3-(phenylselanyl)benzonitrile | 107037-19-4

• 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: 3-(phenylselanyl)benzonitrile
• 英文别名: 3-(phenylseleno)benzonitrile；3-Phenylselanylbenzonitrile；3-phenylselanylbenzonitrile
• CAS: 107037-19-4
• 化学式: C₁₃H₉NSe
• 分子量: 258.181
• InChiKey: UAUJMEMJJRQCBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(phenylselanyl)benzonitrile 在 苯酚 作用下， 生成 2,2'-dicyanodiphenyl diselenide
  参考文献：
  名称：

  Cathodic synthesis of dicyanodiphenyl diselenide from phenylselenobenzonitrile

  摘要：

  DOI：

  10.1016/s0040-4020(01)89796-9
• 作为产物：
  描述：

  4-(phenylselanyl)benzonitrile 生成 3-(phenylselanyl)benzonitrile
  参考文献：
  名称：

  Synthesis of 2-, 3- and 4-(phenylseleno)benzonitrile by electrochemically induced aromatic nucleophilic substitution in acetonitrile

  摘要：

  DOI：

  10.1021/jo00384a008

文献信息

• Metal-free C–Se cross-coupling enabled by photoinduced inter-molecular charge transfer
  作者：Chen Zhu、Serik Zhumagazy、Huifeng Yue、Magnus Rueping

  DOI：10.1039/d1cc06152f

  日期：——

  complexes have been developed. The visible-light induced reactions can be applied for the synthesis of a series of unsymmetrical diaryl selenides employing aryl bromides, aryl iodides as well as aryl chlorides under mild reaction conditions. The scale-up was readily achieved. UV-Vis spectroscopy measurements provide insight into the reaction mechanism.

  已经开发了通过形成电子供体 - 受体（EDA）配合物的无金属 C-Se 交叉偶联。可见光诱导反应可用于在温和的反应条件下使用芳基溴化物、芳基碘化物和芳基氯化物合成一系列不对称的二芳基硒化物。很容易实现放大。紫外-可见光谱测量提供了对反应机制的深入了解。
• Green Synthesis of Diaryl Selenides from Arylboronic Acids and Arylseleninic Acids
  作者：Sébastien Redon、Patrice Vanelle、Vincent Remusat

  DOI：10.1055/a-1733-7607

  日期：2022.3

  A new method of deborylative selanylation using arylboronic acids and arylseleninic acids gave diaryl selenoethers and diarylselenoxide. The present approach requires only equimolar arylseleninic acid and led selectively to selenoethers or selenoxides depending on the solvent. The method is metal-free, base- or oxidant-free, efficient, and environmentally friendly.

  使用芳基硼酸和芳基硒酸进行脱硼硒化的新方法得到二芳基硒醚和二芳基硒氧化物。本方法仅需要等摩尔的芳基硒酸，并根据溶剂选择性地产生硒醚或硒氧化物。该方法无金属、无碱或无氧化剂、高效且环保。
• Cu(<scp>ii</scp>) anchored nitrogen-rich covalent imine network (Cu^II-CIN-1): an efficient and recyclable heterogeneous catalyst for the synthesis of organoselenides from aryl boronic acids in a green solvent
  作者：Susmita Roy、Tanmay Chatterjee、Biplab Banerjee、Noor Salam、Asim Bhaumik、Sk Manirul Islam

  DOI：10.1039/c4ra08909j

  日期：——

  A Cu(ii)-grafted covalent imine framework material has been designed, which catalyzes the C–Se cross-coupling reactions to obtain a library of organoselenides.

  设计了一种Cu（II）嵌入的共价亚胺框架材料，可催化C-Se交叉偶联反应，从而获得一系列的有机硒化合物。
• Nickel-Сatalyzed Carbon–Selenium Bond Formations under Mild Conditions
  作者：Serik Zhumagazy、Chen Zhu、Huifeng Yue、Magnus Rueping

  DOI：10.1055/s-0042-1752655

  日期：——

  offers facile access to various unsymmetrical selenium-containing motifs. The reaction features excellent functional group tolerance, wide substrate scope, good efficiency, and operates under mild reaction conditions. Notably, this protocol could be readily scaled up to gram scale without the loss of yield.

  描述了芳基碘化物和硒醇之间的镍催化 C-Se 交叉偶联。新开发的催化方法可以轻松访问各种不对称的含硒基序。该反应具有优异的官能团耐受性、底物适用范围广、效率高、反应条件温和等特点。值得注意的是，该协议可以很容易地扩大到克级，而不会损失产量。
• Solvent selective phenyl selenylation and phenyl tellurylation of aryl boronic acids catalyzed by Cu(II) grafted functionalized polystyrene
  作者：Susmita Roy、Tanmay Chatterjee、Sk. Manirul Islam

  DOI：10.1016/j.tetlet.2014.12.055

  日期：2015.2

  A solvent-selective methodology for the phenyl selenylation and phenyl tellurylation of aryl boronic acids has been developed for the first time using a polymer supported Cu(II) catalyst. The catalyst was synthesized by anchoring Cu(OAc)(2) onto a functionalized polystyrene with pyridine thiosemicarbazone ligand. It was then characterized properly by SEM, EDAX, FT-IR, TGA, and EPR experiments. The catalyst smoothly catalyzes phenyl selenylation of aryl boronic acids in water and phenyl tellurylation of aryl boronic acids in PEG-600, selectively. Thus a wide variety of unsymmetrical organodiaryl or aryl-heteroaryl selenides and tellurides have been synthesized by this protocol. The catalyst was recycled up to six runs without any appreciable loss of catalytic activity. (C) 2014 Elsevier Ltd. All rights reserved.