1,4-bis-(N-benzimidazolyl)butane | 39677-03-7

• 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: 1,4-bis-(N-benzimidazolyl)butane
• 英文别名: 1,1'-(1,4-butanediyl)bis-1H-benzimidazole；1,4-bis(benzimidazole)butane；1,4-bis(benzimidazol-1-yl)butane；1,1′-(1,4-butanediyl)bis(benzimidazole)；1,4-bis(1H-benzo[d]imidazol-1-yl)butane；1-(4-(1H-benzimidazol-1-yl)butyl)-1H-benzimidazole；1,1′-(1,4-butanediyl)bis-1H-benzimidazole；(1,1'-butane-1,4-diyl)bis(1H-benzimidazole)；1,1'-(1,4-butanediyl)bis(benzimidazole)；1,4-bis(benzoimidazol-1-yl)butane；1,1'-butane-1,4-diylbis(1H-benzimidazole)；1-[4-(benzimidazol-1-yl)butyl]benzimidazole
• CAS: 39677-03-7
• 化学式: C₁₈H₁₈N₄
• 分子量: 290.368
• InChiKey: HZBVLBOHWYTWCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis-(N-benzimidazolyl)butane 在 air 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 1,4-bis (1-methyl-2-oxobenzimidazolin-3-yl) butane
  参考文献：
  名称：

  N,N'-Bridged Derivatives of 2,2'-Bibenzimidazole

  摘要：

  A series of 2,2'-bibenzimidazolium salts has been prepared by N,N'-bridging using dihaloalkanes. These salts may be reduced by either one or two electrons to the corresponding cation radical or neutral 2,2'-bibenzimidazolylidene. The latter species undergoes a chemiluminescent reaction with dioxygen to afford conformationally unique ureaphanes. Two benzimidazole molecules may be joined by N,N'-bridges to form bis(benzimidazolium) salts which may be deprotonated with sodium hydride. Subsequent intramolecular 2,2'-coupling leads to the same 2, 8'-bibenzimidazolinylidenes. The structural features of the ureaphane oxidation products have been studied by X-ray crystallography and NMR. An equimolar mixture of a 2,2'-bibenzimidazolium salt and the corresponding 2,2'-bibenzimidazolinylidene will coproportionate to form the analogous cation radical.

  DOI：

  10.1021/jo00123a034
• 作为产物：
  描述：

  1,4-二溴丁烷 、 苯并咪唑 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到1,4-bis-(N-benzimidazolyl)butane
  参考文献：
  名称：

  Tetrakis（咪唑鎓）大环受体，用于阴离子结合。

  摘要：

  通过双（咪唑鎓）前体化合物的逐步烷基化反应合成了具有可变空腔尺寸的新的（四）咪唑鎓大环受体系统。质子NMR滴定研究表明，大环牢固地结合了卤化物和苯甲酸根阴离子，两个受体系统在竞争性乙腈-水（9：1）溶剂介质中显示出对氟化物的显着选择性。

  DOI：

  10.1039/b510068b

文献信息

• Synthesis and antimicrobial activities of some bridged bis-benzimidazole derivatives
  作者：HASAN KÜÇÜKBAY、ÜLKÜ YILMAZ、NİHAT ŞİRECİ、AYŞE NİLAY GÜVENÇ

  DOI：10.3906/kim-1012-914

  日期：——

  Some bis-benzimidazoles derivatives bearing allyl, crotyl, cinammyl, furfuryl, and thenyl groups were synthesized and their in vitro antimicrobial activity determined against gram-positive and gram-negative bacteria, and fungi by disk-diffusion method. The structures of all new compounds were identified by ^1H-NMR, ^13}C-NMR, and FT-IR spectroscopic techniques and elemental analysis. All the compounds synthesized in this work were examined for their in vitro antimicrobial activities against gram-positive (Staphylococcus aureus and Bacillus megaterium) and gram-negative bacteria (Klebsiella pneumoniae and Escherichia coli), and the yeasts like fungi (Candida globrata and Candida tropicalis). Compared to the reference substances, Cefozine and nystatin, most of the compounds showed high antibacterial and antifungal activities against studied strains with inhibition zones between 8 and 28 mm.

  一些含有烯丙基、烯基、肉桂基、呋喃甲基和苯乙基的双苯并咪唑衍生物被合成，并通过扩散法确定它们对革兰氏阳性和阴性细菌以及真菌的体外抗菌活性。所有新化合物的结构通过^1H-NMR、^13C-NMR和FT-IR光谱技术以及元素分析来鉴定。本工作中合成的所有化合物都经过了体外抗菌活性检测，针对革兰氏阳性细菌（金黄色葡萄球菌和大肠杆菌）、革兰氏阴性细菌（肺炎克雷伯菌和大肠杆菌）以及类似真菌的酵母菌（白色念珠菌和热带念珠菌）。与参考物质，头孢唑啉和制霉菌素相比，大多数化合物显示出对研究菌株的高抗菌和抗真菌活性，抑制区在8到28毫米之间。
• Syntheses and structural characterization of six ionic salts based on bis(benzimidazole)/bis(imidazole) and perchlorometallates of Zn and Cu
  作者：Jianming Pan、Qing Wei、Jingxi Ju、Bin Liu、Shouwen Jin、Zhanghui Lin、Daqi Wang

