1-(4-fluorobenzyl)-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole | 1286706-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-fluorobenzyl)-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole
• 英文别名: 1-[(4-Fluorophenyl)methyl]-4-(naphthalen-1-yloxymethyl)triazole
• CAS: 1286706-53-3
• 化学式: C₂₀H₁₆FN₃O
• 分子量: 333.365
• InChiKey: MMQKAUKRZOEKMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  萘酚 、 (5aR,6R,9S,9aS)-3-((1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1,5,5a,6,9,9a-hexahydro-6,9-methanobenzo[e][1,3,2]-dioxaphosphepine-3-oxide 在 Grubbs catalyst first generation 、 caesium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以40 mg的产率得到1-(4-fluorobenzyl)-4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  “Click”-Capture, Ring-Opening Metathesis Polymerization (ROMP), Release: Facile Triazolation Utilizing ROMP-Derived Oligomeric Phosphates

  摘要：

  Soluble, high-load ring-opening metathesis polymerization (ROMP)-derived oligomeric triazole phosphates (OTP) are reported for application as efficient triazolating reagents of nucleophilic species. Utilizing a "Click"-capture, ROMP, release protocol, the efficient and purification-free, direct triazolation of N-, O-, and S-nucleophilic species was successfully achieved. A variety of OTP derivatives were rapidly synthesized as free-flowing solids on a multigram scale from commercially available materials.

  DOI：

  10.1021/ol200430c

文献信息

• Click reactions catalyzed by Cu(I) complexes supported with dihydrobis(2-mercapto-benzimidazolyl)borate and phosphine ligands
  作者：Dariush Khalili、Roya Evazi、Abdollah Neshat、Jasem Aboonajmi、Farzane Osanlou

  DOI：10.1016/j.ica.2020.119470

  日期：2020.6

  Abstract Four Cu(I) complexes bearing dihydrobis(2-mercapto-benzimidazolyl)borate and phosphine co-ligands were synthesized and their catalytic activity was investigated in azide-alkyne reactions. These complexes were tested as catalyst system and among them a Cu(I) complex bearing tricyclohexylphosphine ligand, [Cu(Bb)(PCy3], showed superior catalytic activity in water. The introduced ligands are advantageous

  摘要合成了四种带有二氢双（2-巯基-苯并咪唑基）硼酸酯和膦共配体的Cu（I）配合物，并研究了它们在叠氮化物-炔烃反应中的催化活性。这些配合物已作为催化剂体系进行了测试，其中带有三环己基膦配体[Cu（Bb）（PCy3）]的Cu（I）配合物在水中表现出优异的催化活性，所引入的配体由于其无毒，强σ-给体作用而具有优势。所选择的催化剂可以在水中干净地制备三唑，根据绿色化学原理，三唑被认为是安全的介质。这些催化剂是通过使碘化铜与钠前体（NaBb）[Bb =二氢双（2-巯基-苯并咪唑基）硼酸酯在选定的磷化氢大分子配体（PPh3，PCy3，PPh2Me，PPh2Py）存在下反应制得的。所有所得的Cu（I）络合物均以单一单体异构体的形式形成，并通过1H，13C 1H}和31P 1H} NMR光谱的组合进行表征。
• Copper Aluminate Spinel in Click Chemistry: An Efficient Heterogeneous Nanocatalyst for the Highly Regioselective Synthesis of Triazoles in Water
  作者：Dariush Khalili、Leila Kavoosi、Ali Khalafi-Nezhad

  DOI：10.1055/s-0039-1690719

  日期：2019.12

  An expeditious protocol for the one-pot synthesis of 1,4-disubstituted (β-hydroxy)-1,2,3-triazoles in an aqueous medium has been developed using copper aluminate nanoparticles. This heterogeneous catalytic system was found to drive a multicomponent click reaction between organic azides (generated in situ from epoxides or halides) and terminal aliphatic or aromatic alkynes in up to 96% yield without

  使用铝酸铜纳米粒子开发了一种在水性介质中一锅合成 1,4-二取代 (β-羟基)-1,2,3-三唑的快速方案。发现这种多相催化系统可以在不需要还原剂的情况下以高达 96% 的产率驱动有机叠氮化物（由环氧化物或卤化物原位生成）和末端脂肪族或芳香族炔烃之间的多组分点击反应。合成了结构多样的 1,2,3-三唑，收率非常好，催化剂可以通过简单的过滤轻松分离、回收和在六个后续循环中重复使用。