4,5-bis(4-chlorophenyl)-1H-imidazole | 68240-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-bis(4-chlorophenyl)-1H-imidazole
• 英文别名: 4,5-Bis(4-chlorophenyl)imidazole；4,5-di(p-chlorophenyl)-1H-imidazole；4,5-di-(4-chlorophenyl)imidazole
• CAS: 68240-86-8
• 化学式: C₁₅H₁₀Cl₂N₂
• 分子量: 289.164
• InChiKey: SCZKETWZLPEUME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-bis(4-chlorophenyl)-1H-imidazole 在 氧气 、 亚甲兰 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以41%的产率得到N,N'-carbonylbis(4-chlorobenzamide)
  参考文献：
  名称：

  Purushothaman, E.; Pillai, V. N. Rajasekharan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 290 - 293

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4'-二氯苯偶酰 在 paraformaldehyde 作用下， 以 formamide 为溶剂， 生成 4,5-bis(4-chlorophenyl)-1H-imidazole
  参考文献：
  名称：

  Substituted imidazoles as cannabinoid receptor modulators

  摘要：

  本发明涉及将这些新型化合物用于选择性拮抗Cannabinoid-1（CB1）受体。因此，本发明的化合物可用作治疗精神病、记忆障碍、认知障碍、偏头痛、神经病、神经炎症性疾病（包括多发性硬化症和吉兰-巴雷综合征）、病毒性脑炎、脑血管意外和头部创伤的炎症后遗症、焦虑症、压力、癫痫、帕金森病和精神分裂症的精神药物。这些化合物还可用于治疗物质滥用障碍，特别是阿片类药物、酒精和尼古丁。这些化合物还可用于治疗与过度食物摄入及相关并发症相关的肥胖或进食障碍。同时还声明了结构式（I）的新型化合物。

  公开号：

  US20030114495A1

文献信息

• Iridium-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols: A Route to Access Branched Ketones and Alcohols
  作者：Sertaç Genç、Süleyman Gülcemal、Salih Günnaz、Bekir Çetinkaya、Derya Gülcemal

  DOI：10.1021/acs.joc.0c01099

  日期：2020.7.17

  Under borrowing hydrogen conditions, NHC–iridium(I) catalyzed the direct or one-pot sequential synthesis of α,α-disubstituted ketones via the alkylation of secondary alcohols with primary alcohols is reported. Notably, the present approach provides a new method for the facile synthesis of α,α-disubstituted ketones and featured with several characteristics, including a broad substrate scope, using easy-to-handle

  据报道，在借用氢的条件下，NHC-铱（I）催化通过仲醇与伯醇的烷基化直接或一锅法连续合成α，α-二取代的酮。值得注意的是，本方法提供了一种易于合成α，α-二取代酮的新方法，该方法具有多种特征，包括广泛的底物范围，使用易于处理的醇作为起始原料，并在有氧条件下进行反应。此外，通过向反应混合物中添加外部氢源，选择性地一锅形成β，β-二取代的醇。
• Synthesis of 4,5-Substituted Imidazoles by a Fast Condensation of 1,2-Diketones and Urotropine in Heterogeneous Medium
  作者：George Bratulescu

  DOI：10.1055/s-0029-1216841

  日期：2009.7

  Starting from 1,2-diketones and urotropine in the presence of ammonium acetate, a simple and efficient solventless microwave-assisted synthesis of 4,5-disubstituted imidazoles was accomplished.

  在氨基乙酸铵存在下，从1,2-二酮和尿素起始物出发，成功实现了一种简单高效的无溶剂微波辅助合成4,5-二取代咪唑的过程。
• Synthesis of some 2,3,6,8-tetraarylimidazo[1,2-a]pyrazine derivatives by using either reflux or microwave irradiation method, and investigation their anticancer activities
  作者：İSMAİL KAYAĞİL、ŞEREF DEMİRAYAK

  DOI：10.3906/kim-1005-649

  日期：——

  In this study, some 2,3,6,8-tetraarylimidazo[1,2-a]pyrazine derivatives were synthesized by reacting 1-(2-aryl-2-oxoethyl)-2-aryloyl-4,5-diarylimidazoles from 2-aryloyl-4,5-diarylimidazole and 2-bromoacetophenone derivatives with ammonium acetate in acetic acid by using the method that was previously developed and repeatedly tested in our studies. Structural elucidation of the compounds was performed by IR, ^1H-NMR, and MASS spectroscopic data and elemental analysis results. Anticancer activities of selected compounds were evaluated and the noticeable activity values were reported.

