1,4-bis(2,6-diisopropylphenyl)-1H-1,2,3-triazole | 1263862-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-bis(2,6-diisopropylphenyl)-1H-1,2,3-triazole
• 英文别名: 1,4-Bis[2,6-di(propan-2-yl)phenyl]triazole；1,4-bis[2,6-di(propan-2-yl)phenyl]triazole
• CAS: 1263862-50-5
• 化学式: C₂₆H₃₅N₃
• 分子量: 389.584
• InChiKey: GZNCYHTYVARASB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(2,6-diisopropylphenyl)-1H-1,2,3-triazole 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.33h， 以93%的产率得到1,4-bis(2,6-diisopropylphenyl)-5-iodo-1H-1,2,3-triazole
  参考文献：
  名称：

  块状碘代三唑四氟硼酸盐作为高活性卤素键供体催化剂†

  摘要：

  催化中心周围的胶体体积是决定催化反应性和选择性的最重要因素之一。本文报道了结构多样的5-碘-3-甲基-1,2,3-三唑鎓盐的合成及其作为2-甲氧基-1的氮杂-Diels-Alder反应的卤素键供体的催化活性的评估，3-丁二烯与亚胺。我们发现，卤素键供体中碘原子周围的位阻显着影响了催化效率。

  DOI：

  10.1039/c8cc05309j
• 作为产物：
  描述：

  2-碘-1,3-二异丙基苯 在 四(三苯基膦)钯 、 Cu(SIMes)Br 、 zinc dibromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 1,4-bis(2,6-diisopropylphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  PEPPSI型1,4-二(2,6-二异丙基苯基)-1,2,3-三唑-5-亚基(tzIPr)钯配合物催化的铃木-宫浦交叉偶联反应

  摘要：

  开发了一种基于 1,4-二(2,6-二异丙基苯基)-1,2,3-三唑-5-亚基 (tzIPr) 的 PEPPSI 型钯配合物作为 Suzuki-Miyaura 交叉偶联反应的优异预催化剂. 无论底物的空间和电子性质如何，该配合物在各种类型的芳基氯化物和芳基硼​​酸之间的交叉偶联反应中都显示出温和条件下的高活性。

  DOI：

  10.1002/ejoc.201201075

文献信息

• Synthetic, Structural, and Catalytic Studies of Well‐Defined Allyl 1,2,3‐Triazol‐5‐ylidene ( <i>tz</i> NHC) Palladium Complexes
  作者：Takahiro Terashima、Sayuri Inomata、Kenichi Ogata、Shin‐ichi Fukuzawa

  DOI：10.1002/ejic.201101383

  日期：2012.3

  identical to those of the corresponding imidazole carbene palladium complexes, and that the tzNHC ligands have stronger donor properties than the imidazole carbene ligands. The relationship between catalytic activity and structure was examined by carrying out a room-temperature Suzuki–Miyaura coupling reaction, and the cinnamylpalladium complex bearing 1,4-bis(2,6-diisopropylphenyl)-3-methyl-1,2,3-triazol-5-ylidene

  制备了一系列烯丙基 1,2,3-三唑-5-亚基 (tzNHC) 钯配合物，并通过 NMR 和 X 射线衍射分析充分表征了配合物的结构。通过研究它们的羰基铱配合物的振动光谱和它们的 X 射线光电子光谱来评估这些配体的供体性质。这些评价表明，tzNHC 钯配合物的结构与相应的咪唑卡宾钯配合物的结构几乎相同，并且 tzNHC 配体比咪唑卡宾配体具有更强的供体性质。通过进行室温 Suzuki-Miyaura 偶联反应和带有 1,4-双（2,6-二异丙基苯基）-3-甲基-1,2 的肉桂基钯配合物，研究了催化活性和结构之间的关系，发现 3-三唑-5-亚基 (TPr) 是活性最高的催化剂。无论取代基的电子和空间性质如何，(肉桂基)(TPr)PdCl 在与芳基氯化物进行的室温反应中都表现出高活性，并且在与空间拥挤的芳基硼酸反应中有效。
• Mono‐ and Di‐Mesoionic Carbene‐Boranes: Synthesis, Structures and Utility as Reducing Agents
  作者：Felix Stein、Marius Kirsch、Julia Beerhues、Uta Albold、Biprajit Sarkar

  DOI：10.1002/ejic.202100273

  日期：2021.6.25

  3-triazol-5-ylidene type are currently popular ligands in organometallic chemistry. Their use in main group chemistry has been rather limited. In this contribution we present mono- and di-MIC-boranes with MICs based on triazolylidenes. The synthesis involves in-situ deprotonation of the corresponding triazolium salts and their reaction with boranes to form the desired compounds. Whereas this reaction route worked

