1,4-dibenzyl-4H-1,2,4-triazol-1-ium chloride | 89315-80-0

• 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: 1,4-dibenzyl-4H-1,2,4-triazol-1-ium chloride
• 英文别名: 1,4-Dibenzyl-1H-[1,2,4]triazol-4-ium；1,4-dibenzyl-1,2,4-triazol-4-ium;chloride
• CAS: 89315-80-0
• 化学式: C₁₆H₁₆N₃*Cl
• 分子量: 285.776
• InChiKey: RYGOPEFOOOBVLA-UHFFFAOYSA-M

物化性质

• 熔点：
  178-181 °C(Solv: 1,4-dioxane (123-91-1))
• 溶解度：
  >42.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)benzenediazonium tetrafluoroborate 、 1,4-dibenzyl-4H-1,2,4-triazol-1-ium chloride 在 三乙烯二胺 、 三乙胺 作用下， 反应 0.08h， 生成
  参考文献：
  名称：

  Becker, H. G. O.; Hoffmann, Gerda; Gwan, Kim Mun, Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 3, p. 325 - 337

  摘要：

  DOI：
• 作为产物：
  描述：

  dichlorobis(2,4-dibenzyl-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)nickel(II) 在 水 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到1,4-dibenzyl-4H-1,2,4-triazol-1-ium chloride
  参考文献：
  名称：

  Facile Hydrolysis of Nickel(II) Complexes with N-Heterocyclic Carbene Ligands

  摘要：

  Metal complexes with N-heterocyclic carbene ligands (NHC) are ubiquitously used in catalysis, where the stability of the metal-ligand framework is a key issue. Our study shows that Ni-NHC complexes may undergo facile decomposition due to the presence of water in organic solvents (hydrolysis). The ability to hydrolyze Ni(NHC)(2)X-2 complexes decreases in the order of NHC = 1,2,4-triazolium > benzimidazolium approximate to imidazolium. Depending on the ligand and substituents, the half reaction time of the complex decomposition may change from several minutes to hours. The nature of the halogen is also an important factor, and the ability for decomposition of the studied complexes decreases in the order of Cl > Br > I. NMR and MS monitoring revealed that Ni-NHC complexes in the presence of water undergo hydrolysis with Ni-C-carbene bond cleavage, affording the corresponding N,N'-dialkylated azolium salts and nickel(II) hydroxide. These findings are of great importance for designing efficient and recyclable catalytic systems, because trace water is a common contaminant in routine synthetic applications.

  DOI：

  10.1021/acs.organomet.5b00856

文献信息

• Pd-PEPPSI complexes based on 1,2,4-triazol-3-ylidene ligands as efficient catalysts in the Suzuki—Miyaura reaction
  作者：A. Yu. Chernenko、A. V. Astakhov、D. V. Pasyukov、P. V. Dorovatovskii、Ya. V. Zubavichus、V. N. Khrustalev、V. M. Chernyshev

  DOI：10.1007/s11172-018-2040-8

  日期：2018.1

  The palladium complexes of the Pd-PEPPSI type with N-heterocyclic carbenes of the 1,2,4-triazole series were synthesized in 76—99% yields by the reactions of PdCl2 with 1,4-di- alkyl-1,2,4-triazolium salts in pyridine in the presence of KBr or KI as sources of halide ions and tetrabutylammonium salts as phase-transfer catalysts. The obtained complexes can be used as efficient catalysts for the Suzuki—Miyaura

  通过 PdCl2 与 1,4-二烷基-1,2 的反应，合成了 Pd-PEPPSI 型与 1,2,4-三唑系列的 N-杂环卡宾的钯配合物，产率为 76-99%，在作为卤离子源的 KBr 或 KI 和作为相转移催化剂的四丁基铵盐存在下，吡啶中的 4-三唑鎓盐。所得配合物可作为Suzuki-Miyaura交叉偶联的高效催化剂，其活性不逊于市售的Pd-PEPPSI催化剂。
• The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation
  作者：Serghei Pogrebnoi、Oleg Radul、Eugenia Stingaci、Lucian Lupascu、Vladimir Valica、Livia Uncu、Anastasia Smetanscaia、Anthi Petrou、Ana Ćirić、Jasmina Glamočlija、Marina Soković、Athina Geronikaki、Fliur Z. Macaev

