2-mesityl-5-phenyl-2H-tetrazole | 1361119-72-3

• 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-mesityl-5-phenyl-2H-tetrazole
• 英文别名: 2-(2,4,6-trimethylphenyl)-5-phenyl-2H-tetrazole；5-Phenyl-2-(2,4,6-trimethylphenyl)tetrazole；5-phenyl-2-(2,4,6-trimethylphenyl)tetrazole
• CAS: 1361119-72-3
• 化学式: C₁₆H₁₆N₄
• 分子量: 264.33
• InChiKey: DJABZWPYAKDYAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4,6-三甲基苯胺 在 tetrafluoroboric acid 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 2-mesityl-5-phenyl-2H-tetrazole
  参考文献：
  名称：

  One-Pot Reactions for Synthesis of 2,5-Substituted Tetrazoles from Aryldiazonium Salts and Amidines

  摘要：

  One-pot sequential reactions of aryldiazonium salts with amidines followed by the treatment of I-2/KI under basic conditions provide 2,5-disubstituted tetrazoles in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, and high yields, making this methodology practical.

  DOI：

  10.1021/acs.orglett.5b03068

文献信息

• Efficient synthesis of 2,5-disubstituted tetrazoles via the Cu2O-catalyzed aerobic oxidative direct cross-coupling of N–H free tetrazoles with boronic acids
  作者：Yu Li、Lian-Xun Gao、Fu-She Han

  DOI：10.1039/c2cc17894j

  日期：——

  We present a new protocol that allows for the synthesis of 2,5-disubstituted tetrazolesvia the direct coupling of N–H free tetrazoles and low toxic boronic acids in the presence of only a catalytic amount of Cu2O (5 mol%) as catalyst and 1 atm of environmentally benign O2 as oxidant, without the need for other additives. This method represents a simple, green, and atom-efficient synthesis of 2,5-disubstituted tetrazoles.

  我们提出了一种新方案，通过自由的四唑（N-H型的四唑）与低毒性的硼酸直接耦合，在仅5 mol%的Cu2O催化剂和1大气压的环境友好型O2作为氧化剂的条件下，无需其他添加剂，实现了2,5-二取代四唑的合成。这一方法简单、环保且原子效率高，为2,5-二取代四唑的合成提供了一条新途径。
• The Development of Copper-Catalyzed Aerobic Oxidative Coupling of H-Tetrazoles with Boronic Acids and an Insight into the Reaction Mechanism
  作者：Chao-You Liu、Yu Li、Jin-Ying Ding、De-Wen Dong、Fu-She Han

  DOI：10.1002/chem.201302857

  日期：2014.2.17

  The development of a highly efficient and practical protocol for the direct CN coupling of H‐tetrazole and boronic acid was presented. A careful and patient optimization of a variety of reaction parameters revealed that this conventionally challenge reaction could indeed proceed efficiently in a very simple system, that is, just by stirring the tetrazoles and boronic acids under oxygen in the presence

  提出了一种高效，实用的方案，用于将H-四唑与硼酸直接进行CN偶联。对各种反应参数的仔细和耐心的优化显示，这种常规的挑战性反应确实可以在非常简单的系统中高效地进行，也就是说，只需在存在不同的Cu I或Cu II的情况下在氧气下搅拌四唑和硼酸即可。在100°C的DMSO中仅负载5 mol％的盐。最重要的是，该反应可以以区域特异性方式非常顺利地进行，从而以高到极好的收率得到2,5-二取代的四唑。一项机理研究表明，四唑和DMSO分别对反应过程中的催化活性铜和溶剂起着至关重要的作用。结果表明，在反应循环中，Cu I催化剂可以通过氧化铜的胺化反应被氧气氧化为Cu II，形成[CuT 2 D]络合物（T =四唑阴离子； D = DMSO）。由此形成的Cu II络合物被证实是真正的催化活性铜物质。即铜II复杂歧化至芳基的Cu III和Cu我在硼酸的存在下进行。轻松消除Cu III物种可提供CN耦合产物。本文介绍的结果不仅为合成2
• Photocatalytic C−H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
  作者：Zhenghui Wen、Ting Wan、Arjun Vijeta、Carla Casadevall、Laura Buglioni、Erwin Reisner、Timothy Noël

  DOI：10.1002/cssc.202101767

  日期：2021.12.6

  Green and versatile! The photocatalytic C(sp2)−H azolation of arenes using heterogeneous carbon nitride is reported. This strategy exhibits a broad substrate scope and is amenable to the late-stage functionalization of several pharmaceuticals. The catalyst can be easily recovered and reused leading to greener and more sustainable routes.

  绿色环保，用途广泛！报道了使用非均相氮化碳对芳烃进行光催化 C(sp 2 )−H 偶氮化。该策略表现出广泛的底物范围，并且适合多种药物的后期功能化。该催化剂可以轻松回收和重复使用，从而形成更环保、更可持续的路线。
• One-Pot Reactions for Synthesis of 2,5-Substituted Tetrazoles from Aryldiazonium Salts and Amidines
  作者：Mani Ramanathan、Yu-Hao Wang、Shiuh-Tzung Liu

  DOI：10.1021/acs.orglett.5b03068

  日期：2015.12.4

  One-pot sequential reactions of aryldiazonium salts with amidines followed by the treatment of I-2/KI under basic conditions provide 2,5-disubstituted tetrazoles in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, and high yields, making this methodology practical.