(R,S)-1-(2-Octyl)imidazole

• 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
• 英文别名: N-(1-methylheptyl)imidazole；1-(1-methylheptyl)-1H-imidazole；1-Octan-2-ylimidazole
• 化学式: C₁₁H₂₀N₂
• 分子量: 180.293
• InChiKey: NEJAGDLRHIFFRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-戊酮 、 (R,S)-1-(2-Octyl)imidazole 在 lithium 、 天然橡胶 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 以65%的产率得到3-[1-(1-methylheptyl)-1H-imidazol-2-yl]pentan-3-ol
  参考文献：
  名称：

  Isoprene-Mediated Lithiation of 1-Alkylimidazoles: Chiral Induction of the Alkyl Substituent

  摘要：

  通过异戊二烯介导的具有氮上二级烷基取代基的咪唑（7、8和13）的锂化反应，随后对不同亲电试剂进行亲核加成，可以制备相应的2-功能化咪唑10、11和14。烷基取代基中立体中心的的存在导致在亲核加成步骤中对消旋化亲电试剂（如三甲基乙醛）产生非对映选择性，生成了预期的咪唑衍生物，总产率很高，但对映体过量率较低（高达26%）。

  DOI：

  10.2174/157017810791514850
• 作为产物：
  描述：

  (R,S)-1-(2-Octyl)imidazole-4,5-dicarbonitrile 在 sodium hydroxide 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 24.5h， 生成 (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

文献信息

• Isoprene-Mediated Lithiation of 1-Alkylimidazoles: Chiral Induction of the Alkyl Substituent
  作者：Isidro M. Pastor、Rosario Torregrosa、Miguel Yus

  DOI：10.2174/157017810791514850

  日期：2010.7.1

  The isoprene-mediated lithiation of imidazoles bearing a secondary alkyl substituent at the nitrogen (7, 8 and 13) and the subsequent nucleophilic addition to different electrophiles allows the preparation of the corresponding 2- functionalized imidazoles 10, 11 and 14. The presence of a stereogenic center in the alkyl substituent induces diastereoselection during the nucleophilic addition step with a prochiral electrophile (i.e. pivalaldehyde), producing the expected imidazole derivative with excellent overall yield, but low de (up to 26%).

  通过异戊二烯介导的具有氮上二级烷基取代基的咪唑（7、8和13）的锂化反应，随后对不同亲电试剂进行亲核加成，可以制备相应的2-功能化咪唑10、11和14。烷基取代基中立体中心的的存在导致在亲核加成步骤中对消旋化亲电试剂（如三甲基乙醛）产生非对映选择性，生成了预期的咪唑衍生物，总产率很高，但对映体过量率较低（高达26%）。
• METHOD FOR PREPARING ACRYLONITRILE DIMER
  申请人：LG CHEM, LTD.

  公开号：EP3950667A1

  公开（公告）日：2022-02-09

  Provided is a method of preparing an acrylonitrile dimer, the method including: supplying an acrylonitrile monomer, a phosphorus-based catalyst, an alcohol solvent, and an ionic liquid to a reactor to perform a dimerization reaction to prepare a single-phase dimerization reaction product (S10); supplying a reactor discharge stream including the dimerization reaction product to a first distillation column, separating the alcohol solvent and an unreacted acrylonitrile monomer from an upper discharge stream, and supplying a lower discharge stream including an acrylonitrile dimer, the ionic liquid, and the phosphorus-based catalyst to a second distillation column (S20); and separating an upper discharge stream including the acrylonitrile dimer and separating a lower discharge stream including the ionic liquid and the phosphorus-based catalyst, in the second distillation column (S30).

  提供了一种制备丙烯腈二聚体的方法，该方法包括向反应器中加入丙烯腈单体、磷系催化剂、醇溶剂和离子液体，进行二聚反应，制备单相二聚反应产物（S10）；将包括二聚反应产物在内的反应器出料流供给第一蒸馏塔，从上层出料流中分离醇溶剂和未反应的丙烯腈单体，并将包括丙烯腈二聚体、离子液体和磷基催化剂在内的下层出料流供给第二蒸馏塔（S20）；在第二蒸馏塔 (S30) 中分离包括丙烯腈二聚体的上部排放流，并分离包括离子液体和磷基催化剂的下部排放流。
• Separations with ionic liquid solvents
  申请人：Chevron Phillips Chemical Company LP

  公开号：US10227274B2

  公开（公告）日：2019-03-12

  Disclosed are systems and methods which provide a process stream comprising a gaseous component, capture the gaseous component from the process stream by an ionic liquid solvent of a separator, and recover a captured gaseous component from the ionic liquid solvent in a regenerator. A second gaseous component from the process stream may be captured by the ionic liquid solvent of the separator, and the second gaseous component may be recovered from the ionic liquid solvent in the regenerator. Alternatively, the second gaseous component from the process stream may be uncaptured by the ionic liquid solvent, and the uncaptured second gaseous component may be recovered from a membrane unit.

  所公开的系统和方法可提供包含气态成分的工艺流，通过分离器的离子液体溶剂从工艺流中捕获气态成分，并在再生器中从离子液体溶剂回收捕获的气态成分。分离器的离子液体溶剂可捕获工艺流中的第二种气体成分，并在再生器中从离子液体溶剂回收第二种气体成分。或者，工艺流中的第二气态成分可能未被离子液体溶剂捕获，未被捕获的第二气态成分可从膜装置中回收。
• 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.
• Réactif utile pour et procédé pour la synthèse d'ester et xanthate transestérifiable
  申请人：RHODIA CHIMIE

  公开号：EP0685442B1

  公开（公告）日：2003-04-23