N,N-diethyl-2-pyridylglyoxylamide | 106910-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-diethyl-2-pyridylglyoxylamide
• 英文别名: N,N-diethyl-α-oxo-2-pyridineacetamide；N,N-diethyl-2-pyridylglyoxamide；N,N-diethyl-2-oxo-2-pyridin-2-ylacetamide
• CAS: 106910-99-0
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: GYRHMZPJESRKAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：

  N,N-二乙基氰乙酰胺 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-2-pyridylglyoxylamide
  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％。
• Synthesis of pyridylglyoxylic acid derivatives via a palladium-catalysed double carbonylation of iodopyridines
  作者：Samuel Couve-Bonnaire、Jean-François Carpentier、Yves Castanet、André Mortreux

  DOI：10.1016/s0040-4039(99)00596-1

  日期：1999.5

  4-Iodopyridiens react with CO and HNEt2 or in the presence of a catalytic amount of PdCl2(PPh3)2 to give the corresponding α-keto amides and esters in fair to high yields.

  4-碘吡啶鎓与CO和HNEt 2或在催化量的PdCl 2（PPh 3）2存在下反应，以相当高的收率得到相应的α-酮酰胺和酯。
• Jones, Gurnos; Mouat, Deborah J.; Tonkinson, Daryl J., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2719 - 2724
  作者：Jones, Gurnos、Mouat, Deborah J.、Tonkinson, Daryl J.

  DOI：——

  日期：——
• Catalytic Synthesis and Asymmetric Reduction of Pyridylglyoxylic Amides and Esters
  作者：Samuel Couve-Bonnaire、Jean-François Carpentier、André Mortreux、Yves Castanet

  DOI：10.1002/1615-4169(20010330)343:3<289::aid-adsc289>3.0.co;2-1

  日期：2001.3.30

  The preparation of 2-pyridyl- and 4-pyridylglyoxylic esters and amides in moderate to high yields via palladium-catalyzed double carbonylation of 2-iodo- and 4-iodopyridines is reported. The effect of temperature, CO pressure, solvent, nature and concentration of nucleophile, nature of catalyst precursor, and substituents on iodopyridines has been investigated. The reduction of 4-pyridylglyoxylate esters into the corresponding alpha -hydroxy esters via ruthenium-catalyzed asymmetric hydrogenation or using alpine-borane proceeded in high yields but poor enantioselectivity. The results for the carbonylation and the hydrogenation catalytic processes are discussed in terms of electronic effects induced by the pyridyl ring.
• JONES, G.;MOUAT, D. J.;TONKINSON, D. J., J. CHEM. SC. PERKIN TRANS., 1985, N 12, 2719-2723
  作者：JONES, G.、MOUAT, D. J.、TONKINSON, D. J.

  DOI：——

  日期：——