2-phenyl-4,5-diidoimidazole | 10045-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-4,5-diidoimidazole
• 英文别名: 4,5-diiodo-2-phenyl-1H-imidazole
• CAS: 10045-66-6
• 化学式: C₉H₆I₂N₂
• 分子量: 395.969
• InChiKey: NJEAORDUNICUGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  2-phenyl-4,5-diidoimidazole 在 sodium sulfite 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以87%的产率得到4-Iodo-2-phenyl-1H-imidazole
  参考文献：
  名称：

  [EN] 6,7-DIHYDROPYRAZOLO[1,5-α]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
  [FR] COMPOSÉS DE 6,7-DIHYDROPYRAZOLO[1,5-Α]PYRAZIN-4(5H)-ONE ET LEUR UTILISATION COMME MODULATEURS ALLOSTÉRIQUES NÉGATIFS DES RÉCEPTEURS MGLUR2

  摘要：

  本发明涉及作为代谢型谷氨酸受体亚型2 ("mGluR2") 的负变构调节剂 (NAMs) 的新型6,7-二氢吡唑并[1,5-α]吡嗪-4(5H)-酮衍生物。该发明还涉及包含这种化合物的药物组合物，用于制备这种化合物和组合物的方法，以及用于预防或治疗涉及代谢型受体的 mGluR2 亚型的疾病的这种化合物和组合物的用途。

  公开号：

  WO2016087487A1
• 作为产物：
  描述：

  2-苯基咪唑 在 K⁽¹⁺⁾*Cl₂I^(1-) 作用下， 以 水 为溶剂， 反应 6.0h， 以89%的产率得到2-phenyl-4,5-diidoimidazole
  参考文献：
  名称：

  水溶液中的芳香碘化。二氯碘酸钾水溶液的新生命

  摘要：

  重新研究使用二氯碘酸钾水溶液（KICl 2）作为芳族化合物的碘化剂，发现该试剂比以前已知的更通用。已发现该试剂可提供优异产率的碘化杂环化合物，如Isatin，咪唑和吡唑。

  DOI：

  10.1016/s0040-4039(01)00105-8

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。
• Aromatic iodination in aqueous solution. A new lease of life for aqueous potassium dichloroiodate
  作者：Simon J Garden、José C Torres、Simone C de Souza Melo、Alexandre S Lima、Angelo C Pinto、Edson L.S Lima

  DOI：10.1016/s0040-4039(01)00105-8

  日期：2001.3

  A re-investigation of the use of aqueous potassium dichloroiodate (KICl2) as an iodinating agent for aromatic compounds has found the reagent to be more generally applicable than previously known. The reagent has been found to give excellent yields of iodinated heterocyclic compounds, such as isatin, imidazole and pyrazole.

  重新研究使用二氯碘酸钾水溶液（KICl 2）作为芳族化合物的碘化剂，发现该试剂比以前已知的更通用。已发现该试剂可提供优异产率的碘化杂环化合物，如Isatin，咪唑和吡唑。
• A Pd-Catalyzed Double Coupling Reaction to 4,5-Disubstituted Imidazole Alkynes
  作者：Guncheol Kim、Sunwha Kang、Youngha Ryu、Gyochang Keum、Myung Joon Seo

  DOI：10.1080/00397919908085793

  日期：1999.2

  Abstract A palladium-catalyzed double coupling reaction of 4,5-diiodoimidazoles 2, which were prepared by diiodination of imidazole, and terminal alkynes provided the corresponding imidazole diynes 3.

  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。
• 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one compounds and their use as negative allosteric modulators of MGLUR2 receptors
  申请人：Janssen Pharmaceutica NV

  公开号：US10072014B2

  公开（公告）日：2018-09-11

  The present invention relates to novel 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as negative allosteric modulators (NAMs) of the metabotropic glutamate receptor subtype 2 (“mGluR2”). The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention or treatment of disorders in which the mGluR2 subtype of metabotropic receptors is involved.

  本发明涉及新型 6,7-二氢吡唑并[1,5-a]吡嗪-4(5H)-酮衍生物作为代谢谷氨酸受体亚型 2（"mGluR2"）的负异位调节剂（NAMs）。本发明还涉及包含此类化合物的药物组合物、制备此类化合物和组合物的工艺，以及使用此类化合物和组合物预防或治疗代谢受体mGluR2亚型参与的疾病。
• Photomodulation of Ionic Interaction and Reactivity: Reversible Photoconversion between Imidazolium and Imidazolinium
  作者：Takuya Nakashima、Masako Goto、Shigekazu Kawai、Tsuyoshi Kawai

  DOI：10.1021/ja802986y

  日期：2008.11.5

  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.