mono-N,N-dimethylamide of malonic acid | 131566-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-N,N-dimethylamide of malonic acid
• 英文别名: N,N-dimethylpropanediamide；N',N'-dimethylpropanediamide
• CAS: 131566-91-1
• 化学式: C₅H₁₀N₂O₂
• mdl: MFCD06666649
• 分子量: 130.147
• InChiKey: BONKBSKIEUBANL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  mono-N,N-dimethylamide of malonic acid 在 palladium on activated charcoal N-甲基吡咯烷酮 、 水 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 2-[4-((S)-1-Amino-2-phenyl-ethyl)-oxazol-2-yl]-N,N-dimethyl-acetamide
  参考文献：
  名称：

  Synthesis ofN,N-Dimethylpropanediamide and its Utility for the Preparation of 2-(Acetamidomethyl)-4-aryloxazoles

  摘要：

  报道了一种实用且易于规模化的N,N-二甲基丙烷二酰胺（1）合成方法。这种双酰胺的用途在于能够从α-溴酮制备几种2,4-取代的噁唑。

  DOI：

  10.1055/s-2004-825607
• 作为产物：
  描述：

  methyl N,N-dimethyl-malonamate 在 氰化钠 、 氨 作用下， 以 甲醇 为溶剂， 以0.41 g的产率得到mono-N,N-dimethylamide of malonic acid
  参考文献：
  名称：

  的构象Ñ α在CDCl -取代肼乙酰胺3，Δδ的酰胺将氢之间的分析的珍贵的帮助，和相关到的构象氮杂β 3 -肽

  摘要：

  我们研究了氯仿溶液中一系列伯酰胺的构象。将经典的NMR工具（例如稀释实验，DMSO和2D-NOESY的影响）与X射线衍射相结合，并分析了双键mid质子之间化学位移Δδ的差异。本研究中为了理解由肼基乙酰胺采用的构象是写给1A和1B作为模型化合物为氮杂- β 3-肽。以这种方式，有可能表明这些化合物的酰胺基充当氢键供体并与两个不同的氢键受体相互作用。我们得出的结论是，肼苯二酚，一种在固态下观察到的特定的分叉H键系统，也是溶液中肼基乙酰胺1a和1b的优选构象。我们的研究结果表明，与所述短距离相互作用Ñ α -氮的孤对电子不仅稳定C8 pseudocycle但也可能有助于氮杂- β的折叠处理3 -肽。鉴于此，它可以解释为什么氮杂β 3 -肽发展比较不同的氢键网络，其等量β 3-肽类似物。我们的工作与肼基肽作为β肽概念的扩展的最新兴趣保持一致。

  DOI：

  10.1021/jo051887q

文献信息

• Conformation-directing effects of a single intramolecular amide-amide hydrogen bond: variable-temperature NMR and IR studies on a homologous diamide series
  作者：Samuel H. Gellman、Gregory P. Dado、Gui Bai Liang、Bruce R. Adams

  DOI：10.1021/ja00004a016

  日期：1991.2

  We have studied intramolecular hydrogen bonding in a homologous series of diamides (compounds 1-6) in methylene chloride, 9:1 carbon tetrachloride/benzene, and acetonitrile. By correlating variable-temperature H-1 NMR and IR measurements, we have shown that the temperature dependence of the amide proton NMR chemical shift (DELTA-delta/DELTA-T) can provide qualitative (and in some cases quantitative) information on the thermodynamic relationship between the intramolecularly hydrogen bonded and non-hydrogen-bonded states of flexible molecules. Among the hydrogen-bonded ring sizes represented in the diamide series, the intramolecular interaction is particularly enthalpically favorable in the nine-membered hydrogen-bonded ring (compound 4). Variable-temperature IR and NMR data indicate that the internally hydrogen bonded state of diamide 4 is 1.4-1.6 kcal/mol more favorable enthalpically than the non-hydrogen-bonded state, in methylene chloride solution; the non-hydrogen-bonded state is 6.8-8.3 eu more favorable entropically in this solvent. In contrast, there appear to be much smaller enthalpy differences between the internally hydrogen bonded and non-hydrogen-bonded states of diamides 2 and 3. Our findings are important methodologically because the temperature dependences of amide proton chemical shifts are commonly used to elucidate peptide conformation in solution. Our results show that previous "rules" for the interpretation of such data are incomplete. In non-hydrogen-bonding solvents, small amide proton DELTA-delta/DELTA-T values have been taken to mean that the proton is either entirely free of hydrogen bonding or completely locked in an intramolecular hydrogen bond over the temperature range studied. We demonstrate that an amide proton can be equilibrating between intramolecularly hydrogen bonded and non-hydrogen-bonded states and still manifest a small chemical shift temperature dependence (implying that the hydrogen-bonded and non-hydrogen-bonded states are of similar enthalpy).
• Conformation of <i>N</i>^α-Substituted Hydrazino Acetamides in CDCl₃, the Precious Help of the Analysis of Δδ between Amidic Hydrogens, and Correlation to the Conformation of Aza-β³-peptides
  作者：Arnaud Salaün、Annaïck Favre、Barbara Le Grel、Michel Potel、Philippe Le Grel

  DOI：10.1021/jo051887q

  日期：2006.1.1

  adopted by hydrazino acetamides 1a and 1b as model compounds for aza-β3-peptides. In this manner, it was possible to show that the amidic group of these compounds acts as a H-bond donor and interacts with two different H-bond acceptors. We concluded that the hydrazinoturn, a specific bifurcated H-bond system observed in the solid state, is also the preferred conformation of hydrazino acetamides 1a and 1b

  我们研究了氯仿溶液中一系列伯酰胺的构象。将经典的NMR工具（例如稀释实验，DMSO和2D-NOESY的影响）与X射线衍射相结合，并分析了双键mid质子之间化学位移Δδ的差异。本研究中为了理解由肼基乙酰胺采用的构象是写给1A和1B作为模型化合物为氮杂- β 3-肽。以这种方式，有可能表明这些化合物的酰胺基充当氢键供体并与两个不同的氢键受体相互作用。我们得出的结论是，肼苯二酚，一种在固态下观察到的特定的分叉H键系统，也是溶液中肼基乙酰胺1a和1b的优选构象。我们的研究结果表明，与所述短距离相互作用Ñ α -氮的孤对电子不仅稳定C8 pseudocycle但也可能有助于氮杂- β的折叠处理3 -肽。鉴于此，它可以解释为什么氮杂β 3 -肽发展比较不同的氢键网络，其等量β 3-肽类似物。我们的工作与肼基肽作为β肽概念的扩展的最新兴趣保持一致。
• Synthesis of<i>N</i>,<i>N</i>-Dimethylpropanediamide and its Utility for the Preparation of 2-(Acetamidomethyl)-4-aryloxazoles
  作者：John A. Ragan、Michael Burmaster、Paul D. Hill

  DOI：10.1055/s-2004-825607

  日期：——

  A practical, readily scaleable synthesis of N,N-dimethylpropanediamide (1) is reported. The utility of this bis-amide is d­emonstrated in the preparation of several 2,4-disubstituted oxazoles from α-bromoketones.

  报道了一种实用且易于规模化的N,N-二甲基丙烷二酰胺（1）合成方法。这种双酰胺的用途在于能够从α-溴酮制备几种2,4-取代的噁唑。