1-(α-Phenylbenzyl)imidazole-4,5-dicarbonitrile | 69840-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(α-Phenylbenzyl)imidazole-4,5-dicarbonitrile
• 英文别名: 1-benzhydryl-1H-imidazole-4,5-dicarbonitrile；1-Benzhydrylimidazole-4,5-dicarbonitrile
• CAS: 69840-48-8
• 化学式: C₁₈H₁₂N₄
• 分子量: 284.32
• InChiKey: QUIVWDKKJIFFTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  531.0±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(α-Phenylbenzyl)imidazole-4,5-dicarbonitrile 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以97%的产率得到1-(α-Phenylbenzyl)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
• 作为产物：
  描述：

  4,5-二氰基咪唑 、 二苯基甲烷 在 二叔丁基过氧化物 、 iron(II) chloride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以95%的产率得到1-(α-Phenylbenzyl)imidazole-4,5-dicarbonitrile
  参考文献：
  名称：

  Direct C–N Coupling of Imidazoles and Benzylic Compounds via Iron-Catalyzed Oxidative Activation of C–H Bonds

  摘要：

  Iron-catalyzed direct C-N bond formation between imidazoles and benzylic hydrocarbons is described. The reaction utilizes an inexpensive iron catalyst-oxidant system that is suitable for the coupling of a range of benzylic C-H bonds with various imidazoles.

  DOI：

  10.1021/jo201253m

文献信息

• Imidazolcarbonsäuren und deren Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Pflanzenwachstumsregulierung bzw. zum Pflanzenschutz
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0000373A1

  公开（公告）日：1979-01-24

  Imidazol-carbonsäuren und deren funktionelle Derivate der Formeln bzw. worin m=0-2,n=1 oder2undm+n=3; R Halogen, Alkyl, Allyl, Hydroxyalkyl, Halogenalkyl, SH, S-Alkyl, CN, Phenyl oder Phenylalkyl, R1 OH, (subst.) Alkoxy, (subst.) Amino, Anilino, Pyrrolidino, Piperidino, Morpholino oder (subst.) Hydrazino, R2 und R3 H, Halogen, Alkyl, CF3, OH, Alkoxy, Halogenalkoxy, S-Alkyl, CN, NO2 oder NHCOCH3 und R. H oder Phenyl bedeuten, sowie deren nicht-toxische Salze mit Säuren und Basen sind vielseitig verwendbare Pflanzenbehandlungsmittel und Antimykotika.

  咪唑羧酸及其功能衍生物式 式中的咪唑羧酸及其官能团衍生物 其中 m=0-2,n=1 或 2andm+n=3； R 是卤素、烷基、烯丙基、羟烷基、卤代烷基、SH、S-烷基、CN、苯基或苯基烷基、 R1 OH、（亚）烷氧基、（亚）氨基、苯胺基、吡咯烷基、哌啶基、吗啉基或（亚）肼基、 R2 和 R3 H、卤素、烷基、CF3、OH、烷氧基、卤代烷氧基、S-烷基、CN、NO2 或 NHCOCH3 以及 R.H 或苯基 以及它们与酸和碱的无毒盐是多功能植物处理剂和抗霉菌剂。
• US4182624A
  申请人：——

  公开号：US4182624A

  公开（公告）日：1980-01-08
• Direct C–N Coupling of Imidazoles and Benzylic Compounds via Iron-Catalyzed Oxidative Activation of C–H Bonds
  作者：Qinqin Xia、Wanzhi Chen、Huayu Qiu

  DOI：10.1021/jo201253m

  日期：2011.9.16

  Iron-catalyzed direct C-N bond formation between imidazoles and benzylic hydrocarbons is described. The reaction utilizes an inexpensive iron catalyst-oxidant system that is suitable for the coupling of a range of benzylic C-H bonds with various imidazoles.
• 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.