1-(4-chlorophenyl)-4-phenyl-1H-imidazole

• 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-chlorophenyl)-4-phenyl-1H-imidazole
• 英文别名: 1-(4-chlorophenyl)-4-phenylimidazole
• 化学式: C₁₅H₁₁ClN₂
• 分子量: 254.719
• InChiKey: CPDGQKJPYYDYQG-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：

  3-(4-chlorophenyl)-5-phenyl-1H-imidazole-2-thione 在 镍 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以49%的产率得到1-(4-chlorophenyl)-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。
• Synthesis of di- and cis -triaryl-3a,4,5,6-tetrahydroimidazo[1,5- b ]isoxazoles and their ring-opening reactions
  作者：Necdet Coşkun、Fatma Tirli Tat、Özden Özel Güven

  DOI：10.1016/s0040-4020(01)00184-3

  日期：2001.4

  diastereoselective cycloaddition with dimethyl acetylenedicarboxylate 2 to give 3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3. Thermally and base induced ring-opening reactions of compounds 3 were demonstrated. cis-6-Phenyl substituted adducts 3d,e undergo ring opening with secondary but not with tertiary amines. The same adducts undergo regio- and diastereoselective Michael addition with sodium methoxide to give

  的Δ 3 -咪唑啉-3-氧化物1经历非对映选择性环加成与乙炔二2，得到3α，4,5,6-四氢咪唑并[1,5- b ]异恶唑3。证明了化合物3的热和碱诱导的开环反应。顺式-6-苯基取代的加合物3d，e与仲胺而不是叔胺一起开环。相同的加合物与甲醇钠一起进行区域和非对映选择性迈克尔加成反应，得到2-甲氧基-3a，5,6-三苯基-六氢-咪唑并[1,5 - b ]异恶唑-2,3-二羧酸二甲酯6。
• 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.
• Copper-catalyzed C–N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride
  作者：Dean P. Phillips、Xue-Feng Zhu、Thomas L. Lau、Xiaohui He、Kunyong Yang、Hong Liu

  DOI：10.1016/j.tetlet.2009.10.041

  日期：2009.12

  The copper-catalyzed C-N coupling of amides to arylhalides usually requires the use of strong alkali metal bases, such as K2CO3, K3PO4, and Cs2CO3, at high temperature. We discovered that CsF is sufficiently basic to promote the cross-coupling of amides and carbamates With aryl halides. Most aryl iodides coupled in high yield at room temperature. This alternative base may be a suitable replacement for substrates that are incompatible with high temperature and strongly basic conditions and can further enhance the chemoselectivity of this reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• The first examples of di- and cis triaryl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles and their ring-opening reactions
  作者：Necdet Coşkun、Fatma Tirli Tat、Özden Özel Güven、Dinçer Ülkü、Cengiz Arıcı

  DOI：10.1016/s0040-4039(00)00864-9

  日期：2000.7

  The Delta(3)-imidazoline 3-oxides 1 undergo diastereoselective cycloaddition with dimethyl acetylenedicarboxylate 2 to give 3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3. Thermal and base induced ring-opening reactions of compounds 3 were demonstrated. (C) 2000 Elsevier Science Ltd. All rights reserved.