  在这项研究中，通过将2-芳酰基-4,5-二芳基咪唑衍生物与2-溴乙酰苯酮衍生物在醋酸中与乙酸铵反应，合成了一些2,3,6,8-四芳基咪唑[1,2-a]吡嗪衍生物，采用的方法在我们的研究中已经开发并反复测试过。对化合物的结构阐明是通过红外光谱、^1H-NMR和质谱数据以及元素分析结果进行的。对选定化合物的抗癌活性进行了评估，并报告了显著的活性值。
• Synthesis, cytotoxic and antibacterial studies of p-benzyl-substituted NHC–silver(I) acetate compounds derived from 4,5-di-p-diisopropylphenyl- or 4,5-di-p-chlorophenyl-1H-imidazole
  作者：Wojciech Streciwilk、Jennifer Cassidy、Frauke Hackenberg、Helge Müller-Bunz、Francesca Paradisi、Matthias Tacke

  DOI：10.1016/j.jorganchem.2013.09.033

  日期：2014.1

  p-substituted benzyl halide derivatives through N-dibenzylation to the symmetrically (3a–j) or through N-monobenzylation followed by N-methylation to the un-symmetrically substituted (5b) imidazolium halides. These halides were further used for the synthesis of the corresponding N-heterocyclic carbene–silver(I) (NHC–silver) acetate complexes 4a–j and 5c. The silver(I) compounds 4b, 4e and 4g were characterised

  4,5-二（p异丙基苯基）-1 ħ -咪唑（图2a）和4,5-二（p -氯苯基）-1- ħ -咪唑（图2b），从适当的取代的苯偶姻制备前体，然后用5反应对位取代的苄基卤化物衍生物可通过N-二苄基化成对称的（3a – j）或通过N-单苄基化，再经N-甲基化成不对称取代的（5b）咪唑鎓卤化物。这些卤化物进一步用于合成相应的N-杂环卡宾-银（I）（NHC-银）乙酸盐络合物4a – j和5c。通过单晶X射线衍射表征银（I）化合物4b，4e和4g。 使用柯比鲍尔圆盘扩散法，对咪唑鎓卤化物3a – j和NHC –醋酸银（I）络合物4a –进行了革兰氏阴性细菌大肠杆菌和革兰氏阳性细菌金黄色葡萄球菌的半定量抗菌研究。g和4i – j。咪唑鎓卤化物前体3a – j在1-5 mm（弱）范围内表现出细菌生长抑制作用，而它们的NHC–银（I）乙酸盐衍生物4a – g和4i – j 被发现可以抑制2-6 mm范围内的细菌生长（从弱到中等）。
• Synthesis and activity of 4,5-diarylimidazoles as human CB1 receptor inverse agonists
  作者：Christopher W. Plummer、Paul E. Finke、Sander G. Mills、Junying Wang、Xinchun Tong、George A. Doss、Tung M. Fong、Julie Z. Lao、Marie-Therese Schaeffer、Jing Chen、Chun-Pyn Shen、D. Sloan Stribling、Lauren P. Shearman,、Alison M. Strack、Lex H.T. Van der Ploeg

  DOI：10.1016/j.bmcl.2004.12.078

  日期：2005.3

  Structure-activity relationship studies directed toward the optimization of 4,5-diarylimidazole-2-carboxamide analogs as human CBI receptor inverse agonists resulted in the discovery of the two amide derivatives 24a and b (hCB1 IC50 = 6.1 and 4.0 nM) which also demonstrated efficacy in overnight feeding studies in the rat for reduction in both food intake and overall body weight. (c) 2005 Elsevier Ltd. All rights reserved.