1,3-bis-(benzimidazol-1-ylmethyl)benzene | 188600-95-5

• 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: 1,3-bis-(benzimidazol-1-ylmethyl)benzene
• 英文别名: 1,3-bis((1H-benzo[d]imidazol-1-yl)methyl)benzene；1,3-bis(benzimidazole-1-ylmethyl)benzene；1,3-Bis(benzimidazol-1-ylmethyl)benzene；1-[[3-(benzimidazol-1-ylmethyl)phenyl]methyl]benzimidazole
• CAS: 188600-95-5
• 化学式: C₂₂H₁₈N₄
• 分子量: 338.412
• InChiKey: SVKWLTSAJZQGAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  602.4±65.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1,3-bis-(benzimidazol-1-ylmethyl)benzene 在 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 1,1'-[1,3-phenylenebis(methylene)]-bis-2,2’-iodo-3,3’-methyl-1H-benzimidazolium bis(trifluoromethanesulfonate)
  参考文献：
  名称：

  氢键诱导的氢键诱导的氢原子转移至C═N键

  摘要：

  制备了几种双齿二氢咪唑啉，并研究了用汉茨酯还原氢转移C═N键的催化剂。观察到喹啉和亚胺的高效反应，催化剂负载量低至2摩尔％。使用NMR研究和等温量热滴定法阐明了卤素键的存在。XB供体的结合常数也使用等温量热滴定法（ITC）进行测量。

  DOI：

  10.1021/ol501259q
• 作为产物：
  描述：

  苯并咪唑 、 间二溴苄 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以68%的产率得到1,3-bis-(benzimidazol-1-ylmethyl)benzene
  参考文献：
  名称：

  1,3,4-恶二唑在苯并咪唑啉酮的光谱，光学和电化学性质中的作用研究

  摘要：

  1，3，4-恶二唑（OXD）基二氯环糊精的合成已通过N-烷基化途径完成，UV-vis光谱证明不存在电荷转移相互作用。电化学研究表明，OXD单元干扰了苯并咪唑并苯二酚的特征氧化还原特性。

  DOI：

  10.1016/j.tetlet.2008.10.142

文献信息

• Cholesterol-Appended Benzimidazolium Salts: Synthesis, Aggregation, Sensing, Dye Adsorption, and Semiconducting Properties
  作者：Santanu Panja、Subhratanu Bhattacharya、Kumaresh Ghosh

  DOI：10.1021/acs.langmuir.7b01713

  日期：2017.8.22

  A series of cholesterol-appended benzimidazolium salts 1–9 have been designed and synthesized. They have been explored in gel chemistry. The gelation of the benzimidazolium salts is dependent on the nature of the counteranions. In addition, the gelation behavior of the gelators is linked with the presence of both π-stacking and cholesteryl motifs. Whereas bisbenzimidazolium salt 2 forms a gel in d

  已经设计并合成了一系列胆固醇附加的苯并咪唑鎓盐1–9。他们已经在凝胶化学中进行了探索。苯并咪唑盐的凝胶化取决于抗衡阴离子的性质。另外，胶凝剂的胶凝行为与π-堆积和胆固醇基序的存在有关。而bisbenzimidazolium盐2所形成的凝胶在二甲亚砜/ H 2 O（1：1，V / V）本身，在类似条件下，monobenzimidazolium盐4和6表现出凝胶化在F的存在-离子和验证F的视觉传感-。作为应用，凝胶相为2有效去除废水中的有毒染料。此外，所有凝胶均在较宽的电压范围内显示出热活化的半导体特性。
• Bis (benzimidazole) derivatives serving as potassium blocking agents
  申请人：Neurosearch A/S

  公开号：US06194447B1

  公开（公告）日：2001-02-27

  This invention relates to novel potassium channel blocking agents, and their use in the preparation of pharmaceutical compositions. Moreover the invention is directed to pharmaceutical compositions useful for the treatment or alleviation of diseases or disorders associated with the activity of potassium channels, in particular asthma, cystic fibrosis, chronic obstructive pulmonary disease and rhinorrhea, convulsions, vascular spasms, coronary artery spasms, renal disorders, polycystic kidney disease, bladder spasms, urinary incontinence, bladder outflow obstruction, irritable bowel syndrome, gastrointestinal dysfunction, secretory diarrhoea, ischaemia, cerebral ischaemia, ischaemic hearth disease, angina pectoris, coronary hearth disease, traumatic brain injury, psychosis, anxiety, depression, dementia, memory and attention deficits, Alzheimer's disease, dysmenorrhea, narcolepsy, Reynaud's disease, intermittent claudication, Sjorgren's syndrome, migraine, arrhythmia, hypertension, absence seizures, myotonic muscle dystrophia, xerostomi, diabetes type II, hyperinsulinemia, premature labor, baldness, cancer, and immune suppression.

