1-tert-butyl 2-methyl 4-benzyl-5,6-dihydro-5-hydroxypyrazine-1,2(4H)-dicarboxylate | 1138808-21-5

• 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: 1-tert-butyl 2-methyl 4-benzyl-5,6-dihydro-5-hydroxypyrazine-1,2(4H)-dicarboxylate
• 英文别名: 1-O-tert-butyl 6-O-methyl 4-benzyl-3-hydroxy-2,3-dihydropyrazine-1,6-dicarboxylate
• CAS: 1138808-21-5
• 化学式: C₁₈H₂₄N₂O₅
• 分子量: 348.399
• InChiKey: JXVHDHNWIIFZAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 2-methyl 4-benzyl-5,6-dihydro-5-hydroxypyrazine-1,2(4H)-dicarboxylate 、 苄胺 在 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到1-tert-butyl 2-methyl 4-benzyl-5-(benzylamino)-5,6-dihydropyrazine-1,2(4H)-dicarboxylate
  参考文献：
  名称：

  Reactivity of 5-hydroxy-5,6-dihydro-4H-pyrazines—easy and efficient access to ring-fused polycyclic diazinic systems

  摘要：

  An efficient synthesis of functionalized 1,4-diazinic hemiaminals starting from methyl-4H-1,4-oxazine-3-carboxylate moiety is reported. Given that various polycyclic heterocyclic frameworks could be easily obtained, this strategy may provide an efficient method to access a library Of Compounds based on privileged Substructures that are of interest in drug discovery. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.152
• 作为产物：
  描述：

  4-(tert-butoxycarbonyl)-3-methoxycarbonyl-4H-[1,4]oxazine 、 苄胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以100%的产率得到1-tert-butyl 2-methyl 4-benzyl-5,6-dihydro-5-hydroxypyrazine-1,2(4H)-dicarboxylate
  参考文献：
  名称：

  Nucleophilic Addition onto Methyl-4H-1,4-oxazine-3-carboxylate Moiety: Short Access to 1,4-Diazine Privileged Substructures

  摘要：

  To determine the synthetic potential of the original 1,4-oxazine ring, which appears as a valuable building block for the synthesis of more complex derivatives, Michael-type nucleophilic additions were studied. According to the nature of the nucleophile, either acyclic or cyclic derivatives were isolated. In the presence of primary amines, a short and efficient access to diazinic hemiaminals was described.

  DOI：

  10.1021/jo900291f

文献信息

• Nucleophilic Addition onto Methyl-4<i>H</i>-1,4-oxazine-3-carboxylate Moiety: Short Access to 1,4-Diazine Privileged Substructures
  作者：Elise Claveau、Isabelle Gillaizeau、Justyna Kalinowska-Tluscik、Pascal Bouyssou、Gérard Coudert

  DOI：10.1021/jo900291f

  日期：2009.4.3

  To determine the synthetic potential of the original 1,4-oxazine ring, which appears as a valuable building block for the synthesis of more complex derivatives, Michael-type nucleophilic additions were studied. According to the nature of the nucleophile, either acyclic or cyclic derivatives were isolated. In the presence of primary amines, a short and efficient access to diazinic hemiaminals was described.
• Reactivity of 5-hydroxy-5,6-dihydro-4H-pyrazines—easy and efficient access to ring-fused polycyclic diazinic systems
  作者：Elise Claveau、Isabelle Gillaizeau、Gérard Coudert

  DOI：10.1016/j.tetlet.2009.03.152

  日期：2009.7

  An efficient synthesis of functionalized 1,4-diazinic hemiaminals starting from methyl-4H-1,4-oxazine-3-carboxylate moiety is reported. Given that various polycyclic heterocyclic frameworks could be easily obtained, this strategy may provide an efficient method to access a library Of Compounds based on privileged Substructures that are of interest in drug discovery. (C) 2009 Elsevier Ltd. All rights reserved.