2-[2-[2-[2-(2-cyclooctyn-1-yloxy)ethoxy]ethoxy]ethoxy]ethanol | 1150109-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[2-[2-[2-(2-cyclooctyn-1-yloxy)ethoxy]ethoxy]ethoxy]ethanol
• 英文别名: 2-[2-[2-(2-Cyclooct-2-yn-1-yloxyethoxy)ethoxy]ethoxy]ethanol；2-[2-[2-(2-cyclooct-2-yn-1-yloxyethoxy)ethoxy]ethoxy]ethanol
• CAS: 1150109-77-5
• 化学式: C₁₆H₂₈O₅
• 分子量: 300.395
• InChiKey: VPOMUGUHICMVTN-UHFFFAOYSA-N

物化性质

• 沸点：
  423.1±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2-[2-[2-(2-cyclooctyn-1-yloxy)ethoxy]ethoxy]ethoxy]ethanol 在 lithium aluminium tetrahydride 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.92h， 生成
  参考文献：
  名称：

  Nanoliposomes presenting on surface a cis-glycofused benzopyran compound display binding affinity and aggregation inhibition ability towards Amyloid β1-42 peptide

  摘要：

  Nanoliposomes decorated on their surface with ligands for A beta-peptides, the key morphological features of Alzheimer's disease (AD), have been synthesized and characterized for their ability to target A beta-peptide aggregates. A tricyclic benzopyrane-glycofused structure has been exploited as A beta-peptide ligand, which was linked to liposomes via a copper-free, chemoselective, biocompatible click chemistry reaction. The tricyclic-decorated liposomes presented a mean diameter in the nanomolar range (150-200 nm), a negative z-potential and a good stability, at least up to one month. Integrity studies performed in the presence of serum proteins indicated that these decorated nanoliposomes fulfill the requirements for in vivo applications. NMR experiments carried out with A beta-(1-42) oligomers using both surface functionalized and plain (control) liposomes, revealed that the binding ability of the nanoliposomes was mediated by the presence of the tricyclic ligand on their surface. Finally ThT assay carried out with tricyclic-decorated liposomes showed significant decrease in thioflavine T fluorescence after 24 h, suggesting a significant inhibition/delay of A beta(1-42) aggregation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.085
• 作为产物：
  描述：

  8,8-dibromobicyclo[5.1.0]octane 在 吡啶 、 potassium tert-butylate 、 silver perchlorate 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 64.0h， 生成 2-[2-[2-[2-(2-cyclooctyn-1-yloxy)ethoxy]ethoxy]ethoxy]ethanol
  参考文献：
  名称：

  Nanoliposomes presenting on surface a cis-glycofused benzopyran compound display binding affinity and aggregation inhibition ability towards Amyloid β1-42 peptide

  摘要：

  Nanoliposomes decorated on their surface with ligands for A beta-peptides, the key morphological features of Alzheimer's disease (AD), have been synthesized and characterized for their ability to target A beta-peptide aggregates. A tricyclic benzopyrane-glycofused structure has been exploited as A beta-peptide ligand, which was linked to liposomes via a copper-free, chemoselective, biocompatible click chemistry reaction. The tricyclic-decorated liposomes presented a mean diameter in the nanomolar range (150-200 nm), a negative z-potential and a good stability, at least up to one month. Integrity studies performed in the presence of serum proteins indicated that these decorated nanoliposomes fulfill the requirements for in vivo applications. NMR experiments carried out with A beta-(1-42) oligomers using both surface functionalized and plain (control) liposomes, revealed that the binding ability of the nanoliposomes was mediated by the presence of the tricyclic ligand on their surface. Finally ThT assay carried out with tricyclic-decorated liposomes showed significant decrease in thioflavine T fluorescence after 24 h, suggesting a significant inhibition/delay of A beta(1-42) aggregation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.085