  这项发明涉及新型钾通道阻滞剂，以及它们在制备药物组合物中的应用。 此外，该发明针对用于治疗或缓解与钾通道活性相关的疾病或障碍的药物组合物，特别是哮喘、囊性纤维化、慢性阻塞性肺病和鼻涕、痉挛、血管痉挛、冠状动脉痉挛、肾脏疾病、多囊肾病、膀胱痉挛、尿失禁、膀胱排出道梗阻、肠易激综合征、胃肠功能障碍、分泌性腹泻、缺血、脑缺血、缺血性心脏病、心绞痛、冠状动脉心脏病、创伤性脑损伤、精神病、焦虑、抑郁症、痴呆、记忆和注意力缺陷、阿尔茨海默病、痛经、嗜睡症、雷诺氏病、间歇性跛行、Sjorgren综合征、偏头痛、心律失常、高血压、缺席性癫痫发作、肌肉肌无力症、口干症、糖尿病II型、胰岛素过多症、早产、秃头、癌症和免疫抑制。
• Pyridinophanes as Two-Centre Phase-Transfer Catalyst for N-Alkylation Reaction
  作者：Perumal Rajakumar、Manickam Dhanasekaran

  DOI：10.1055/s-2006-926304

  日期：——

  The synthetic utility of water-soluble pyridinophanes 1 and 2 as an efficient two-centre phase-transfer catalyst for N-alkylation of indoles, imidazole, benzimidazole and benzotriazole has been explored. Application of such pyridinophanes for the synthesis of various precyclophanes involving bis-N alkylation is also described.

  已经探索了水溶性吡啶啉 1 和 2 作为有效的双中心相转移催化剂用于吲哚、咪唑、苯并咪唑和苯并三唑的 N-烷基化的合成效用。还描述了此类吡啶啉在合成涉及双-N烷基化的各种前环烷中的应用。
• Acridine-based macrocyclic fluorescent sensors: self-assembly behavior characterized by crystal structures and a tunable bathochromic-shift in emission induced by H2PO4−via adjusting the ring size and rigidity
  作者：Dawei Zhang、Xiaozhi Jiang、Haiqiang Yang、Alexandre Martinez、Meiyuan Feng、Zhiyun Dong、Guohua Gao

  DOI：10.1039/c3ob27500k

  日期：——

  In this paper, a series of novel acridine derived bisbenzimidazolium macrocyclic fluorescent sensors were designed and synthesized. X-ray crystal structures demonstrated the self-assembly behavior of these cyclophanes in the solid state driven by hydrogen bond and π–π interactions. Anion binding studies of these sensors revealed a significant effect of the macrocyclic size and rigidity for H2PO4− sensing via the obvious turn-on as well as bathochromic-shift in fluorescence emission. Different cavity size or rigidity of the sensors showed different bathochromic-shifts (from 36 to 126 nm) in fluorescence emission induced by H2PO4−, which resulted in significant color changes of fluorescence from blue to orange red, orange, green and blue-green respectively. The unique fluorescence response toward H2PO4− may be attributed to H2PO4−-induced assembly of sensors forming the excimer between two acridine rings to a different extent.

  在本文中，设计并合成了一系列新型的由氨基吖啶衍生的双苯并咪唑鎓宏环荧光传感器。X射线晶体结构展示了这些环芳烃在固态下以氢键和π-π相互作用驱动的自组装行为。这些传感器的阴离子结合研究揭示了宏环大小和刚性的显著影响，特别是在H2PO4⁻的探测中，通过荧光发射的明显开启以及红移效应。传感器的不同腔体大小或刚性在H2PO4⁻诱导的荧光发射中显示出不同的红移（从36到126纳米），导致荧光颜色从蓝色变化为橙红色、橙色、绿色和蓝绿色。对H2PO4⁻的独特荧光响应可能归因于H2PO4⁻诱导的传感器组装，形成两个氨基吖啶环之间的激发态二聚体，且程度不同。
• Benzimidazolium-based chemosensors: selective recognition of H₂PO₄⁻, HP₂O₇³⁻, F⁻ and ATP through fluorescence and gelation studies
  作者：Kumaresh Ghosh、Debasis Kar、Debashis Sahu、Bishwajit Ganguly

  DOI：10.1039/c5ra06301a

  日期：——

  Benzimidazolium-based receptors 1 and 2 exhibit sensing properties towards different anions such as H₂PO₄⁻, HP₂O₇³⁻ and F⁻ under identical condition. Experimental results are correlated with the theoretical findings.

  苯并咪唑基受体1和2在相同条件下对不同阴离子（如H2PO4-、HP2O7^3-和F^-）具有感应性能。实验结果与理论发现相关联。