Tert-butyl 2-(2-bromo-5-formyl-3-hydroxyphenoxy)acetate | 1160109-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Tert-butyl 2-(2-bromo-5-formyl-3-hydroxyphenoxy)acetate
• CAS: 1160109-57-8
• 化学式: C₁₃H₁₅BrO₅
• 分子量: 331.163
• InChiKey: FGNUBXATILDAKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-bromo-3,5-bis(methoxymethoxy)benzene 、 Tert-butyl 2-(2-bromo-5-formyl-3-hydroxyphenoxy)acetate 在 正丁基锂 、 三丁基氯化锡 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以15.67 g的产率得到tert-butyl 2-((4-formyl-6-hydroxy-3',5'-bis(methoxymethoxy)-[1,1'-biphenyl]-2-yl)oxy)acetate
  参考文献：
  名称：

  Site-Specific Installation and Study of Electroactive Units in Every Layer of Dendrons

  摘要：

  Whereas encapsulation of functional groups at the core of dendrimers is well-understood, very little is known about their intermediate layers or even the periphery. Here we report oil a systematic investigation of every layer of dendrimers by incorporating a single ferrocene unit in well-defined locations in dendrons. Site-specific incorporation of the ferrocene unit was achieved by utilizing the dendrimer sequencing methodology. We show here that the redox potential values of ferrocene at intermediate layers were remarkably different from those at the core and the periphery. Although redox potential values were location-dependent, no significant change in the rate of heterogeneous electron transfer (k(0)) was observed with respect to locations. This was attributed to the possibility that free rotation of dendrimer nullifies the distance between the electrode and ferrocene unit. Finally, we also show that no Faradaic current was observed for the amphiphilic assemblies of these dendrons, whereas the same dendron did exhibit significant Faradaic current in nonassembling solvent environments.

  DOI：

  10.1021/jo902109u
• 作为产物：
  描述：

  在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到Tert-butyl 2-(2-bromo-5-formyl-3-hydroxyphenoxy)acetate
  参考文献：
  名称：

  Site-Specific Installation and Study of Electroactive Units in Every Layer of Dendrons

  摘要：

  Whereas encapsulation of functional groups at the core of dendrimers is well-understood, very little is known about their intermediate layers or even the periphery. Here we report oil a systematic investigation of every layer of dendrimers by incorporating a single ferrocene unit in well-defined locations in dendrons. Site-specific incorporation of the ferrocene unit was achieved by utilizing the dendrimer sequencing methodology. We show here that the redox potential values of ferrocene at intermediate layers were remarkably different from those at the core and the periphery. Although redox potential values were location-dependent, no significant change in the rate of heterogeneous electron transfer (k(0)) was observed with respect to locations. This was attributed to the possibility that free rotation of dendrimer nullifies the distance between the electrode and ferrocene unit. Finally, we also show that no Faradaic current was observed for the amphiphilic assemblies of these dendrons, whereas the same dendron did exhibit significant Faradaic current in nonassembling solvent environments.

  DOI：

  10.1021/jo902109u

文献信息

• Site-Specific Installation and Study of Electroactive Units in Every Layer of Dendrons
  作者：Malar A. Azagarsamy、Kothandam Krishnamoorthy、Kulandaivelu Sivanandan、S. Thayumanavan

  DOI：10.1021/jo902109u

  日期：2009.12.18

  Whereas encapsulation of functional groups at the core of dendrimers is well-understood, very little is known about their intermediate layers or even the periphery. Here we report oil a systematic investigation of every layer of dendrimers by incorporating a single ferrocene unit in well-defined locations in dendrons. Site-specific incorporation of the ferrocene unit was achieved by utilizing the dendrimer sequencing methodology. We show here that the redox potential values of ferrocene at intermediate layers were remarkably different from those at the core and the periphery. Although redox potential values were location-dependent, no significant change in the rate of heterogeneous electron transfer (k(0)) was observed with respect to locations. This was attributed to the possibility that free rotation of dendrimer nullifies the distance between the electrode and ferrocene unit. Finally, we also show that no Faradaic current was observed for the amphiphilic assemblies of these dendrons, whereas the same dendron did exhibit significant Faradaic current in nonassembling solvent environments.