1,5-bis(4-benzyloxyphenyl)-3-phenyl-6-oxoverdazyl | 1446527-13-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,5-bis(4-benzyloxyphenyl)-3-phenyl-6-oxoverdazyl
• CAS: 1446527-13-4
• 化学式: C₃₄H₂₇N₄O₃
• 分子量: 539.613
• InChiKey: SZFXXSJNQITBJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-bis(4-benzyloxyphenyl)-3-phenyl-6-oxoverdazyl 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.0h， 以51%的产率得到1,5-bis(4-hydroxyphenyl)-3-phenyl-6-oxoverdazyl
  参考文献：
  名称：

  Functional Group Transformations in Derivatives of 6-Oxoverdazyl

  摘要：

  Transformations of functional groups, such as OCH2Ph, OCOPh, NO2 and I, in 1,3,5-triphenyl-6-oxoverdazyls la le were investigated in order to expand the range of synthetic tools for incorporation of the verdazyl system into more complex molecular architectures and to increase spin delocalization. Thus, Pd-catalyzed debenzylation of the OCH2Ph group or basic hydrolysis of the OCOPh group gave the phenol functionality, which was acylated, but could not be alkylated. Orthogonal deprotection of diphenol functionality was also demonstrated in radical 1c. Pt-catalyzed reduction of the NO2 group led to the aniline derivative, which was acylated. Attempted C-C coupling reactions to iodophenyl derivatives le and Se were unsuccessful. Selected verdazyl radicals were characterized by EPR and electronic absorption spectroscopy, and results were analyzed with the aid of DFT computational methods.

  DOI：

  10.1021/jo400843y
• 作为产物：
  描述：

  benzaldehyde 4-benzyloxyphenylhydrazone 在 吡啶 、 CN^(1-)*Fe⁽³⁺⁾*K⁽¹⁺⁾ 、 四丁基溴化铵 、 sodium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1,5-bis(4-benzyloxyphenyl)-3-phenyl-6-oxoverdazyl
  参考文献：
  名称：

  Functional Group Transformations in Derivatives of 6-Oxoverdazyl

  摘要：

  Transformations of functional groups, such as OCH2Ph, OCOPh, NO2 and I, in 1,3,5-triphenyl-6-oxoverdazyls la le were investigated in order to expand the range of synthetic tools for incorporation of the verdazyl system into more complex molecular architectures and to increase spin delocalization. Thus, Pd-catalyzed debenzylation of the OCH2Ph group or basic hydrolysis of the OCOPh group gave the phenol functionality, which was acylated, but could not be alkylated. Orthogonal deprotection of diphenol functionality was also demonstrated in radical 1c. Pt-catalyzed reduction of the NO2 group led to the aniline derivative, which was acylated. Attempted C-C coupling reactions to iodophenyl derivatives le and Se were unsuccessful. Selected verdazyl radicals were characterized by EPR and electronic absorption spectroscopy, and results were analyzed with the aid of DFT computational methods.

  DOI：

  10.1021/jo400843y

文献信息

• Functional Group Transformations in Derivatives of 6-Oxoverdazyl
  作者：Marcin Jasiński、Jason S. Gerding、Aleksandra Jankowiak、Krzysztof Gębicki、Jarosław Romański、Katarzyna Jastrzębska、Ajan Sivaramamoorthy、Kristein Mason、Donavan H. Evans、Małgorzata Celeda、Piotr Kaszyński

  DOI：10.1021/jo400843y

  日期：2013.8.2

  Transformations of functional groups, such as OCH2Ph, OCOPh, NO2 and I, in 1,3,5-triphenyl-6-oxoverdazyls la le were investigated in order to expand the range of synthetic tools for incorporation of the verdazyl system into more complex molecular architectures and to increase spin delocalization. Thus, Pd-catalyzed debenzylation of the OCH2Ph group or basic hydrolysis of the OCOPh group gave the phenol functionality, which was acylated, but could not be alkylated. Orthogonal deprotection of diphenol functionality was also demonstrated in radical 1c. Pt-catalyzed reduction of the NO2 group led to the aniline derivative, which was acylated. Attempted C-C coupling reactions to iodophenyl derivatives le and Se were unsuccessful. Selected verdazyl radicals were characterized by EPR and electronic absorption spectroscopy, and results were analyzed with the aid of DFT computational methods.