2-(氯甲基)-1-乙基-1H-苯并咪唑 | 66947-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(氯甲基)-1-乙基-1H-苯并咪唑
• 英文名称: 2-(chloromethyl)-1-ethyl-benzimidazole
• 英文别名: 2-(chloromethyl)-1-ethyl-1H-benzo[d]imidazole；1H-Benzimidazole, 2-(chloromethyl)-1-ethyl-；2-(chloromethyl)-1-ethylbenzimidazole
• CAS: 66947-93-1
• 化学式: C₁₀H₁₁ClN₂
• 分子量: 194.664
• InChiKey: NGOCULQAUYHTQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-(氯甲基)-1-乙基-1H-苯并咪唑 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 生成 2-(Azidomethyl)-1-ethylbenzimidazole
  参考文献：
  名称：

  Synthesis of new 1,2,3-triazole linked benzimidazole molecules as anti-proliferative agents

  摘要：

  One pot click chemistry is used to link triazole and benzimidazole pharmacophore to get N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)aniline and its derivatives. Flexible linkages in the form of -CH2-R or -O-R/-N-R were designed during synthesis. All the newly synthesized compounds were characterized by FT-IR and NMR spectroscopy as well as high-resolution mass spectrometry. Selected compounds were screened for in vitro anti-proliferative activity using National Cancer Institute (NCI)-60 human tumor cell line screening program. The most potent structure N-((1-((1H-benzo[d] imidazol-2-yl) methyl)-1H-1,2,3-triazol-4-yl) methyl)-4-chloroaniline 7e showed 40% growth inhibition in renal cancer cell line (UO-31) at 10 mu M concentration.

  DOI：

  10.1080/00397911.2017.1289412
• 作为产物：
  描述：

  (1-乙基-1H-苯并咪唑-2-基)甲醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到2-(氯甲基)-1-乙基-1H-苯并咪唑
  参考文献：
  名称：

  锰与过氧化氢配合物催化的高效脂肪族CH键氧化

  摘要：

  开发了含有苯并咪唑环和富电子吡啶环的四齿氮配体，所得锰配合物在简单烷烃的CH氧化中表现出良好的活性。特别地，通过使用环境友好的H 2 O 2作为末端氧化剂，环状脂肪族烷烃以非常高的收率（高达89％）转化为酮。该方案也成功地用于苄基CH氧化中，从而使相应的酮具有很好的选择性。此外，锰络合物对复杂分子的CH-H键氧化显示出在后期化学合成中以良好的选择性组装醇的潜在效用。

  DOI：

  10.1002/asia.201800068

文献信息

• Substituent-dependent structures and catalysis of benzimidazole-tethered N-heterocyclic carbene complexes of Ag(i), Ni(ii) and Pd(ii)
  作者：Fuwei Li、Jian Jin Hu、Lip Lin Koh、T. S. Andy Hor

  DOI：10.1039/c000722f

  日期：——

  Homoleptic cationic benzimidazole-imidazolin-2-ylidene N-heterocyclic carbene (NHC = L) complexes of NiII and PdII have been prepared directly from the ligand precursor in salt form [H.L]Cl and from the transmetallation route via AgI. The N-tether of the imidazolinylidene ring imposes a significant influence on the nuclearity of the intermediate Ag(I)-NHC complexes and the geometric isomer outcome of the d8 products. Use of a benzyl-substituted NHC gives [Ag4(LBn)2Cl4], 2a (from [HLBn]Cl, 1a, and Ag2O) (Bn = benzyl), which shows an alignment of four silver atoms bridged by the difunctional C–N ligands and chlorides. Its transmetallation with NiCl2(PPh3)4 and PdCl2(MeCN)2 results in double-metal salts 2[M(LBn)2]2+[Ag4Cl8]4− (M = Ni (3a) and Pd (4a)). The nuclearity of the Ag4 aggregate is maintained in the transmetallation process. Their Ag-free forms [M(LBn)2]Cl2 (M = Ni (5) and Pd (6)) were prepared by direct deprotonation of 1a with M(OAc)2. The two carbenic carbon donor are cis- to each other in both 3a and 4a, thus imposing the weaker σ-benzimidazole nitrogen donor to be trans to them. A sterically demanding mesityl pendant however gives the dinuclear dissymmetic [Ag2(LMes)2Cl2], 2b (Mes = mesityl) that shows a 12-membered metallomacrocyclic ring with a 2-coordinated [AgI(NHC)2] and 4-coordinated [AgI(Imd)2Cl2] (Imd = imidazole). Transmetallation of the latter, or direct metallation from [HLMes]Cl, 1b, gives [M(LMes)2]Cl2 (M = Ni (3b) and Pd (4b)) with the two carbonic carbon trans to each other. The catalytic potential of 3b and 4b, which are more effective than 5 and 6, has been demonstrated by their high activities in Ni-catalyzed Kumada at room temperature and Pd-catalyzed Heck couplings of aryl and/or heteroaryl halides, respectively.

