2-(苯并咪唑-1-基)乙酸乙酯 | 55175-50-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(苯并咪唑-1-基)乙酸乙酯
• 英文名称: ethyl 2-(1H-benzo[d]imidazol-1-yl)acetate
• 英文别名: 1-(ethoxycarbonylmethyl)benzimidazole；1H-Benzimidazole-1-acetic acid, ethyl ester；ethyl 2-(benzimidazol-1-yl)acetate
• CAS: 55175-50-3
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD00449812
• 分子量: 204.228
• InChiKey: QQNQPNGPSKOQAD-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C
• 沸点：
  344.3±44.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(苯并咪唑-1-基)乙酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 苯并咪唑-1-乙酸
  参考文献：
  名称：

  苯并咪唑衍生物制备中的均裂取代和类碳反应：（2-环烷基-1-苯并咪唑基）-N，N-二乙基乙酰胺的合成和性质

  摘要：

  描述了（2-环烷基-1-苯并咪唑基）-N，N-二乙基乙酰胺7a-e的制备和初步生物学评价。制备化合物 7a - d 的关键步骤是 (i) 苯并咪唑的均裂环烷基化，其中银催化的环烷羧酸 1a - d 被过二硫酸盐氧化脱羧作为烷基自由基的来源，以及 (ii) ) 由铜青铜生成的乙氧基羰基卡宾对苯并咪唑进行 N-烷基化-催化重氮乙酸乙酯分解。

  DOI：

  10.1002/ardp.19853180503
• 作为产物：
  描述：

  邻苯二胺 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 2-(苯并咪唑-1-基)乙酸乙酯
  参考文献：
  名称：

  Synthesis of benzimidazolyl-1,3,4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents

  摘要：

  To affiliate multiple bioactivities in a compact heteronuclei, two series of benzimidazole based 1,3,4-oxadiazoles were synthesized and assessed in vitro for their efficacy as antimicrobial agents against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, Shigella flexneri), four fungi (Aspergillus niger, Aspergillus fumigants, Aspergillus clavatus, Candida albicans) and Mycobacterium tuberculosis H37Rv and best results were observed amongst the N-benzothiazolylaetamide series. The lipophilicity (LogP) influence on the biological profile (MICs) of the prepared products was also discussed. Upon biological screening, it was observed that the majority of the compounds were found to possess a significant broad spectrum antimicrobial (3.12-25 mu g/mL of MIC) and antitubercular (6.25-25 mu g/mL of MIC) potential. The structural assignments of the new products were done on the basis of IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.033

文献信息

• Synthesis and catalytic application of cyclopentadienyl nickel(II) N-heterocyclic carbene complexes
  作者：Deniz Demir Atli

  DOI：10.1080/00958972.2020.1786543

  日期：2020.5.18

  A series of ester-functionalized benzimidazolium salts 2a–c were prepared by quaternization of 1-(ethoxycarbonyl)methyl}benzimidazole (1) with 3,5-dimethylbenzyl bromide, 2,5-dimethylbenzyl chlori...

  通过 1-(乙氧基羰基) 甲基}苯并咪唑 (1) 与 3,5-二甲基苄基溴、2,5-二甲基苄基氯...
• 6-substituted pyrazolo (3,4-d)pyrimidin-4-ones and compositions and
  申请人：Sanofi Winthrop, Inc.

  公开号：US05656629A1

  公开（公告）日：1997-08-12

  6-Substituted pyrazolo[3,4 -d]pyrimidin-4-one derivatives, pharmaceutical compositions containing them and methods for effecting c-GMP-phosphodiesterase inhibition and for treating heart failure and/or hypertension.

