2,4,5-trichloro-2-phenyl-2H-imidazole | 59206-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,5-trichloro-2-phenyl-2H-imidazole
• 英文别名: 2-phenyl-2,4,5-trichloro-2H-imidazole；2,4,5-Trichloro-2-phenylimidazole
• CAS: 59206-98-3
• 化学式: C₉H₅Cl₃N₂
• 分子量: 247.511
• InChiKey: LQBRHNIPQIFBLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(1-萘基)乙胺 、 2,4,5-trichloro-2-phenyl-2H-imidazole 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.17h， 生成 ((R)-1-Naphthalen-1-yl-ethyl)-{5-[(E)-(R)-1-naphthalen-1-yl-ethylimino]-2-phenyl-5H-imidazol-4-yl}-amine
  参考文献：
  名称：

  Fünfring-Cycloamidine - Neue farbige Heterocyclen mit ungewöhnlichen Eigenschaften. I. Synthese und spektrale Besonderheiten

  摘要：

  The cycloaddition of benzamidines with bis-imidoylchlorides 1 derived from oxalic acid was investigated. For example, treatment of benzamidine with 1 gives the new 4H-imidazoles (3a-1) in yields up to 92%. Because of rapid H-transfer processes in solution, the NMR-spectra of 3a-1 show only a single signal set. Apart from prototropism, 3c shows interesting properties as an amphoteric heterocycle. The protonation of 3c is accompanied by a change of color to orange to blue. Probably, protonation takes place on the exocyclic imino nitrogen to give a cyanine type chromophor. The resulting cation can also be regarded as an antiaromatic 1,3-diazacyclopentadienylium system. In order to investigate the influence of exocyclic substituents at nitrogen on the UV/VIS absorption, compounds 3d-h were synthesized. Whereas electron withdrawing groups cause hypsochromic shifts of the first UV/VIS absorption band, the dimethylamino group shifts this band bathochromically as exemplified by 3e. This novel cycloamidine shows strong acidochromism with bathochromic shifts of more than Delta-lambda-(max)=150 nm.

  DOI：

  10.1002/prac.199733901132
• 作为产物：
  描述：

  2-苯基咪唑 以68%的产率得到
  参考文献：
  名称：

  BUECHEL K.-H.; ERDMANN H., CHEM. BER. , 1976, 109, NO 5, 1638-1642

  摘要：

  DOI：

文献信息

• US3997552A
  申请人：——

  公开号：US3997552A

  公开（公告）日：1976-12-14
• Fünfring-Cycloamidine - Neue farbige Heterocyclen mit ungewöhnlichen Eigenschaften. I. Synthese und spektrale Besonderheiten
  作者：Jens Atzrodt、Jörg Brandenburg、Christian Käpplinger、Rainer Beckert、Wolfgang Günther、Helmar Görls、Jürgen Fabian

  DOI：10.1002/prac.199733901132

  日期：——

  The cycloaddition of benzamidines with bis-imidoylchlorides 1 derived from oxalic acid was investigated. For example, treatment of benzamidine with 1 gives the new 4H-imidazoles (3a-1) in yields up to 92%. Because of rapid H-transfer processes in solution, the NMR-spectra of 3a-1 show only a single signal set. Apart from prototropism, 3c shows interesting properties as an amphoteric heterocycle. The protonation of 3c is accompanied by a change of color to orange to blue. Probably, protonation takes place on the exocyclic imino nitrogen to give a cyanine type chromophor. The resulting cation can also be regarded as an antiaromatic 1,3-diazacyclopentadienylium system. In order to investigate the influence of exocyclic substituents at nitrogen on the UV/VIS absorption, compounds 3d-h were synthesized. Whereas electron withdrawing groups cause hypsochromic shifts of the first UV/VIS absorption band, the dimethylamino group shifts this band bathochromically as exemplified by 3e. This novel cycloamidine shows strong acidochromism with bathochromic shifts of more than Delta-lambda-(max)=150 nm.
• BUECHEL K.-H.; ERDMANN H., CHEM. BER. <CHBE-AM>, 1976, 109, NO 5, 1638-1642
  作者：BUECHEL K.-H.、 ERDMANN H.

  DOI：——

  日期：——