ethyl N-[N-benzyloxycarbonylsarcosyl]-2-ethoxycarbonylsarcosinate | 865879-16-9

• 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: ethyl N-[N-benzyloxycarbonylsarcosyl]-2-ethoxycarbonylsarcosinate
• CAS: 865879-16-9
• 化学式: C₁₉H₂₆N₂O₇
• 分子量: 394.425
• InChiKey: WKZZQCZBBJAQGA-UHFFFAOYSA-N

物化性质

• 沸点：
  517.8±50.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  102.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl N-[N-benzyloxycarbonylsarcosyl]-2-ethoxycarbonylsarcosinate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 81.0h， 生成 肌氨酸酐
  参考文献：
  名称：

  The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones

  摘要：

  Alkoxycarbonylpiperazine-2,5-diones are versatile precursors for the alpha-functionalisation of piperazine-2,5-diones. The alkoxycarbonyl group activates the a-carbon position to alkylation reactions and this provides a mild and selective method for the extension of the carbon framework of piperazine-2,5-diones. In addition, the alkoxycarbonyl group can be converted to the carboxy group, which in turn can be 'deleted' or manipulated for the installation of carbon and/or heteroatom substituents where desired, the latter via N-acyliminium chemistry. We also demonstrate that hydroxymethylpiperazine-2,5-diones complement carboxypiperazinediones as precursors for the generation of N-acyliminium ions. (c) 2005 Elsevier Ltd. All-rights reserved.

  DOI：

  10.1016/j.tet.2005.06.084
• 作为产物：
  描述：

  diethyl 2-(benzyl(methyl)amino)propanedioate 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 ethyl N-[N-benzyloxycarbonylsarcosyl]-2-ethoxycarbonylsarcosinate
  参考文献：
  名称：

  The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones

  摘要：

  Alkoxycarbonylpiperazine-2,5-diones are versatile precursors for the alpha-functionalisation of piperazine-2,5-diones. The alkoxycarbonyl group activates the a-carbon position to alkylation reactions and this provides a mild and selective method for the extension of the carbon framework of piperazine-2,5-diones. In addition, the alkoxycarbonyl group can be converted to the carboxy group, which in turn can be 'deleted' or manipulated for the installation of carbon and/or heteroatom substituents where desired, the latter via N-acyliminium chemistry. We also demonstrate that hydroxymethylpiperazine-2,5-diones complement carboxypiperazinediones as precursors for the generation of N-acyliminium ions. (c) 2005 Elsevier Ltd. All-rights reserved.

  DOI：

  10.1016/j.tet.2005.06.084

文献信息

• The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones
  作者：Christina L.L. Chai、John A. Elix、Paul B. Huleatt

  DOI：10.1016/j.tet.2005.06.084

  日期：2005.9

  Alkoxycarbonylpiperazine-2,5-diones are versatile precursors for the alpha-functionalisation of piperazine-2,5-diones. The alkoxycarbonyl group activates the a-carbon position to alkylation reactions and this provides a mild and selective method for the extension of the carbon framework of piperazine-2,5-diones. In addition, the alkoxycarbonyl group can be converted to the carboxy group, which in turn can be 'deleted' or manipulated for the installation of carbon and/or heteroatom substituents where desired, the latter via N-acyliminium chemistry. We also demonstrate that hydroxymethylpiperazine-2,5-diones complement carboxypiperazinediones as precursors for the generation of N-acyliminium ions. (c) 2005 Elsevier Ltd. All-rights reserved.