4-((4-nitrophenyl)ethynyl)benzonitrile | 2832-79-3

• 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: 4-((4-nitrophenyl)ethynyl)benzonitrile
• 英文别名: 4-[(4-Nitrophenyl)ethynyl]benzonitrile；4-[2-(4-nitrophenyl)ethynyl]benzonitrile
• CAS: 2832-79-3
• 化学式: C₁₅H₈N₂O₂
• 分子量: 248.241
• InChiKey: ZFJBOETVAXZZOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((4-nitrophenyl)ethynyl)benzonitrile 在 一水合肼 作用下， 80.0 ℃ 、551.59 kPa 条件下， 反应 0.5h， 以80%的产率得到4-(2-(4-氨基苯基)乙炔基)苯甲腈
  参考文献：
  名称：

  Solid supported rhodium(0) nanoparticles: an efficient catalyst for chemo- and regio-selective transfer hydrogenation of nitroarenes to anilines under microwave irradiation

  摘要：

  A Solid-supported rhodium(0) (SS-Rh) catalyst has been developed and applied for the chemo- and regioselective reduction of nitroarenes functionalized with C-C multiple bonds and dinitroarenes to their corresponding amines respectively using hydrazine hydrate (N2H4 center dot H2O) as a reducing source under mild microwave irradiation (MWI) conditions. The present methodology also shows excellent compatibility with a broad range of structurally diverse reducible functional groups. The catalyst can be recovered by simple filtration and reused for 13 cycles with consistent activity hence reduces the cost of the catalyst assertively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.047
• 作为产物：
  描述：

  4-溴苯腈 在 potassium phosphate 、 copper(l) iodide 、 8-羟基喹啉 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 4-((4-nitrophenyl)ethynyl)benzonitrile
  参考文献：
  名称：

  铜催化的脱丙酮 Sonogashira 偶联

  摘要：

  已经开发了一种方便的无钯和无膦方案，用于从叔炔丙醇和（杂）芳基卤化物组装内部炔烃。所提出的串联方法包括碱基促进的逆向 Favorskii 裂解，然后是铜催化的 C(sp)–C(sp 2 ) 交叉偶联。使用廉价的试剂（例如催化剂、添加剂、碱和溶剂）和良好的官能团耐受性使该程序实用且具有成本效益。该方法的合成效用通过源自天然甾体激素的乙烯基碘化物的平滑炔基化得到证实。

  DOI：

  10.1039/d2ob01267g

文献信息

• Porous organic polymer with <i>in situ</i> generated palladium nanoparticles as a phase-transfer catalyst for Sonogashira cross-coupling reaction in water
  作者：Ying Dong、Yun-Qi Chen、Jing-Jing Jv、Yue Li、Wen-Han Li、Yu-Bin Dong

  DOI：10.1039/c9ra04103f

  日期：——

  Pd(PPh3)4 catalysed in situ one-pot Suzuki cross-coupling reaction between imidazolium attached dibromobenzene and 1,3,5-tri(4-pinacholatoborolanephenyl)benzene. Besides the high thermal and chemical stability, the obtained Pd@PTC-POP can be used as a highly active and reusable phase-transfer solid catalyst to promote the Sonogashira coupling reaction in water. The obtained results indicate that the Pd@PTC-POP

  通过咪唑连接的二溴苯和 1,3 之间的 Pd(PPh 3 ) 4催化原位单锅 Suzuki 交叉偶联反应，很容易制备出一种新的负载 Pd 纳米颗粒和咪唑鎓离子液体修饰的Pd@PTC-POP有机聚合物， 5-三(4-频哪醇硼烷苯基)苯。除了具有较高的热稳定性和化学稳定性外，所获得的Pd@PTC-POP还可用作高活性和可重复使用的相转移固体催化剂，以促进水中的 Sonogashira 偶联反应。所得结果表明，Pd@PTC-POP本文可以创建一个多功能的固相转移催化剂家族，以促进在水中进行的广泛反应。
• Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction in solvent-free conditions
  作者：Sara S. E. Ghodsinia、Batool Akhlaghinia、Roya Jahanshahi

