1-(2,6-diisopropylphenyl)-4-phenyl-1H-1,2,3-triazole | 1254815-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,6-diisopropylphenyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-[2,6-Di(propan-2-yl)phenyl]-4-phenyltriazole；1-[2,6-di(propan-2-yl)phenyl]-4-phenyltriazole
• CAS: 1254815-47-8
• 化学式: C₂₀H₂₃N₃
• 分子量: 305.423
• InChiKey: QMHOTFSJXHUGFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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-(2,6-diisopropylphenyl)-4-phenyl-1H-1,2,3-triazole 在 silver(l) oxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 66.0h， 生成
  参考文献：
  名称：

  PEPPSI-type palladium 1,2,3-triazolin-5-ylidene complexes – Synthesis, structure and catalytic properties in Suzuki-Miyaura coupling

  摘要：

  Palladium complexes of the general formula [PdCl2(tzNHC)(pyridine)] bearing a series 1,2,3-triazolin-5-ylidene (tzNHC) ligands were synthesized and characterized by spectroscopic methods and X-ray analysis. Complexes exhibit catalytic activity in the Suzuki-Miyaura coupling of boronic acids with aryl bromides.

  DOI：

  10.1016/j.ica.2018.06.028
• 作为产物：
  描述：

  2,6-二异丙基苯胺 在 盐酸 、 copper(II) sulfate 、 sodium ascorbate 、 sodium nitrite 作用下， 生成 1-(2,6-diisopropylphenyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  亲核 Fe 催化中的氧化还原活性三唑鎓衍生配体 - 反应性分布和区域选择性 O-烯丙基化的发展

  摘要：

  三唑鎓衍生的 N-杂环卡宾 (aNHC) 配体通过相应三唑鎓盐的去质子化很容易获得，被证明是各种烯丙基取代反应中的通用配体。相应的三唑鎓盐是由叠氮化物和炔烃通过 1,3-偶极环加成和 N-烷基化反应形成的。这些配体的独特性质是在其释放形式时是两性离子的，并作为强氧化还原活性 σ-供体配体。凭借这些特性，这些配体能够开发出前所未有的 Fe 催化的烯丙基碳酸酯区域选择性芳氧基化。

  DOI：

  10.1002/ejoc.201300902

文献信息

• Crystalline 1H-1,2,3-Triazol-5-ylidenes: New Stable Mesoionic Carbenes (MICs)
  作者：Gregorio Guisado-Barrios、Jean Bouffard、Bruno Donnadieu、Guy Bertrand

  DOI：10.1002/anie.201001864

  日期：2010.6.28

  MICs: A short modular synthesis allows the preparation of novel stable heterocycles that feature a lone pair of electrons on a carbon center. The donor properties of these mesoionic compounds are greater than those of classical N‐heterocyclic carbenes; they are accessible by deprotonation of the corresponding conjugate acids using comparatively mild bases.

  Click 制造 MICs：短的模块化合成允许制备新型稳定杂环，其特征是碳中心上有一对孤对电子。这些介离子化合物的供体性质大于经典的 N-杂环卡宾；它们可以通过使用相对温和的碱去质子化相应的共轭酸来获得。
• Influence of steric demand on ruthenium-catalyzed cycloaddition of sterically hindered azides
  作者：Venkata S. Sadu、Sirisha Sadu、Seji Kim、In-Taek Hwang、Ki-Jeong Kong、Kee-In Lee

  DOI：10.1039/c6ra25403a

  日期：——

  The RuAAC of sterically hindered 2,2-diaryl-2-azidoamines and terminal alkynes resulted in the unprecedented formation of 1,4-disubstituted-1,2,3-triazoles. A control experiment with 2-(azidomethyl)pyrrolidine revealed the usual selectivity with RuAAC and the reactions of azides with intermediate bulkiness gave mixtures of 1,4- and 1,5-regioisomers. The results suggest that the steric demands could

  空间受阻的2,2-二芳基-2-叠氮基胺和末端炔烃的RuAAC导致空前形成1,4-二取代-1,2,3-三唑。用2-（叠氮甲基）吡咯烷的对照实验表明，通常用RuAAC具有选择性，叠氮化物在中等体积下的反应得到1，4-和1，5-区域异构体的混合物。结果表明，空间需求可以基本消除RuAAC的偏好和对区域选择性的影响。
• Ruthenium(<scp>ii</scp>) and osmium(<scp>ii</scp>) 1,2,3-triazolylidene organometallics: a preliminary investigation into the biological activity of ‘click’ carbene complexes
  作者：Kelly J. Kilpin、Stéphanie Crot、Tina Riedel、Jonathan A. Kitchen、Paul J. Dyson

