Ethyl 3-(4-methoxyphenyl)benzotriazole-5-carboxylate | 1295605-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 3-(4-methoxyphenyl)benzotriazole-5-carboxylate
• 英文别名: ethyl 3-(4-methoxyphenyl)benzotriazole-5-carboxylate
• CAS: 1295605-98-9
• 化学式: C₁₆H₁₅N₃O₃
• 分子量: 297.313
• InChiKey: SZCFXNLSZSTTFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-4-甲氧基苯胺 在 盐酸 、 1,3-双(二苯基膦)丙烷 、 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.25h， 生成 Ethyl 3-(4-methoxyphenyl)benzotriazole-5-carboxylate
  参考文献：
  名称：

  1,7-Palladium Migration via C−H Activation, Followed by Intramolecular Amination: Regioselective Synthesis of Benzotriazoles

  摘要：

  A novel 1,7-palladium migration-cyclization-dealkylation sequence for the regioselective synthesis of benzotriazoles has been developed. These reactions proceed in excellent yields with high regioselectivities. The mechanism of the reaction has also been investigated.

  DOI：

  10.1021/ja2007438

文献信息

• Synthesis of functionized N-arylbenzotriazoles via palladium catalyzed intramolecular amination
  作者：Dachao Wang、Xiaoting Gan、Lewei Zhou、Hanyu Shu、Jun Zhou

  DOI：10.1016/j.tetlet.2021.153587

  日期：2022.1

  The functionalized benzotriazoles are prepared by palladium catalyzed intramolecular amination of 2-bromodiaryltriazene. By screening the reaction conditions, such as ligand, solvent, base and reaction concentration, the optimal reaction conditions were obtained, and 28 functionalized benzotriazole derivatives were successfully prepared up to 99% yield. The method is easy to operate and has good tolerance

  功能化的苯并三唑是通过钯催化的 2-溴二芳基三氮烯的分子内胺化制备的。通过对配体、溶剂、碱和反应浓度等反应条件进行筛选，得到了最佳反应条件，成功制备了28种功能化苯并三唑衍生物，收率高达99%。该方法操作简单，对多种官能团具有良好的耐受性。
• 一种钯催化N-芳基苯并三氮唑衍生物的合成方法
  申请人：长沙理工大学

  公开号：CN113582936A

  公开（公告）日：2021-11-02

  本发明公开了一种钯催化N‑芳基苯并三氮唑衍生物的合成方法，其特征在于，包括如下步骤：在钯催化剂、配体和碱的存在条件下，溴取代的芳基三氮烯在有机溶剂中加热条件下进行反应，反应完全之后，经后处理得到所述的N‑芳基苯并三氮唑衍生物。该合成方法操作简单，底物官能团适用范围广泛，能够高产率和高选择性的制备N‑芳基苯并三氮唑衍生物。
• 1,7-Palladium Migration via C−H Activation, Followed by Intramolecular Amination: Regioselective Synthesis of Benzotriazoles
  作者：Jun Zhou、Jianjun He、Binjie Wang、Weijun Yang、Hongjun Ren

  DOI：10.1021/ja2007438

  日期：2011.5.11

  A novel 1,7-palladium migration-cyclization-dealkylation sequence for the regioselective synthesis of benzotriazoles has been developed. These reactions proceed in excellent yields with high regioselectivities. The mechanism of the reaction has also been investigated.