1-(2-azidoethoxy)-5-hydroxynaphthalene | 1350517-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-azidoethoxy)-5-hydroxynaphthalene
• 英文别名: 5-(2-azidoethoxy)naphthalene-1-ol；5-(2-Azidoethoxy)naphthalen-1-ol；5-(2-azidoethoxy)naphthalen-1-ol
• CAS: 1350517-28-0
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: FZYTZFHNBWSALP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-azidoethoxy)-5-hydroxynaphthalene 在 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(2-((5-hydroxynaphthalen-1-yl)oxy)ethyl)amine
  参考文献：
  名称：

  Fluorescent reporters of monoamine transporter distribution and function

  摘要：

  Serotonin is a monoamine serving as a chemical messenger in diverse brain regions, as well as in blood and various other organs. We synthesized six ethylamine functionalized fluorophores as fluorescent probes for serotonin. The one with best spectral properties and aqueous solubility, 6-amino-2-(2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione, was studied in detail both in vivo and in vitro. It was shown to act as a ligand for serotonin transporter (SERT) without acute cerebral or cardiovascular toxicity or adverse effects. Fluorescent serotonin analogs can be used for direct visualization of SERT distribution and activity in live tissue. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.007
• 作为产物：
  描述：

  1,5-二羟基萘 、 tosylethylazide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以57%的产率得到1-(2-azidoethoxy)-5-hydroxynaphthalene
  参考文献：
  名称：

  Fluorescent reporters of monoamine transporter distribution and function

  摘要：

  Serotonin is a monoamine serving as a chemical messenger in diverse brain regions, as well as in blood and various other organs. We synthesized six ethylamine functionalized fluorophores as fluorescent probes for serotonin. The one with best spectral properties and aqueous solubility, 6-amino-2-(2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione, was studied in detail both in vivo and in vitro. It was shown to act as a ligand for serotonin transporter (SERT) without acute cerebral or cardiovascular toxicity or adverse effects. Fluorescent serotonin analogs can be used for direct visualization of SERT distribution and activity in live tissue. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.007

文献信息

• Design and synthesis of a bis-macrocyclic host and guests as building blocks for small molecular knots
  作者：Elizabeth A Margolis、Rebecca J Keyes、Stephen D Lockey、Edward E Fenlon

  DOI：10.3762/bjoc.16.192

  日期：——

  molecular knots. The modular second-generation approach to small trefoil knots described herein involves electrostatic interactions between an electron-rich bis-macrocyclic host compound and electron-deficient guests in the threading step. The bis-macrocyclic host was synthesized in eight steps and 6.6% overall yield. Ammonium and pyridinium guests were synthesized in 4–5 steps. The TLC knot-forming sequence

  以前，线切割（TLC）方法已显示出有望成为合成分子结的一种新方法。本文所述的小三叶结的模块化第二代方法涉及在穿线步骤中富电子的双大环主体化合物与缺电子的客体之间的静电相互作用。双大环主体以八步合成，总收率为6.6％。铵和吡啶鎓客体以4-5个步骤合成。进行了TLC结形成序列，并产生了具有预期分子量的产物，但是，不幸的是，进一步的表征并未就产物的拓扑产生决定性的结果。
• Fluorescent reporters of monoamine transporter distribution and function
  作者：Sharanappa M. Bagale、Adrienne S. Brown、Melissa M. Carballosa Gonzalez、Alberto Vitores、Teresa L. Micotto、N.S. Saleesh Kumar、Ian D. Hentall、James N. Wilson

  DOI：10.1016/j.bmcl.2011.10.007

  日期：2011.12

  Serotonin is a monoamine serving as a chemical messenger in diverse brain regions, as well as in blood and various other organs. We synthesized six ethylamine functionalized fluorophores as fluorescent probes for serotonin. The one with best spectral properties and aqueous solubility, 6-amino-2-(2-aminoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione, was studied in detail both in vivo and in vitro. It was shown to act as a ligand for serotonin transporter (SERT) without acute cerebral or cardiovascular toxicity or adverse effects. Fluorescent serotonin analogs can be used for direct visualization of SERT distribution and activity in live tissue. (C) 2011 Elsevier Ltd. All rights reserved.