diazidomethylanthracene | 1231728-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diazidomethylanthracene
• 英文别名: methyl-2-C-(5-prop-2-ynylamino-5-deoxy-2,3-di-O-isopropylidne-β-D-ribofuranosyl) acetate
• CAS: 1231728-36-1
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: FHZXQRJLOBFHNW-JULQROHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diazidomethylanthracene 、 9,10-bis(azidomethyl)anthracene 在 铜 、 copper(II) sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以68%的产率得到dimethyl 2,2'-(6,6'-(1,1'-(anthracene-9,10-diylbis(methylene))bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene)bis(azanediyl)bis(methylene)bis(2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-6,4-diyl))diacetate
  参考文献：
  名称：

  A water-soluble ribosyl-based fluorescent sensor for Hg2+ and Cu2+ ions

  摘要：

  A water-soluble ribosyl-based fluorescent sensor 5 was prepared. The sensor contains an anthracene as the fluorophore and a set of complex groups as recognition sites, which bears two triazole ring spacers linked to two ribosyl carboxylic acids groups. The association constants of 5 in water are 2.15 x 10(5) M-1 and 9.57 x 10(4) M-1 for Cu2+ and Hg2+ ions, respectively, and both metals formed complexes with 5 at a 1:1 metal to ligand ratio. The binding of 5 to Cu2+ shows a broad pH range (5-10) and a low detection limit (57 ppb) in water, thus indicating it an efficient and promising cation probe. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.02.003
• 作为产物：
  描述：

  3-溴丙炔 、 methyl 2-C-(5-amino-5-deoxy-2,3-di-O-isopropylidene-β-D-ribofuranosyl)acetate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以62%的产率得到diazidomethylanthracene
  参考文献：
  名称：

  A water-soluble ribosyl-based fluorescent sensor for Hg2+ and Cu2+ ions

  摘要：

  A water-soluble ribosyl-based fluorescent sensor 5 was prepared. The sensor contains an anthracene as the fluorophore and a set of complex groups as recognition sites, which bears two triazole ring spacers linked to two ribosyl carboxylic acids groups. The association constants of 5 in water are 2.15 x 10(5) M-1 and 9.57 x 10(4) M-1 for Cu2+ and Hg2+ ions, respectively, and both metals formed complexes with 5 at a 1:1 metal to ligand ratio. The binding of 5 to Cu2+ shows a broad pH range (5-10) and a low detection limit (57 ppb) in water, thus indicating it an efficient and promising cation probe. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.02.003

文献信息

• Effect of bis-triazoles on a ribose-based fluorescent sensor
  作者：Huei-Jyun Huang、Hau-Yu Fang、Jiun-Ly Chir、An-Tai Wu

  DOI：10.1002/bio.1263

  日期：2011.11

  We synthesized two ribosyl-based fluorescent sensors. Both sensors have an anthracene as the fluorophore, but they differ in the recognition site for metal ions. One (3) has two ribosyl esters, and the other (6) has two triazole groups linked to two ribosyl esters. Among the metal ions examined in MeOH, compound 3 displayed a large chelation-enhanced fluorescence (CHEF) effect with Hg2+ and Cu2+ ions, and compound 6 displayed a large chelation-quenched fluorescence (CHQF) effect with Cu2+ and Ni2+ ions. The results demonstrated that the absence (sensor 3) and presence (sensor 6) of an incorporated bis-triazole group in a ribosyl-based fluorescent sensor conferred different preferences and distinct binding modes for metal ions. Copyright © 2010 John Wiley & Sons, Ltd.

  我们合成了两种基于核糖基的荧光传感器。两种传感器都以蒽作为荧光团，但它们在金属离子的识别位点上有所不同。一个 (3) 具有两个核糖酯，另一个 (6) 具有两个与两个核糖酯连接的三唑基团。在MeOH中检测的金属离子中，化合物3与Hg2+和Cu2+离子表现出较大的螯合增强荧光（CHEF）效应，化合物6与Cu2+和Ni2+离子表现出较大的螯合猝灭荧光（CHQF）效应。结果表明，基于核糖基的荧光传感器中不存在（传感器 3）和存在（传感器 6）双三唑基团赋予金属离子不同的偏好和不同的结合模式。版权所有 © 2010 约翰威利父子有限公司