4-n-butyl-1-(o-tolyl)-1H-1,2,3-triazole | 1027335-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-n-butyl-1-(o-tolyl)-1H-1,2,3-triazole
• 英文别名: 4-Butyl-1-(2-methylphenyl)triazole
• CAS: 1027335-43-8
• 化学式: C₁₃H₁₇N₃
• 分子量: 215.298
• InChiKey: DDMQVJICTDJFGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  4-n-butyl-1-(o-tolyl)-1H-1,2,3-triazole 在 silver hexafluoroantimonate 、 重水 、 copper(II) acetate monohydrate 、 丙烯酸乙酯 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以96%的产率得到C₁₃H₁₅⁽²⁾H₂N₃
  参考文献：
  名称：

  Ruthenium(II)-catalyzed cross-dehydrogenative C–H alkenylations by triazole assistance

  摘要：

  Ruthenium(II) carboxylate complexes allowed for efficient cross-dehydrogenative alkenylations of N-aryl-1,2,3-triazoles. The twofold C-H functionalizations occurred with excellent chemo-, regio-, site- and diastereoselectivities, and ample substrate scope. The versatile ruthenium(II) catalyst proved tolerant of moisture, air, and various electrophilic functional groups. Mechanistic studies were in good agreement with an initial C-H metalation by a cationic ruthenium(II) carboxylate, along with a subsequent migratory insertion of the olefin. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.033
• 作为产物：
  描述：

  2-碘代甲苯 、 1-己炔 在 copper(l) iodide 、 sodium azide 、 sodium ascorbate 、 N,N'-二甲基乙二胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 以78%的产率得到4-n-butyl-1-(o-tolyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  辅助钌催化的CH键活化：羧酸作为助催化剂，通常用于非极性溶剂中的直接芳基化。

  摘要：

  催化量的芳族羧酸MesCO H通过一致的去质子化-金属化机理在无极性溶剂中实现了钌催化的直接芳基化，具有无与伦比的广泛范围。

  DOI：

  10.1021/ol800773x

文献信息

• Palladium-Catalyzed Direct Arylations of 1,2,3-Triazoles with Aryl Chlorides using Conventional Heating
  作者：Lutz Ackermann、Rubén Vicente、Robert Born

  DOI：10.1002/adsc.200800016

  日期：2008.3.25

  Generally applicable, palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides were accomplished through conventional heating at reaction temperatures of 105–120 °C. Thereby, intra- and intermolecular CH bond functionalizations were achieved with a variety of differently substituted chlorides as electrophiles, bearing numerous valuable functional groups.

  通常适用的是，通过在105-120°C的反应温度下进行常规加热来实现1,2,3-三唑与芳基氯化物的钯催化直接芳基化。因此，用各种不同取代的氯化物作为亲电子体，实现了分子内和分子间的CH键官能化，并带有许多有价值的官能团。
• C–H arylations of 1,2,3-triazoles by reusable heterogeneous palladium catalysts in biomass-derived γ-valerolactone
  作者：Xu Tian、Fanzhi Yang、Dace Rasina、Michaela Bauer、Svenja Warratz、Francesco Ferlin、Luigi Vaccaro、Lutz Ackermann

  DOI：10.1039/c6cc03468c

  日期：——

  C-H arylations were accomplished with a user-friendly heterogeneous palladium catalyst in the biomass-derived [gamma]-valerolactone (GVL) as an environmentally-benign reaction medium. The user-friendly protocol was characterized by ample substrate scope and...

  在用户友好的非均相钯催化剂中，在环境友好的反应介质中，在生物质衍生的γ-戊内酯（GVL）中实现CH芳基化。该用户友好协议的特点是具有足够的承印物范围和...
• Catalytic Direct Arylations in Polyethylene Glycol (PEG): Recyclable Palladium(0) Catalyst for C−H Bond Cleavages in the Presence of Air
  作者：Lutz Ackermann、Rubén Vicente

  DOI：10.1021/ol9020354

  日期：2009.11.5

  Two protocols for ruthenium- or palladium-catalyzed direct arylations in user-friendly polyethylene glycol (PEG) were devised, which set the stage for the development of user-friendly palladium(0)-catalyzed C−H bond functionalizations in the presence of air with a recyclable phosphine ligand-free palladium complex.

  设计了两种在用户友好的聚乙二醇（PEG）中钌或钯催化的直接芳基化的方案，为在空气存在下用户友好的钯（0）催化的CH键功能化的发展奠定了基础与可回收的不含膦配体的钯配合物。
• Ruthenium(II)‐Catalyzed Late‐Stage Incorporation of N‐Aryl Triazoles and Tetrazoles with Sulfonium Salts via C–H Activation
  作者：Hendrik Simon、Agnese Zangarelli、Tristan Bauch、Lutz Ackermann

  DOI：10.1002/anie.202402060

  日期：——

  The unprecedented ruthenium-catalyzed late-stage functionalization with easily accessible sulfonium salts enabled the C−H arylation of medicinally relevant N-aryl triazoles and tetrazoles.

  前所未有的钌催化后期功能化与易于获得的锍盐实现了医学相关的N-芳基三唑和四唑的 C−H 芳基化。
• Copper-Catalyzed “Click” Reaction/Direct Arylation Sequence: Modular Syntheses of 1,2,3-Triazoles
  作者：Lutz Ackermann、Harish K. Potukuchi、Dirk Landsberg、Rubén Vicente

  DOI：10.1021/ol801078r

  日期：2008.7.17

  Inexpensive copper catalysts enabled modular one-pot multicomponent syntheses of fully decorated triazoles through a sustainable "click" reaction/direct arylation sequence.