  均配正离子苯并咪唑-咪唑啉亚基N-杂环卡宾（NHC = L）NiII和PdII配合物可以通过盐形式的配体前驱体[H.L]Cl以及通过AgI的转金属路线来直接制备。咪唑啉亚基环的N-连接对中间体Ag(I)-NHC配合物的核数和d8产物的几何异构体结果产生了显著影响。使用苯甲基取代的NHC得到[Ag4(LBn)2Cl4]，2a（由[HLBn]Cl，1a，和Ag2O制备）（Bn = 苯甲基），显示出四个银原子通过双功能的C-N配体和氯化物桥接的对齐。其与NiCl2(PPh3)4和PdCl2(MeCN)2的转金属反应得到了双金属盐2[M(LBn)2]2+[Ag4Cl8]4-（M = Ni (3a) 和 Pd (4a)）。Ag4聚集体的核数在转金属过程中得以保持。它们的Ag-free形式[M(LBn)2]Cl2（M = Ni (5) 和 Pd (6)）是通过1a与M(OAc)2的直接去质子化制备的。两个卡宾碳供体在3a和4a中都是cis相对的，因此使较弱的σ-苯并咪唑氮供体与其相对。然而，空间位阻较大的甲基苯基悬挂物给出了二核不对称的[Ag2(LMes)2Cl2]，2b（Mes = 甲基苯基），显示出具有2配位的[AgI(NHC)2]和4配位的[AgI(Imd)2Cl2]（Imd = 咪唑）的12元金属大环。后者的转金属反应，或直接从[HLMes]Cl，1b，金属化得到了[M(LMes)2]Cl2（M = Ni (3b) 和 Pd (4b)），其中两个碳碳彼此相对。3b和4b的催化潜力，它们比5和6更有效，已经通过它们在室温下Ni催化的Kumada和Pd催化的芳基和/或杂芳基卤化物的Heck偶联反应中的高活性得到了证明。
• Bicyclic Benzimidazole Compounds and Their Use as Metabotropic Glutamate Receptor Potentiators
  申请人：Egle Ian

  公开号：US20090192169A1

  公开（公告）日：2009-07-30

  Compounds of Formula I: wherein A, B, D, L, R 1 , R 2 , R 3 , R 4 , m, and n are as defined for Formula I in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

  式I的化合物： 其中A、B、D、L、R1、R2、R3、R4、m和n的定义如描述中所定义。本发明还涉及制备这些化合物的方法，以及用于制备的新中间体，含有这些化合物的药物组合物，以及这些化合物在治疗中的应用。
• Synthesis, structural characterization and catalytic activity of benzimidazole-functionalized Pd(II) <i>N</i> -heterocyclic carbene complexes
  作者：Yalin Diao、Rong Hao、Junfeng Kou、Mingyu Teng、Guoli Huang、Yegao Chen