文献信息

• Controlled density glycodendron microarrays for studying carbohydrate–lectin interactions
  作者：Antonio Di Maio、Anna Cioce、Silvia Achilli、Michel Thépaut、Corinne Vivès、Franck Fieschi、Javier Rojo、Niels-C. Reichardt

  DOI：10.1039/d1ob00872b

  日期：——

  functionalised glycans. The non-covalent immobilisation of dendrons on the ITO surface by hydrophobic interaction allowed us to study dendron surface density and SPAAC conversion rate by in situ MALDI-TOF MS analysis. By diluting the dendron surface density we could study how the carbohydrate–lectin interactions became exclusively dependant on the valency of the immobilised glycodendron.

  通过在疏水性氧化铟锡 (ITO) 涂层载玻片上进行片上合成，构建了具有确定化合价的糖松微阵列，并用于多种植物和人类凝集素的凝集素-碳水化合物结合研究。通过固定化环辛炔树突和叠氮官能化聚糖之间的点状应变促进叠氮-炔环加成（SPAAC）制备以不同价态呈递糖表位的糖苷元。通过疏水相互作用将树枝状分子非共价固定在 ITO 表面上，使我们能够通过原位MALDI-TOF MS 分析来研究树枝状分子表面密度和 SPAAC 转化率。通过稀释树突表面密度，我们可以研究碳水化合物-凝集素相互作用如何完全依赖于固定化糖突的化合价。
• SERS enhancement of silver nanoparticles prepared by a template-directed triazole ligand strategy
  作者：Heba A. Kashmery、David G. Thompson、Ruggero Dondi、Samuel Mabbott、Duncan Graham、Alasdair W. Clark、Glenn A. Burley

  DOI：10.1039/c5cc02883c

  日期：——

  A one-pot method to prepare silver nanoparticle (AgNP) nanotags using the Tollens' reagent is described.

  描述了一种使用 Tollens' 试剂制备银纳米颗粒 (AgNP) 纳米标记的一锅法方法。
• Lallana, Enrique; Fernandez-Megia, Eduardo; Riguera, Ricardo, Journal of the American Chemical Society, 2009, vol. 131, p. 5748 - 5750
  作者：Lallana, Enrique、Fernandez-Megia, Eduardo、Riguera, Ricardo

  DOI：——

  日期：——
• Nanoliposomes presenting on surface a cis-glycofused benzopyran compound display binding affinity and aggregation inhibition ability towards Amyloid β1-42 peptide
  作者：Cristina Airoldi、Spyridon Mourtas、Francisco Cardona、Cristiano Zona、Erika Sironi、Giuseppe D'Orazio、Eleni Markoutsa、Francesco Nicotra、Sophia G. Antimisiaris、Barbara La Ferla

  DOI：10.1016/j.ejmech.2014.07.085

  日期：2014.10

  Nanoliposomes decorated on their surface with ligands for A beta-peptides, the key morphological features of Alzheimer's disease (AD), have been synthesized and characterized for their ability to target A beta-peptide aggregates. A tricyclic benzopyrane-glycofused structure has been exploited as A beta-peptide ligand, which was linked to liposomes via a copper-free, chemoselective, biocompatible click chemistry reaction. The tricyclic-decorated liposomes presented a mean diameter in the nanomolar range (150-200 nm), a negative z-potential and a good stability, at least up to one month. Integrity studies performed in the presence of serum proteins indicated that these decorated nanoliposomes fulfill the requirements for in vivo applications. NMR experiments carried out with A beta-(1-42) oligomers using both surface functionalized and plain (control) liposomes, revealed that the binding ability of the nanoliposomes was mediated by the presence of the tricyclic ligand on their surface. Finally ThT assay carried out with tricyclic-decorated liposomes showed significant decrease in thioflavine T fluorescence after 24 h, suggesting a significant inhibition/delay of A beta(1-42) aggregation. (C) 2014 Elsevier Masson SAS. All rights reserved.