3-(methoxycarbonyl)-1,4-dimethylpiperazine-2,5-dione | 1140526-62-0

• 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-(methoxycarbonyl)-1,4-dimethylpiperazine-2,5-dione
• 英文别名: methyl 1,4-Dimethyl-3,6-dioxopiperazine-2-carboxylate
• CAS: 1140526-62-0
• 化学式: C₈H₁₂N₂O₄
• 分子量: 200.194
• InChiKey: GKODXPGMLGVDLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1-(phenylthio)-1H-1,2,4-triazole 、 3-(methoxycarbonyl)-1,4-dimethylpiperazine-2,5-dione 在 奎宁 作用下， 以 甲苯 、 苯 为溶剂， 反应 18.0h， 以99%的产率得到3-phenylsulfanyl-3-(methoxycarbonyl)-1,4-dimethylpiperazine-2,5-dione
  参考文献：
  名称：

  Efficient organocatalytic α-sulfenylation of substituted piperazine-2,5-diones

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.05.031
• 作为产物：
  描述：

  methyl 2-{N-methyl-2-[methyl(phenoxycarbonyl)amino]-acetamido}acetate 在 sodium hydride 、 叔丁醇 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.0h， 以55%的产率得到3-(methoxycarbonyl)-1,4-dimethylpiperazine-2,5-dione
  参考文献：
  名称：

  Dieckmann环化路线到Piperazine-2,5-diones

  摘要：

  通过Dieckmann环化（NaH，THF）形成CH 2 -N（R）C（O）CH 2 N（R'）CO 2 Ph类型的亚结构，其中末端亚甲基（CH 2）与氮相邻在链的另一端封闭在氨基甲酸苯酯单元的羰基上。R和R'是烷基，并且末端亚甲基被酮羰基，腈，酯或磷酰基活化。原料通过标准的酰化和氧化工艺组装而成，其起始原料为β-（烷基氨基）醇，（烷基氨基）乙腈，（烷基氨基）酯或（烷基氨基）甲基膦酸酯。

  DOI：

  10.1021/jo3007144

文献信息

• 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.
• A Dieckmann Cyclization Route to Piperazine-2,5-diones
  作者：Claude Larrivée Aboussafy、Derrick L. J. Clive

  DOI：10.1021/jo3007144

  日期：2012.6.1

  Piperazine-2,5-diones are formed by Dieckmann cyclization (NaH, THF) of substructures of the type CH2-N(R)C(O)CH2N(R′)CO2Ph in which the terminal methylene (CH2) that is adjacent to nitrogen closes onto the carbonyl group of the phenyl carbamate unit at the other end of the chain. R and R′ are alkyl groups, and the terminal methylene is activated by a ketone carbonyl, a nitrile, an ester, or a phosphoryl

  通过Dieckmann环化（NaH，THF）形成CH 2 -N（R）C（O）CH 2 N（R'）CO 2 Ph类型的亚结构，其中末端亚甲基（CH 2）与氮相邻在链的另一端封闭在氨基甲酸苯酯单元的羰基上。R和R'是烷基，并且末端亚甲基被酮羰基，腈，酯或磷酰基活化。原料通过标准的酰化和氧化工艺组装而成，其起始原料为β-（烷基氨基）醇，（烷基氨基）乙腈，（烷基氨基）酯或（烷基氨基）甲基膦酸酯。
• 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.