(R,S)-1-(2-Octyl)imidazole-4,5-dicarboxylic acid | 162824-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R,S)-1-(2-Octyl)imidazole-4,5-dicarboxylic acid
• CAS: 162824-39-7
• 化学式: C₁₃H₂₀N₂O₄
• 分子量: 268.313
• InChiKey: OVYLNVXRQJGGEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.42
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R,S)-1-(2-Octyl)imidazole-4,5-dicarboxylic acid 以 二苯醚 为溶剂， 反应 0.5h， 以81%的产率得到(R,S)-1-(2-Octyl)imidazole
  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：

  (R,S)-1-(2-Octyl)imidazole-4,5-dicarbonitrile 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以77%的产率得到(R,S)-1-(2-Octyl)imidazole-4,5-dicarboxylic 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

文献信息

• Stereospecific synthesis of 1-alkylimidazole derivatives via mitsunobu reactions
  作者：Maurizio Botta、Vincenzo Summa、Gianna Trapassi、Edith Monteagudo、Federico Corelli

  DOI：10.1016/s0957-4166(00)86167-4

  日期：1994.1

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 1 under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 2, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 4 in good overall yield and high enantiomeric excess. The absolute stereochemistry of the compounds has been confirmed by synthesizing 4c through an independent route.