2-(4-hexyl-1H-1,2,3-triazol-1-yl)-1-(naphthalene-6-yl)ethanone | 1370006-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-hexyl-1H-1,2,3-triazol-1-yl)-1-(naphthalene-6-yl)ethanone
• 英文别名: 2-(4-Hexyltriazol-1-yl)-1-naphthalen-2-ylethanone
• CAS: 1370006-19-1
• 化学式: C₂₀H₂₃N₃O
• 分子量: 321.422
• InChiKey: OXCKIPFUMQQMML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-辛炔 、 2-azido-1-(2-naphthyl)ethanone 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 为溶剂， 反应 0.27h， 以95%的产率得到2-(4-hexyl-1H-1,2,3-triazol-1-yl)-1-(naphthalene-6-yl)ethanone
  参考文献：
  名称：

  A Rapid Click Chemistry Using Beta-Cyclodextrin Immobilized on Glass Micro-Particles

  摘要：

  玻璃微粒（GMP）的表面经过β-环状糊精功能化（→ GMP-β-CD），并通过X射线光电子能谱（XPS）进行表征。GMP-β-CD被用作芳香族叠氮化物与末端炔烃之间点击反应的相转移催化剂。对于苄基叠氮化物和苯烯的点击反应，当加入0.8克GMP-β-CD/毫摩尔苄基叠氮化物时，反应时间从5.8小时减少到10分钟。经过10个循环后的XPS分析确认，GMP-β-CD的改性表面在重复使用后没有变化或降解。

  DOI：

  10.2174/1570178611310040008

文献信息

• Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction in Water Using Cyclodextrin as a Phase Transfer Catalyst
  作者：Jung-Ah Shin、Yeong-Gweon Lim、Kyung-Hee Lee

  DOI：10.1021/jo3000095

  日期：2012.4.20

  1,4-Disubstituted-1,2,3-triazoles were obtained in excellent yields from azides and terminal alkynes in H2O in the presence of catalytic amount of beta-cyclodextrin as a phase transfer catalyst. Also, a one-pot CuAAC reaction was carried out successfully, affording 1,4-disubstituted-1,2,3-triazoles in good to high yields starting from an alkyl bromide, sodium azide, and terminal alkyne.
• Continuous process for click reactions using glass micro-reactor functionalized with β-cyclodextrin
  作者：Muhammad Nazir Tahir、Riaz-ul Qamar、Ahmad Adnan、Eunae Cho、Seunho Jung

  DOI：10.1016/j.tetlet.2013.04.042

  日期：2013.6

  A micro-reactor based on glass micro-chip functionalized with beta-cyclodextrin was prepared and used to develop a flow process for click reactions of aromatic azides and acetylenes. Products with 97-99% yield were obtained within a few minutes. Modified surface remained stable and almost no degradation was observed after 50 h of continuous use. (C) 2013 Elsevier Ltd. All rights reserved.