3-(N,N-penta-1,5-diyl-glyoxylamido)-pyridine | 88584-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(N,N-penta-1,5-diyl-glyoxylamido)-pyridine
• 英文别名: 1-(piperidin-1-yl)-2-(pyridin-3-yl)ethane-1,2-dione；1-(piperidin-1-yl)-2-(pyridine-3-yl)ethane-1,2-dione；1-(Piperidin-1-yl)-2-(pyridin-3-yl)ethane-1,2-dione；1-piperidin-1-yl-2-pyridin-3-ylethane-1,2-dione
• CAS: 88584-89-8
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: KFNRSXJXCMLCAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1-(piperidin-1-yl)-2-(pyridin-3-yl)ethanone 在 air 、 四丁基溴化铵 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以81%的产率得到3-(N,N-penta-1,5-diyl-glyoxylamido)-pyridine
  参考文献：
  名称：

  Cesium carbonate promoted aerobic oxidation of arylacetamides: an efficient access to N-substituted α-keto amides

  摘要：

  A novel cesium carbonate promoted aerobic oxidation reaction to prepare N-substituted alpha-keto amides in the presence of catalytic amount of tetra-n-butylammonium bromide was described. This reaction provides a very simple and convenient route from easily available arylacetamides in good to high yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.099

文献信息

• NIS-Catalyzed Reactions: Amidation of Acetophenones and Oxidative Amination of Propiophenones
  作者：Manjunath Lamani、Kandikere Ramaiah Prabhu

  DOI：10.1002/chem.201202703

  日期：2012.11.12

  Single‐step amination: The N‐iodosuccinimide (NIS)‐catalyzed amidation of acetophenone derivatives by using tert‐butylhydroperoxide (TBHP) as an oxidant is presented. A variety of acetyl derivatives of heterocyclic compounds were easily converted to their corresponding ketoamides under these conditions. A new, NIS‐catalyzed amination of propiophenone and its derivatives in the presence of TBHP to furnish

  单步胺化：介绍了使用叔丁基过氧化氢（TBHP）作为氧化剂的N-碘琥珀酰亚胺（NIS）催化的苯乙酮衍生物酰胺化反应。在这些条件下，杂环化合物的各种乙酰基衍生物很容易转化为它们相应的酮酰胺。在TBHP存在下，一种新的NIS催化的苯乙酮及其衍生物的胺化反应可提供相应的2-氨基酮衍生物，这是首次报道的苯乙酮衍生物的单步胺化反应。
• Homogeneous catalytic aminocarbonylation of nitrogen-containing iodo-heteroaromatics. Synthesis of N-substituted nicotinamide related compounds
  作者：Attila Takács、Balázs Jakab、Andrea Petz、László Kollár

  DOI：10.1016/j.tet.2007.07.017

  日期：2007.10

  Various primary and secondary amines, including amino acid methyl esters, were used as nucleophiles in palladium-catalysed aminocarbonylation of 2-iodopyridine, 3-iodopyridine and iodopyrazine. N-Substituted nicotinamides and 3-pyridyl-glyoxylamides (2-oxo-carboxamide type derivatives) of potential biological importance can be obtained from 3-iodopyridine as a result of simple and double carbon monoxide

  各种伯胺和仲胺，包括氨基酸甲酯，在钯催化的2-碘吡啶，3-碘吡啶和碘吡嗪的氨基羰基化反应中用作亲核试剂。具有潜在生物学重要性的N-取代的烟酰胺和3-吡啶基-乙二酰乙酰胺（2-氧代-羧酰胺型衍生物）可以分别通过简单和两次一氧化碳插入而从3-碘吡啶获得。后面的例子可以通过使用升高的一氧化碳压力以合成上可接受的产率获得。相反，仅通过使用2-碘吡啶和碘吡嗪在整个压力范围内获得N-烷基/芳基-甲酰胺。