N,N-bis[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]prop-2-yn-1-amine | 1034194-08-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-bis[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]prop-2-yn-1-amine
• 英文别名: N,N-bis((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)propargylamine；N,N-bis[(1-benzyltriazol-4-yl)methyl]prop-2-yn-1-amine
• CAS: 1034194-08-5
• 化学式: C₂₃H₂₃N₇
• 分子量: 397.483
• InChiKey: BYSNSUAVYZKNEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]prop-2-yn-1-amine 在 copper diacetate 、 sodium ascorbate 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 2-(4-((bis((1-benzyl-1H-1,2,3,triazol-4-yl)methyl)amino)methyl)-1H-1,2,3,-triazol-1-yl)methylcarboxylic acid
  参考文献：
  名称：

  Development of Biocompatible Cu(I)‐Microdevices for Bioorthogonal Uncaging and Click Reactions

  摘要：

  Transition‐metal‐catalyzed bioorthogonal reactions emerged a decade ago as a novel strategy to implement spatiotemporal control over enzymatic functions and pharmacological interventions. The use of this methodology in experimental therapy is driven by the ambition of improving the tolerability and PK properties of clinically‐used therapeutic agents. The preclinical potential of bioorthogonal catalysis has been validated in vitro and in vivo with the in situ generation of a broad range of drugs, including cytotoxic agents, anti‐inflammatory drugs and anxiolytics. In this article, we report our investigations towards the preparation of solid‐supported Cu(I)‐microdevices and their application in bioorthogonal uncaging and click reactions. A range of ligand‐functionalized polymeric devices and off‐on Cu(I)‐sensitive sensors were developed and tested under conditions compatible with life. Last, we present a preliminary exploration of their use for the synthesis of PROTACs through CuAAC assembly of two heterofunctional mating units.

  DOI：

  10.1002/chem.202400611
• 作为产物：
  描述：

  苄基叠氮 在 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 copper(II) sulfate 、 sodium ascorbate 、 三甲基乙酸 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 叔丁醇 为溶剂， 生成 N,N-bis[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]prop-2-yn-1-amine
  参考文献：
  名称：

  One-pot synthesis of TBTA-functionalized coordinating polymers

  摘要：

  DOI：

  10.1016/j.reactfunctpolym.2014.05.008

文献信息

• Polymeric ligands as homogeneous, reusable catalyst systems for copper assisted click chemistry
  作者：Mieke Lammens、Jared Skey、Sofie Wallyn、Rachel O’Reilly、Filip Du Prez

  DOI：10.1039/c0cc01451f

  日期：——

  Tris-(benzyltriazolylmethyl)amine (TBTA) has been immobilized onto a styrenic monomer and subsequently copolymerized with styrene to afford catalytically active and reusable copolymers for the CuAAC reaction.

  三（苄基噻唑基甲基）胺（TBTA）已被固定到一类苯乙烯单体上，并随后与苯乙烯共聚合，以获得具有催化活性和可重复使用的共聚物，可用于CuAAC反应。
• Structural Determinants of Alkyne Reactivity in Copper-Catalyzed Azide-Alkyne Cycloadditions
  作者：Xiaoguang Zhang、Peiye Liu、Lei Zhu

  DOI：10.3390/molecules21121697

  日期：——

  This work represents our initial effort in identifying azide/alkyne pairs for optimal reactivity in copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. In previous works, we have identified chelating azides, in particular 2-picolyl azide, as "privileged" azide substrates with high CuAAC reactivity. In the current work, two types of alkynes are shown to undergo rapid CuAAC reactions under

  这项工作代表了我们为确定在铜催化的叠氮化物-炔烃环加成（CuAAC）反应中具有最佳反应性而需要的叠氮化物/炔烃对的初步工作。在以前的工作中，我们已经将螯合叠氮化物，特别是2-picolyl叠氮化物确定为具有高CuAAC反应性的“特权”叠氮化物底物。在当前的工作中，两种类型的炔烃在铜（II）-（通过诱导期）和铜（I）催化的条件下均会发生快速的CuAAC反应。第一种炔烃带有相对酸性的乙炔基CH键，而第二种炔烃则包含N-（三唑基甲基）丙炔基部分，可产生自加速作用。提供了在铜（II）-和铜（I）催化的条件下的反应性等级。关于其他反应参数如加速配体的观察
• One-pot synthesis of TBTA-functionalized coordinating polymers
  作者：Alireza Movahedi、Kasper Moth-Poulsen、Johnas Eklöf、Magnus Nydén、Nina Kann

  DOI：10.1016/j.reactfunctpolym.2014.05.008

  日期：2014.9
• Development of Biocompatible Cu(I)‐Microdevices for Bioorthogonal Uncaging and Click Reactions
  作者：Melissa van de L'Isle、Stephen Croke、Teresa Valero、Asier Unciti‐Broceta

  DOI：10.1002/chem.202400611

  日期：——

  Transition‐metal‐catalyzed bioorthogonal reactions emerged a decade ago as a novel strategy to implement spatiotemporal control over enzymatic functions and pharmacological interventions. The use of this methodology in experimental therapy is driven by the ambition of improving the tolerability and PK properties of clinically‐used therapeutic agents. The preclinical potential of bioorthogonal catalysis has been validated in vitro and in vivo with the in situ generation of a broad range of drugs, including cytotoxic agents, anti‐inflammatory drugs and anxiolytics. In this article, we report our investigations towards the preparation of solid‐supported Cu(I)‐microdevices and their application in bioorthogonal uncaging and click reactions. A range of ligand‐functionalized polymeric devices and off‐on Cu(I)‐sensitive sensors were developed and tested under conditions compatible with life. Last, we present a preliminary exploration of their use for the synthesis of PROTACs through CuAAC assembly of two heterofunctional mating units.