1,5-bis(4-hydroxyphenyl)-3-phenyl-6-oxoverdazyl | 1446527-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,5-bis(4-hydroxyphenyl)-3-phenyl-6-oxoverdazyl
• CAS: 1446527-21-4
• 化学式: C₂₀H₁₅N₄O₃
• 分子量: 359.364
• InChiKey: NENRPEIDMJSEHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-bis(4-hydroxyphenyl)-3-phenyl-6-oxoverdazyl 、 对氰基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以82%的产率得到1,5-bis(4-(4-cyanobenzoyloxy)phenyl)-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-benzoyloxyphenylhydrazone 在 吡啶 、 四乙基溴化铵 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 1,5-bis(4-hydroxyphenyl)-3-phenyl-6-oxoverdazyl
  参考文献：
  名称：

  3-Substituted 6-oxoverdazyl bent-core nematic radicals: synthesis and characterization

  摘要：

  含有6-氧代苯并氮氧自由基作为中心角单元的弯曲核向列体表现出罕见的向列相行为。

  DOI：

  10.1039/c5ra04119h

文献信息

• Molecular engineering of liquid crystalline derivatives of 6-oxoverdazyl
  作者：Piotr Kaszynski、Marcin Jasiński、Sylwia Ciastek、Szymon Kapuscinski、Krzysztof Gebicki

  DOI：10.3998/ark.5550190.p009.800

  日期：——

  available positions on the heterocycle can be substituted with wedge-shaped or rod-like groups in combination with a small substituent, which leads to different molecular architectures and diverse organization of the mesophase. Several of these architectures have been realized experimentally and materials exhibiting columnar and calamitic phases have been obtained. Compounds with some other combination of

  6-Oxoverdazyl 是一种 π 离域稳定自由基，被认为是顺磁性自组织材料的中心结构元素。杂环上的三个可用位置可以被楔形或棒状基团取代，并结合一个小的取代基，从而导致不同的分子结构和中间相的不同组织。这些结构中的一些已经通过实验实现，并且已经获得了表现出柱状和棒状相的材料。具有一些其他取代基组合的化合物没有表现出液晶行为。该分析还指出了一些可能适合形成液晶相的新分子结构。最后，讨论了盘状衍生物的磁化率和光伏测量结果。
• Induction of smectic polymorphism in bent-core derivatives of the 6-oxoverdazyl by partial fluorination of alkyl chains
  作者：Sylwia Ciastek、Piotr Kaszyński、Damian Pociecha、Marcin Jasiński

  DOI：10.1039/c6ra21383a

  日期：——

  A series of bent-core mesogens 2[m,n] derived from the 6-oxoverdazyl radical and containing partially fluorinated alkyl tails was prepared and investigated by thermal, optical, XRD and EPR methods. In contrast to non-fluorinated analogs, the series 2[m,n] exhibits SmA and SmC phases with thermal stability dependent on the degree of fluorination and the F/H ratio (m/n) in the alkyl chain.

  制备了一系列由6-氧过氧二氮杂基衍生并包含部分氟化烷基尾部的弯曲核液晶元2 [ m，n ]，并通过热，光学，XRD和EPR方法对其进行了研究。与非氟化类似物相反，系列2 [ m，n ]表现出SmA和SmC相，其热稳定性取决于氟化程度和烷基链中的F / H比（m / n）。
• 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.
• 3-Substituted 6-oxoverdazyl bent-core nematic radicals: synthesis and characterization
  作者：Sylwia Ciastek、Marcin Jasiński、Piotr Kaszyński

  DOI：10.1039/c5ra04119h

  日期：——

  Bent-core mesogens containing the 6-oxoverdazyl as the central angular unit exhibit rare nematic behavior.

  含有6-氧代苯并氮氧自由基作为中心角单元的弯曲核向列体表现出罕见的向列相行为。