3-benzyloxycarbonyl-1-methylpiperazine-2,5-dione | 519141-03-8

• 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: 3-benzyloxycarbonyl-1-methylpiperazine-2,5-dione
• 英文别名: 1-methyl-3-benzyloxycarbonylpiperazine-2,5-dione；Benzyl 4-methyl-3,6-dioxopiperazine-2-carboxylate
• CAS: 519141-03-8
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: MUELQJOAKBVIEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  526.9±50.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyloxycarbonyl-1-methylpiperazine-2,5-dione 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 49.0h， 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：

  二苄基马来酸酯 在 aluminum amalgam 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium nitrite 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 58.0h， 生成 3-benzyloxycarbonyl-1-methylpiperazine-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

文献信息

• Multi-purpose functionality for the structural elaboration of the piperazine-2,5-dione motif
  作者：Christina L.L. Chai、John A. Elix、Paul B. Huleatt

  DOI：10.1016/s0040-4039(02)02571-6

  日期：2003.1

  Mild methods for controlled C- and N-alkylation of 3-benzyloxycarbonylpiperazine-2,5-diones are reported. The benzyloxylcarbonyl substituent can also serve as latent functionality for N-acyliminium ion formation and subsequent trapping enables installation of new carbon and/or heteroatom substituents. (C) 2002 Elsevier Science Ltd. All rights reserved.