1-benzyl-1'-decyl-1H,1'H-4,4'-bi(1,2,3-triazole) | 1204429-03-7

• 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: 1-benzyl-1'-decyl-1H,1'H-4,4'-bi(1,2,3-triazole)
• 英文别名: 1-Benzyl-4-(1-decyltriazol-4-yl)triazole；1-benzyl-4-(1-decyltriazol-4-yl)triazole
• CAS: 1204429-03-7
• 化学式: C₂₁H₃₀N₆
• 分子量: 366.509
• InChiKey: BFVZHKZEEQSBRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(phenylmethyl)-4-[2-(trimethylsilyl)ethynyl]-1H-1,2,3-triazole 在 potassium fluoride 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 17.5h， 生成 1-benzyl-1'-decyl-1H,1'H-4,4'-bi(1,2,3-triazole)
  参考文献：
  名称：

  Synthesis of Unsymmetrical 1,1′-Disubstituted Bis(1,2,3-triazole)s Using Monosilylbutadiynes

  摘要：

  Bis(1,2,3-triazole)s have attracted recent interest as coordinating ligands for transition metals. Here we report a rapid, modular method for the synthesis of 1,1'-disubstituted-4,4'-linked unsymmetrical bis(1,2,3-triazole)s. The method employs sequential copper catalyzed azide-alkyne cycloaddition and deprotection steps on a monosilylbutadlyne. TMS (trimethylsilyl) and TIPS (trilsopropylsilyl) were both investigated with TIPS being the preferred protecting group due to increased stability. The reactions were amenable to one-pot synthesis, and an optimized one-pot, three-step procedure was developed.

  DOI：

  10.1021/ol102852z

文献信息

• An easy access to unsymmetrically substituted 4,4′-bi-1,2,3-triazoles
  作者：Vito Fiandanese、Daniela Bottalico、Giuseppe Marchese、Angela Punzi、Francesca Capuzzolo

  DOI：10.1016/j.tet.2009.10.078

  日期：2009.12

  A convenient synthesis of 4-alkynyl-1,2,3-triazoles and novel unsymmetrically substituted 4,4'-bi-1,2,3-triazole derivatives has been devised starting from easily available 1-trimethylsilyi-1,3-butadiyne. The starting compound was reacted with several azides, leading to 4-(silylalkynyl)-1,2,3-triazoles, which were easily transformed into 4-arylalkynyl-1,2,3-triazoles by a Pd catalyzed coupling reaction with aryl halides, or into novel 4,4'-bi-1,2,3-triazole derivatives by a subsequent cyclization reaction with azides. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Unsymmetrical 1,1′-Disubstituted Bis(1,2,3-triazole)s Using Monosilylbutadiynes
  作者：Bradley C. Doak、Martin J. Scanlon、Jamie S. Simpson

  DOI：10.1021/ol102852z

  日期：2011.2.4

  Bis(1,2,3-triazole)s have attracted recent interest as coordinating ligands for transition metals. Here we report a rapid, modular method for the synthesis of 1,1'-disubstituted-4,4'-linked unsymmetrical bis(1,2,3-triazole)s. The method employs sequential copper catalyzed azide-alkyne cycloaddition and deprotection steps on a monosilylbutadlyne. TMS (trimethylsilyl) and TIPS (trilsopropylsilyl) were both investigated with TIPS being the preferred protecting group due to increased stability. The reactions were amenable to one-pot synthesis, and an optimized one-pot, three-step procedure was developed.