tert-butyl (2-(4-(3-((2-(2-(2-azidoethoxy)ethoxy)ethyl)thio)propyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)-1H-indol-3-yl)ethyl)carbamate | 1365565-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl (2-(4-(3-((2-(2-(2-azidoethoxy)ethoxy)ethyl)thio)propyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)-1H-indol-3-yl)ethyl)carbamate
• 英文别名: tert-butyl N-[2-[4-[3-[2-[2-(2-azidoethoxy)ethoxy]ethylsulfanyl]propyl]-5-(oxan-2-yloxy)-1H-indol-3-yl]ethyl]carbamate
• CAS: 1365565-82-7
• 化学式: C₂₉H₄₅N₅O₆S
• 分子量: 591.772
• InChiKey: RNQUYFUBVZHKPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  41
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-羟基色胺盐酸盐 在 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 邻二甲苯 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 9.84h， 生成 tert-butyl (2-(4-(3-((2-(2-(2-azidoethoxy)ethoxy)ethyl)thio)propyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)-1H-indol-3-yl)ethyl)carbamate 、 tert-butyl 4-(3-((2-(2-(2-azidoethoxy)ethoxy)ethyl)thio)propyl)-3-(2-((tert-butoxycarbonyl)amino)ethyl)-5-((tetrahydro-2H-pyran-2-yl)-oxy)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Synthesis of Dopamine and Serotonin Derivatives for Immobilization on a Solid Support

  摘要：

  The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.

  DOI：

  10.1021/jo2025477

文献信息

• Synthesis of Dopamine and Serotonin Derivatives for Immobilization on a Solid Support
  作者：Erik Daa Funder、Anne Bjørnskov Jensen、Thomas Tørring、Anne Louise Bank Kodal、Ane Rebolledo Azcargorta、Kurt Vesterager Gothelf

  DOI：10.1021/jo2025477

  日期：2012.4.6

  The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.