(1-((6-(azidomethyl)quinolin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methanol | 1375006-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (1-((6-(azidomethyl)quinolin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methanol
• 英文别名: [1-[[6-(Azidomethyl)quinolin-2-yl]methyl]triazol-4-yl]methanol；[1-[[6-(azidomethyl)quinolin-2-yl]methyl]triazol-4-yl]methanol
• CAS: 1375006-72-6
• 化学式: C₁₄H₁₃N₇O
• 分子量: 295.304
• InChiKey: SNPFTHIHVSWGRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2，6-二甲基喹啉 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 偶氮二异丁腈 、 copper diacetate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 (1-((6-(azidomethyl)quinolin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methanol
  参考文献：
  名称：

  Chemoselective Sequential “Click” Ligation Using Unsymmetrical Bisazides

  摘要：

  Unsymmetrical bisazides containing chelating and nonchelating azido groups undergo chemoselective three-component copper(I)-catalyzed azide-alkyne conjugation reactions with two different alkyne molecules. In conjunction with the reactivity gap between aromatic and aliphatic alkynes, a bistriazole molecule can be generated with excellent regioselectivity by mixing two alkynes and a bisazide in a single reaction container. This method is applicable in aqueous solutions at neutral pH, which may lend utilities in bioconjugation applications.

  DOI：

  10.1021/ol300899n

文献信息

• UMSYMMETRICAL BISAZIDES FOR CHEMOSELECTIVE SEQUENTIAL LIGATION
  申请人：The Florida State University Research Foundation, Inc.

  公开号：US20140018541A1

  公开（公告）日：2014-01-16

  Unsymmetrical bisazides containing chelating and non-chelating azido groups undergo chemoselective three-component copper(I)-catalyzed azide-alkyne conjugation reactions with two different alkyne molecules. In conjunction with the reactivity gap between aromatic and aliphatic alkynes, a bistriazole molecule can be generated with an excellent regioselectivity by mixing two alkynes and a bisazide in a single reaction container. This method is applicable in aqueous solutions at neutral pH, which may lend utilities in bioconjugation applications.

  含有螯合和非螯合偶氮基团的不对称双偶联物可通过选择性化学反应，在两种不同的炔烃分子中，与三元铜(I)催化偶联反应发生反应。结合芳香族和脂肪族炔烃之间的反应性差异，通过在单个反应容器中混合两种炔烃和一个双偶氮基团，可以生成一个具有极佳区域选择性的双三唑分子。这种方法适用于中性pH值的水溶液中，可能在生物偶联应用中发挥作用。
• US8871940B2
  申请人：——

  公开号：US8871940B2

  公开（公告）日：2014-10-28
• Chemoselective Sequential “Click” Ligation Using Unsymmetrical Bisazides
  作者：Zhao Yuan、Gui-Chao Kuang、Ronald J. Clark、Lei Zhu

  DOI：10.1021/ol300899n

  日期：2012.5.18

  Unsymmetrical bisazides containing chelating and nonchelating azido groups undergo chemoselective three-component copper(I)-catalyzed azide-alkyne conjugation reactions with two different alkyne molecules. In conjunction with the reactivity gap between aromatic and aliphatic alkynes, a bistriazole molecule can be generated with excellent regioselectivity by mixing two alkynes and a bisazide in a single reaction container. This method is applicable in aqueous solutions at neutral pH, which may lend utilities in bioconjugation applications.