1,3-二苄基-1H-苯并[D]咪唑-3-氯化物 | 36339-13-6

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 1,3-二苄基-1H-苯并[D]咪唑-3-氯化物
• 英文名称: 1,3-dibenzylbenzimidazolium chloride
• 英文别名: N,N'-dibenzylbenzimidazolium chloride；1,3-dibenzyl-1H-benzimidazol-3-ium chloride；1,3-dibenzyl-1H-benzo[d]imidazol-3-ium chloride；1,3-dibenzylbenzimidazol-3-ium;chloride
• CAS: 36339-13-6
• 化学式: C₂₁H₁₉N₂*Cl
• 分子量: 334.848
• InChiKey: CSFOFEZIBMHEPB-UHFFFAOYSA-M

物化性质

• 熔点：
  210-212 °C(Solv: dichloromethane (75-09-2))
• 溶解度：
  DMSO（轻微，超声处理），甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1,3-二苄基-1H-苯并[D]咪唑-3-氯化物 在 sodium hypochlorite 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到1,3-dibenzyl-1,3-dihydro-2H-benzo[d]imidazol-2-one
  参考文献：
  名称：

  2-咪唑酮和2-亚氨基咪唑的合成

  摘要：

  已经开发了将咪唑鎓盐直接转化为相应的 2-咪唑酮或 2-亚氨基咪唑衍生物的方便方法。用商业漂白剂处理盐导致在 C2 处有效氧化并形成相应的咪唑酮。或者，用N-氯酰胺处理盐以良好的产率提供相应的保护的2-氨基衍生物。

  DOI：

  10.1021/ol2022438
• 作为产物：
  描述：

  氯化苄 在 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 1,3-二苄基-1H-苯并[D]咪唑-3-氯化物
  参考文献：
  名称：

  Synthesis and applications of novel imidazole and benzimidazole based sulfonic acid group functionalized Brönsted acidic ionic liquid catalysts

  摘要：

  In this study, a variety of imidazole/benzimidazole based sulfonic acid group functionalized Bronsted acidic ionic liquids (BAILs) were synthesized. Catalytic activities of BAILS were assessed using multicomponent coupling reactions. Catalytic activities of BAILs were high when compared with those of solid acid catalysts such as H-ZSM-5. H-BETA, and sulfonic acid functionalized SBA-15 catalysts. The Hammett acidity order determined from UV-visible spectroscopy of BAILS is consistent with their activity order observed in acid-catalyzed reactions. Theoretical studies demonstrate that the hydrogen bonding plays a key role in tuning the acidity of BAILs. Recycling experiments suggest that these novel BAILS can be reused without significant loss in catalytic activity. Novel BAILS offer several attractive features such as low cost, high catalytic activity, and recyclability. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.06.003
• 作为试剂：
  描述：

  对硝基苯甲醛 、 alpha-氯乙酰苯 在 1,3-二苄基-1H-苯并[D]咪唑-3-氯化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.28h， 以82%的产率得到1-(4-硝基苯基)-3-苯基丙烷-1,3-二酮
  参考文献：
  名称：

  Nucleophilic acylation of α-haloketones with aldehydes: an umpolung strategy for the synthesis of 1,3-diketones

  摘要：

  The first example of N-heterocyclic carbene (NHC)-promoted intermolecular acylation of alpha-haloketones with aldehydes and alpha,beta-unsaturated aldehydes (enals) is reported. The protocol involves carbonyl umpolung reactivity of aldehydes and enals in which the carbonyl carbon attacks nucleophilically on electrophilic terminal of alpha-haloketones to afford 1,3-diketones and alpha,beta-unsaturated 1,3-diketones, respectively. Short reaction time, ambient temperature, operational simplicity, and high yields are the salient features of the present procedure. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.175

文献信息

• Synthesis of Imidazolidinone, Imidazolone, and Benzimidazolone Derivatives through Oxidation Using Copper and Air
  作者：Dazhi Li、Thierry Ollevier

  DOI：10.1021/acs.orglett.9b00973

  日期：2019.5.17

  synthetic method of urea derivatives using copper and air was developed. These mild conditions provided moderate to very good yields for 15 examples (53–93%), while low yields were obtained with sterically hindered substrates (3 examples). The reaction was found to go through an in situ generated copper–N-heterocyclic carbene, which was then oxidized into cyclic urea derivatives possessing alkyl, benzyl

  开发了一种利用铜和空气合成尿素衍生物的新方法。这些温和的条件为15个实例提供了中等至非常高的产量（53-93％），而空间受阻的底物却获得了低产量（3个实例）。发现该反应通过原位生成的铜-N-杂环卡宾，然后被氧化成具有烷基，苄基，芳基，羟基，Boc保护的和叔胺基的环状脲衍生物。
• Synthesis and structures of 1,3,1′,3′-tetrabenzyl-2,2′-biimidazolidinylidenes (electron-rich alkenes), their aminal intermediates and their degradation products
  作者：Bekir Çetinkaya、Engin Çetinkaya、José A. Chamizo、Peter B. Hitchcock、Hatam A. Jasim、Hasan Küçükbay、Michael F. Lappert

