N-(4′-methoxy-[1,1′-biphenyl]-4-yl)acetamide | 2221-22-9

• 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: N-(4′-methoxy-[1,1′-biphenyl]-4-yl)acetamide
• 英文别名: N-(4'-methoxy-[1,1'-biphenyl]-4-yl)acetamide；N-(4'-methoxybiphenyl-4-yl)acetamide；4'-methoxybiphenyl-4-acetanilide；N-(4'-methoxy-biphenyl-4-yl)-acetamide；N-(4'-Methoxy-biphenyl-4-yl)-acetamid；4'-Acetamino-4-methoxy-diphenyl；N-[4-(4-methoxyphenyl)phenyl]acetamide
• CAS: 2221-22-9
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: DVGUYVDUSBITJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4′-methoxy-[1,1′-biphenyl]-4-yl)acetamide 在 氢氧化钾 作用下， 生成 4-甲氧基-联苯-4-胺
  参考文献：
  名称：

  Iwanow; Panaiotow, Doklady Akademii Nauk SSSR, 1953, vol. 93, p. 1041

  摘要：

  DOI：
• 作为产物：
  描述：

  4'-hydroxy-4-acetylaminobiphenyl 生成 N-(4′-methoxy-[1,1′-biphenyl]-4-yl)acetamide
  参考文献：
  名称：

  DE85988

  摘要：

  公开号：

文献信息

• A base-free, one-pot diazotization/cross-coupling of anilines with arylboronic acids
  作者：Fanyang Mo、Di Qiu、Yubo Jiang、Yan Zhang、Jianbo Wang

  DOI：10.1016/j.tetlet.2010.11.099

  日期：2011.1

  Pd-catalyzed one-pot diazotization/cross-coupling is realized for the synthesis of biaryls directly from anilines and arylboronic acids.

  实现了钯催化的一锅重氮化/交叉偶联，可直接从苯胺和芳基硼酸合成联芳基。
• Liquid-Assisted Grinding Accelerating: Suzuki–Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions
  作者：Zhi-Jiang Jiang、Zhen-Hua Li、Jing-Bo Yu、Wei-Ke Su

  DOI：10.1021/acs.joc.6b01938

  日期：2016.10.21

  studied using mechanical Suzuki–Miyaura reaction of aryl chlorides as the model reaction. Catalytic systems of Davephos and PCy3 are tested respectively showing strong influences from different liquids. Unexpected improvement of yield over 55% is observed using alcohols as additives, which is explained by in situ formed alkoxides and their participation in oxidative addition. Further expansion of substrates

  使用芳基氯化物的Suzuki-Miyaura机械反应作为模型反应，研究了液体辅助研磨的效果。分别测试了Davephos和PCy 3的催化体系，显示出不同液体的强烈影响。使用醇作为添加剂时，收率意外提高了55％以上，这可通过原位形成的醇盐及其参与氧化加成反应来解释。使用Pd（OAc）2 / PCy 3 / MeOH系统进一步扩展底物，可以以高到高收率获得所需的产物。
• Cost‐effective bio‐derived mesoporous carbon nanoparticles‐supported palladium catalyst for nitroarene reduction and Suzuki–Miyaura coupling by microwave approach
  作者：S. Supriya、Guddekoppa S. Ananthnag、Vijayendra S. Shetti、B.M. Nagaraja、Gurumurthy Hegde

  DOI：10.1002/aoc.5384

  日期：2020.3

  at 160 °C using 12 mol% of Pd/CNS (0.36% actual Pd content). The reduction of nitroarenes into their respective amino compounds was achieved in 10–20 min (conversion up to 100%); by contrast, the Suzuki–Miyaura reactions yielded up to 98% at 150 °C with 10 mol% of Pd/CNS catalyst. The products were identified using gas chromatography and nuclear magnetic resonance spectroscopy. The catalyst was isolated

  通过将Pd固定在槟榔仁衍生的碳纳米球（CNSs）上，合成了一种新的非均相催化剂。中枢神经系统无需任何进一步的活化过程，即可在其表面容纳3％的Pd。新型Pd / CNS材料用于还原硝基芳烃以及溴芳烃与芳基硼酸的Suzuki-Miyaura偶联反应。反应在微波辐射下于160°C使用12 mol％的Pd / CNS（实际Pd含量为0.36％）进行。在10至20分钟内将硝基芳烃还原为各自的氨基化合物（转化率高达100％）；相反，使用10 mol％的Pd / CNS催化剂，Suzuki-Miyaura反应在150°C时的收率高达98％。使用气相色谱法和核磁共振波谱法鉴定产物。从反应混合物中分离出催化剂，并重新使用而活性没有明显损失。因此，本工作介绍了单源多孔CNS作为Pd的有效催化载体，在成本和效率方面建立了现有Pd / C的替代品。
• Reusable resin plug-bound palladium catalysts for organic synthesis
  作者：Butrus Atrash、John Reader、Mark Bradley

  DOI：10.1016/s0040-4039(03)00977-8

  日期：2003.6

  Resin plugs, a unique and conveniently handled form of resin, prepared by sintering high-density polyethylene (HDPE) with pre-functionalised resins, were derivatised and loaded with palladium(0). These 'plugs' were used in the preparation of a Suzuki reaction based library and the removal of allyl ester protecting groups. The 'plugs of catalyst' were easily separated from the reaction mixture and were re-used multiple times with minimal loss of activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology
  作者：Riina K. Arvela、Nicholas E. Leadbeater、Michael S. Sangi、Victoria A. Williams、Patricia Granados、Robert D. Singer

  DOI：10.1021/jo048531j

  日期：2005.1.1

  We present here a reassessment of our transition-metal free Suzuki-type coupling protocol. We believe that, although the reaction can be run without the need for addition of a metal catalyst, palladium contaminants down to a level of 50 ppb found in commercially available sodium carbonate are responsible for the generation of the biaryl rather than, as previously suggested, an alternative non-palladium-mediated pathway. We present a revised methodology for Suzuki couplings using ultralow palladium concentrations for use with aryl and vinyl boronic acids and discuss the effects of the purity of the boronic acid on the reaction.