2-(p-bromophenyl)-4-formyl-1,2,3-triazole | 13322-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(p-bromophenyl)-4-formyl-1,2,3-triazole
• 英文别名: 2-(4-bromo-phenyl)-2H-[1,2,3]triazole-4-formaldehyde；2-(4-Bromphenyl)-2H-1,2,3-triazol-4-aldehyd；2-(p-Bromphenyl)-2H-1,2,3-triazol-aldehyd-(4)；2-p-Bromphenyl-4-formyl-1,2,3-triazol；2-(4-bromo-phenyl)-2H-[1,2,3]triazole-4-carbaldehyde；2-(4-bromophenyl)-4-formyl-1,2,3-triazole；2-(4-Bromophenyl)-2H-1,2,3-triazole-4-carbaldehyde；2-(4-bromophenyl)triazole-4-carbaldehyde
• CAS: 13322-18-4
• 化学式: C₉H₆BrN₃O
• 分子量: 252.07
• InChiKey: HOIKSIPJDQCYRU-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C
• 沸点：
  401.0±51.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-bromophenyl)-4-formyl-1,2,3-triazole 在 硫酸 、 sodium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 6.08h， 生成 N',N'''-(2-(2-(4-bromophenyl)-2H-1,2,3-triazol-4-yl)-5-oxofuran-3,4(2H,5H)-diylidene)di(benzohydrazide)
  参考文献：
  名称：

  Synthesis of 4-[2-(p-bromophenyl)triazol-4-yl]-2-hydroxytetronimide and some derivatives: bromophenyltriazolyl analogs of imino-l-ascorbic acid

  摘要：

  DOI：

  10.1016/s0008-6215(00)81803-0
• 作为产物：
  描述：

  2-苯基-1,2,3-三唑-4-甲醛 以 水 为溶剂， 生成 2-(p-bromophenyl)-4-formyl-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of 4-[2-(p-bromophenyl)triazol-4-yl]-2-hydroxytetronimide and some derivatives: bromophenyltriazolyl analogs of imino-l-ascorbic acid

  摘要：

  DOI：

  10.1016/s0008-6215(00)81803-0

文献信息

• An Intramolecular Charge Transfer and Aggregation Induced Emission Enhancement Fluorescent Probe Based on 2‐Phenyl‐1,2,3‐triazole for Highly Selective and Sensitive Detection of Homocysteine and Its Application in Living Cells
  作者：Yicheng Chu、Zhengfeng Xie、Daijiao Zhuang、Yongshuang Yue、Yuhua Yue、Wei Shi、Shun Feng

  DOI：10.1002/cjoc.201900323

  日期：2019.12

  homocysteine (Hcy). Moreover, APTC has excellent optical properties such as intramolecular charge transfer (ICT) and aggregation induced emission enhancement (AIEE) characteristics, indicating its extensive application potentiality. What's more, APTC displayed rapid, high selectivity and specificity towards homocysteine over cysteine/glutathione. The detection limit of APTC for Hcy was as low as 2.198×10–8

  在这项工作中，合理设计了一种新的简单且易于合成的开启探针2-（4-蒽-9-苯基）-2 H- [1,2,3]三唑-4-甲醛（APTC），用于同型半胱氨酸（Hcy）。此外，APTC具有出色的光学性质，例如分子内电荷转移（ICT）和聚集诱导发射增强（AIEE）特性，表明其广泛的应用潜力。此外，与半胱氨酸/谷胱甘肽相比，APTC对同型半胱氨酸显示出快速，高度的选择性和特异性。APTC用于同型半胱氨酸的检出限为低至2.198×10 -8莫尔-1，响应时间仅为5分钟。APTC已成功应用于检测硅胶板和活细胞中的Hcy，这表明APTC作为Hcy的选择性探针具有良好的稳定性和生物相容性。最后，使用1 H NMR滴定实验和质谱对机理进行了研究。
• 5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and New Cyclic C-Glycoside Analogues from Carbohydrate Precursors with MAO-B, Antimicrobial and Antifungal Activities
  作者：Mohamed Mohamed El-Sadek、Seham Yassen Hassan、Nagwa Said Abd El-Dayem、Galila Ahmed Yacout

  DOI：10.3390/molecules17067010

  日期：——

  Cyclization of acyclic C-glycoside derivatives 1a,b to 2a,b as the major isomers, and 4a,b as the minor isomers were carried out. The isopropylidene derivatives 3a,b were prepared, as well as the hydrazide derivative 6, which was condensed with a variety of aldehydes to give hydrazones 7a–e which were also prepared from the compounds 12a–e. Acetylation of 7a,d gave the corresponding acetyl derivatives 8a,d, respectively. In addition, the dicarbonyl compound 9 was prepared in the hydrate form, which reacted with a number of aroylhydrazines to give the corresponding bisaroyl-hydrazones 10a–d, which were cyclized into 1,3,4-oxadiazoles 11a–d. Furthermore, two of the prepared compounds were examined to show the ability to activate MAO-B. In addition a number of prepared compounds showed antibacterial and antiviral activities.

