1,1'-bis[(R)-α-methylbenzyl]-4,4'-bis(1H-1,2,3-triazole) | 1365691-22-0

• 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: 1,1'-bis[(R)-α-methylbenzyl]-4,4'-bis(1H-1,2,3-triazole)
• CAS: 1365691-22-0
• 化学式: C₂₀H₂₀N₆
• 分子量: 344.419
• InChiKey: RYZVKZSGPHKEJE-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,1'-bis[(R)-α-methylbenzyl]-4,4'-bis(1H-1,2,3-triazole) 、 trimethoxonium tetrafluoroborate 以 二氯甲烷 为溶剂， 以55%的产率得到
  参考文献：
  名称：

  Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

  摘要：

  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.

  DOI：

  10.1021/ol3004657
• 作为产物：
  描述：

  1,4-双(三甲硅基)-1,3-丁二炔 、 [(R)-1-叠氮乙基]苯 在 吡啶 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 24.0h， 以88%的产率得到1,1'-bis[(R)-α-methylbenzyl]-4,4'-bis(1H-1,2,3-triazole)
  参考文献：
  名称：

  Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

  摘要：

  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.

  DOI：

  10.1021/ol3004657

文献信息

• Site-Selective N-Dealkylation of 1,2,3-Triazolium Salts: A Metal-Free Route to 1,5-Substituted 1,2,3-Triazoles and Related Bistriazoles
  作者：Zaira Monasterio、Aitziber Irastorza、José I. Miranda、Jesus M. Aizpurua

  DOI：10.1021/acs.orglett.6b01177

  日期：2016.5.20

  carrying latent “click” functionality, followed by a nucleophile-promoted N1-dealkylation of the resulting strongly electrophilic intermediate triazolium salts, provides an efficient route to 1,5-disubstituted 1,2,3-triazoles. The azide and alkyne groups incorporated by N-alkylation can be submitted to further copper-catalyzed azide–alkyne and Huisgen cycloadditions to provide bis(1,2,3-triazoles)

  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）。