4'-acetylbiphenyl-2-carbonitrile

• 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'-acetylbiphenyl-2-carbonitrile
• 英文别名: 4-acetyl-2'-cyanobiphenyl；2-(4-Acetylphenyl)benzonitrile
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: LMVQQIJOEAKLPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-acetylbiphenyl-2-carbonitrile 、 乙醛酸 生成
  参考文献：
  名称：

  DE2047806

  摘要：

  公开号：
• 作为产物：
  描述：

  4'-acetyl-[1,1'-biphenyl]-2-carbaldehyde 在 O-(4-(trifluoromethyl)benzoyl)hydroxylamine 、 三氟乙酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 48.0h， 以70%的产率得到4'-acetylbiphenyl-2-carbonitrile
  参考文献：
  名称：

  Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source

  摘要：

  The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Bronsted acid. Several aliphatic, aromatic, and alpha,beta-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.

  DOI：

  10.1021/acs.orglett.5b02547

文献信息

• Cubical Palladium Nanoparticles on C@Fe3O4 for Nitro reduction, Suzuki-Miyaura Coupling and Sequential Reactions
  作者：Basuvaraj Suresh Kumar、Arlin Jose Amali、Kasi Pitchumani

  DOI：10.1016/j.molcata.2016.08.003

  日期：2016.11

  Abstract Cubical Pd nanoparticles incorporated magnetically recyclable nanoreactor (Pd cNPs/C@Fe 3 O 4 ) are found to be efficient catalysts for the hydrogenation or aromatic nitrocompounds, Suzuki-Miyaura coupling and the sequential reaction of C C coupling followed by reduction of nitrobiphenyl substrates. A variety of aryl iodides, bromides and chlorides were coupled with phenylboronic acids to

  摘要 已发现掺入磁可回收纳米反应器 (Pd cNPs/C@Fe 3 O 4 ) 的立方 Pd 纳米粒子是氢化或芳族硝基化合物、Suzuki-Miyaura 偶联和 CC 偶联随后还原硝基联苯底物的顺序反应的有效催化剂。多种芳基碘化物、溴化物和氯化物与苯基硼酸偶联形成相应的联芳基产物，并对多种硝基芳族化合物进行加氢，收率高，TON。嵌入过量100}表面的钯立方纳米粒子（Pd cNPs）的催化活性优于嵌入混合表面刻面的Pd球形纳米粒子（Pd sNPs）。即使经过五次重复循环，催化效率也保持不变。观察到的催化活性增强归因于 Pd cNPs/C@Fe 3 O 4 催化剂表面存在的高密度低配位 Pd 100} 原子，这已通过 HR-TEM 研究得到证实。此外，该催化剂是真正的多相催化剂，高度稳定，不需要任何有毒配体，在硝基还原和 Suzuki-Miyaura 偶联反应中具有广泛的底物范围，以及以
• Amine-Catalyzed Direct Photoarylation of Unactivated Arenes
  作者：Xingliang Zheng、Luo Yang、Weiyuan Du、Aishun Ding、Hao Guo

  DOI：10.1002/asia.201301371

  日期：2014.2

  Constructing biaryls through direct aromatic CH functionalization of unactivated arenes has become a popular topic in organic chemistry. Many efficient methods have been developed. In this Communication, a direct arylation of unactivated arenes with a broad range of aryl iodides is reported. This reaction proceeds through a new type of amine‐catalyzed single electron transfer initiated radical coupling

  通过未活化的芳烃的直接芳族CH官能化构建联芳基已成为有机化学中的热门话题。已经开发了许多有效的方法。在该通报中，报道了未活化的芳烃与多种芳基碘化物的直接芳基化。该反应通过新型的胺催化的单电子转移引发的自由基偶联过程进行，从而在室温下紫外线辐射下以高收率形成联芳基。仅20mol％的TMEDA用作催化剂。该转化不需要其他添加剂，从而避免使用有毒的过渡金属催化剂，强碱或大量其他有机添加剂。此更环保协议提供一种新的策略，以实现直接芳族C H功能化，并提供了一个经济高效且对环境有益的联芳基新实例。
• The 1,3-Diaminobenzene-Derived Aminophosphine Palladium Pincer Complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A Highly Active Suzuki-Miyaura Catalyst with Excellent Functional Group Tolerance
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/adsc.200900848

  日期：——

  The rapidly prepared 1,3‐diaminobenzene‐derived aminophosphine pincer complex C6H3[NHP(piperidinyl)2]2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side‐product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable

  快速制备的1,3-二氨基苯衍生的氨基膦钳形配合物C 6 H 3 [NHP（哌啶基）2 ] 2 Pd（Cl）}（1）是一种有效的Suzuki催化剂，具有出色的官能团耐受性。仅很少检测到副产物形成，例如均偶联，去溴化或原去硼，如果这样，在所有情况下均低于5％的水平。提出的反应方案是普遍适用的。实验观察表明，钯纳米颗粒的催化活性形式1。
• Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki–Miyaura coupling without intentionally added base
  作者：Aiichiro Nagaki、Yuya Moriwaki、Jun-ichi Yoshida

  DOI：10.1039/c2cc36197c

  日期：——

  We found that an integrated flow microreactor system enables the preparation of boronic esters bearing electrophilic functional groups using organolithium chemistry and that it allows for their use in Suzuki-Miyaura cross-coupling without intentionally added base. Based on this method, cross-coupling of two aryl halides bearing electrophilic functional groups was accomplished to obtain the corresponding

  我们发现，集成的流动微反应器系统能够使用有机锂化学方法制备带有亲电官能团的硼酸酯，并且可以将其用于Suzuki-Miyaura交叉偶联中而无需故意添加碱。基于此方法，完成了两个带有亲电官能团的芳基卤化物的交叉偶联，以一次获得相应的联芳基化合物。
• Synthesis of Biphenyl-2-carbonitrile Derivatives via a Palladium-Catalyzed sp² C−H Bond Activation Using Cyano as a Directing Group
  作者：Wu Li、Zhipeng Xu、Peipei Sun、Xiaoqing Jiang、Min Fang

  DOI：10.1021/ol103075n

  日期：2011.3.18

  Pd-II-catalyzed aromatic C-H bond activation using cyano as a directing group was carried out in TFA medium. Biphenyl-2-carbonitrile derivatives were therefore synthesized from aryl nitriles and aryl halides in moderate to good yields.