N,N-diethyl-α-oxo-3-pyridineacetamide | 84039-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-diethyl-α-oxo-3-pyridineacetamide
• 英文别名: N,N-diethyl-2-oxo-2-(pyridin-3-yl)acetamide；N,N-diethyl-3-pyridylglyoxamide；N,N-diethyl-2-oxo-2-pyridin-3-ylacetamide
• CAS: 84039-67-8
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: JPBMDMOYKBKYFE-UHFFFAOYSA-N

物化性质

• 沸点：
  323.3±34.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  烟酸甲酯 在 sodium hypochlorite 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 N,N-diethyl-α-oxo-3-pyridineacetamide
  参考文献：
  名称：

  A Strategy for the Synthesis of Aryl α-Ketoamides Based upon the Acylation of Anions Derived from Cyanomethylamines Followed by Oxidative Cleavage

  摘要：

  [GRAPHICS]Cyanomethylamines, prepared by alkylation of amines with chloroacetonitrile, were deprotonated using NaHDMS in THF, reacted with heteroaryl or substitutedphenyl esters, and then oxidized by adding Clorox(TM) to afford aryl alpha-ketoamides in a single operation In good overall yields.

  DOI：

  10.1021/ol010297l

文献信息

• Double carbonylation of aryl iodides with diethylamine catalyzed by dinuclear palladium complexes
  作者：Naofumi Tsukada、Yoichi Ohba、Yoshio Inoue

  DOI：10.1016/j.jorganchem.2003.08.014

  日期：2003.12

  Dinuclear palladium complexes bridged by a novel PNNP ligand, N,N′-bis[(2-diphenylphosphino)phenylformamidinate (dpfam), were found to be very efficient and selective catalysts for the double carbonylation of iodobenzene with diethylamine using K3PO4 as base and 1,4-dioxane as solvent with a TON up to 105 and selectivity of 96%.

  已发现由新型PNNP配体N，N'-双[（2-二苯基膦基）苯基甲ami酸盐（dpfam）桥接的双核钯络合物是非常有效的选择性催化剂，可使用K 3 PO 4作为二乙胺与二乙胺进行双羰基化反应。碱和1,4-二恶烷作为溶剂，TON高达10 5，选择性为96％。
• Catalytic double carbonylation of organohalogen compounds promoted by palladium complexes
  作者：Fumiyuki Ozawa、Hidehiko Soyma、Takakazu Yamamoto、Akio Yamamoto

  DOI：10.1016/s0040-4039(00)87621-2

  日期：1982.1

  Various organohalogem compounds can be catalytically converted into α-keto amides on reaction with carbon monoxide and amines. Tertiary phosphine-coordinated palladium compounds are particularly suitable as the double carbonylation catalyst.

  与一氧化碳和胺反应后，各种有机卤代烃化合物可催化转化为α-酮酰胺。叔膦配位的钯化合物特别适合作为双羰基化催化剂。
• Aryl-palladium-NHC complex: efficient phosphine-free catalyst precursors for the carbonylation of aryl iodides with amines or alkynes
  作者：Chunyan Zhang、Jianhua Liu、Chungu Xia

  DOI：10.1039/c4ob01878h

  日期：——

  aryl-palladium-NHC compounds was prepared according to the reported methods and their catalytic activity in the carbonylation of aryl iodides to synthesize α-keto amides and alkynones was examined. These practical aryl-palladium-NHC complexes have shown highly efficient catalyzed carbonylation and Sonogashira carbonylation reactions, with high turnover number in synthesis of α-keto amides (TON = 4300) and in synthesis

  根据报道的方法制备了一系列芳基-钯-NHC化合物，并研究了它们在芳基碘化物羰基化反应中合成α-酮酰胺和炔烃的催化活性。这些实用的芳基-钯-NHC配合物已显示出高效的催化羰基化和Sonogashira羰基化反应，在合成α-酮酰胺（TON = 4300）和炔烃（TON = 980）时具有很高的转化率。
• Palladium nanoparticles on a pyridinium supported ionic liquid phase: a recyclable and low-leaching palladium catalyst for aminocarbonylation reactions
  作者：Bernadett Adamcsik、Enikő Nagy、Béla Urbán、Péter Szabó、Péter Pekker、Rita Skoda-Földes

  DOI：10.1039/d0ra03406a

  日期：——

  A new SILP (Supported Ionic Liquid Phase) palladium catalyst was prepared and characterized by 13C and 29Si CP MAS NMR, DTG, FTIR and TEM. The presence of the grafted pyridinium cations on the surface of the support was found to result in the formation of highly dispersed Pd nanoparticles with their diameter in the range of 1–2 nm. The catalyst was proved to be active not only in the aminocarbonylation

  制备了一种新型 SILP（负载型离子液相）钯催化剂，并通过13 C 和29表征Si CP MAS NMR、DTG、FTIR 和 TEM。发现载体表面上接枝吡啶鎓阳离子的存在导致形成高度分散的 Pd 纳米粒子，其直径在 1-2 nm 范围内。该催化剂被证明不仅在一些模型化合物的氨基羰基化中具有活性，而且在活性药物成分的合成中也具有活性。首次在氨基羰基化中进行催化剂回收和钯浸出研究，生成 CX-546（1-(1,4-benzodioxan-6-ylcarbonyl)piperidine）、吗氯贝胺、Nikethamide 和非那雄胺的前体。后一反应证明，在多相催化剂的帮助下，不仅芳基碘化物，而且碘代烯烃都可以转化为产物。结果表明，在不同底物的反应中，应始终对条件进行微调，以达到最佳结果。还观察到钯损失在很大程度上取决于反应伙伴的性质。
• OZAWA, FUMIYUKI;SOYAMA, HIDEHIKO;YAMAMOTO, TAKAKAZU;YAMAMOTO, AKIO, TETRAHEDRON LETT., 1982, 23, N 33, 3383-3386
  作者：OZAWA, FUMIYUKI、SOYAMA, HIDEHIKO、YAMAMOTO, TAKAKAZU、YAMAMOTO, AKIO

  DOI：——

  日期：——