4-(azidodiphenylmethyl)-1-benzyl-5-butyl-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(azidodiphenylmethyl)-1-benzyl-5-butyl-1H-1,2,3-triazole
• 英文别名: 4-[Azido(diphenyl)methyl]-1-benzyl-5-butyltriazole；4-[azido(diphenyl)methyl]-1-benzyl-5-butyltriazole
• 化学式: C₂₆H₂₆N₆
• 分子量: 422.533
• InChiKey: PENXJKBZVHCRCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  45.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-己炔 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 4-(azidodiphenylmethyl)-1-benzyl-5-butyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Regioselective Rapid Synthesis of Fully Substituted 1,2,3-Triazoles Mediated by Propargyl Cations

  摘要：

  Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also -90 degrees C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.

  DOI：

  10.1021/ol402387w

文献信息

• Acid-mediated synthesis of fully substituted 1,2,3-triazoles: multicomponent coupling reactions, mechanistic study, synthesis of serine hydrolase inhibitor and its derivatives
  作者：Huan Zhang、Hiroki Tanimoto、Tsumoru Morimoto、Yasuhiro Nishiyama、Kiyomi Kakiuchi

  DOI：10.1016/j.tet.2014.10.076

  日期：2014.12

  We describe the full details of multicomponent coupling reactions in acid-mediated synthesis of fully substituted 1,2,3-triazoles syntheses, and their applications to bioactive molecule synthesis. For substitution with wide range of nucleophiles, selection of acids or activating reagents was important, and various types of multicomponent coupling reactions were demonstrated, allowing functionalization with alcohols, amines, thiol, azide, and carbon nucleophiles. Four-component couplings including double triazolations were also tested. The efficiency of this method was demonstrated by the synthesis of serine hydrolase inhibitor and its novel substituted derivatives. (C) 2014 Elsevier Ltd. All rights reserved.
• Regioselective Rapid Synthesis of Fully Substituted 1,2,3-Triazoles Mediated by Propargyl Cations
  作者：Huan Zhang、Hiroki Tanimoto、Tsumoru Morimoto、Yasuhiro Nishiyama、Kiyomi Kakiuchi

  DOI：10.1021/ol402387w

  日期：2013.10.18

  Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also -90 degrees C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.