  DOI：10.1039/c3dt52584h

  日期：——

  Taking advantage of the facile and versatile synthetic properties of ‘click’ 1,2,3-triazolylidene N-heterocyclic carbenes (tzNHC's), a range of new organometallic Ru(II) and Os(II) arene complexes containing functionalised tzNHC ligands, [M(η6-p-cymene)(tzNHC)Cl2] [M = Ru(II), Os(II)], have been synthesised and fully characterised, including the X-ray crystal structure of one of the Os(II) complexes. The tzNHC ligands remain coordinated to the metal centres under relevant physiological conditions, and following binding to the model protein, ubiquitin. The in vitro cytotoxicity of the compounds towards human ovarian cancer cells is dependent on the substituent on the tzNHC ligand but is generally <50 μM and in some cases <1 μM, whilst still retaining a high degree of selectivity towards cancer cells over healthy cells (1.85 μM in A2780 ovarian cancer cells versus 435 μM in human embryonic kidney cells in one case).

  利用“点击”1,2,3-噻唑烯N-杂环卡宾（tzNHC）的合成特性，我们合成了一系列新型有机金属Ru(II)和Os(II)芳烃配合物，这些配合物含有功能化的tzNHC配体，[M(η6-p-香叶醇)(tzNHC)Cl2] [M = Ru(II), Os(II)]，并进行了全面表征，包括其中一个Os(II)配合物的X射线晶体结构。tzNHC配体在相关生理条件下持续与金属中心配位，并在与模型蛋白泛素结合后保持这一状态。这些化合物对人类卵巢癌细胞的体外细胞毒性取决于tzNHC配体上的取代基，通常低于50 μM，在某些情况下甚至低于1 μM，同时对癌细胞相对于健康细胞保持了较高的选择性（在一种情况下，A2780卵巢癌细胞中的毒性为1.85 μM，而人类胚胎肾细胞中的毒性为435 μM）。
• Activating Azides and Alkynes for the Click Reaction with [Cu( <i>a</i> NHC) ₂ I] or [Cu( <i>a</i> NHC) ₂ ] ⁺ ( <i>a</i> NHC = Triazole‐Derived Abnormal Carbenes): Structural Characterization and Catalytic Properties
  作者：Stephan Hohloch、Damaris Scheiffele、Biprajit Sarkar

  DOI：10.1002/ejic.201300150

  日期：2013.8.6

  single-crystal X-ray diffraction analyses. In 6, the copper(I) center is tricoordinated, and its geometry is in between trigonal planar and T-shaped. In halide-free 11, the copper(I) center is linearly coordinated by two abnormal-carbene ligands. All complexes were tested as catalysts in the Huisgen [3+2] cycloaddition reaction between azides and alkynes, and they showed excellent efficiencies under neat conditions

  中性含碘铜 (I) 络合物 [Cu(aNHC)2I] aNHC = 1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (for 6) 和 3-甲基-1-[2-(甲硫基)苯基]-4-苯基-1,2,3-triazol-5-ylidene (for 7)} 和阳离子、无卤化物的铜 (I) 配合物 [Cu(aNHC)2 ](BF4) aNHC = 1-benzyl-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene (for 8), 3-methyl-1,4-diphenyl-1,2,3 -triazol-5-ylidene (for 9), 3-methyl-1-[2-(methylthio)phenyl]-4-phenyl-1,2,3-triazol-5-ylidene (for 10), and 1-mesityl
• Convergent synthesis of trifunctional molecules by three sequential azido-type-selective cycloadditions
  作者：Suguru Yoshida、Kimiyuki Kanno、Isao Kii、Yoshihiro Misawa、Masatoshi Hagiwara、Takamitsu Hosoya

  DOI：10.1039/c8cc01195h

  日期：——

  A facile strategy for the synthesis of trifunctional molecules involving three sequential selective triazole-forming reactions is proposed. This method exploits three kinds of mechanistically different azido-type-selective cycloadditions. Three different azidophiles could be efficiently connected to a triazido platform molecule with three types of azido groups in a consecutive manner, which rendered

  提出了一种容易的合成三官能分子的策略，涉及三个连续的选择性三唑形成反应。该方法利用了三种机械上不同的叠氮基类型选择性环加成反应。可以以连续的方式将三种不同的亲氮化合物有效地连接到具有三种类型的叠氮基团的三叠氮平台分子上，这使得实用的三官能分子易于获得。