1-(phenylmethyl)-4-[2-(trimethylsilyl)ethynyl]-1H-1,2,3-triazole | 1204428-86-3

• 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-(phenylmethyl)-4-[2-(trimethylsilyl)ethynyl]-1H-1,2,3-triazole
• 英文别名: 4-(trimethylsilylethynyl)-1-benzyl-1H-1,2,3-triazole；1-benzyl-4-((trimethylsilyl)ethynyl)-1H-1,2,3-triazole；2-(1-Benzyltriazol-4-yl)ethynyl-trimethylsilane；2-(1-benzyltriazol-4-yl)ethynyl-trimethylsilane
• CAS: 1204428-86-3
• 化学式: C₁₄H₁₇N₃Si
• 分子量: 255.395
• InChiKey: CSDJOMMRUZOJMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(phenylmethyl)-4-[2-(trimethylsilyl)ethynyl]-1H-1,2,3-triazole 在 potassium fluoride 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以89%的产率得到1-benzyl-4-ethynyl-1H-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
• 作为产物：
  描述：

  1,4-双(三甲硅基)-1,3-丁二炔 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 甲基锂 作用下， 以 四氢呋喃 、 乙醚 、 水 、 叔丁醇 为溶剂， 反应 3.5h， 生成 1-(phenylmethyl)-4-[2-(trimethylsilyl)ethynyl]-1H-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

• A Lantern‐Shaped Pd(II) Cage Constructed from Four Different Low‐Symmetry Ligands with Positional and Orientational Control: An Ancillary Pairings Approach
  作者：Dan Preston、Jack D. Evans

  DOI：10.1002/anie.202314378

  日期：2023.12.4

  One of the key challenges of metallo‐supramolecular chemistry is to maintain the ease of self‐assembly but, at the same time, create structures of increasingly high levels of complexity. In palladium(II) quadruply stranded lantern‐shaped cages, this has been achieved through either 1) the formation of heteroleptic (multi‐ligand) assemblies, or 2) homoleptic assemblies from low‐symmetry ligands. Heteroleptic cages formed from low‐symmetry ligands, a hybid of these two approaches, would add an additional rich level of complexity but no examples of these have been reported. Here we use a system of ancillary complementary ligand pairings at the termini of cage ligands to target heteroleptic assemblies: these complementary pairs can only interact (through coordination to a single Pd(II) metal ion) between ligands in a cis position on the cage. Complementarity between each pair (and orthogonality to other pairs) is controlled by denticity (tridentate to monodentate or bidentate to bidentate) and/or hydrogen‐bonding capability (AA to DD or AD to DA). This allows positional and orientational control over ligands with different ancillary sites. By using this approach, we have successfully used low‐symmetry ligands to synthesise complex heteroleptic cages, including an example with four different low‐symmetry ligands.

  摘要 金属超分子化学面临的主要挑战之一是保持自组装的简易性，同时创造出复杂程度越来越高的结构。在钯(II)四股灯笼形笼子中，实现这一目标的方法是：1）形成异配体（多配体）组装体；或 2）由低对称性配体形成同配体组装体。由低对称性配体形成的异极笼是这两种方法的混合体，将增加额外的复杂性，但目前还没有这方面的实例报道。在这里，我们利用笼状配体末端的辅助互补配体配对系统来实现异方性组装：这些互补配对只能在笼状配体上处于顺式位置的配体之间相互作用（通过与单个钯（II）金属离子配位）。每对配体之间的互补性（以及与其他配体之间的正交性）受齿性（三叉齿性与单齿性或双齿性与双齿性）和/或氢键能力（AA 与 DD 或 AD 与 DA）的控制。这样就可以对具有不同辅助位点的配体进行位置和方向控制。通过使用这种方法，我们成功地利用低对称性配体合成了复杂的异性笼，包括一个含有四种不同低对称性配体的例子。
• 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.
• 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.
• N-heterocyclic carbene platinum-butadiyne Click/iClick complexes. Towards blue-violet phosphorescence
  作者：Ru He、Jhonti Chakraborty、Tanjila Islam、Hadi D. Arman、Wendell P. Griffith、Adam S. Veige、Kirk S. Schanze

  DOI：10.1016/j.jorganchem.2022.122440

  日期：2022.10