N,N-bis-(tert-butoxycarbonyl)-2,5-bis-methoxycarbonyl-1,4-dihydropyrazine | 773896-53-0

• 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: N,N-bis-(tert-butoxycarbonyl)-2,5-bis-methoxycarbonyl-1,4-dihydropyrazine
• 英文别名: N,N-bis(tert-butoxycarbonyl)-2,5-bismethoxycarbonyl-1,4-dihydropyrazine；1,4-Di-tert-butyl 2,5-dimethyl pyrazine-1,2,4,5-tetracarboxylate；1-O,4-O-ditert-butyl 2-O,5-O-dimethyl pyrazine-1,2,4,5-tetracarboxylate
• CAS: 773896-53-0
• 化学式: C₁₈H₂₆N₂O₈
• 分子量: 398.413
• InChiKey: FSYAFTAGVDAPMN-UHFFFAOYSA-N

物化性质

• 熔点：
  155.0-156.0 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  453.1±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N-bis-(tert-butoxycarbonyl)-2,5-bis-methoxycarbonyl-1,4-dihydropyrazine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到吡嗪-2,5-二羧酸二甲酯
  参考文献：
  名称：

  Synthesis and reactivity of a 1,4-dihydropyrazine derivative

  摘要：

  N,N-Bis-(tert-butoxycarbonyl)-2,5-bis-methoxycarbonyl-1,4-dihydropyrazine can be obtained in high yield by treatment of the methyl ester of N-(4-toluenesulfonyl)-N-(tert-butoxycarbonyl)-alpha,beta-didehydroalanine with dimethylaminopyridine and potassium carbonate. This compound was used as substrate in Michael addition reactions with several types of nucleophiles. The electrochemical behaviour of this pyrazine derivative was also studied by cyclic voltammetry and by controlled potential electrolysis. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.06.127
• 作为产物：
  描述：

  甲基2-(N-(叔丁基氧羰基)-4-甲基苯磺酰氨基)丙烯酸酯 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以85%的产率得到N,N-bis-(tert-butoxycarbonyl)-2,5-bis-methoxycarbonyl-1,4-dihydropyrazine
  参考文献：
  名称：

  Photochemical oxidation of N,N-bis- (tert-butoxycarbonyl)-1,4-dihydropyrazine derivatives

  摘要：

  摘要：通过使用中压汞灯照射，研究了N,N-双(叔丁氧羰基)-1,4-二氢吡嗪的光化学氧化反应。主要产物已被分离，并通过光谱方法和单晶X射线衍射分析确定了它们的结构。建议光氧化是氧气对双键的[2+2]环加成反应。

  DOI：

  10.1515/hc-2014-0202

文献信息

• Photochemical oxidation of <i>N</i>,<i>N</i>-bis- (<i>tert</i>-butoxycarbonyl)-1,4-dihydropyrazine derivatives
  作者：Hong-bo Tan、Xiu-qing Song、Hong Yan

  DOI：10.1515/hc-2014-0202

  日期：2015.4.1

  The photochemical oxidation of N,N-Bis-(tert-butoxycarbonyl)-1,4-dihydropyrazines was investigated by irradiation using a medium-pressure mercury lamp. The main products were isolated, and their structures were determined by spectral methods and single crystal X-ray diffraction analysis. Photooxygenation is suggested to be a [2+2] cycloaddition reaction of oxygen to the double bond.

  摘要：通过使用中压汞灯照射，研究了N,N-双(叔丁氧羰基)-1,4-二氢吡嗪的光化学氧化反应。主要产物已被分离，并通过光谱方法和单晶X射线衍射分析确定了它们的结构。建议光氧化是氧气对双键的[2+2]环加成反应。
• Synthesis and reactivity of a 1,4-dihydropyrazine derivative
  作者：Anabela Rodrigues、Paula M.T. Ferreira、Luís S. Monteiro

  DOI：10.1016/j.tet.2004.06.127

  日期：2004.9

  N,N-Bis-(tert-butoxycarbonyl)-2,5-bis-methoxycarbonyl-1,4-dihydropyrazine can be obtained in high yield by treatment of the methyl ester of N-(4-toluenesulfonyl)-N-(tert-butoxycarbonyl)-alpha,beta-didehydroalanine with dimethylaminopyridine and potassium carbonate. This compound was used as substrate in Michael addition reactions with several types of nucleophiles. The electrochemical behaviour of this pyrazine derivative was also studied by cyclic voltammetry and by controlled potential electrolysis. (C) 2004 Published by Elsevier Ltd.