N-(4-cyanophenyl)-N-phenylacetamide

• 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-cyanophenyl)-N-phenylacetamide
• 英文别名: N-phenyl-4-cyanoacetanilide
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: AMPUKXMJPCKYRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 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：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-碘氰基苯 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 39.0h， 生成 N-(4-cyanophenyl)-N-phenylacetamide
  参考文献：
  名称：

  Metal-Free N-Arylation of Secondary Amides at Room Temperature

  摘要：

  The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.

  DOI：

  10.1021/acs.orglett.5b01079

文献信息

• Palladium-Catalyzed Intermolecular Coupling of Aryl Halides and Amides
  作者：Jingjun Yin、Stephen L. Buchwald

  DOI：10.1021/ol005654r

  日期：2000.4.1

  [formula: see text] The first general intermolecular C-N bond-forming reactions between aryl halides and amides were realized using a palladium catalyst with Xantphos as the ligand. Aryl triflates, carbamates, and sulfonamides are also viable substrates for the amidations, which proceed at 45-110 degrees C with 1-4 mol% of Pd catalyst in 66-99% yields and exhibit good functional group compatibility

  芳卤化物和酰胺之间的第一个一般的分子间CN键形成反应是使用以黄磷为配体的钯催化剂实现的。芳基三氟甲磺酸酯，氨基甲酸酯和磺酰胺也是酰胺化的可行底物，它们在45-110℃下以1-4 mol％的Pd催化剂进行，收率为66-99％，并具有良好的官能团相容性。
• Exploiting the Marcus inverted region for first-row transition metal–based photoredox catalysis
  作者：Amy Y. Chan、Atanu Ghosh、Jonathan T. Yarranton、Jack Twilton、Jian Jin、Daniela M. Arias-Rotondo、Holt A. Sakai、James K. McCusker、David W. C. MacMillan

  DOI：10.1126/science.adj0612

  日期：2023.10.13

  Second- and third-row transition metal complexes are widely employed in photocatalysis, whereas earth-abundant first-row transition metals have found only limited use because of the prohibitively fast decay of their excited states. We report an unforeseen reactivity mode for productive photocatalysis that uses cobalt polypyridyl complexes as photocatalysts by exploiting Marcus inverted region behavior

  第二和第三行过渡金属络合物广泛应用于光催化，而地球上丰富的第一行过渡金属由于其激发态的快速衰减而仅具有有限的用途。我们报告了一种不可预见的高效光催化反应模式，该模式利用钴聚吡啶配合物作为光催化剂，利用马库斯倒置区域行为，将激发态能量的增加与激发态寿命的增加结合起来。这些钴 (III) 配合物凭借其强大的氧化还原电位和足够长的激发态寿命可以参与双分子反应，催化氧化 C(sp 2 )–芳基酰胺与具有挑战性的位阻芳基硼酸的 N 偶联。更一般地说，结果意味着发色团可以设计为增加激发态寿命，同时增加激发态能量，为使用相对丰富的金属作为光氧化还原催化剂提供了途径。
• Dharmasena, Priyanthi M.; Oliveira-Campos, Ana-M. F.; Raposo, M. Manuela M., Journal of Chemical Research, Miniprint, 1994, # 8, p. 1601 - 1611
  作者：Dharmasena, Priyanthi M.、Oliveira-Campos, Ana-M. F.、Raposo, M. Manuela M.、Shannon, Patrick V. R.

  DOI：——

  日期：——
• A facile N-arylation of acetanilides with arynes
  作者：James C. Haber、Michael A. Lynch、Stacey L. Spring、Anthony D. Pechulis、Joseph Raker、Yi Wang

  DOI：10.1016/j.tetlet.2011.08.146

  日期：2011.11

  An efficient, mild and transition-metal-free method for the N-arylation of acetanilides, leading to a range of unsymmetrical diarylamine products is reported. Reactions of ortho-silylaryl triflates with acetanilides in the presence of tetrabutylammonium triphenyldifluorosilicate (TBAT) in toluene afforded the desired products in good to excellent yields. Regioselectivity was also observed when unsymmetrical aryne precursors were used. (C) 2011 Elsevier Ltd. All rights reserved.
• Metal-Free <i>N</i>-Arylation of Secondary Amides at Room Temperature
  作者：Fredrik Tinnis、Elin Stridfeldt、Helena Lundberg、Hans Adolfsson、Berit Olofsson

  DOI：10.1021/acs.orglett.5b01079

  日期：2015.6.5

  The arylation of secondary acyclic amides has been achieved with diaryliodonium salts under mild and metal-free conditions. The methodology has a wide scope, allows synthesis of tertiary amides with highly congested aryl moieties, and avoids the regioselectivity problems observed in reactions with (diacetoxyiodo)benzene.