乙基N-(羟基氨基甲酰)甘氨酸酯 | 157166-51-3

• 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
• 中文名称: 乙基N-(羟基氨基甲酰)甘氨酸酯
• 中文别名: 甘氨酸,N-[(羟氨基)羰基]-,乙基酯(9CI)
• 英文名称: ethyl 2-(3-hydroxyureido)acetate
• 英文别名: Ethyl 2-(hydroxycarbamoylamino)acetate
• CAS: 157166-51-3
• 化学式: C₅H₁₀N₂O₄
• 分子量: 162.145
• InChiKey: QOXOHGLGIFSMNR-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙基N-(羟基氨基甲酰)甘氨酸酯 在 四丁基高碘酸铵 作用下， 生成 ethyl 2-(oxocarbamoylamino)acetate
  参考文献：
  名称：

  Nitroxyl (HNO) release from new functionalized N-hydroxyurea-derived acyl nitroso-9,10-dimethylanthracene cycloadducts

  摘要：

  A thermal retro-Diels-Alder decomposition of N-hydroxyurea-derived acyl nitroso compounds and 9,10-dimethylanthracene cycloadducts followed by acyl nitroso compound hydrolysis produces nitrous oxide, evidence for the formation of nitroxyl, the one-electron reduced form of nitric oxide that has drawn considerable attention for its potential roles in biological systems. EPR and NMR spectroscopy provide further evidence for nitroxyl formation and kinetic information, respectively. Such compounds may prove to be useful alternative nitroxyl donors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.062
• 作为产物：
  描述：

  异氰酰乙酸乙酯 在 羟胺 作用下， 以91%的产率得到乙基N-(羟基氨基甲酰)甘氨酸酯
  参考文献：
  名称：

  Nitroxyl (HNO) release from new functionalized N-hydroxyurea-derived acyl nitroso-9,10-dimethylanthracene cycloadducts

  摘要：

  A thermal retro-Diels-Alder decomposition of N-hydroxyurea-derived acyl nitroso compounds and 9,10-dimethylanthracene cycloadducts followed by acyl nitroso compound hydrolysis produces nitrous oxide, evidence for the formation of nitroxyl, the one-electron reduced form of nitric oxide that has drawn considerable attention for its potential roles in biological systems. EPR and NMR spectroscopy provide further evidence for nitroxyl formation and kinetic information, respectively. Such compounds may prove to be useful alternative nitroxyl donors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.062

文献信息

• Different Reactivity of Hydroxylamine with Carbamoyl Azides and Carbamoyl Cyanides: Synthesis of Hydroxyureas and Carbamoyl Amidoximes
  作者：Jairo Paz、Carlos Pérez-Balado、Beatriz Iglesias、Luis Muñoz

  DOI：10.1021/jo1014855

  日期：2010.12.3

  The carbamoylating agents carbamoyl azides and carbamoyl cyanides (aka cyanoformamides) react with hydroxylamine in different ways, leading in the first case to N-hydroxyureas and, in the case of carbamoyl cyanides, to carbamoyl amidoxime derivatives. The synthetic procedure developed for the latter type of compound, which represents an interesting precursor for heterocyclic structures, allowed the

  氨基甲酰基化剂氨基甲酰基叠氮化物和氨基甲酰基氰化物（又名氰基甲酰胺）以不同的方式与羟胺反应，在第一种情况下生成N-羟基脲，在氨基甲酰基氰化物的情况下，生成氨基甲酰基a肟肟衍生物。为后一种类型的化合物开发的合成方法代表了杂环结构的一种有趣的前体，可以高效地制备各种实例。在比较异丙基和苄基衍生物的实验值和计算出的13 C和15 N NMR化学位移值的基础上，提出了mid胺肟部分中双键的Z构型。
• Semicarbazones from <i>N</i>-Hydroxyureas and Amines: A Novel Entry in the Reactivity of the Acyl Nitroso Group
  作者：Jairo Paz、Carlos Pérez-Balado、Beatriz Iglesias、Luis Muñoz

  DOI：10.1021/ol2003226

  日期：2011.4.1

  The condensation of carbamoyl nitroso compounds, obtained by oxidation of N-hydroxyureas, with amines unexpectedly afforded semicarbazones (aka carbamoyl hydrazones). Although the substitution of the nitrosyl moiety might compete to afford the corresponding urea, an excess of amine led to the semicarbazone as the major product, which is presumably formed via isomerization of an initially generated acyl azo compound.
• Nitroxyl (HNO) release from new functionalized N-hydroxyurea-derived acyl nitroso-9,10-dimethylanthracene cycloadducts
  作者：Bu-Bing Zeng、Jinming Huang、Marcus W. Wright、S. Bruce King

  DOI：10.1016/j.bmcl.2004.08.062

  日期：2004.11

  A thermal retro-Diels-Alder decomposition of N-hydroxyurea-derived acyl nitroso compounds and 9,10-dimethylanthracene cycloadducts followed by acyl nitroso compound hydrolysis produces nitrous oxide, evidence for the formation of nitroxyl, the one-electron reduced form of nitric oxide that has drawn considerable attention for its potential roles in biological systems. EPR and NMR spectroscopy provide further evidence for nitroxyl formation and kinetic information, respectively. Such compounds may prove to be useful alternative nitroxyl donors. (C) 2004 Elsevier Ltd. All rights reserved.