(E)-N-(benzimidazol-1-yl)-1-phenyl-methanimine | 81949-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (E)-N-(benzimidazol-1-yl)-1-phenyl-methanimine
• 英文别名: 1-benzylideneaminobenzimidazole；benzoimidazol-1-yl-benzylidene-amine；benzaldehyde benzimidazol-1-ylimine；Benzaldehyd-benzimidazol-1-ylimin；1-Benzylidenamino-benzimidazol；N-(1H-benzimidazol-1-yl)-N-benzylideneamine；(E)-N-(benzimidazol-1-yl)-1-phenylmethanimine
• CAS: 81949-11-3
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: OPGLONOADIEPAF-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-(benzimidazol-1-yl)-1-phenyl-methanimine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 1-[(E)-benzylideneamino]-3-butyl-1',3'-diisopropylspiro[benzimidazolidine-2,5'-imidazolidine]-2',4'-dithione
  参考文献：
  名称：

  Carbene-Mediated Transformations of 1-(Benzylideneamino)benzimidazoles

  摘要：

  Carbene-mediated transformations of N-(3-butyl-benzimidazol-3-ium-1-yl)-1-arylmethanimine iodides with carbon disulfide and benzoyl isothiocyanate gave the corresponding NHC center dot CS(2) betaines in 68-85% and benzoyl-[1-butyl-3-[(E)-(aryl)-methyleneamino]benzimidazol-1-ium-2-carbothioyl]azanides, respectively, in 74-85% yields. However, reaction with excess isopropyl isothiocyanate in NaH/THF at room temperature yielded the 1-butyl-1',3'-diisopropyl-3-[(E)-(aryl)methyleneamino]spiro[benzimidazole-2,5'-imidazolidine]-2',4'-dithiones (74-77%).

  DOI：

  10.1021/jo200088s
• 作为产物：
  描述：

  苯并咪唑 在 硫酸 、 potassium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 (E)-N-(benzimidazol-1-yl)-1-phenyl-methanimine
  参考文献：
  名称：

  Carbene-Mediated Transformations of 1-(Benzylideneamino)benzimidazoles

  摘要：

  Carbene-mediated transformations of N-(3-butyl-benzimidazol-3-ium-1-yl)-1-arylmethanimine iodides with carbon disulfide and benzoyl isothiocyanate gave the corresponding NHC center dot CS(2) betaines in 68-85% and benzoyl-[1-butyl-3-[(E)-(aryl)-methyleneamino]benzimidazol-1-ium-2-carbothioyl]azanides, respectively, in 74-85% yields. However, reaction with excess isopropyl isothiocyanate in NaH/THF at room temperature yielded the 1-butyl-1',3'-diisopropyl-3-[(E)-(aryl)methyleneamino]spiro[benzimidazole-2,5'-imidazolidine]-2',4'-dithiones (74-77%).

  DOI：

  10.1021/jo200088s

文献信息

• 10.1080/17415993.2024.2394627
  作者：Khodykina, Evgeniya、Pobedinskaya, Diana、Borodkina, Inna、Astakhov, Alexander、Demidov, Oleg、Metelitsa, Anatoly、Chernyshev, Victor、Kolodina, Alexandra

  DOI：10.1080/17415993.2024.2394627

  日期：——

  An efficient approach to the synthesis of novel 2,3-diaryl-3,4-dihydro-2H-benzo[4,5]imidazo[2,1-b][1,3,4]thiadiazines via a base-catalyzed intramolecular cyclization of 2-arylmethylthio-N-arylidene...

  通过碱催化分子内合成新型2,3-二芳基-3,4-二氢-2H-苯并[4,5]咪唑并[2,1-b][1,3,4]噻二嗪的有效方法2-芳基甲硫基-N-亚芳基的环化...
• Oxidation of 1-aminobenzimidazoles. Synthesis and properties of 1,1?-azobenzimidazoles
  作者：A. F. Pozharskii、I. M. Nanavyan、V. V. Kuz'menko、A. I. Chernyshev、Yu. V. Orlov、N. A. Klyuev

  DOI：10.1007/bf00481518

  日期：1989.11
• Kuz'menko, V.V.; Pozharskii, A.F.; Kuz'menko, T.A., Russian Journal of Organic Chemistry, 1993, vol. 29, # 9, p. 1577 - 1581
  作者：Kuz'menko, V.V.、Pozharskii, A.F.、Kuz'menko, T.A.、Kryshtalyuk, O.V.

  DOI：——

  日期：——
• Push-Pull Triazenes Derived from 1-(Benzylideneamino)- and 1-(Sulfonimido)-azolylidenes
  作者：Davit Jishkariani、C. Dennis Hall、Aydin Demircan、Blake J. Tomlin、Peter J. Steel、Alan R. Katritzky

  DOI：10.1021/jo302697q

  日期：2013.4.5

  In-situ-generated neutral 1-(benzylideneamino)- and novel anionic 1-(sulfonimido)-azolylidenes react with organic azides to afford diverse classes of push-pull triazenes and triazene salts. The scope of the heterocyclic core and substituents at the N1 and N3 positions of NHC precursors together with the thermal properties of resulting compounds were examined.
• Carbene-Mediated Transformations of 1-(Benzylideneamino)benzimidazoles
  作者：Alan R. Katritzky、Davit Jishkariani、Rajeev Sakhuja、C. Dennis Hall、Peter J. Steel

  DOI：10.1021/jo200088s

  日期：2011.5.20

  Carbene-mediated transformations of N-(3-butyl-benzimidazol-3-ium-1-yl)-1-arylmethanimine iodides with carbon disulfide and benzoyl isothiocyanate gave the corresponding NHC center dot CS(2) betaines in 68-85% and benzoyl-[1-butyl-3-[(E)-(aryl)-methyleneamino]benzimidazol-1-ium-2-carbothioyl]azanides, respectively, in 74-85% yields. However, reaction with excess isopropyl isothiocyanate in NaH/THF at room temperature yielded the 1-butyl-1',3'-diisopropyl-3-[(E)-(aryl)methyleneamino]spiro[benzimidazole-2,5'-imidazolidine]-2',4'-dithiones (74-77%).