4-ciano-t-azobenzene cation radical | 92594-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-ciano-t-azobenzene cation radical
• 英文别名: (E)-(4-phenyldiazenyl)benzonitrile；(E)-4-(phenyldiazenyl)benzonitrile；4-(phenyldiazenyl)benzonitrile；p-phenylazobenzonitrile；4-ciano-t-azobenzene；4-Cyanoazobenzol
• CAS: 92594-44-0
• 化学式: C₁₃H₉N₃
• 分子量: 207.235
• InChiKey: KFGLGJJFHLSWSU-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.51
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-ciano-t-azobenzene cation radical 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 以21%的产率得到(E)-(4-(phenyldiazenyl)phenyl)methanamine
  参考文献：
  名称：

  Reversible Laser-Induced Bending of Pseudorotaxane Crystals

  摘要：

  This study investigated the dynamic photo-response of pseudorotaxane crystals with azobenzene and ferrocenyl groups in the axle component. X-ray crystallography showed pseudorotaxanes with a methylazobenzene group and a dibromophenylene ring in the cyclic component to exhibit twisting of the trans-azobenzene groups at torsion angles of 17 degrees and 38 degrees, respectively. Repeated alternating laser irradiation of the crystals at 360 and 445 nm produced bending of 20-30 degrees in opposite directions, with no evidence of decay. Under 44S nm irradiation, bending took place within 0.3 s. A crystal of nonsubstituted pseudorotaxane showed bending of only 2 degrees under 360 nm irradiation due to multiple pi-pi interactions between the planar trans-azobenzene groups. The pseudorotaxane crystals have two chromophores, bent rapidly and reversibly on irradiation at rates depending on the molecular structure.

  DOI：

  10.1021/jacs.7b10998
• 作为产物：
  描述：

  生成 4-ciano-t-azobenzene cation radical
  参考文献：
  名称：

  Design of phase-transition molecular solar thermal energy storage compounds: compact molecules with high energy densities

  摘要：

  研究各种带有不同功能基团的紧凑偶氮苯衍生物，以实现每克超过300焦耳的光子和热能储存。

  DOI：

  10.1039/d1cc03742k

文献信息

• Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines Leading to Aromatic Azo Compounds using Dioxygen as an Oxidant
  作者：Chun Zhang、Ning Jiao

  DOI：10.1002/anie.201001651

  日期：2010.8.16

  In the air tonight: A novel approach to symmetric and unsymmetric aromatic azo compounds from simple anilines catalyzed by inexpensive CuBr has been disclosed. Air (or dioxygen) was used as an oxidant under mild reaction conditions, with H2O as the byproduct, to make this transformation environmentally benign and very easy to handle.

  今晚在空气中：已经公开了一种由廉价的溴化铜催化的简单苯胺中的对称和不对称芳族偶氮化合物的新颖方法。在温和的反应条件下，使用空气（或双氧）作为氧化剂，并以H 2 O作为副产物，使这种转化在环境上无害且非常易于处理。
• AgNO₃ as nitrogen source for rhodium(<scp>iii</scp>)-catalyzed synthesis of 2-aryl-2H-benzotriazoles from azobenzenes
  作者：Jixing Li、Hui Zhou、Jinlong Zhang、Huameng Yang、Gaoxi Jiang

  DOI：10.1039/c6cc04341k

  日期：——

  A new approach has been established for Rh(iii)-catalyzed direct aza oxidative cyclization of non-prefunctionalized azobenzenes to provide 2-aryl-2H-benzotriazoles in good yields.

  已建立一种新方法，用于Rh(iii)催化的非预功能化偶氮苯直接氮杂氧化环化，以高产率提供2-芳基-2H-苯并三唑。
• Visible-Light-Mediated Hydroacylation of Azobenzenes with α-Keto Acids
  作者：Jingya Yang、Menghui Song、Hongyan Zhou、Ganggang Wang、Ben Ma、Yuanyuan Qi、Congde Huo

  DOI：10.1021/acs.orglett.0c03039

  日期：2020.11.6

  A visible-light-mediated protocol for the hydroacylation of azobenzenes with α-keto acids has been developed. In the absence of any catalyst or additive, decarboxylative hydroacylation proceeded smoothly under visible-light irradiation at room temperature. A wide range of azobenzenes and α-keto acids were well-tolerated and afforded hydroacylation products in high to excellent yields. Preliminary investigations

  已经开发了一种可见光介导的方案，用于将偶氮苯与α-酮酸加氢酰化。在不存在任何催化剂或添加剂的情况下，在室温下在可见光照射下，脱羧加氢酰化反应顺利进行。宽范围的偶氮苯和α-酮酸具有良好的耐受性，并能以高到极好的收率提供加氢酰化产物。初步研究表明，光活性偶氮苯吸收可见光以实现转化。
• Synthesis of Redshifted Azobenzene Photoswitches by Late-Stage Functionalization
  作者：David B. Konrad、James A. Frank、Dirk Trauner

  DOI：10.1002/chem.201505061

  日期：2016.3.18

  of tetra‐ortho‐chloro azobenzenes has been developed, which relies on direct palladium(II)‐catalyzed C−H activation of pre‐existing standard azobenzenes. This late‐stage functionalization has a broad substrate scope and can be used to create a variety of useful building blocks for the construction of more elaborate redshifted photopharmaceuticals. This method is used to prepare red‐AzCA‐4, a photoswitchable

  偶氮苯是多才多艺，可他们之间循环光电继电器反式-与顺光构型。此异构化所需的波长基本上从UV通过四偏移到可见范围邻-chlorination。这些卤代偶氮苯显示出独特的光开关特性，但它们的合成仍然有限且效率低下。合成四邻位的一种新的通用方法已经开发了氯代偶氮苯，它依赖于钯（II）对预先存在的标准偶氮苯的直接CH-H活化作用。后期功能化具有广泛的底物范围，可用于创建各种有用的构建基块，用于构建更精细的红移光药物。这种方法被用来制备红- AZCA-4 ，一个光可香草素，使可见光的阳离子通道TRPV1的光学控制。
• Calculated oxidation potentials predict reactivity in Baeyer–Mills reactions
  作者：Robert J. Tombari、Jeremy R. Tuck、Noah Yardeny、Phillip W. Gingrich、Dean J. Tantillo、David E. Olson

  DOI：10.1039/d1ob01450a

  日期：——

  The Baeyer–Mills reaction is widely utilized to synthesize azobenzenes, but often produces azoxybenzene as an undesired byproduct. Here, we use a computational approach to predict the outcomes of Baeyer–Mills reactions.

  巴耶尔-米尔斯反应被广泛用于合成偶氮苯，但通常会产生偶氧苯作为不希望的副产物。在这里，我们使用计算方法来预测巴耶尔-米尔斯反应的结果。