1-allyl-3-benzylbenzimidazolium bromide

• 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: 1-allyl-3-benzylbenzimidazolium bromide
• 英文别名: 1-Benzyl-3-prop-2-enylbenzimidazol-1-ium;bromide
• 化学式: Br*C₁₇H₁₇N₂
• 分子量: 329.239
• InChiKey: LVBGJBKSGMETBV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.17
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-allyl-3-benzylbenzimidazolium bromide 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 bis(1-allyl-3-benzylbenzimidazolium)palladium(II) bromide
  参考文献：
  名称：

  单和双-N-杂环卡宾银（I）和钯（II）配合物：合成，表征，晶体结构和体外抗癌研究

  摘要：

  摘要具有丁基和烯丙基取代基的苯并咪唑鎓盐1具有与银（I）中心的两种配位行为，其中bis-NHC配合物2在室温下形成，而mono-NHC配合物3在室温下形成。高温。但是，在相同的反应条件下类似盐与氧化银（I）的反应不会导致形成单-NHC配合物，而会生成双-NHC配合物。通过用钯（II）源处理相应的银配合物，获得了一系列的钯（II）-NHC配合物4、5、10和11。所有新化合物都通过各种光谱和分析技术进行了表征。另外，通过单晶X射线衍射法明确地确定了单NHC银络合物3的结构。

  DOI：

  10.1016/j.poly.2016.09.065
• 作为产物：
  描述：

  苯并咪唑 在 18-冠醚-6 氢氧化钾 作用下， 以 甲苯 、 苯 为溶剂， 反应 10.0h， 生成 1-allyl-3-benzylbenzimidazolium bromide
  参考文献：
  名称：

  Synthesis and antitumour activity of trimethylsilylpropyl substituted benzimidazoles

  摘要：

  The quaternisation of N-substituted benzimidazoles by heating with various alkyl, allyl, propargyl and benzyl chlorides and bromides leads to the formation of benzimidazolinium salts. The interaction of N-monosubstituted benzimidazoles with various salts (CuCl2, ZnCl2, CoCl2, PdCl2, and AgNO3) Yielded stable sol-id complexes. Potential cytotoxic activity of synthesised benzimidazolinium salts and benzimidazole metal complexes was tested in vitro on four monolayer tumour cell Hues: MG-22A (mouse hepatoma), HT-1080 (human fibrosarcoma), B16 (mouse melanoma), Neuro 2A (mouse neuroblastoma) and normal mouse fibroblast cells. A preliminary analysis of the structure-activity relationship for the benzimidazole derivatives clearly indicates that the character of substituents in the benzimidazole ring has strong influence on the cytotoxic activity. The insertion of the silicon atom into the N-alkyl chain increases the cytotoxic activity of benzimidazolinium salts significantly, which show a very significant potency in vitro against all studied tumour cell lines, being particularly active in experiments with B16 (mouse melanoma). TD, for the most active compounds are in the range 0.001-0.008 mug ml(-1). Cytotoxicity of benzimidazole metal complexes (L2MX2) strongly depends on the metal nature. 1-(3-Trimethylsilylpropyl)benzimidazole in dose 1 mg kg(-1) inhibits carcinoma S-180 tumour growth by 62% (on ICR mice). (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01241-7

文献信息

• Rearrangement of Electron-RichN-Allyldibenzotetraazafulvalenes –An Experimental and Theoretical Study
  作者：Christian Holtgrewe、Christian Diedrich、Tania Pape、Stefan Grimme、F. Ekkehardt Hahn

  DOI：10.1002/ejoc.200600087

  日期：2006.7

  halides 9a–d initially results in the formation of the N-allyldibenzotetraazafulvalenes 10. These electron-rich olefins rearrange to give 1,1′,2′,3′-tetraalkyl-1′,2′-dihydro-2,2′-bibenzimidazoles 13, either by a 3-aza-Cope rearrangement or by a homolytic N-alkyl bond cleavage and addition of the radical at the 2′-position of the bibenzimidazole. Alternatively, double N-alkyl bond cleavage gives rise

  N-烯丙基苯并咪唑鎓卤化物 9a-d 的去质子化最初导致形成 N-烯丙基二苯并四氮杂富瓦烯 10。这些富电子烯烃重排得到 1,1',2',3'-四烷基-1',2'-二氢-2,2'-联苯并咪唑 13，通过 3-氮杂-Cope 重排或通过均裂 N-烷基键断裂和在联苯并咪唑的 2'-位添加自由基。或者，双 N-烷基键断裂产生 1,1'-二烷基-2,2'-联苯并咪唑 14。所有反应途径均通过在 DFT/B3-LYP/TZVP//DFT/ 上使用量子化学计算进行研究BP86/SV(P) 水平，通过将自由基的激活参数和协同重排机制与实验获得的产品进行比较。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Non-symmetrically substituted N-heterocyclic carbene–Ag(I) complexes of benzimidazol-2-ylidenes: Synthesis, crystal structures, anticancer activity and transmetallation studies
  作者：Rosenani A. Haque、Mohammed Z. Ghdhayeb、Srinivasa Budagumpi、Abbas Washeel Salman、Mohamed B. Khadeer Ahamed、Amin Malik Shah Abdul Majid

  DOI：10.1016/j.ica.2012.09.013

  日期：2013.1

  Non-symmetrically substituted benzimidazolium salts (1 and 2) having bromide counterion undergo metallation with Ag2O at stiochiometric ratio, giving mononuclear bis-carbene Ag(I) complexes (3 and 4), active as anticancer agents against Human Colorectal (HCT 116) cell lines. Both the complexes provide good activity (IC50 = 13.9 mu M for 3 and 14.6 mu M for 4) in the anticancer studies and so distinctly better than the ligand precursors (IC50 = 119.3 mu M for 1, and 70.0 mu M for 2). The molecular structure of Ag complexes 3 and 4 is elucidated by X-ray diffraction studies. The Pd(II)- and Au(I)-NHC complexes (5 and 6) were synthesized from 4 via the technique of transmetallation. However, attempts to produce transmetallated complexes using 3 were unsuccessful. (C) 2012 Elsevier B.V. All rights reserved.