  DOI：10.1039/a802123f

  日期：——

  substituted enetetramines 9 and 3 have been studied. From HNR(CH2)2NRH and CH(NMe2)2OBut or CH(OMe)2NMe2, two new intermediates along the pathway to 9, namely the orthoamide 11 and the bis(orthoamide) 12 were isolated. Each of 11 and 12 was converted into 9 by refluxing in toluene. Photolysis of 9 yielded the isomer 10, while thermolysis of 9 gave the di(debenzylated) product 1,1′-dibenzyl-2,2′-biimidazoline

  已研究了苄基（R）取代的四胺（9）和（3）。从HNR（CH 2）2 NRH和CH（NMe 2）2 OBu t或CH（OMe）2 NMe 2中，分离出两个通往9的新中间体，即邻酰胺11和双邻酰胺12。通过在甲苯中回流，将11和12中的每一个转化为9。9的光解生成异构体10，而9的热解生成二（去苄基化）产物1,1'-二苄基-2,2'-联咪唑啉13。至3的路线（R = R'= CH 2 Ph）类似于用于9的那些，涉及1,2-C 6 H 4 [N（R）H] 2与CH（OMe）2的缩合NMe 2或1,3-二苄基苯并咪唑氯化物8（X = Cl）与NaH之间的反应未得到预期的烯四胺3（9的二苯并类似物），取而代之的是双（脱苄基）产物15。加热orthoamide 1,2--R NC 6 H ^ 4 N（R）C （H）NME 2，从CH制备（NME 2）2 OBU吨和1,2--C 6 H ^ 4 [N（H）R]
• New 4-vinylbenzyl-substituted bis(NHC)-Pd(II) complexes: Synthesis, characterization and the catalytic activity in the direct arylation reaction
  作者：Yetkin Gök、Aydın Aktaş、Hülya Erdoğan、Yakup Sarı

  DOI：10.1016/j.ica.2017.12.019

  日期：2018.2

  substituted bis(NHC)-Pd(II) complexes and their catalytic activity in direct arylation reaction. The bis(NHC)-Pd(II) complexes have been prepared from Ag(I)NHC complexes by transmetallation method. The complexes have been characterized by using 1H NMR, 13C NMR, FTIR spectroscopy and elemental analysis techniques. Also, all the complexes showed excellent activity as catalysts in the direct arylation reaction

  摘要这项研究包含了新的4-乙烯基苄基取代的双（NHC）-Pd（II）配合物的合成及其在直接芳基化反应中的催化活性。由Ag（I）NHC配合物通过金属转移法制备了双（NHC）-Pd（II）配合物。通过使用1 H NMR，13 C NMR，FTIR光谱和元素分析技术对复合物进行了表征。另外，所有配合物在直接芳基化反应中均表现出优异的催化剂活性。
• Mechanism studies of oxidation and hydrolysis of Cu(I)–NHC and Ag–NHC in solution under air
  作者：Dazhi Li、Thierry Ollevier

  DOI：10.1016/j.jorganchem.2019.121025

  日期：2020.1

  The decomposition of copper(I)–NHC and silver-NHC complexes in solution under air was studied. The Cu(I)–NHCs were oxidized into urea derivatives and hydrolysed into imidazoliums or benzimidazoliums. The decomposition of Ag–NHC with a saturated backbone led to ring-opening product, while the Ag–NHC with an unsaturated backbone led to imidazolium and Ag-bisNHC complex. The effects of steric property

  研究了溶液中空气中铜（I）-NHC和银-NHC配合物的分解。Cu（I）–NHCs被氧化成脲衍生物，然后水解成咪唑或苯并咪唑。具有饱和主链的Ag–NHC的分解导致开环产物，而具有不饱和主链的Ag–NHC的分解导致咪唑和Ag-bisNHC络合物。使用理论计算研究了空间特性，亲水性和NHC与O 2和H 2 O的结合能对Cu（I）-NHC分解的影响。立体位阻对Cu（I）–NHC的稳定性起着重要作用。提出了Cu（I）-NHC和Ag-NHC分解的途径。
• Highly efficient carbene and polycarbene catalysis of the transesterification reaction
  作者：Konstantin A. Marichev、Nikolai I. Korotkikh、Alan H. Cowley、Vagiz Sh. Saberov、Nataliya V. Glinyanaya、Gennady F. Rayenko、Oles P. Shvaika

  DOI：10.24820/ark.5550190.p010.034

  日期：——

  Highly efficient carbene and polycarbene catalysis of the transesterification reaction of ethyl benzoate in methanol has been observed and results in values of TON as high as 4000–6150 at a molar ratio of ester to methanol of 1:18 at room temperature. The most effective catalysts were found to be the individual carbenes or in situ generated carbenes, namely adamantyl and aromatic substituted cyclic

  已经观察到苯甲酸乙酯在甲醇中的酯交换反应的高效卡宾和聚卡宾催化，并且在室温下酯与甲醇的摩尔比为 1:18 时，TON 值高达 4000-6150。发现最有效的催化剂是单独的卡宾或原位生成的卡宾，即金刚烷基和芳族取代的环状化合物和聚合卡宾。这些反应都不需要使用分子筛。聚合咪唑-2-亚基催化剂用于从葵花油中高效生产生物柴油燃料。