4-cyclohexyl-1-phenyl-1H-1,2,3-triazole | 1159096-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-cyclohexyl-1-phenyl-1H-1,2,3-triazole
• 英文别名: 4-Cyclohexyl-1-phenyltriazole
• CAS: 1159096-41-9
• 化学式: C₁₄H₁₇N₃
• 分子量: 227.309
• InChiKey: ITFKYFRKJLPIHL-UHFFFAOYSA-N

物化性质

• 熔点：
  82.5-96.1 °C(Solvent: Diethyl ether)
• 沸点：
  390.1±35.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  4-cyclohexyl-1-phenyl-1H-1,2,3-triazole 、 二苯基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以27%的产率得到4-cyclohexyl-5-(diphenylphosphanyl)-1-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

  摘要：

  Twelve 1,5-disubtituted and fourteen 5-sub-stituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesized and used as ligands for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. Bulky substrates were tested, and lead-like product formation was demonstrated. The online tool SambVca2.0 was used to assess steric parameters of ligands and preliminary buried volume determination using XRD-obtained data in a small number of cases proved to be informative. Two modeling approaches were compared for the determination of the buried volume of ligands where XRD data was not available. An approach with imposed steric restrictions was found to be superior in leading to buried volume determinations that closely correlate with observed reaction conversions. The online tool LLAMA was used to determine lead-likeness of potential Suzuki-Miyaura cross-coupling products, from which 10 of the most lead-like were successfully synthesized. Thus, confirming these readily accessible triazole-containing phosphines as highly suitable ligands for reaction screening and optimization in drug discovery campaigns.

  DOI：

  10.1021/acs.organomet.8b00539
• 作为产物：
  描述：

  环己氯化镁 在 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 0.16h， 生成 4-cyclohexyl-1-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  一种可扩展的无金属，无叠氮化物和无卤的三唑制备方法。

  摘要：

  已开发出一种可扩展的，无金属，无叠氮化物和无卤素的方法，用于合成取代的1,2,3-三唑。该反应通过α-酮缩醛，甲苯磺酰脲和伯胺的3组分偶联而进行。在α-酮缩醛和胺偶合伙伴中，官能团的耐受性均十分出色，从而能够以优异的产率获得4-，1,4-，1,5-和1,4,5-取代的三唑。这种稳健的方法导致了稠密官能化的1,2,3-三唑，这些化合物仍然难以通过叠氮化物-炔烃环加成（AAC，CuAAC，RuAAC）方法制备，并且可以在间歇式或流式反应器中进行规模化。还描述了脂族胺或苯胺的化学选择性反应的方法，揭示了这种新颖且用途广泛的转化的一些潜力。

  DOI：

  10.1002/anie.201915944

文献信息

• Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon
  作者：Francisco Alonso、Yanina Moglie、Gabriel Radivoy、Miguel Yus

  DOI：10.1039/c1ob05735a

  日期：——

  An easy-to-prepare, reusable and versatile catalyst consisting of oxidised copper nanoparticles on activated carbon has been fully characterised and found to effectively promote the multicomponent synthesis of 1,2,3-triazoles from organic halides, diazonium salts, and aromatic amines in water at a low copper loading.

  一种易于制备、可重复使用且具有多功能性的催化剂，由氧化铜纳米颗粒负载于活性炭上构成，经过充分表征并发现其能有效促进1,2,3-三唑的多组分合成。该合成过程以有机卤化物、重氮盐和芳香胺为原料，在水相中进行，且铜的用量较低。
• Waste-minimised copper-catalysed azide–alkyne cycloaddition in Polarclean as a reusable and safe reaction medium
  作者：Lorenzo Luciani、Emily Goff、Daniela Lanari、Stefano Santoro、Luigi Vaccaro

  DOI：10.1039/c7gc03022c

  日期：——

  Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide–alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium.

  在这里，我们报告了一种通常有用的有机反应的第一个例子，即铜催化的偶氮化物-炔烃环加成反应，在Polarclean/水混合物中作为反应介质进行。
• Unsupported Copper Nanoparticles in the 1,3-Dipolar Cycloaddition of Terminal Alkynes and Azides
  作者：Francisco Alonso、Yanina Moglie、Gabriel Radivoy、Miguel Yus

  DOI：10.1002/ejoc.200901446

  日期：2010.4

  Readily prepared copper nanoparticles were found to catalyse the 1,3-dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3-triazoles were prepared in

  发现现成的铜纳米粒子可催化叠氮化物和炔烃的 1,3-偶极环加成，其速率可与微波化学相媲美。纳米颗粒的制备和点击反应都是在温和的条件下进行的，反应时间很短，并且没有任何稳定添加剂或配体。以极好的收率制备了多种 1,2,3-三唑。在不同的反应性研究和氘化实验的基础上假设了一种反应机制。铜(I) 炔化物被证明是真正的中间体。
• Copper nanoparticles in click chemistry: an alternative catalytic system for the cycloaddition of terminal alkynes and azides
  作者：Francisco Alonso、Yanina Moglie、Gabriel Radivoy、Miguel Yus

  DOI：10.1016/j.tetlet.2009.02.220

  日期：2009.5

  Readily prepared copper nanoparticles have been found to effectively catalyse the 1,3-dipolar cycloaddition of a variety of azides and alkynes furnishing the corresponding 1,2,3-triazoles in excellent yields. Both the preparation of the nanoparticles and the click reaction proceed in short reaction times.

  已经发现现成的铜纳米粒子可有效催化各种叠氮化物和炔烃的1,3-偶极环加成反应，并以极高的收率提供相应的1,2,3-三唑。纳米颗粒的制备和点击反应都在短的反应时间内进行。
• Copper(I) Heteroleptic Bis(NHC) and Mixed NHC/Phosphine Complexes: Syntheses and Catalytic Activities in the One-Pot Sequential CuAAC Reaction of Aromatic Amines
  作者：Shuai Guo、Miao Hui Lim、Han Vinh Huynh

  DOI：10.1021/om400911u

  日期：2013.12.9

  A series of 2-coordinate heteroleptic Cu(I) complexes of the general formula [Cu(IPr)(L)]PF6 (2-5, L = NHC or phosphine) have been synthesized via either (i) chlorido substitution by phosphine or in situ generated free NHC or (ii) the Ag-NHC transfer protocol using [CuCl(IPr)] (1) as a precursor (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene). The reactions of precursor 1 with diphosphine ligands afforded 3-coordinate heteroleptic Cu(I) complexes of the type [Cu(IPr)(L-2)]PF6 (6 and 7, L-2 = diphosphine). Complexes 1-7 have been subjected to a catalytic one-pot sequential CuAAC study, in which aromatic amines serve as the precursors to aryl azides. Hetero-bis(NHC) complexes 2-4 proved to be generally superior compared to their mixed NHC/phosphine counterparts 5-7. Overall, complex [Cu(Bn-2-imy)(IPr)]PF6 (2), bearing the Bn-2-imy (Bn-2-imy = 1,3-dibenzyl-imidazolin-2-ylidene) coligand, showed the best catalytic performance.