  DOI：10.1007/s11164-021-04466-y

  日期：2021.8

  characterization of the catalyst. It was found that the Co3O4/TSCN has a high performance to promote Sonogashira–Hagihara cross-coupling reaction in solvent-free conditions. Interestingly, the architecture of the catalyst provides not only the high dispersion loading of the Co3O4 NPs on the support, but also facilitates the favorable mass transfer through the catalyst structure. The catalyst could be readily

  受三壳周期性介孔有机硅空心球合成的启发，已通过包括硬模板技术和热模板技术在内的组合路线，建立了一种直接可控的制备嵌入三壳石墨氮化碳中的Co 3 O 4 NP的方法。浸渍方法。一系列的各种技术，如FT-IR，XRD，BET，TEM，FE-SEM，EDX，EDX作图，TGA和ICP-OES已用于催化剂的全面表征。发现Co 3 O 4/ TSCN在无溶剂条件下具有促进Sonogashira-Hagihara交叉偶联反应的高性能。有趣的是，催化剂的结构不仅提供了Co 3 O 4 NP在载体上的高分散负载，而且还促进了通过催化剂结构的有利的质量传递。通过过滤方法可以容易地从反应混合物中分离出催化剂，并再次使用多达五次，而催化活性没有明显降低。 图形概要 Co 3 O 4 / TSCN作为新型可持续分级催化剂的优异催化性能已在无溶剂条件下用于无Pd / Cu的Sonogashira-Hagihara交叉偶联反应中
• Photosensitizer-free, visible light-mediated recyclable gold-catalyzed cross-coupling of aryldiazonium salts and alkynyltrimethylsilanes
  作者：Jiajia Li、Junmin Chen、Hefeng Zhu、Mingzhong Cai

  DOI：10.1039/d3nj02853d

  日期：——

  temperature to afford diverse arylalkynes in moderate to good yields with high functional group tolerance, including aryl halides incompatible with traditional cross-coupling. This new heterogenized gold(I) catalyst could be easily recovered through a simple centrifugation process and reused at least nine times without any significant drop in its catalytic efficiency.

  通过(4-(氯甲基)苯乙基)三甲氧基硅烷与SBA - 15缩合，然后与( 2-(二苯基膦)苯基)甲醇和Me 2 SAuCl，然后用AgNTf 2处理并通过不同的物理化学技术进行表征。存在 10 mol% SBA-15-Ph 3 PAuNTf 2时，四氟硼酸芳基重氮盐和炔基三甲基硅烷的无光敏剂交叉偶联反应在蓝色 LED 照射下在乙腈中在室温下顺利进行，以中等至良好的产率提供多种芳基炔烃，具有高官能团耐受性，包括与传统交叉偶联不相容的芳基卤化物。这种新型多相金（I）催化剂可以通过简单的离心过程轻松回收，并重复使用至少九次，而催化效率不会出现任何显着下降。
• Click-Reagent Version of Sonogashira Coupling Protocol to Conjugated Fluorescent Alkynes with No or Reduced Homocoupling
  作者：Subhendu Sekhar Bag、Rajen Kundu、Manas Das

  DOI：10.1021/jo200005n

  日期：2011.4.1

  A click-reagent version of the Sonogashira-coupling protocol has been developed. Diarylalkynes with donor and/or acceptor substituents have been synthesized via this protocol at moderate to excellent yields and with no or drastically reduced quantities of undesired homocoupled side products. This protocol is green-solvent compatible, air-insensitive, and effective under microwave conditions.
• Acetylenes and α-Chlorostilbenes vis Phosphonate Anion
  作者：Hans Zimmer、Peter Jenö Bercz、Otto J. Maltenieks、Melvyn W. Moore

  DOI：10.1021/ja01090a058

  日期：1965.6