2,5-bis-(imidazolmethyl)pyrrole | 454677-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,5-bis-(imidazolmethyl)pyrrole
• 英文别名: 2,5-bis[(imidazol-1-yl)methyl]pyrrole；2,5-bis((1H-imidazol-1-yl)methyl)-1H-pyrrole；1-[[5-(imidazol-1-ylmethyl)-1H-pyrrol-2-yl]methyl]imidazole
• CAS: 454677-73-7
• 化学式: C₁₂H₁₃N₅
• 分子量: 227.269
• InChiKey: QAQPORZELJAANS-UHFFFAOYSA-N

物化性质

• 沸点：
  518.2±40.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-bis-(imidazolmethyl)pyrrole 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 bis(3-N-benzylimidazole)dichloropalladium(II)
  参考文献：
  名称：

  Pyrrole pincers containing imidazole, pyrazole and 1,2,4-triazole groups

  摘要：

  Pincer compounds containing a central pyrrole linked through methylene groups in the 2,5-positions to two N-imidazole, N-pyrazole and N-1,2,4-triazole heterocyles have been prepared via a common quaternary amine precursor. Alkylation of the imidazole groups using methyl iodide or benzyl bromide gave imidazolium compounds. The methylated iodide salt was characterised crystallographically, showing significant pyrrole I center dot center dot center dot HN, imidazolium I center dot center dot center dot HC and imidazolium I center dot center dot center dot(sp(2)-C) interactions leading to a U-shaped conformation of the cationic pincer compound. The alkylated cations which were investigated as precursors to pyrrole-carbene pincer ligands, but all attempts to either coordinate palladium or deprotonate using silver oxide led to cleavage of the heterocycles from the central pyrrole. The result was the formation of palladium and silver complexes containing 3-N-methylimidazole (3-N-MeIm) or 3-N-benzylimidazole (3-N-BzIm) ligands: (3-N-MeIm)PdI2, (3-N-MeIm)PdCl2 and [(3-N-MeIm)(2)Ag]I, with the (3-N-MeIm)PdI2 complex characterised by crystallography. Pyrazole, 3,5-dimethylpyrazole and 1,2,4-triazole pincer compounds were prepared, the latter characterised by a molecular structure determination. The pyrazole and 1,2,4-triazole pincers coordinate directly to palladium through the deprotonated central pyrrolyl and neutral N-donors on the flanking heterocycles. (C) 2014 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.07.022
• 作为产物：
  描述：

  咪唑 、 1,1'-(1H-pyrrole-2,5-diyl)bis(N,N,N-trimethylmethanaminium) diiodide 在 氢氧化钾 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以90%的产率得到2,5-bis-(imidazolmethyl)pyrrole
  参考文献：
  名称：

  两种双咪唑连接的环烷的合成与结构表征：“碳烯卟啉”配体的前体

  摘要：

  描述了咪唑鎓连接的环烷[ 1 ] [PF 6 ] 2和[ 2 ] [PF 6 ] 2的合成和光谱表征。环环烷[ 1 ] [PF 6 ] 2包含两个由2,6-双（甲基）-吡啶单元和2,5-双（甲基）-吡咯单元桥接的咪唑环。环烷[ 2 ] [PF 6 ] 2包含两个由两个2,5-双（甲基）-吡咯单元桥接的咪唑环。环烷[ 1 ] [PF 6 ] 2和[ 2 ] [PF 6 ] 2 X射线晶体学已在结构上对其进行了表征。

  DOI：

  10.1016/s0040-4039(02)00557-9

文献信息

• Synthesis of novel NHC-pyrrole-NHC C-N-C Pincer proligands
  作者：Hong Jiang、Hong Ding、Kaiqi Ge、Pei Guang、Yunfei Li、Xiang Liu、Guangsheng Pang、Yanhui Shi

  DOI：10.1515/hc-2012-0108

  日期：2012.10.1

  Two novel pyrrole-functionalized bis(benzoimidazolium) salts, which are novel NHC-pyrrole-NHC C-N-C Pincer proligands were synthesized in high yield. Both of these compounds are fully characterized by ¹H and ¹³C NMR, IR and elemental analysis.

