3-(ethoxycarbonyl)-1,4-dimethylpiperazine-2,5-dione | 865879-15-8

• 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-(ethoxycarbonyl)-1,4-dimethylpiperazine-2,5-dione
• 英文别名: 3-ethoxycarbonyl-1,4-dimethylpiperazine-2,5-dione；Ethyl 1,4-dimethyl-3,6-dioxopiperazine-2-carboxylate
• CAS: 865879-15-8
• 化学式: C₉H₁₄N₂O₄
• 分子量: 214.221
• InChiKey: GTCBMTHCKKTTCW-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68 °C
• 沸点：
  400.8±45.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(ethoxycarbonyl)-1,4-dimethylpiperazine-2,5-dione 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 17.0h， 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 (methylamino)malonate 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 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 82.0h， 生成 3-(ethoxycarbonyl)-1,4-dimethylpiperazine-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

• Direct organocatalytic coupling of carboxylated piperazine-2,5-diones with indoles through conjugate addition of carbon nucleophiles to indolenine intermediates
  作者：Ramin Dubey、Bogdan Olenyuk

  DOI：10.1016/j.tetlet.2009.11.068

  日期：2010.1

  Organocatalytic conjugate addition of diketopiperazines to indoles was achieved in good to excellent yields through electrophilic indolenine intermediates generated under mild conditions. Screening of catalysts and solvents at different temperatures was performed in order to achieve high product yields.

  通过在温和条件下产生的亲电假吲哚中间体，以良好到优异的收率实现了二酮哌嗪与吲哚的有机催化共轭加成。在不同温度下对催化剂和溶剂进行筛选以实现高产率。
• Enantioselective organocatalytic α-sulfenylation of substituted diketopiperazines
  作者：Nathan W. Polaske、Ramin Dubey、Gary S. Nichol、Bogdan Olenyuk

  DOI：10.1016/j.tetasy.2009.10.037

  日期：2009.12

  The asymmetric organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported, with cinchona alkaloids as chiral Lewis bases and electrophilic sulfur transfer reagents. Catalyst loadings, the type of sulfur transfer reagent, temperature and solvent were investigated in order to optimize the reaction conditions. The effects of ring substitution and the type of catalyst on the yield and enantioselectivity of the reaction are reported. (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient organocatalytic α-sulfenylation of substituted piperazine-2,5-diones
  作者：Ramin Dubey、Nathan W. Polaske、Gary S. Nichol、Bogdan Olenyuk

  DOI：10.1016/j.tetlet.2009.05.031

  日期：2009.7

  Organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported through the use of cinchona alkaloids as Lewis bases and electrophilic sulfur transfer reagents. 1-Phenylsulfanyl[1,2,4]triazole, a novel Sulfur transfer reagent, gave excellent product yields with a number of substituted piperazine-2,5-diones under mild conditions. Catalyst loading, stoichiometry Of Sulfur electrophile, temperature, and solvent were optimized to achieve high product yields. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.