3,6-dihexylpyrazine-2,5-dicarbaldehyde | 1384607-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-dihexylpyrazine-2,5-dicarbaldehyde
• CAS: 1384607-66-2
• 化学式: C₁₈H₂₈N₂O₂
• 分子量: 304.433
• InChiKey: QLRXCSOBFNSNAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(5-bromothiophen-2-yl)methyl]triphenylphosphonium bromide 、 3,6-dihexylpyrazine-2,5-dicarbaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以55%的产率得到2,5-bis((E)-2-(5-bromothiophen-2-yl)vinyl)-3,6-dihexylpyrazine
  参考文献：
  名称：

  Regioselective double Boekelheide reaction: first synthesis of 3,6-dialkylpyrazine-2,5-dicarboxaldehydes from dl-alanine

  摘要：

  Pyrazine-2,5-dicarboxaldehyde was synthesized on a multi-gram scale by MnO2 oxidation of 2,5-bis(hydroxymethyl)pyrazine, which in turn was obtained from 2,5-dimethylpyrazine employing double Boekelheide reaction as a key step as reported previously. This reaction was subsequently utilized in a regioselective fashion as a key step to synthesize efficiently, for the first time, 3,6-di(long-chain)alkylpyrazine-2,5-dicarboxaldehydes starting from DL-alanine. These monomers are certain to have importance as electron deficient and chemically versatile components for new materials development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.057
• 作为产物：
  描述：

  (3,6-dihexylpyrazine-2,5-diyl)dimethanol 在 manganese(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 以88%的产率得到3,6-dihexylpyrazine-2,5-dicarbaldehyde
  参考文献：
  名称：

  Regioselective double Boekelheide reaction: first synthesis of 3,6-dialkylpyrazine-2,5-dicarboxaldehydes from dl-alanine

  摘要：

  Pyrazine-2,5-dicarboxaldehyde was synthesized on a multi-gram scale by MnO2 oxidation of 2,5-bis(hydroxymethyl)pyrazine, which in turn was obtained from 2,5-dimethylpyrazine employing double Boekelheide reaction as a key step as reported previously. This reaction was subsequently utilized in a regioselective fashion as a key step to synthesize efficiently, for the first time, 3,6-di(long-chain)alkylpyrazine-2,5-dicarboxaldehydes starting from DL-alanine. These monomers are certain to have importance as electron deficient and chemically versatile components for new materials development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.057