methyl 4-benzyl-5-cyano-1,4,5,6-tetrahydropyrazine-2-carboxylate | 1138808-32-8

• 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: methyl 4-benzyl-5-cyano-1,4,5,6-tetrahydropyrazine-2-carboxylate
• 英文别名: methyl 4-benzyl-3-cyano-2,3-dihydro-1H-pyrazine-6-carboxylate
• CAS: 1138808-32-8
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: RFDXMAKMNAUJOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 1-tert-butyl 2-methyl 4-benzyl-5,6-dihydro-5-hydroxypyrazine-1,2(4H)-dicarboxylate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到methyl 4-benzyl-5-cyano-1,4,5,6-tetrahydropyrazine-2-carboxylate
  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

• 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.
• 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.