  DOI：10.3390/antibiotics11050588

  日期：——

  voriconazole, etc. Thus, the interest in developing new azoles with an extended spectrum of activity still attracts the interest of the scientific community. Herein, we report the synthesis of a series of triazolium salts, an evaluation of their antifungal activity, and docking studies. Ketoconazole and bifonazole were used as reference drugs. All compounds showed good antifungal activity with MIC/MFC

  由于可用于抗真菌治疗的有效药物数量有限，真菌病原体的控制越来越困难。此外，人类和真菌都是真核生物；由于对相关人体靶点的抑制作用，抗真菌药物可能具有显着的毒性。此外，另一个问题是真菌对唑类药物的耐药性增加，例如氟康唑、酮康唑、伏立康​​唑等。因此，开发具有扩展活性的新唑类药物的兴趣仍然吸引了科学界的兴趣。在此，我们报告了一系列三唑鎓盐的合成，对其抗真菌活性的评估以及对接研究。酮康唑和联苯苄唑用作参考药物。所有化合物均显示出良好的抗真菌活性，MIC/MFC 在 0.0003 至 0.2/0.0006-0 范围内。4毫克/毫升。化合物19在 MIC/MFC 的所有测试中表现出最好的活性，分别在 0.009 至 0.037 mg/mL 和 0.0125-0.05 mg/mL 范围内。所有化合物似乎都比两种参考药物更有效。对接研究与实验结果一致。
• A New Mode of Operation of Pd-NHC Systems Studied in a Catalytic Mizoroki–Heck Reaction
  作者：Alexander V. Astakhov、Oleg V. Khazipov、Andrey Yu. Chernenko、Dmitry V. Pasyukov、Alexey S. Kashin、Evgeniy G. Gordeev、Victor N. Khrustalev、Victor M. Chernyshev、Valentine P. Ananikov

  DOI：10.1021/acs.organomet.7b00184

  日期：2017.5.22

  Metal complexes bearing N-heterocyclic carbene (NHC) ligands are typically considered the system of choice for homogeneous catalysis with well-defined molecular active species due to their stable metal ligand framework. A detailed study involving 19 different Pd-NHC complexes with imidazolium, benzimidazolium, and triazolium ligands has been carried out in the present work and revealed a new mode of operation of metal-NHC systems. The catalytic activity of the studied Pd-NHC systems is predominantly determined by the cleavage of the metal NHC bond, while the catalyst performance is strongly affected by the stabilization of in situ formed metal clusters. In the present study, the formation of Pd nanopartides was observed from a broad range of metal complexes with NHC ligands under standard Mizoroki-Heck reaction conditions. A mechanistic analysis revealed two different pathways to connect Pd-NHC complexes to "cocktail"-type catalysis: (i) reductive elimination from a Pd(II) intermediate and the release of NHC-containing byproducts and (ii) dissociation of NHC ligands from Pd intermediates. Metal-NHC systems are ubiquitously applied in modern organic synthesis and catalysis, while the new mode of operation revealed in the present study guides catalyst design and opens a variety of novel opportunities. As shown by experimental studies and theoretical calculations, metal dusters and nanopartides can be readily formed from M-NHC complexes after formation of new M-C or M-H bonds followed by C-NHC or H-NHC coupling. Thus, a combination of a classical molecular mode of operation and a novel cocktail-type mode of operation, described in the present study, may be anticipated as an intrinsic feature of M-NHC catalytic systems.
• Abenhaiem David, Diez-Barra Enrique, de la Hoz Antonio, Loupy Andre, Sanc+, Heterocycles, 38 (1994) N 4, S 793-802
  作者：Abenhaiem David, Diez-Barra Enrique, de la Hoz Antonio, Loupy Andre, Sanc+

  DOI：——

  日期：——
• BECKER, H. G. O.;HOFFMANN, GERDA;GWAN, KIM MUN;KNUPFER, L., J. PRAKT. CHEM., 330,(1988) N 3, C. 325-337
  作者：BECKER, H. G. O.、HOFFMANN, GERDA、GWAN, KIM MUN、KNUPFER, L.

  DOI：——

  日期：——