4,5-diiodo-1-methyl-2-phenyl-1H-imidazole | 221534-29-8

• 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-diiodo-1-methyl-2-phenyl-1H-imidazole
• 英文别名: 4,5-Diiodo-1-methyl-2-phenylimidazole
• CAS: 221534-29-8
• 化学式: C₁₀H₈I₂N₂
• 分子量: 409.996
• InChiKey: HEARGAGDZVRLFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-methyl-2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 、 4,5-diiodo-1-methyl-2-phenyl-1H-imidazole 在 palladium diacetate 、 cesium fluoride 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以9%的产率得到4,4'-(1-methyl-2-phenyl-1H-imidazole-4,5-diyl)bis(5-methyl-2-phenylthiazole)
  参考文献：
  名称：

  Photomodulation of Ionic Interaction and Reactivity: Reversible Photoconversion between Imidazolium and Imidazolinium

  摘要：

  An interconversion system between imidazolium and imidazolinium has been proposed for the first time. Imidazolium and imidazolinium cations exhibit different reactivity due to the difference in the aromaticity and charge localization structure, which is successfully controlled by means of photoirradiation in the present system. A 4,5-dithiazolylimidazolium salt was prepared and studied as a new class of photochromic materials modulating electrostatic interactions and chemical reactivities. The photochromic 4,5-dithiazolylimidazolium showed reversible photoconversions between imidazolium open-form and imidazolinium closed-form upon successive irradiation with UV and visible light. The imidazolinium closed-form exhibited characteristic solvato- and ionochromisms in which the absorption maximum shifted by more than 80 nm depending on the solvent polarity and counteranions, whereas the imidazolium open-form showed no such solvent-dependent property. Because the corresponding nonionic 4,5-dithiazolylimidazole also did not exhibit the solvent-dependent absorption profile both in open- and closed-forms, the appearance of these chromisms in imidazolinium closed-form was attributed to the change in the extent of ionic interaction, which was brought about by the photoconversion of imidazolium to imidazolinium. The photoderived strong ionic interaction of imidazolinium with counteranion was further applied to the photocontrolled nucleophilic reaction system. Whereas the imidazolium open-form was inert to nucleophiles such as sodium methoxide, the imidazolinium closed-form was reactive to the nucleophilic reaction, demonstrating a photogated reaction system.

  DOI：

  10.1021/ja802986y
• 作为产物：
  描述：

  1-甲基-2-苯基-1H-咪唑 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5-diiodo-1-methyl-2-phenyl-1H-imidazole
  参考文献：
  名称：

  钯催化双偶联反应生成 4,5-二取代咪唑炔

  摘要：

  摘要 通过咪唑二碘化制备的4,5-二碘咪唑2与末端炔烃在钯催化下进行双偶联反应得到相应的咪唑二炔3。

  DOI：

  10.1080/00397919908085793

文献信息

• Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus
  作者：Mebarek Bahnous、Abdelmalek Bouraiou、Meryem Chelghoum、Sofiane Bouacida、Thierry Roisnel、Farida Smati、Chafia Bentchouala、Philippe C. Gros、Ali Belfaitah

  DOI：10.1016/j.bmcl.2013.01.004

  日期：2013.3

  Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods

  通过咪唑，1-甲基咪唑和2-苯基-1-甲基咪唑为关键中间体，通过适当的合成途径，合成了几种新的高度官能化的咪唑鎓衍生物。用圆盘扩散法和MIC法评价了所制备化合物对大肠杆菌，金黄色葡萄球菌，铜绿假单胞菌和沙门氏菌的抗菌活性。报告了六种化合物的晶体X射线结构。
• Synthesis and Chemistry of 4,5-Dimagnesioimidazole Dianions
  作者：Ralf H.-J. Butz、Stephen D. Lindell

  DOI：10.1021/jo0161680

  日期：2002.4.1

  procedure for the generation of 4,5-dimagnesioimidazoles is described. N-Protected 2-substituted 4,5-diiodoimidazoles were treated with i-PrMgCl (2.4 equiv) in THF at 0-5 degrees C. The resulting vicinal dianions reacted with electrophiles to give 4,5-disubstituted imidazoles in 27-71% yields.

  描述了一种产生4,5-二甲氨基咪唑的实验方便的方法。N-保护的2-取代的4,5-二碘咪唑在THF中0-5℃下用i-PrMgCl（2.4当量）处理。生成的邻位二价阴离子与亲电试剂反应，得到27-71％的4,5-二取代的咪唑产量。
• Ligands for asymmetric reactions
  申请人：——

  公开号：US20040260091A1

  公开（公告）日：2004-12-23

  The invention relates to a process for the manufacture of ligands capable of forming metal complexes and such complexes; novel ligands with new backbones, complexes thereof with transition metals, the use of complexes of said ligands with transition metals as catalysts, as well as novel intermediates for the manufacture of said ligands. The ligand complexes are useful in stereoselective synthesis, especially hydrogenation, of various organic molecules. Especially, the process according to the invention is directed to the synthesis of compounds of the formulae IA and IIA, wherein the substituents have the meanings given in the description, and to novel compounds of these formulae as ligands. 1

  本发明涉及一种制备能够形成金属配合物的配体及其配合物的工艺；带有新骨架的新型配体，以及与过渡金属的复合物，所述配体与过渡金属的复合物的用途作为催化剂，以及用于制备所述配体的新型中间体。所述配体复合物在立体选择性合成中特别有用，特别是在各种有机分子的氢化反应中。特别地，本发明的工艺针对式IA和IIA化合物的合成，其中取代基具有所述描述中给出的含义，以及这些式的新型化合物作为配体。
• LIGANDS FOR ASYMMETRIC REACTIONS
  申请人：Solvias AG

  公开号：EP1483273A2

  公开（公告）日：2004-12-08
• US7094907B2
  申请人：——

  公开号：US7094907B2

  公开（公告）日：2006-08-22