  DOI：10.1080/00958972.2014.966701

  日期：2014.11.17

  [(H2L1)(CuCl4)]·H2O (2), [(H2L2)(ZnCl4)] (3) (L2 = 1-(3-(1H-benzimidazol-1-yl)propyl)-1H-benzimidazole), [( H2L2)(CuCl4)] (4), [(H2L3)(CuCl4)]·H2O (5) (L3 = 1- (4-(1H-benzimidazol-1-yl)butyl)-1H-benzimidazole), and [(H2L4)(ZnCl4)]·H2O (6) (L4 = 3,6-bis(imidazol-1-yl)pyridazine)), derived from bis(benzimidazole)/bis(imidazole) and metal(II) chloride dihydrate (zinc(II) chloride and copper(II) chloride dihydrate)

  六种盐，([(H2L1)(ZnCl4)] (1) (L1 = 1,1'-双(苯并咪唑基)甲烷), [(H2L1)(CuCl4)]·H2O (2), [(H2L2)(ZnCl4 )] (3) (L2 = 1-(3-(1H-苯并咪唑-1-基)丙基)-1H-苯并咪唑), [( H2L2)(CuCl4)] (4), [(H2L3)(CuCl4)] ·H2O (5) (L3 = 1- (4-(1H-苯并咪唑-1-基)丁基)-1H-苯并咪唑), 和 [(H2L4)(ZnCl4)]·H2O (6) (L4 = 3,6 -双（咪唑-1-基）哒嗪）），衍生自双（苯并咪唑）/双（咪唑）和金属（II）氯化物二水合物（氯化锌（II）和氯化铜（II）二水合物），并表征为红外、X 射线结构分析、元素分析和热重分析。所有化合物中阳离子的芳环都是平面的。X 射线衍射分析表明，所有配合物都具有由阳离子和氯金属阴离子之间的氢键构成的
• Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes
  作者：Alexander V. Aksenov、Alexander N. Smirnov、Nicolai A. Aksenov、Asiyat S. Bijieva、Inna V. Aksenova、Michael Rubin

  DOI：10.1039/c5ob00131e

  日期：——

  PPA-induced umpolung triggers efficient nucleophilic addition of unactivated anilines to nitroalkanes to afford benzoxazoles and benzimidazoles.

  PPA诱导的极性反转触发了对未活化苯胺与硝基烷烃的高效亲核加成，生成苯并噁唑和苯并咪唑。
• Two new coordination polymers of Co(II) with 1,1′-(1,4-butanediyl)bis(benzimidazole)
  作者：Jian-Fang Ma、Jing-Fu Liu、Ying-Chun Liu、Yan Xing、Heng-Qing Jia、Yong-Hua Lin

  DOI：10.1039/b004787m

  日期：——

  Two new compounds, [CoL2(H2O)2](NO3)2·8H2O (1) and [CoL(H2O)2(CH3CO2)2]·H2O (2), were obtained from self-assembly of the corresponding metal salts with 1,1′-(1,4-butanediyl)bis(benzimidazole) (L). In 1, each cobalt ion is coordinated to four nitrogen atoms from four molecules of L, and to two water molecules. Metal ions are bridged by L ligands to form infinite (4, 4) networks that contain 44-membered rings. The (4, 4) networks of 1 stack in a parallel fashion, resulting in the formation of large channels in the material. In 2, each cobalt ion is coordinated to two N atoms from two L molecules, two water molecules and two carboxylate O atoms from two acetate anions. Each L molecule is coordinated to two cobalt ions, acting as a bridging ligand as in 1. The bridged cobalt ions form an infinite zigzag chain structure.

  两个新化合物，[CoL2(H2O)2](NO3)2·8H2O (1) 和 [CoL(H2O)2(CH3CO2)2]·H2O (2)，是通过相应金属盐与1,1'-(1,4-丁二烯)双(苯咪唑)(L)的自组装获得的。在1中，每个钴离子与四个L分子的四个氮原子和两个水分子配位。金属离子由L配体桥连，形成无限的（4, 4）网络，包含44元环。1的（4, 4）网络以平行方式堆叠，最终形成材料中的大通道。在2中，每个钴离子与两个L分子的两个氮原子、两个水分子和两个来自两个乙酸根阴离子的羧酸氧原子配位。每个L分子与两个钴离子配位，充当桥接配体，如同在1中一样。桥接的钴离子形成无限之字形链结构。
• Synthesis and microwave-assisted catalytic activity of novel bis-benzimidazole salts bearing furfuryl and thenyl moieties in Heck and Suzuki cross-coupling reactions
  作者：Ülkü Yılmaz、Nihat Şireci、Selma Deniz、Hasan Küçükbay

  DOI：10.1002/aoc.1633

  日期：——

  A mixture of bis‐benzimidazole salts (1–7), Pd(OAc)2 and K2CO3 in DMF H2O catalyzes, in high yield, the Suzuki and Heck cross‐coupling reactions assisted by microwave irradiation in a short time. In particular, the yields of the Heck and Suzuki reactions with aryl bromides were found to be nearly quantative. The synthesized bis‐benzimidazole salts (1–7) were identified by 1H13C NMR, IR spectroscopic

  的双苯并咪唑盐（A混合物1-7），加入Pd（OAc）2和K 2 CO 3在DMF  ħ 2个Ó催化，以高收率，铃木和的Heck交叉偶联通过微波辐射辅助的反应在短时间。特别地，发现与芳基溴化物的Heck和Suzuki反应的产率几乎是定量的。将合成的双苯并咪唑盐（1 - 7）通过确定1个ħ  13 C NMR，IR光谱法和微量分析。版权所有©2010 John Wiley＆Sons，Ltd.