4-methyl-2-(o-tolyl)-2H-benzo[d][1,2,3]triazole | 107922-57-6

• 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-methyl-2-(o-tolyl)-2H-benzo[d][1,2,3]triazole
• 英文别名: 4-Methyl-2-(2-methylphenyl)benzotriazole
• CAS: 107922-57-6
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: UFXSLFZLBPPCJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2'-偶氮甲苯 在 叔丁基过氧化氢 、 叠氮基三甲基硅烷 、 palladium diacetate 作用下， 以 癸烷 、 二甲基亚砜 为溶剂， 反应 28.0h， 以58%的产率得到4-methyl-2-(o-tolyl)-2H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of 2-Aryl-2H-Benzotriazoles from Azoarenes and TMSN₃

  摘要：

  Substrate-directed ortho C-H amination of azoarenes using TMSN3 as the source of nitrogen leading to the synthesis of 2-aryl-2H-benzotriazoles has been accomplished with the help of Pd/TBHP combinations. An intermolecular o-azidation (C-N bond formation) followed by an intramolecular N-N bond formation via nucleophilic attack of one of the azo nitrogen onto the o-azide nitrogen leads to cyclization with the expulsion of N-2.

  DOI：

  10.1021/acs.joc.5b01706

文献信息

• AgNO₃ as nitrogen source for rhodium(<scp>iii</scp>)-catalyzed synthesis of 2-aryl-2H-benzotriazoles from azobenzenes
  作者：Jixing Li、Hui Zhou、Jinlong Zhang、Huameng Yang、Gaoxi Jiang

  DOI：10.1039/c6cc04341k

  日期：——

  A new approach has been established for Rh(iii)-catalyzed direct aza oxidative cyclization of non-prefunctionalized azobenzenes to provide 2-aryl-2H-benzotriazoles in good yields.

  已建立一种新方法，用于Rh(iii)催化的非预功能化偶氮苯直接氮杂氧化环化，以高产率提供2-芳基-2H-苯并三唑。
• Synthesis of 2-Aryl-2<i>H</i>-benzotrizoles from Azobenzenes and <i>N</i>-Sulfonyl Azides through Sequential Rhodium-Catalyzed Amidation and Oxidation in One Pot
  作者：Taekyu Ryu、Jiae Min、Wonseok Choi、Woo Hyung Jeon、Phil Ho Lee

  DOI：10.1021/ol501250t

  日期：2014.6.6

  An efficient synthetic method of 2-aryl-2H-benzotriazoles from nonprefunctionalized azobenzenes and N-sulfonyl azides via sequential Rh-catalyzed amidation (C-N bond formation) and oxidation (N-N bond formation) with PhI(OAc)(2) in one pot is reported.
• Dal Monte; Veggetti, Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1958, vol. 16, p. 1
  作者：Dal Monte、Veggetti

  DOI：——

  日期：——
• Palladium-Catalyzed Synthesis of 2-Aryl-<i>2H</i>-Benzotriazoles from Azoarenes and TMSN₃
  作者：Nilufa Khatun、Anju Modi、Wajid Ali、Bhisma K. Patel

  DOI：10.1021/acs.joc.5b01706

  日期：2015.10.2

  Substrate-directed ortho C-H amination of azoarenes using TMSN3 as the source of nitrogen leading to the synthesis of 2-aryl-2H-benzotriazoles has been accomplished with the help of Pd/TBHP combinations. An intermolecular o-azidation (C-N bond formation) followed by an intramolecular N-N bond formation via nucleophilic attack of one of the azo nitrogen onto the o-azide nitrogen leads to cyclization with the expulsion of N-2.