5-Amino-1-(2-octyl)imidazole-4-carbonitrile | 162824-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Amino-1-(2-octyl)imidazole-4-carbonitrile
• 英文别名: 5-Amino-1-octan-2-ylimidazole-4-carbonitrile
• CAS: 162824-48-8
• 化学式: C₁₂H₂₀N₄
• 分子量: 220.318
• InChiKey: QMICNKMKPMYNGH-UHFFFAOYSA-N

物化性质

• 沸点：
  421.0±30.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Amino-1-(2-octyl)imidazole-4-carbonitrile 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-Amino-1-(2-octyl)imidazole-4-carboxylic acid
  参考文献：
  名称：

  Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

  DOI：

  10.1021/jo00112a023
• 作为产物：
  描述：

  (±)-4-氨基辛烷 、 对苯二磺酸氨基丙二酰丁氰 、 原甲酸三乙酯 生成 5-Amino-1-(2-octyl)imidazole-4-carbonitrile
  参考文献：
  名称：

  Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

  DOI：

  10.1021/jo00112a023

文献信息

• Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles
  作者：Federico Corelli、Vincenzo Summa、Alessandra Brogi、Edith Monteagudo、Maurizio Botta

  DOI：10.1021/jo00112a023

  日期：1995.4

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.