  1,2,3-三唑-5-亚基类型的介离子卡宾 (MIC) 是目前有机金属化学中流行的配体。它们在主族化学中的应用相当有限。在这篇文章中，我们介绍了基于三唑基的 MIC 的单和双 MIC-硼烷。该合成涉及相应三唑鎓盐的原位去质子化以及它们与硼烷反应形成所需化合物。尽管该反应路线对于衍生自三唑的 1,4-区域异构体的所有三唑鎓盐均运行良好，但对于衍生自 1,5-取代三唑的亚甲基桥连双三唑鎓盐，我们观察到双-三唑鎓和具有新的 NB 键的三唑硼烷的形成。所有化合物均通过多核 NMR 光谱、质谱、和单晶X射线衍射。此外，MIC-硼烷用作还原剂，用于将醛的 C=O 还原为相应的醇。
• Copper(I) 1,2,3-Triazol-5-ylidene Complexes as Efficient Catalysts for Click Reactions of Azides with Alkynes
  作者：Tatsuhito Nakamura、Takahiro Terashima、Kenichi Ogata、Shin-ichi Fukuzawa

  DOI：10.1021/ol102858u

  日期：2011.2.18

  Complexes of copper with 1,4-diphenyl, 1,4-dimesityl, and 1-(2,6-diisopropylphenyl)-4-(3,5-xylyl)-1,2,3-triazol-5-ylidene (abnormal NHC = N-heterocyclic carbene) were prepared by consecutive treatment of the corresponding azolium salts with silver oxide and copper chloride. The new CuCl(aNHC) complexes efficiently catalyzed click reactions of azides with alkynes to give 1,4-substituted 1,2,3-triazoles

  铜与1,4-二苯基，1,4-二苯甲基和1-（2,6-二异丙基苯基）-4-（3,5-二甲苯基）-1,2,3-三唑-5-亚烷基的配合物（异常通过用氧化银和氯化铜连续处理相应的偶氮盐制备NHC ＝N-杂环卡宾。新的CuCl（aNHC）配合物可有效催化叠氮化物与炔烃的点击反应，在室温下以短时间反应以优异的收率得到1,4-取代的1,2,3-三唑。CuCl（TPh）对于位阻叠氮化物与炔烃之间的反应特别有效。
• 2-Ethynylpyridine-Promoted Rapid Copper(I) Chloride Catalyzed Azide-Alkyne Cycloaddition Reaction in Water
  作者：Shin-ichi Fukuzawa、Hidekatsu Hiroki、Kenichi Ogata

  DOI：10.1055/s-0032-1318488

  日期：——

  The copper(I) chloride catalyzed reaction of azides with alkynes in water at room temperature was promoted by the addition of a catalytic amount of 2-ethynylpyridine, affording the corresponding 1,4-disubstituted 1,2,3-triazoles in good yields after a specific reaction time. The catalytic system could be successfully applied to electron-rich, electron-poor, and sterically crowded substrates. A study

  加入催化量的 2-乙炔基吡啶促进了氯化铜（I）在室温下催化叠氮化物与炔烃在水中的反应，得到相应的 1,4-二取代 1,2,3-三唑，反应后产率良好。特定的反应时间。该催化体系可成功应用于富电子、缺电子和空间拥挤的基材。对吡啶衍生物的加成效应的研究表明，炔基和 2-吡啶基对于活化铜催化剂是必不可少的。
• Copper(I) Complexes of Mesoionic Carbene: Structural Characterization and Catalytic Hydrosilylation Reactions
  作者：Stephan Hohloch、Fenja Duecker、Margarethe van der Meer、Biprajit Sarkar

  DOI：10.3390/molecules20047379

  日期：——

  Two series of different Cu(I)-complexes of “click” derived mesoionic carbenes are reported. Halide complexes of the type (MIC)CuI (with MIC = 1,4-(2,6-diisopropyl)-phenyl-3-methyl-1,2,3-triazol-5-ylidene (for 1b), 1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (for 1c)) and cationic complexes of the general formula [Cu(MIC)2]X (with MIC =1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene, X = CuI2− (for 2á), 1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene, X = BF4− (for 2a), 1,4-(2,6-diisopropyl)phenyl-3-methyl-1,2,3-triazol-5-ylidene, X = BF4− (for 2b), 1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene, X = BF4− (for 2c)) have been prepared from CuI or [Cu(CH3CN)4](BF4) and the corresponding ligands, respectively. All complexes were characterized by elemental analysis and standard spectroscopic methods. Complexes 2á and 1b were studied by single-crystal X-ray diffraction analysis. Structural analysis revealed 2á to adopt a cationic form as [Cu(MIC)2](CuI2) and comparison of the NMR spectra of 2á and 2a confirmed this conformation in solution. In contrast, after crystallization complex 1b was found to adopt the desired neutral form. All complexes were tested for the reduction of cyclohexanone under hydrosilylation condition at elevated temperatures. These complexes were found to be efficient catalysts for this reaction. 2c was also found to catalyze this reaction at room temperature. Mechanistic studies have been carried out as well.

  100℃,100℃,10“C,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃,100℃