N,N-dibutyl-2-oxoacetamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-dibutyl-2-oxoacetamide
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: HIUKCFDTTJWUSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  一氧化碳 、 lithium dibutylamide 在 水 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以100%的产率得到N,N-dibutyl-2-oxoacetamide
  参考文献：
  名称：

  Aggregation studies of lithium dialkylamides. The role of aggregates in the carbonylation reaction

  摘要：

  C-13 NMR spectroscopy and isotopic exchange in carbonylation intermediates have been successfully employed to characterize aggregation of lithium dialkylamides in THF solution. It is shown that lithium (3-oxapentamethylene)amide forms a 1:1 mixed aggregate with morpholine. The aggregate remains even in diluted THF solution. Lithium pentamethyleneamide also forms aggregates with piperidine while the less acidic amines do not form mixed aggregates with the corresponding lithium dialkylamide either in the solid state or in THF solution. The product composition in the carbonylation reaction of lithium dialkylamides is highly dependent on their aggregation states, and this phenomenon can be successfully used for synthetic purposes.

  DOI：

  10.1021/jo00059a042

文献信息

• New Insights into the Chemistry of Lithium Carbamoyls:  Characterization of an Adduct (R₂NC(O)CLi(OLi)NR₂)
  作者：Norma S. Nudelman、Guadalupe E. García Liñares

  DOI：10.1021/jo9908445

  日期：2000.3.1

  the reaction mixtures showed the presence of similar intermediates in all cases: adducts of this type have not been reported before. These dilithiated intermediates were trapped with methyl iodide giving the corresponding doubly methylated derivatives. Isolation of substituted glyoxylamides and quantitative determination of the products yields constitute further evidence of the whole reaction scheme

  二环己基氨基锂与N，N-二丁基甲酰胺，1-甲酰基哌啶和4-甲酰基吗啉的反应研究表明，由这些化合物引起的平衡向加合物的形成转变，该加合物迅速塌陷为二环己胺，并衍生出锂化的氨基甲酰基阴离子最初的二取代甲酰胺。氨基甲酸锂的进一步反应导致形成新的加合物，其中锂化的碳与N，O和羰基官能团键合。反应混合物的（13）C NMR分析表明，在所有情况下都存在相似的中间体：以前没有这种类型的加合物的报道。这些二片化中间体被碘甲烷截留，得到相应的双甲基化衍生物。
• Development of an organo- and enzyme-catalysed one-pot, sequential three-component reaction
  作者：Angela Kinnell、Thomas Harman、Matilda Bingham、Alan Berry、Adam Nelson

  DOI：10.1016/j.tet.2012.02.010

  日期：2012.9

  A one-pot, three-component process is described which involves both organo- and enzyme-catalysed carbon-carbon bond-forming steps. In the first step, an organocatalyst catalyses the aldol reaction between acetaldehyde and a glyoxylamide. After dilution with additional aqueous buffer, and addition of pyruvate and an aldolase enzyme variant, a second aldol reaction occurs to yield a final product. Crucially, it was possible to develop a reaction in which both the organo- and enzyme-catalysed reactions could be performed in the same aqueous buffer system. The reaction described is the first example of a one-pot, three-component reaction in which the two carbon-carbon bond-forming processes are catalysed using the combination of an organocatalyst and an enzyme. (C) 2012 Elsevier Ltd. All rights reserved.
• Aggregation studies of lithium dialkylamides. The role of aggregates in the carbonylation reaction
  作者：N. S. Nudelman、E. Lewkowicz、J. J. P. Furlong

  DOI：10.1021/jo00059a042

  日期：1993.3

  C-13 NMR spectroscopy and isotopic exchange in carbonylation intermediates have been successfully employed to characterize aggregation of lithium dialkylamides in THF solution. It is shown that lithium (3-oxapentamethylene)amide forms a 1:1 mixed aggregate with morpholine. The aggregate remains even in diluted THF solution. Lithium pentamethyleneamide also forms aggregates with piperidine while the less acidic amines do not form mixed aggregates with the corresponding lithium dialkylamide either in the solid state or in THF solution. The product composition in the carbonylation reaction of lithium dialkylamides is highly dependent on their aggregation states, and this phenomenon can be successfully used for synthetic purposes.