N-methyl glyoxamide | 57122-20-0

• 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-methyl glyoxamide
• 英文别名: N-Methylglyoxylamid；N-methyl-2-oxoacetamide
• CAS: 57122-20-0
• 化学式: C₃H₅NO₂
• mdl: MFCD19219650
• 分子量: 87.0782
• InChiKey: NOFKDVPQXNNKCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-乙炔-1H-吲唑 、 N-methyl glyoxamide 在 盐酸羟胺 、 chloroamine-T 、 铜 、 copper(II) sulfate 、 sodium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 生成 5-(1H-indazol-5-yl)-N-methylisoxazole-3-carboxamide
  参考文献：
  名称：

  Scaffold oriented synthesis. Part 3: Design, synthesis and biological evaluation of novel 5-substituted indazoles as potent and selective kinase inhibitors employing [2+3] cycloadditions

  摘要：

  We report the synthesis and biological evaluation of 5-substituted indazoles and amino indazoles as kinase inhibitors. The compounds were synthesized in a parallel synthesis fashion from readily available starting materials employing [2+3] cycloaddition reactions and were evaluated against a panel of kinase assays. Potent inhibitors were identified for numerous kinases such as Rock2, Gsk3 beta, Aurora2 and Jak2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.007
• 作为产物：
  描述：

  dimethylaminotartaramide 在 高碘酸 作用下， 以 四氢呋喃 为溶剂， 生成 N-methyl glyoxamide
  参考文献：
  名称：

  通过亚氨基酰胺获得具有芳基硼酸的α-功能化甘氨酸衍生物

  摘要：

  开发了一种有效的方法，用于亚氨基酰胺与芳基硼酸的 α-芳基化。针对该芳基化反应检查了不同的底物。对于N-苯基亚氨基酰胺的α-芳基化，由于苯基的吸电子特性，酰胺与亚胺醇之间的互变异构化更加困难。因此，观察到低反应速率和低转化率。这种现象支持我们之前提出的α-氨基酸衍生物芳基化机制。同时，该方法为α-功能化甘氨酸衍生物的合成提供了一种替代方法。

  DOI：

  10.1055/s-0029-1218266

文献信息

• Access to α-Functionalized Glycine Derivatives with Arylboronic Acid via Imino Amides
  作者：Chao-Jun Li、Liang Zhao、Xiaohong Liao

  DOI：10.1055/s-0029-1218266

  日期：2009.11

  An efficient approach was developed for the α-arylation of imino amides with arylboronic acids. Different substrates were examined for this arylation reaction. For the α-arylation of N-phenylimino amide, due to the electron-withdrawing properties of the phenyl group, the tautomerization between the amide and the iminol is more difficult. Thus, low reaction rate and low conversion were observed. This

  开发了一种有效的方法，用于亚氨基酰胺与芳基硼酸的 α-芳基化。针对该芳基化反应检查了不同的底物。对于N-苯基亚氨基酰胺的α-芳基化，由于苯基的吸电子特性，酰胺与亚胺醇之间的互变异构化更加困难。因此，观察到低反应速率和低转化率。这种现象支持我们之前提出的α-氨基酸衍生物芳基化机制。同时，该方法为α-功能化甘氨酸衍生物的合成提供了一种替代方法。
• Scaffold oriented synthesis. Part 3: Design, synthesis and biological evaluation of novel 5-substituted indazoles as potent and selective kinase inhibitors employing [2+3] cycloadditions
  作者：Irini Akritopoulou-Zanze、Brian D. Wakefield、Alan Gasiecki、Douglas Kalvin、Eric F. Johnson、Peter Kovar、Stevan W. Djuric

  DOI：10.1016/j.bmcl.2011.01.007

  日期：2011.3

  We report the synthesis and biological evaluation of 5-substituted indazoles and amino indazoles as kinase inhibitors. The compounds were synthesized in a parallel synthesis fashion from readily available starting materials employing [2+3] cycloaddition reactions and were evaluated against a panel of kinase assays. Potent inhibitors were identified for numerous kinases such as Rock2, Gsk3 beta, Aurora2 and Jak2. (C) 2011 Elsevier Ltd. All rights reserved.
• Asymmetric [3+2]-cyclization of α-imino amide surrogates to construct 3,4-diaminopyrrolidine-2,5-diones
  作者：Peiran Ruan、Cefei Zhang、Jin Wu、Fengnan Xiao、Yongyan Zhang、Qingfa Tan、Zhishan Su、Xiaoming Feng、Xiaohua Liu

  DOI：10.1039/d3cc01203d

  日期：——

  Using novel α-imino amide surrogates and chiral guanidine, diaminopyrrolidines derivatives could be obtained with good results and versatile application value. The role of guanidine was demonstrated by DFT calculations.

  利用新型α-亚氨基酰胺代用品和手性胍，获得了二氨基吡咯烷衍生物，结果良好，具有广泛的应用价值。DFT 计算证明了胍的作用。