  DOI：10.1002/aoc.3030

  日期：2013.9

  Two Pd(II)–NHC complexes bearing benzimidazole and pyridine groups have been successfully prepared and fully characterized by NMR and X‐ray diffraction analysis. The structure of palladium complexes are a typical square‐planar with palladium surrounded by two pairs of trans‐arranged benzimidazole and carbene ligands. The Pd–NHC complexes have been proved to be a highly efficient catalyst for the Mizoroki–Heck

  已经成功制备了两个带有苯并咪唑和吡啶基团的Pd（II）-NHC配合物，并通过NMR和X射线衍射分析对其进行了全面表征。钯配合物的结构是典型的方形平面，钯被两对反式排列的苯并咪唑和卡宾配体包围。已证明Pd-NHC络合物是温和条件下芳基卤化物与各种取代丙烯酸酯的Mizoroki-Heck偶联反应的高效催化剂，产率高。版权所有©2013 John Wiley＆Sons，Ltd.
• Synthesis, structural characterization of benzimidazole-functionalized Ni(II) and Hg(II) N-heterocyclic carbene complexes and their applications as efficient catalysts for Friedel–Crafts alkylations
  作者：Guoli Huang、Hongsheng Sun、Xiaojie Qiu、Yingzhong Shen、Juli Jiang、Leyong Wang

  DOI：10.1016/j.jorganchem.2011.04.039

  日期：2011.9

  L1 = 3-(1-ethyl-1H-benzimidazol-2-yl)methyl)-1-((6-methylpyridin-2-yl)methyl)imidazolyl-idene), [Ni(L2)2(CH3CN)](PF6)2 (3b, L2 = 3-(1-ethyl-1H-benzimidazol-2-yl)methyl)-1-((6-methylpyridin-2-yl)-methyl)benzimidazolylidene), and [Hg(L1)2(CH3CN)2](PF6)2 (4) have been successfully prepared and fully characterized by NMR, ESI-MS spectroscopy, and X-ray diffraction analysis. The nickel complexes reveal

  [Ni（L 1）2 ]（PF 6）2（3a，L 1  = 3-（1-乙基-1 H-苯并咪唑-2-基）甲基）-1-（（6-甲基吡啶-2-基） （Ni（L 2）2（CH 3 CN）]（PF 6）2（3b，L 2  = 3-（1-乙基-1 H-苯并咪唑-2-基）甲基）-1- （（6-甲基吡啶-2--2-基）-甲基）苯并咪唑基亚烷基）和[Hg（L 1）2（CH 3 CN）2 ]（PF 6）2（4）已成功制备，并已通过NMR，ESI-MS光谱和X射线衍射分析进行了全面表征。镍络合物显示出具有两个卡宾配体和苯并咪唑基团的顺式构型的平面结构。事实证明，镍络合物3b是在室温下以中等至优异的产率将吲哚与β-硝基苯乙烯进行吲哚的Friedel-Crafts烷基化的高效催化剂。的晶体堆积结构4个的是双链1D超分子链通过链间的苯并咪唑环和吡啶形成的显示环面-面π - π堆积相互作用。
• Ionically tagged benzimidazole palladium(II) complex: preparation and catalytic application in cross-coupling reactions
  作者：Li Zhang、Junliang Wu、Lijun Shi、Chungu Xia、Fuwei Li

  DOI：10.1016/j.tetlet.2011.05.079

  日期：2011.7

  An imidazolium chloride tagged palladium(II) complex has been conveniently prepared and structurally analyzed. It is active toward cross-coupling of arylboronic acid with aryl halide and benzoyl chloride, giving moderate to high yield of the desired biaryls and aryl ketones, respectively. The present phosphine-free (N–N)Pd(II) complex could be efficiently recycled at least four times with minor decrease

  方便地制备了咪唑鎓氯化物标记的钯（II）配合物并进行了结构分析。它对芳基硼酸与芳基卤化物和苯甲酰氯的交叉偶联具有活性，分别给出中等至高收率的所需联芳基和芳基酮。目前的无膦（N–N）Pd（II）复合物可以有效地循环至少四次，而在Suzuki-Miyaura水溶液中的反应活性则略有下降。