1-(4-bromophenyl)-4-phenyl-1H-imidazole | 79221-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-bromophenyl)-4-phenyl-1H-imidazole
• 英文别名: 1-(4-Bromophenyl)-4-phenylimidazole
• CAS: 79221-05-9
• 化学式: C₁₅H₁₁BrN₂
• 分子量: 299.17
• InChiKey: ZSDPRZMPVINHHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(4-Bromophenyl)-4-phenyl-2,3-dihydro-1H-imidazole-2-thione 在 镍 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以47%的产率得到1-(4-bromophenyl)-4-phenyl-1H-imidazole
  参考文献：
  名称：

  Ali, Akhtar; Saksena, R. K., Journal of the Indian Chemical Society, 1981, vol. 58, p. 624 - 625

  摘要：

  DOI：

文献信息

• Thermal rearrangements of tetrahydroimidazo[1,5-b]isoxazole-2,3-dicarboxylates. Synthesis of 3H-imidazol-1-ium ylides and their silver derivatives
  作者：Necdet Coşkun、Meliha Çetin

  DOI：10.1016/j.tet.2010.01.037

  日期：2010.3

  Isoxazolines 2 from the cycloaddition of imidazoline 3-oxides 1 with DMAD undergo rearrangement to 3,4-dihydro-2H-imidazol-1-ium-1-(1,2-bis-methoxycarbonyl-2-oxo-ethanides) 3, which spontaneously undergo elimination to give 3H-imidazol-1-ium-1-(1,2-bis-methoxycarbonyl-2-oxo-ethanides) 5 or 1H-imidazoles 6 when heated in toluene at reflux. The presence of the aromatic ring at C-6 decelerated the conversion

  异恶唑啉2从咪唑啉-3-氧化物环加成1与DMAD经历重排，以3,4-二氢-2- ħ咪唑-1-鎓-1-（1,2-双-甲氧基羰基-2-氧代ethanides）3，当在甲苯中加热回流时，其自发消除，得到3 H-咪唑-1-鎓-1-（1,2-双-甲氧基羰基-2-氧代乙烷）5或1 H-咪唑6。C-6上芳环的存在降低了转化率，并提高了5的收率。极性比甲苯强的溶剂（例如DMSO）可实现2到6的定量转化在温和条件下，而在极性较小的溶剂（如CCl 4）中，反应速率降低，5的收率提高。C-2未取代的内鎓盐5用银处理过的2 O或硝酸银3中的的Et存在下3 Ñ在室温下，得到C-2的金属化衍生物9在良好的产率。
• Tandem Insertion–Cyclization Reaction of Isocyanides in the Synthesis of 1,4-Diaryl-1<i>H</i>-imidazoles: Presence of<i>N</i>-Arylformimidate Intermediate
  作者：Benjamin Pooi、Jeongbin Lee、Kyujin Choi、Hajime Hirao、Soon Hyeok Hong

  DOI：10.1021/jo501652w

  日期：2014.10.3

  A straightforward and high-yielding synthesis of 1,4-diaryl-1H-imidazoles is reported. 1,4-Diaryl-1H-imidazoels have been difficult to access in ambient conditions, but our method utilizes two different facets of isocyanide reactivity to achieve it. The reaction is believed to involve (1) NHC-copper-catalyzed isocyanide insertion into alcohol to form an N-arylformimidate intermediate and (2) subsequent base-promoted cycloaddition with benzyl isocyanide derivatives There is cooperation between these two processes through the deprotonation of benzyl isocyanide by KOtBu. The deprotonation gives tert-butyl alcohol and the benzyl isocyanide anion which are used for the first and second steps of the reaction, respectively. Various control and kinetic experiments were carried out to gain an in-depth understanding of the reaction mechanism and isocyanide reactivity. The reaction mechanism determined by density functional theory calculations was consistent with the experimental data and provided detailed explanations for the reactivity trends.
• ALI A.; SAKSENA R. K., J. INDIAN CHEM. SOC., 1981, 58, NO 6, 624-625
  作者：ALI A.、 SAKSENA R. K.

  DOI：——

  日期：——