β-catenin信号抑制剂，并评估了它们对能量代谢的影响。最重要的抑制剂之一化合物3a促进了Axin的稳定，从而导致蛋白酶体降解β-catenin，并随后抑制了细胞中Wnt /β-catenin的信号传导。用化合物3a处理肝细胞和高脂饮食喂养的小鼠导致肝脂质蓄积明显减少。而且，化合物3a改善了高脂饮食喂养小鼠的葡萄糖耐量，而没有明显的毒性，同时下调了参与葡萄糖和脂肪酸代谢的基因。预期将进一步开发新的抑制剂来治疗代谢紊乱。
• 1H and13C NMR spectroscopy of substituted 1,2,3-triazoles
  作者：Xiao-Wen Sun、Peng-Fei Xu、Zi-Yi Zhang

  DOI：10.1002/(sici)1097-458x(199806)36:6<459::aid-omr297>3.0.co;2-h

  日期：1998.6

  1‐Aryl‐4‐carboxy‐5‐methyl‐1,2,3‐triazoles were prepared by the condensation of aryl azides with ethyl acetoacetate. The structures of these compounds were characterized by MS, IR and 1H and 13C NMR spectroscopy. The measured and calculated 13C chemical shifts of the aromatic carbons were compared. ©1998 John Wiley & Sons, Ltd.

  1-芳基-4-羧基-5-甲基-1,2,3-三唑是通过芳基叠氮化物与乙酰乙酸乙酯缩合制备的。这些化合物的结构通过 MS、IR 和 1H 和 13C NMR 光谱表征。比较测量和计算的芳族碳的 13C 化学位移。©1998 John Wiley & Sons, Ltd.
• Synthesis of 1,2,4- and 1,3,4-oxadiazoles from 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides
  作者：N. D. Obushak、N. T. Pokhodylo、N. I. Pidlypnyi、V. S. Matiichuk

  DOI：10.1134/s1070428008100217

  日期：2008.10

  5-Substituted 2-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazoles were synthesized by reaction of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides with the corresponding 5-substituted 1H-tetrazoles. 5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carbonyl chloride reacted with N'-hydroxybenzimidamides to give 3-aryl-5-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazoles. Reactions of 4-(5-methyl-1H-1,2,3-triazol-1-yl)benzoic acid with N'-hydroxybenzimidamides resulted in the formation of 3-aryl-5-[4-(5-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,2,4-oxadiazoles.
• Chu; Sun; Zhang, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 9, p. 854 - 856
  作者：Chu、Sun、Zhang、Li、Liao

  DOI：——

  日期：——
• Studies on Condensed Heterocyclic Compounds XVII. Synthesis of 6-(1-Aryl-5-methyl-1,2,3-triazol-4-yl)-3-phenyl-s-triazolo[3,4-<i>b</i>]-1,3,4-thiadiazoles
  作者：Xiao-Wen Sun、Yan Zhang、Zi-Yi Zhang

  DOI：10.1002/jccs.199800080

  日期：1998.8

  AbstractTreatment of 4‐amino‐5‐mercapto‐3‐phenyl‐1,2,4‐triazole 2 with 1‐aryl‐4‐carboxy‐5‐methyl‐1,2,3‐triazoles 1a‐1j in a one‐step reaction yielded several 6‐(1‐aryl‐5‐methyl‐1,2,3‐triazol‐4‐yl)‐3‐phenyl‐s‐triazolo[3,4‐b]‐1,3,4‐thiadiazoles 3a‐3j. The structures of all the products were established on the basis of elemental analyses and spectral data. The fragmentation of the mass spectra of 3a‐3j under electron impact was discussed.