3-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)-7-hydroxycoumarin | 1428675-25-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)-7-hydroxycoumarin
• 英文别名: 3-[4-(Aminomethyl)triazol-1-yl]-7-hydroxychromen-2-one
• CAS: 1428675-25-5
• 化学式: C₁₂H₁₀N₄O₃
• 分子量: 258.236
• InChiKey: FGRIHYDEFPZTNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  炔丙胺 、 3-叠氮基-7-羟基氧杂萘邻酮 在 copper(II) sulfate 、 sodium ascorbate 、 三(3-羟丙基三唑甲基)胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 3-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)-7-hydroxycoumarin
  参考文献：
  名称：

  铜催化的叠氮化物-炔烃环加成催化的天然肽配体的选择

  摘要：

  铜催化的叠氮化物-炔烃环加成反应（CuAAC）是在有机反应和生物系统中进行连接的强大工具。然而，这种连接过程在活细胞中的使用受到与未结合的铜离子相关的毒性的限制。作为创建能够进行细胞表达的基于肽的加速配体的初步尝试，我们在带有候选配体和炔烃底物的固相合成珠上进行了此类物质的合成和选择。确定了一个简单的含组氨酸的基序（HXXH），并在固溶相优化后发现，可产生单周转系统，在无配体反应中显示出中等速率加速。发现不同炔烃的CuAAC反应速率和产率对肽配体有反应，

  DOI：

  10.1021/acs.bioconjchem.7b00161

文献信息

• Highly-efficient and versatile fluorous-tagged Cu(<scp>i</scp>)-catalyzed azide–alkyne cycloaddition ligand for preparing bioconjugates
  作者：Lingyi Sun、Yongkang Gai、Carolyn J. Anderson、Dexing Zeng

  DOI：10.1039/c5cc06858d

  日期：——

  A novel ligand for CuAAC has been developed, which demonstrates not only superior catalytic efficiency but also the ease of removing toxic copper species. Additionally, no transchelation was observed while applying this ligand in the preparation of radio-metal based radiopharmaceutics.

  已开发出一种新型的CuAAC配体，不仅表现出优越的催化效率，而且易于去除有毒的铜物种。此外，在制备基于放射金属的放射性药物时，使用该配体时未观察到任何转位螯合作用。
• CU(I)-CATALYZED AZIDE-ALKYNE CYCLOADDITIONS (CUAAC) LIGANDS AND METHODS FOR CARRYING OUT CU(I)-CATALYZED AZIDE-ALKYNE CYCLOADDITION REACTIONS
  申请人：UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCACATION

  公开号：US20170297008A1

  公开（公告）日：2017-10-19

  A Cu(I)-Catalyzed Azide-Alkyne Cycloadditions (CuAAC) ligand comprising: a catalytic core; a fluorous tag; and a linker binding the fluorous tag to the catalytic core. A method for carrying out a Cu(I)-Catalyzed Azide-Alkyne Cycloaddition reaction, comprising: combining in a solution an alkyne-tagged component, an azide-tagged component and a Cu(I)-Catalyzed Azide-Alkyne Cycloadditions (CuAAC) ligand comprising: a catalytic core; a fluorous tag; and a linker binding the fluorous tag to the catalytic core; filtering the solution through a solid phase extraction filter to remove Cu(I)-ligand catalyst and/or excess ligand.

  一种Cu(I)催化的叠氮-炔烃环加成（CuAAC）配体，包括：一个催化核心；一个氟亲疏标签；以及将氟亲疏标签与催化核心结合的连接剂。一种进行Cu(I)催化的叠氮-炔烃环加成反应的方法，包括：在溶液中混合一个炔基标记的组分，一个叠氮基标记的组分以及一个Cu(I)催化的叠氮-炔烃环加成（CuAAC）配体，包括：一个催化核心；一个氟亲疏标签；以及将氟亲疏标签与催化核心结合的连接剂；将溶液通过固相萃取滤器过滤以去除Cu(I)-配体催化剂和/或过量配体。
• Versatile post-functionalization of the external shell of cowpea chlorotic mottle virus by using click chemistry
  作者：C. A. Hommersom、B. Matt、A. van der Ham、J. J. L. M. Cornelissen、N. Katsonis

  DOI：10.1039/c4ob00505h

  日期：——

  We present the modification of the outer protein shell of cowpea chlorotic mottle virus (CCMV) with linear and strained alkyne groups for post-functionalization by click chemistry.

  我们介绍了利用线性和应变炔基对菜豆黄化莴苣花叶病毒（CCMV）的外蛋白质壳进行修饰，以便进行点击化学后修饰的方法。
• Cu(I)-catalyzed azide-alkyne cycloadditions (CuAAC) ligands and methods for carrying out Cu(I)-catalyzed azide-alkyne cycloaddition reactions
  申请人：UNIVERSITY OF PITTSBURGH—OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：US10758895B2

  公开（公告）日：2020-09-01

  A Cu(I)-Catalyzed Azide-Alkyne Cycloadditions (CuAAC) ligand comprising: a catalytic core; a fluorous tag; and a linker binding the fluorous tag to the catalytic core. A method for carrying out a Cu(I)-Catalyzed Azide-Alkyne Cycloaddition reaction, comprising: combining in a solution an alkyne-tagged component, an azide-tagged component and a Cu(I)-Catalyzed Azide-Alkyne Cycloadditions (CuAAC) ligand comprising: a catalytic core; a fluorous tag; and a linker binding the fluorous tag to the catalytic core; filtering the solution through a solid phase extraction filter to remove Cu(I)-ligand catalyst and/or excess ligand.

  一种 Cu(I)-Catalyzed Azide-Alkyne Cycloadditions (CuAAC) 配体，包括：催化核心；荧光标记；以及将荧光标记与催化核心结合的连接体。一种进行 Cu(I)催化叠氮-炔环加成反应的方法，包括：在溶液中结合炔标记组分、叠氮标记组分和 Cu(I)-Catalyzed Azide-Alkyne Cycloadditions (CuAAC) 配体，配体包括：催化核心；多孔标记；以及将多孔标记与催化核心结合的连接体；通过固相萃取过滤器过滤溶液以除去 Cu(I)-ligand 催化剂和/或过量配体。
• Relative Performance of Alkynes in Copper-Catalyzed Azide–Alkyne Cycloaddition
  作者：Alexander A. Kislukhin、Vu P. Hong、Kurt E. Breitenkamp、M. G. Finn

  DOI：10.1021/bc300672b

  日期：2013.4.17

  Copper-catalyzed azide-alkyne cycloaddition (CuAAC) has found numerous applications in a variety of fields. We report here only modest differences in the reactivity of various classes of terminal alkynes under typical bioconjugative and preparative organic conditions. Propargyl compounds represent an excellent combination of azide reactivity, ease of installation, and cost. Electronically activated propiolamides are slightly more reactive, at the expense of increased propensity for Michael addition. Certain alkynes, including tertiary propargyl carbamates, are not suitable for bioconjugation due to copper-induced fragmentation. A fluorogenic probe based on such reactivity is available in one step from rhodamine 110 and can be useful for optimization of CuAAC conditions.