1-benzyl-4-ethynyl-1H-1,2,3-triazole | 79318-05-1

• 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-benzyl-4-ethynyl-1H-1,2,3-triazole
• 英文别名: 1-benzyl-4-ethynyl-1,2,3-triazole；1-Benzyl-4-ethynyltriazole
• CAS: 79318-05-1
• 化学式: C₁₁H₉N₃
• 分子量: 183.213
• InChiKey: BLZYIWDCXVDXJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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-benzyl-4-ethynyl-1H-1,2,3-triazole 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 2-benzyl-3’-methyl-4,5-dihydro-2,3,3a,5a,6,7-hexaazaindaceniumditrifluoromethanesulfonate
  参考文献：
  名称：

  1,2,3-三唑鎓盐的位点选择性N-脱烷基化：通往1,5-取代的1,2,3-三唑和相关双三唑的无金属途径

  摘要：

  1-（新戊酰氧基甲基）-1,2,3-三唑与带有潜在“喀哒”官能团的烷基三氟甲磺酸酯的N3-烷基化，然后由亲核试剂促进所得的强亲电中间体三唑鎓盐的N1-去烷基化，提供了一条有效的途径1,5-二取代的1,2,3-三唑。通过N-烷基化结合的叠氮化物和炔基可进一步用于铜催化的叠氮化物-炔烃和Huisgen环加成反应，以提供具有前所未有的1,5 / 1,4取代模式的双（1,2,3-三唑）。

  DOI：

  10.1021/acs.orglett.6b01177
• 作为产物：
  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

文献信息

• ‘Click’ Synthesis of Nonsymmetrical 4,4′-Bis(1,2,3-triazolium) Salts
  作者：Jesus Aizpurua、Maialen Sagartzazu-Aizpurua、Itxaso Azcune、José Miranda、Zaira Monasterio、Eva García-Lecina、Raluca Fratila

  DOI：10.1055/s-0030-1260061

  日期：2011.9

  demonstrated that triazolium alkynes were more reactive than their triazole counterparts in CuAAC reactions, especially with aromatic azides. The N-alkylation site integrity was maintained in all the triazolium salts prepared. alkylation - catalysis - cycloaddition - heterocycles - 1,2,3-triazolium salts

  非对称取代的4,4'-双（1,2,3-三唑鎓）盐是通过铜（I）催化的3-烷基-4-的“咔嗒” [2 + 3]环加成反应以完全位点特异性的方式制备的乙炔基1,2,3-三唑鎓盐与烷基和芳基叠氮化物。竞争实验表明，三唑鎓炔在CuAAC反应中比三唑对应物更具反应性，尤其是与芳族叠氮化物反应时。在所有制备的三唑鎓盐中均保持N-烷基化位点的完整性。 烷基化-催化-环加成-杂环-1,2,3-三唑鎓盐
• A Nucleobase-Discriminating Pyrrolo-dC Click Adduct Designed for DNA Fluorescence Mismatch Sensing
  作者：Xin Ming、Frank Seela

  DOI：10.1002/chem.201103385

  日期：2012.7.27

  03), is maintained in oligonucleotides. Compound 5 was used as a nucleobase‐discriminating fluorescence sensor in duplex DNA. Excellent mismatch discrimination was observed when 5 was positioned opposite the four canonical nucleosides. Compound 5 has the potential to be used for SNP detection in long DNA targets when conventional techniques such as high resolution melt analysis fail.

  合成了与1,2,3-三唑骨架连接的新的pyrrolo-dC Click加合物（4和5），并制备了寡核苷酸。三唑体系要么直接连接到吡咯基部分（5），要么通过正丁基接头（4）连接。在寡核苷酸中保留了核苷5（Φ = 0.32）的量子产率，它是8-甲基吡咯并-dC（1 b，Φ = 0.026）或长接头衍生物4（Φ = 0.03）的量子产率的10倍。化合物5用作双链DNA中区分核碱基的荧光传感器。当5个位于四个规范核苷对面时，观察到极好的错配判别。当常规技术（例如高分辨率熔解分析）失败时，化合物5可能会用于长DNA靶中的SNP检测。
• “Click” Synthesis of Nonsymmetrical Bis(1,2,3-triazoles)
  作者：Jesus M. Aizpurua、Itxaso Azcune、Raluca M. Fratila、Eva Balentova、Maialen Sagartzazu-Aizpurua、Jose I. Miranda

  DOI：10.1021/ol1003127

  日期：2010.4.2

  Unsymmetrically 1,1'-disubstituted 4,4'-bis-1H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole intermediates 5: (a) the stepwise Swern oxidation/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadlyne 9. The method is highlighted by its compatibility with orthogonally protected and functionalized saccharide-peptide hybrids and its ability to be extended to the trisubstituted counterparts 12.
• Tikhonova, L. G.; Serebryakova, E. S.; Proidakov, A. G., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 4, p. 645 - 648
  作者：Tikhonova, L. G.、Serebryakova, E. S.、Proidakov, A. G.、Sokolova, I. E.、Vereshchagin, L. I.

  DOI：——

  日期：——
• Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes
  作者：Jesus M. Aizpurua、Maialen Sagartzazu-Aizpurua、Zaira Monasterio、Itxaso Azcune、Claudio Mendicute、Jose I. Miranda、Eva García-Lecina、Ainhoa Altube、Raluca M. Fratila

  DOI：10.1021/ol3004657

  日期：2012.4.6

  Mesoionic 4,4'-bis(1,2,3-triazole-5,5'-diylidene) Rh(I) complexes having a C2 chiral 4,4'-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC. Computational analysis of the MICs involved in the reaction suggested the formation of a highly stable and unprecedented cation-carbene intermediate species, which could be evidenced experimentally by cyclic voltammetry analysis.