4-((1H-1,2,3-triazol-1-yl)methyl)benzonitrile | 118618-40-9

• 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: 4-((1H-1,2,3-triazol-1-yl)methyl)benzonitrile
• 英文别名: 4-[(1H-1,2,3-Triazol-1-yl)methyl]benzonitrile；4-(triazol-1-ylmethyl)benzonitrile
• CAS: 118618-40-9
• 化学式: C₁₀H₈N₄
• mdl: MFCD25956228
• 分子量: 184.2
• InChiKey: XPHNLXFWMCRONM-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  400.2±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((1H-1,2,3-triazol-1-yl)methyl)benzonitrile 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以77%的产率得到1-(p-carboxy-benzyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Biagi; Livi; Scartoni, Farmaco, Edizione Scientifica, 1988, vol. 43, # 7-8, p. 597 - 611

  摘要：

  DOI：
• 作为产物：
  描述：

  对氰基溴化苄 生成 4-((1H-1,2,3-triazol-1-yl)methyl)benzonitrile
  参考文献：
  名称：

  BOHLMANN, ROLF;STREHLKE, PETER;HENDERSON, DAVID;SCHNEIDER, MARTIN;NISHINO+

  摘要：

  DOI：

文献信息

• Water-soluble NHC-Cu catalysts: applications in click chemistry, bioconjugation and mechanistic analysis
  作者：Heriberto Díaz Velázquez、Yara Ruiz García、Matthias Vandichel、Annemieke Madder、Francis Verpoort

  DOI：10.1039/c4ob01350f

  日期：——

  A series of novel bis(NHC) Cu(i) catalysts enables the production of triazoles with different substitution patterns and bioconjugation via “click” chemistry under homogeneous and/or heterogeneous catalytic conditions in aqueous media.

  一系列新型双(NHC)铜(i)催化剂使得在水性介质中通过均相和/或非均相催化条件，生产具有不同取代模式和生物共轭的三唑类化合物，通过“点击”化学方法。
• Self-Assembled Polymeric Pyridine Copper Catalysts for Huisgen Cycloaddition with Alkynes and Acetylene Gas: Application in Synthesis of Tazobactam
  作者：Hao Hu、Aya Ohno、Takuma Sato、Toshiaki Mase、Yasuhiro Uozumi、Yoichi M. A. Yamada

  DOI：10.1021/acs.oprd.8b00429

  日期：2019.4.19

  Novel convoluted polymeric pyridine copper(I) catalysts PVPy-Cu were developed for the Huisgen cyclization of organic azides using alkynes and acetylene gas. They were readily prepared based on our molecular convolution of CuSO4·5H2O and poly(4-vinylpyridine) (PVPy) in the presence of sodium ascorbate with and without various sodium salts in water. Their structural investigation was conducted using

  开发了新型旋绕的聚合吡啶铜（I）催化剂PVPy-Cu，用于使用炔烃和乙炔气对有机叠氮化物进行惠斯根环合。根据我们在水中有无各种钠盐的抗坏血酸钠存在下，我们的CuSO 4 ·5H 2 O和聚（4-乙烯基吡啶）（PVPy）的分子卷积可以轻松地制备它们。他们使用XANES和EXAFS以及DFT计算进行了结构研究。使用100至800 mol ppm Cu的PVPy-Cu水中的Cu，可进行多种炔烃和乙炔气体的Huisgen环加成反应，其周转数高达10000。该催化体系用于他他巴坦的合成，是细菌β-内酰胺酶的抑制剂。
• Synthesis of 2-alkyl triazoles with solvothermal conditions
  作者：Youcai Ma、Xiaohui Zhang、Yawen Yang、Liangzhen Hu、Yan Xiong

  DOI：10.1016/j.tet.2022.132765

  日期：2022.5

  straightforward access to 2-alkyl triazoles with alkyl halides as the readily available alkylation reagents, by using a well-organized nucleophilic substitution strategy under metal-free and solvothermal conditions has been developed. Various alkyl substitutions on 2-site of triazoles occurred and were mainly examined in the text. Particularly, the reactions between linear bisbromo alkanes and 1,2,3-triazoles

  通过在无金属和溶剂热条件下使用组织良好的亲核取代策略，开发了一种直接使用烷基卤化物作为容易获得的烷基化试剂的 2-烷基三唑的通用协议。三唑的 2 位发生了各种烷基取代，主要在文中进行了检查。特别是直链双溴烷烃与1,2,3-三唑反应生成溴烷基三唑和双三唑，溴烷基三唑的再烷基化通过三唑的加成实现。该程序方便，通常提供 2-烷基化产物，在目前的合成方法下，这种产物略显稀缺。
• Synthesis and structure–activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors
  作者：Jérémie Doiron、Al Haliffa Soultan、Ryan Richard、Mamadou Mansour Touré、Nadia Picot、Rémi Richard、Miroslava Čuperlović-Culf、Gilles A. Robichaud、Mohamed Touaibia

  DOI：10.1016/j.ejmech.2011.05.074

  日期：2011.9

  A series of bis- and mono-benzonitrile or phenyl analogues of letrozole 1, bearing (1,2,3 and 1,2,5)-triazole or imidazole, were synthesized and screened for their anti-aromatase activities. The unsubstituted 1,2,3-triazole 10a derivative displayed inhibitory activity comparable with that of the aromatase inhibitor, letrozole I. Compound 10a, bearing a 1,2,3-triazole, is also 10000-times more tightly binding than the corresponding analogue 25 bearing a 1,2,5-triazole, which confirms the importance of a nitrogen atom at position 3 or 4 of the 5-membered ring needed for high activity. The effect on human epithelial adrenocortical carcinoma cell line (H295R) proliferation was also evaluated. The compound 10j (IC50 = 4.64 mu M), a letrozole 1 analogue bearing para-cyanophenoxymethylene-1,2,3-triazole decreased proliferation rates of H295R cells by 76 and 99% in 24 and 72 h respectively. Computer calculations, using quantum ab initio structures, suggest a possible correlation between anti-aromatase activity and the distance between the nitrogen in position 3 or 4 of triazole nitrogen and the cyano group nitrogen. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Huisgen Cycloaddition with Acetylene Gas by Using an Amphiphilic Self-Assembled Polymeric Copper Catalyst
  作者：Yasuhiro Uozumi、Yoichi M. A. Yamada、Hiroshi Yoshida、Aya Ohno、Takuma Sato、Toshiaki Mase

  DOI：10.3987/com-16-s(s)57

  日期：——

  A copper-mediated Huisgen cycloaddition, aka the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC), of flammable acetylene gas and a variety of organic azides proceeded smoothly by using our amphiphilic self-assembled polymeric copper catalyst MPPI-Cu to give the corresponding triazoles in high yield. MPPI-Cu was readily reused without loss of catalytic activity. The XAFS and DFT calculation studies revealed the local structure near Cu atom of an active species MPPI-Cu(I).