3-phenyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine
• 英文别名: 2-(4-trifluoromethylphenyl)-3-benzimidazo[1,2-a]pyridine；3-Phenyl-2-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine
• 化学式: C₂₀H₁₃F₃N₂
• 分子量: 338.332
• InChiKey: XECGJVRTQDSDMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-4'-(三氟甲基)苯乙酮 在 四(三苯基膦)钯 sodium hydroxide 、 N-碘代丁二酰亚胺 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 12.5h， 生成 3-phenyl-2-(4-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  2,3-Diarylimidazo[1,2-a]pyridines as potential inhibitors of UV-induced keratinocytes apoptosis: synthesis, pharmacological properties and interactions with model membranes and oligonucleotides by NMR

  摘要：

  Four 2,3-diarylimidazo[1,2-alpha]pyridines (I, 1a-c) were synthesized as inhibitors of UV-induced apoptosis and showed quite different properties. First, only the pyridinyl derivative I showed protection in molt cells. From the supposed intracellular target, phospholipid membrane models were studied by H-1, H-2 and P-31 NMR spectroscopy. All these molecules can incorporate the membrane bilayer of small unilamellar vesicles of lecithin (SUV). However, I is clearly closed to the external polar head of the lipids, and is relatively mobile in the layer. Conversely, the other molecules are strongly immobilized in the deep part of the external layer. P-31 solid-state NMR spectra recorded on phospholipid dispersions (multilayers vesicles (MLV)) completely excluded any detergent effect or any modification of temperature transition. The only structural or dynamic effect observed was a homogeneous, but limited, reduction in the chemical shift anisotropy in the presence of 1, in agreement with its superficial location. H-2 NMR experiment performed on the same model using perdeuterated phospholipids showed no significant fluidity reduction at the level of terminal CD3 groups in the presence of la-c, according to their deep location. Finaly, their interactions with synthetic oligonucleotide, d(CGATCG)(2) was studied showing non specific interactions of la on the external GC pair, while no interaction was observed with the other derivatives. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2004.10.009

文献信息

• Metal-free C–H arylation of imidazoheterocycles with aryl hydrazines
  作者：Sourav Jana、Sadhanendu Samanta、Avik K. Bagdi、Valerii Z. Shirinian、Alakananda Hajra

  DOI：10.1039/c8ra01474d

  日期：——

  A simple and efficient metal-free arylation of imidazo[1,2-a]pyridines at the C-3 position with arylhydrazine has been achieved at room temperature under ambient air conditions. Various 2,3-disubstituted imidazopyridines and imidazothiazoles were synthesized with high yields. The present methodology demonstrates the usefulness of commercially available aryl hydrazine as an arylating agent.

  在室温和环境空气条件下，已经实现了在 C-3 位的咪唑并[1,2- a ]吡啶与芳基肼的简单有效的无金属芳基化。以高产率合成了各种 2,3-二取代的咪唑并吡啶和咪唑噻唑。本方法证明了可商购的芳基肼作为芳基化剂的有用性。
• 苯并咪唑类化合物的合成方法及其农用生物 活性
  申请人：青岛农业大学

  公开号：CN108794471B

  公开（公告）日：2020-04-28

  本发明提出一种苯并咪唑类化合物的合成方法及其农用生物活性，属于有机合成领域，该方法所用原料成本低，反应体系无需加热、能耗低，环境友好、产物产率高，为苯并咪唑类化合物的合成提供了一种崭新的方法。该技术方案包括向反应容器中分别加入苯基咪唑类化合物和酚类化合物，在醋酸钯和异丙醇作用下，于20‑25℃下蓝色LED灯光照条件下反应4‑6小时；反应结束后，进行柱色谱分离，得到苯并咪唑类化合物。本发明能够应用于苯并咪唑类化合物的制备以及农作物的病菌防治中。