  合成了两种新型吡咯功能化的双(苯并咪唑)盐，这些盐是新型的NHC-吡咯-NHC C-N-C Pincer 前体配体，收率很高。这两种化合物均通过¹H和¹³C NMR、IR和元素分析进行了全面表征。

• Metallacycles and methods of making the same
  申请人：Lu Kuang-Lieh

  公开号：US20090082574A1

  公开（公告）日：2009-03-26

  The present invention provides for novel metallacycles and processes for making the same.

  本发明提供了一种新型金属环化合物和制备方法。
• Metal complexes of N-heterocyclic carbenes as radiopharmaceuticals and antibiotics
  申请人：Youngs Wiley

  公开号：US20070021401A1

  公开（公告）日：2007-01-25

  A method for inhibiting microbial growth comprises administering an effective amount of a silver complex of a N-heterocyclic amine. A method for treating cancer cells or a method for imaging one or more tissues of a patient includes administering an effective amount of a complex of a N-heterocyclic amine and a radioactive metal. A method for treating urinary tract infections utilizing silver complexes of N-heterocyclic carbenes. N-heterocyclic carbenes of the present invention may be represented by the formula wherein Z is a heterocyclic group, and R 1 and R 2 are, independently or in combination, hydrogen or a C 1 -C 12 organic group selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, arylalkyl, alkylaryl, heterocyclic, and alkoxy groups and substituted derivatives thereof.

  一种抑制微生物生长的方法包括给予有效量的N-杂环胺的银络合物。一种治疗癌细胞或成像患者一个或多个组织的方法包括给予有效量的N-杂环胺和放射性金属的络合物。一种利用N-杂环卡宾银络合物治疗尿路感染的方法。本发明的N-杂环卡宾可以用以下式表示，其中Z是杂环基，而R1和R2是独立或组合的氢或选择自烷基、环烷基、烯基、环烯基、炔基、芳基、芳基烷基、烷基芳基、杂环和烷氧基和其取代衍生物的C1-C12有机基。
• Metal Complexes of N-Heterocyclic Carbenes as Radiopharmaceuticals and Antibiotics
  申请人：Youngs Wiley J.

  公开号：US20080267867A1

  公开（公告）日：2008-10-30

  A method for inhibiting microbial growth comprises administering an effective amount of a silver complex of a N-heterocyclic amine. A method for treating cancer cells or a method for imaging one or more tissues of a patient includes administering an effective amount of a complex of a N-heterocyclic amine and a radioactive metal. N-heterocyclic carbenes of the present invention may be represented by formula (I) wherein Z is a heterocyclic group, and R 1 and R 2 are, independently or in combination, hydrogen or a C 1 -C 12 organic group selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, arylalkyl, alkylaryl, heterocyclic, and alkoxy groups and substituted derivatives thereof.

  一种抑制微生物生长的方法包括给予一种N-杂环胺的银络合物有效量。一种治疗癌细胞或成像患者的一个或多个组织的方法包括给予一种N-杂环胺和放射性金属的络合物有效量。本发明的N-杂环卡宾可以用式(I)表示，其中Z是一个杂环基团，R1和R2独立或组合地是氢或C1-C12有机基团，所述有机基团选自烷基，环烷基，烯基，环烯基，炔基，芳基，芳基烷基，烷基芳基，杂环和其取代衍生物。
• [EN] METAL COMPLEXES OF N-HETEROCYCLIC CARBENES AS RADIOPHARMACEUTICALS AND ANTIBIOTICS<br/>[FR] COMPLEXES METALLIQUES DE CARBENES N-HETEROCYCLIQUES UTILES COMME PRODUITS RADIOPHARMACEUTIQUES ET ANTIBIOTIQUES
  申请人：UNIV AKRON

  公开号：WO2005023760A3

  公开（公告）日：2006-10-12