  将无环 C-糖苷衍生物 1a,b 环化成主要异构体 2a,b 和次要异构体 4a,b。制备出了异亚丙基衍生物 3a、b 以及酰肼衍生物 6，后者与多种醛缩合生成了酰肼 7a-e，这些酰肼也是由化合物 12a-e 制备而成的。对 7a,d 进行乙酰化处理后，可分别得到相应的乙酰基衍生物 8a,d。此外，还制备了水合物形式的二羰基化合物 9，该化合物与一些酰肼反应生成相应的双酰肼 10a-d，然后环化成 1,3,4-噁二唑 11a-d。此外，研究还发现其中两种化合物具有激活 MAO-B 的能力。此外，一些制备的化合物还显示出抗菌和抗病毒活性。
• An efficient protocol for the one-pot synthesis of 4-(2-(4-bromophenyl)-1,2,3-triazol-4-yl)-3,4-dihydropyrimidin-2(1H)-ones/thiones catalyzed by Mg(NO3)2
  作者：Chenjiang Liu、Xinhai Zhao、Yanping Li

  DOI：10.1002/jhet.517

  日期：2011.1

  A series of novel 4‐(2‐(4‐bromophenyl)‐1,2,3‐triazol‐4‐yl)‐3,4‐dihydropyrimidin‐2(1H)‐ones/thiones were prepared by condensing 2‐(4‐bromophenyl)‐4‐formyl‐1,2,3‐triazole with 1,3‐dicarbonyl compound and urea or thiourea using Mg(NO3)2 as an efficient and cheap catalyst. The satisfactory results were obtained with excellent yields and short reaction time. J. Heterocyclic Chem., (2010).

  一系列新颖的4-（2-（4-溴苯基）-1,2,3-三唑-4-基）-3,4-二氢嘧啶-2（ħ） -酮/硫酮通过缩合2-（制备4-溴苯基）-4-甲酰基1,2,3-三唑与1,3-二羰基化合物以及尿素或硫脲，使用Mg（NO 3）2作为有效而廉价的催化剂。以优异的产率和短的反应时间获得了满意的结果。J.杂环化​​学。（2010）。
• Highly selective and sensitive fluorescent probe possessing AIEE and ICT properties for rapid detection of Pb ²⁺ in aqueous medium and its applications in living cells
  作者：Songsong Xue、Zhengfeng Xie、Yicheng Chu、Wei Shi、Yucheng Liu、Yunhui Zhao

  DOI：10.1002/bio.4151

  日期：2022.1

  In this paper, a novel rapid, highly selective and sensitive Pb2+ fluorescent probe (E)-N′-((2-(4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)-2H-1,2,3-triazol-4-yl)methylene) (DBTBH) was synthesized. The probe DBTBH not only exhibited more excellent selectivity and sensitivity to Pb2+ detection compared with other analytes (include metal ions and anions) in H2O:THF solution (v:v = 9:1, 10 mM Tris–HCl, 1 mM

  在本文中，一种新型的快速、高选择性和灵敏的 Pb 2+荧光探针 (E)-N'-((2-(4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)-合成了2H-1,2,3-三唑-4-基）亚甲基）（DBTBH）。探针DBTBH不仅表现出更优异的选择性和灵敏度对Pb 2+与其他分析物相比，检测（包括金属离子和阴离子）H中2 ○：THF溶液（V：V  = 9：1，的10mM的Tris-HCl，1 mM KI，pH 7.4)，但也具有优异的光学特性，如聚集诱导发射增强 (AIEE) 和分子内电荷转移 (ICT)。探针DBTBH对 Pb 2+ 的检测限为 4.49 × 10 -8 M. 通过1 H NMR 滴定和 HR-MS验证了可能的机制。此外，成功检测铅2+通过DBTBH实际水样和HeLa细胞中表示，DBTBH有选择性识别铅的巨大潜力2+自然环境和生物系统。这些发现将为未来设计更好的
• Synthesis and Spectral Characterization of Some Novel Thiazolyl-Pyrazoline Derivatives Containing 1,2,3-Triazole Moiety
  作者：Hai Shi、Fang-Ming Liu、Song-Wei Shen

  DOI：10.1080/10426507.2010.494647

  日期：2011.1.31

  A series of novel 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-(4-aryl-2-thiazoyl)pyrazolines 6a-6r were synthesized using 2-aryl-4-formyl-1,2,3-triazoles 1a, b as the starting materials. Thus, reacting 1a, b with 1-arylethanones 2a-2c gave 1-aryl-3-(2-aryl-1,2,3-triazol4- yl)-2-propen-1-ones 3a-3f. The reaction of the latter with thiosemicarbazide afforded 3-aryl-5-(2-aryl-1,2,3-triazol-4-yl)-1-thiocarbamoyl-pyrazolines 4a-4f, which condensed with 2-bromo-1-arylethanones 5a-5c to afford the target compounds 6a-6r. The chemical structures of the compounds were verified by means of their IR, (1)H NMR, ESI-MS spectroscopic data, and elemental analysis.