  6-取代嘧啶并[3,4 -d]嘧啶-4-酮衍生物，含有它们的药物组合物以及用于影响c-GMP-磷酸二酯酶抑制和治疗心力衰竭和/或高血压的方法。
• Synthesis of β-hydroxyacetamides from unactivated ethyl acetates under base-free conditions and microwave irradiation
  作者：Eugenio Hernández-Fernández、Pedro Pablo Sánchez-Lara、Mario Ordóñez、Oscar Abelardo Ramírez-Marroquín、Francisco G. Avalos-Alanís、Susana López-Cortina、Víctor M. Jiménez-Pérez、Tannya Rocio Ibarra-Rivera

  DOI：10.1016/j.tetasy.2014.11.015

  日期：2015.1

  unactivated ethyl esters with achiral and chiral 1,2-amino alcohols under microwave irradiation and base-free conditions is described. This procedure provides a convenient method for the synthesis of β-hydroxyacetamides bearing pyrazole, imidazole, and benzimidazole groups in high yields and without racemization. The protocol described herein is environmentally friendly and allows for the preparation of a

  的酰胺化未活化乙酯与非手性和手性1,2-二氨基微波照射和游离碱条件下醇进行说明。该过程提供了β-hydroxyacetamides轴承吡唑，咪唑和苯并咪唑基团以高产率和无外消旋作用的合成的便利方法。本文所描述的协议是环境友好的，并且允许的各种β-hydroxyacetamides，这是在恶唑啉和生物学感兴趣的其它衍生物的合成中的关键中间体的制备。
• Solid–Liquid Phase Alkylation of<i>N</i>-Heterocycles: Microwave-Assisted Synthesis as an Environmentally Friendly Alternative
  作者：Mátyás Milen、Alajos Grün、Erika Bálint、András Dancsó、György Keglevich

  DOI：10.1080/00397910903226166

  日期：2010.7.12

  The solid–liquid phase alkylation of a variety of five-membered N-heterocycles (carbazole, imidazole, benzimidazole, and indole-3-carbaldehyde) was carried out under different conditions. The use of alkali carbonate in dimethylformamide or in MeCN (in the latter case, in the presence of a phase-transfer catalyst) is a suitable method to prepare the corresponding N-alkylated products in an efficient

  多种五元 N-杂环（咔唑、咪唑、苯并咪唑和吲哚-3-甲醛）的固液相烷基化反应在不同条件下进行。在二甲基甲酰胺或 MeCN（在后一种情况下，在相转移催化剂的存在下）中使用碱金属碳酸盐是一种以有效方式制备相应 N-烷基化产物的合适方法。在大多数情况下，无溶剂、微波辅助反应是传统方法的一种环保替代方法。
• Palladium–benzimidazolium salt catalyst systems for Suzuki coupling: development of a practical and highly active palladium catalyst system for coupling of aromatic halides with arylboronic acids
  作者：Wen Huang、Jianping Guo、Yuanjing Xiao、Miaofen Zhu、Gang Zou、Jie Tang

  DOI：10.1016/j.tet.2005.06.060

  日期：2005.10

  be as low as 0.0001 mol% and 0.01–0.1 mol% for iodide and bromide substrates, respectively. The coupling of unactivated aromatic chlorides with arylboronic acids also gave good results using Cs2CO3 as base with a 2 mol% palladium loading. The electronic factors from aromatic halides exert a significant influence on the Suzuki coupling catalyzed by the PdCl2–2 system while the electronic effect from

  钯-苯并咪唑盐催化剂体系已针对Suzuki偶联进行了研究。对于来自钯-咪唑鎓盐类似物的苯并咪唑鎓盐中的氮取代基，尚未发现不同的取代作用。已经确定了实用且高活性的钯催化剂体系PdCl 2 / N，N'-二苄基苯并咪唑鎓氯化物2用于芳族卤化物与芳基硼酸的Suzuki偶联。各种芳族卤化物与芳基硼酸与PdCl 2 – 2的偶联催化剂体系获得了良好的优异收率。对于碘化物和溴化物底物，钯的有效载量可能分别低至0.0001 mol％和0.01-0.1 mol％。未活化的芳族氯化物与芳基硼酸的偶合也以使用Cs 2 CO 3为碱，钯含量为2mol％的情况给出了良好的结果。从芳族卤化物的电子因素施加在铃木一个显著影响通过的PdCl联接器催化2 - 2系统而来自芳基的对应电子效应是可忽略的。芳香族卤化物与适度的空间位阻也可以与使用的PdCl苯基硼酸情侣平稳2 - 2催化剂体系。