2-(4-chlorophenyl)-4-phenyl-1-p-tolyl-2,5-dihydro-1H-imidazole-3-oxide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4-chlorophenyl)-4-phenyl-1-p-tolyl-2,5-dihydro-1H-imidazole-3-oxide
• 英文别名: 2-(4-Chlorophenyl)-3-(4-methylphenyl)-1-oxido-5-phenyl-2,4-dihydroimidazol-1-ium；2-(4-chlorophenyl)-3-(4-methylphenyl)-1-oxido-5-phenyl-2,4-dihydroimidazol-1-ium
• 化学式: C₂₂H₁₉ClN₂O
• 分子量: 362.859
• InChiKey: ZMTRGKRFZIBLBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  32
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-4-phenyl-1-p-tolyl-2,5-dihydro-1H-imidazole-3-oxide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(4-Chlorophenyl)-3-hydroxy-1-(4-methylphenyl)-4-phenylimidazolidine
  参考文献：
  名称：

  Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring–chain tautomerism

  摘要：

  Imidazolin-3-oxides I were reduced with NaBH4 in THF at reflux to give the corresponding 2,3,5-triarylimidazolidin-l-oles 2, which are proved to be in a ring-chain-ring tautomeric equilibrium with N-2-aminoethyl nitrones 3 and 3,5,6-triphenyl-1,2,5-oxadiazinanes 4. The ratios of the ring and chain form are determined by the substituent at the reaction centre and can be described by the equation logK(x) = p sigma(+) + logK(x=H). These are the first examples of a novel three-component ring-chain-ring tautomeric equilibrium characterized by a Hammett-type equation. The stability of the ring form was favoured by electron-withdrawing substituents. Treatment of the equilibrium mixture of 2, 3 and 4 with phenylisocyanate in refluxing toluene gives selectively the corresponding O-carbamoylated imidazolidines 5; cis-5 was shown to isomerize to trans-5 on heating. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.058
• 作为产物：
  描述：

  2-bromo-1-phenyl-ethanone oxime 、 4-氯苯甲醛 、 乙烷,三氯氟- 以 乙醇 为溶剂， 反应 3.33h， 生成 2-(4-chlorophenyl)-4-phenyl-1-p-tolyl-2,5-dihydro-1H-imidazole-3-oxide
  参考文献：
  名称：

  A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles

  摘要：

  Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2008.11.002

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。
• A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles
  作者：Lei Lu、Weiguo Cao、Jie Chen、Hui Zhang、Jiaping Zhang、Huiyun Chen、Jiamei Wei、Hongmei Deng、Min Shao

  DOI：10.1016/j.jfluchem.2008.11.002

  日期：2009.3

  Methyl 2-perfluoroalkynoates 2 reacted readily with cyclic nitrones 1 via 1,3-dipolar cycloaddition at room temperature to give 2-perfluoroalkyl-3a,4,5,6-tetrahydroimidazo[1,5-b]isoxazoles 3 in good to excellent yields with high diastereoselectivity and regioselectivity. (C) 2008 Elsevier B.V. All rights reserved.
• Imidazolidin-1-oles, N-2-aminoethyl nitrones and 1,2,5-oxadiazinanes. A novel ring–chain tautomerism
  作者：Necdet Coşkun、Oktay Asutay

  DOI：10.1016/j.tetlet.2007.05.058

  日期：2007.7

  Imidazolin-3-oxides I were reduced with NaBH4 in THF at reflux to give the corresponding 2,3,5-triarylimidazolidin-l-oles 2, which are proved to be in a ring-chain-ring tautomeric equilibrium with N-2-aminoethyl nitrones 3 and 3,5,6-triphenyl-1,2,5-oxadiazinanes 4. The ratios of the ring and chain form are determined by the substituent at the reaction centre and can be described by the equation logK(x) = p sigma(+) + logK(x=H). These are the first examples of a novel three-component ring-chain-ring tautomeric equilibrium characterized by a Hammett-type equation. The stability of the ring form was favoured by electron-withdrawing substituents. Treatment of the equilibrium mixture of 2, 3 and 4 with phenylisocyanate in refluxing toluene gives selectively the corresponding O-carbamoylated imidazolidines 5; cis-5 was shown to isomerize to trans-5 on heating. (C) 2007 Elsevier Ltd. All rights reserved.