3-diazo-N-methyl-2-oxopropanamide | 36261-17-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-diazo-N-methyl-2-oxopropanamide
• 英文别名: Diazo-brenztraubensaeure-N-methylamid
• CAS: 36261-17-3
• 化学式: C₄H₅N₃O₂
• 分子量: 127.103
• InChiKey: XRYLLQYSWXJQHT-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-diazo-N-methyl-2-oxopropanamide 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 1-amino-1,2,5,6-tetrahydro-1,2,3-triazine-5,6-dione
  参考文献：
  名称：

  Zalesov, V. V.; Vyaznikova, N. G.; Shurov, S. N., Russian Journal of Organic Chemistry, 1995, vol. 31, # 7, p. 1005 - 1010

  摘要：

  DOI：
• 作为产物：
  描述：

  重氮甲烷 、 3-(2,3-二氢-5-苯并呋喃)-丙酸 生成 3-diazo-N-methyl-2-oxopropanamide
  参考文献：
  名称：

  3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor

  摘要：

  A series of substituted 3-hydroxy-quinolin-2-one derivatives 6 was synthesized and evaluated as inhibitors of [H-3]-glycine and [H-3]-AMPA binding to rat cortical membranes. These compounds were generally found to be more potent ligands for the NMDA-associated glycine binding site than the AMPA receptor. Affinity for the glycine site was found to be influenced by both the electronic and steric properties associated with the C-4 substituent and the nature and pattern of substitution of the aromatic ring. The most active compound in this series, 6y, displaces [H-3]-glycine with an IC50 of 29 nM.

  DOI：

  10.1016/0960-894x(96)00031-5

文献信息

• Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: experimental investigation and theoretical rationalization
  作者：Hengzhen Qi、Xinyao Li、Jiaxi Xu

  DOI：10.1039/c0ob00783h

  日期：——

  The stereoselectivity of the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents was investigated experimentally by determination of the product stereochemistry and theoretically via DFT calculations. The results indicate that imines preferentially attack the less sterically hindered exo-side of the ketenes to generate zwitterionic intermediates. Subsequently, for cyclic imines, the intermediates undergo a conrotatory ring closure directly to produce β-lactams, while for linear imines, the imine moiety of the intermediates isomerizes to more stable intermediates, which further undergo a conrotatory ring closure to afford trans-β-lactams. The steric hindrance and the isomerization, rather than the torquoelectronic effect, play crucial roles in controlling the stereoselectivity in the practical Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents, although the unaccessible borylketene with a powerful electron acceptor group controls the stereoselectivity torquoelectronically, in theory.

  通过确定产物立体化学和基于密度泛函理论（DFT）的计算，实验上研究了涉及带有电子受体取代基的单取代乙烯酮的斯陶丁格反应的立体选择性。结果表明，亚胺优先攻击乙烯酮上立体障碍较小的外侧，生成内鎓离子中间体。随后，对于环状亚胺，中间体直接进行协同环合反应生成β-内酰胺；而对于线性亚胺，中间体的亚胺部分异构化为更稳定的中间体，后者进一步进行协同环合反应，产生反式β-内酰胺。在实际涉及带有电子受体取代基的单取代乙烯酮的斯陶丁格反应中，立体障碍和异构化而不是扭曲电子效应在控制立体选择性中起着关键作用，尽管在理论上，具有强电子受体基团的不可获得的硼乙烯酮通过扭曲电子效应控制立体选择性。
• Stereochemistry and Mechanistic Insight in the [2^k+2ⁱ+2ⁱ] Annulations of Ketenes and Imines
  作者：Zhanhui Yang、Wei He、Baoxiang Cheng、Jiaxi Xu

  DOI：10.1021/acs.joc.6b00279

  日期：2016.6.3

  products due to the occurrence of the stepwise nucleophilic annulation. However, in the [2k+2i+2i] annulations of seven-membered cyclic imine dibenzo[b,f][1,4]oxazepine, the zwitterionic aza-butadiene-type intermediates exclusively undergo exo hetero-Diels–Alder cycloadditions with another molecule of imine to yield (2,4)-trans-(4,5)-trans-[2k+2i+2i] annuladducts stereospecifically, regardless of the ketene

  以六元3,4-二氢异喹啉为亚胺探针，研究了一个烯酮分子与两个亚胺分子的环化反应[[2 k +2 i +2 i ]的环化反应中的立体化学和机理。提出了一种协同的杂Diels-Alder环加成机理来解释立体化学结果。在大多数情况下，从烯酮和亚胺生成的两性离子2-氮杂-1,3-丁二烯型中间体会与第二个亚胺分子发生内杂-Diels -Alder环加成反应。对于带有给电子取代基的烯酮，（2,4）-顺式-（4,5）-顺式-[2 k +2 i +2 i]年环化合物是立体定向形成的，而对于带有电子接受取代基的烯酮，（2,4）-顺式-（4,5）-反式-[2 k +2 i +2 i ]年环化合物是立体定向生成的。芳氧基烯酮和3,4-二氢异喹啉的[2 k +2 i +2 i ]环由于逐步的亲核环化而产生立体发散产物。然而，在[2 ķ 2我2我] 7元环亚胺二苯并annulations [ b，˚F] [1,4]
• Viomycin. Part II. The structure of the chromophore
  作者：B. W. Bycroft、D. Cameron、L. R. Croft、A. Hassanali-Walji、A. W. Johnson、T. Webb

  DOI：10.1039/p19720000827

  日期：——

  unit of viomycin is shown to be the monoureide of C-formylglycine, which is present in peptide combination. Hydrogenolysis of viomycin followed by hydrolysis yields alanine, which is not present in viomycin hydrolysates and which is derived from the chromophore. Other reactions of viomycin which involve the chromophore are discussed. The rate of evolution of urea during mild hydrolyses of viomycin is shown

  显示出维霉素的发色单元是C-甲酰基甘氨酸的单脲，其存在于肽组合中。维霉素的氢解然后水解产生丙氨酸，丙氨酸不存在于维霉素水解产物中，其衍生自发色团。讨论了涉及生色团的紫霉素的其他反应。尿素轻度水解过程中尿素的释放速率显示出与生色团的损失速率相对应。不稳定的产品，去氨脲霉素，可以与尿素重新组合以重建抗生素。
• Posyagin, G. S.; Zalesov, V. V.; Andreichikov, Yu. S., Journal of general chemistry of the USSR, 1989, vol. 59, # 11.1, p. 2184 - 2187
  作者：Posyagin, G. S.、Zalesov, V. V.、Andreichikov, Yu. S.、Posyagina, E. Yu.、Vyaznikova, N. G.

  DOI：——

  日期：——