3-羧基-1,3,4-三甲基哌嗪-2,5-二酮 | 519141-24-3

• 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: 3-羧基-1,3,4-三甲基哌嗪-2,5-二酮
• 英文名称: 3-carboxyl-1,3,4-trimethylpiperazine-2,5-dione
• 英文别名: 1,2,4-Trimethyl-3,6-dioxopiperazine-2-carboxylic acid
• CAS: 519141-24-3
• 化学式: C₈H₁₂N₂O₄
• 分子量: 200.194
• InChiKey: YSGCDJRHKLAHJW-UHFFFAOYSA-N

物化性质

• 沸点：
  473.7±45.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羧基-1,3,4-三甲基哌嗪-2,5-二酮 在 碘苯二乙酸 、 三氟化硼乙醚 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 20.17h， 生成 3-allyl-1,3,4-trimethylpiperazine-2,5-dione
  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：

  在 palladium on activated charcoal 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 97.0h， 生成 3-羧基-1,3,4-三甲基哌嗪-2,5-二酮
  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.