4,5-diphenyl-1-(2-phenylethyl)imidazole 3-oxide | 63235-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-diphenyl-1-(2-phenylethyl)imidazole 3-oxide
• 英文别名: 1-Oxido-4,5-diphenyl-3-(2-phenylethyl)imidazol-1-ium
• CAS: 63235-61-0
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: JMRNYRWWYKADPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  30.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-diphenyl-1-(2-phenylethyl)imidazole 3-oxide 在 2,2,4,4-tetramethyl-3-thioxocyclobutanone 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以88%的产率得到1-Phenethyl-4,5-diphenyl-1,3-dihydro-imidazole-2-thione
  参考文献：
  名称：

  First Examples of Reactions of AzoleN-Oxides with Thioketones: A Novel Type of Sulfur-Transfer Reaction

  摘要：

  The reactions of 1,4,5-trisubstituted imidazole 3-oxides 1a-k with cyclobutanethiones 5a,b in CHCl3 at room temperature give imidazole-2(3H)-thiones 9a-k in high yield. The second product formed in this reaction is 2,2,4,4-tetramethylcyclobutane-1,3-dione (6a; Scheme 2). Similar reactions occur with 1 and adamantanethione (5c) as thiocarbonyl compound, as well as with 1,2,4-triazole-4-oxide derivative 10 and 5a (Scheme 3). A reaction mechanism by a two-step formation of the formal cycloadduct of type 7 via zwitterion 16 is proposed in Scheme 5. Spontaneous decomposition of 7 yields the products of this novel sulfur-transfer reaction. The starting imidazole 3-oxides are conveniently prepared by heating a mixture of 1,3,5-trisubstituted hexahydro-1,3,5-triazines 3 and alpha-(hydroxyimino) ketones 2 in EtOH (cf: Scheme 1). As demonstrated in the case of 9d, a 'one-pot' procedure allows the preparation of 9 without isolation of the imidazole 3-oxides 1. The reaction of Ic with thioketene 12 leads to a mixture of four products (Scheme 4). The minor products, 9c and the ketene 15, result from an analogous sulfur-transfer reaction (Path a in Scheme 5), whereas the parent imidazole 14 and thiiranone 13 are the products of an oxygen-transfer reaction (Path b in Scheme 5).

  DOI：

  10.1002/(sici)1522-2675(19980909)81:9<1585::aid-hlca1585>3.0.co;2-n
• 作为产物：
  描述：

  Alpha-联苯酰一肟 、 1,3,5-triphenethylhexahydro-1,3,5-triazine 以 乙醇 为溶剂， 反应 2.0h， 以74%的产率得到4,5-diphenyl-1-(2-phenylethyl)imidazole 3-oxide
  参考文献：
  名称：

  First Examples of Reactions of AzoleN-Oxides with Thioketones: A Novel Type of Sulfur-Transfer Reaction

  摘要：

  The reactions of 1,4,5-trisubstituted imidazole 3-oxides 1a-k with cyclobutanethiones 5a,b in CHCl3 at room temperature give imidazole-2(3H)-thiones 9a-k in high yield. The second product formed in this reaction is 2,2,4,4-tetramethylcyclobutane-1,3-dione (6a; Scheme 2). Similar reactions occur with 1 and adamantanethione (5c) as thiocarbonyl compound, as well as with 1,2,4-triazole-4-oxide derivative 10 and 5a (Scheme 3). A reaction mechanism by a two-step formation of the formal cycloadduct of type 7 via zwitterion 16 is proposed in Scheme 5. Spontaneous decomposition of 7 yields the products of this novel sulfur-transfer reaction. The starting imidazole 3-oxides are conveniently prepared by heating a mixture of 1,3,5-trisubstituted hexahydro-1,3,5-triazines 3 and alpha-(hydroxyimino) ketones 2 in EtOH (cf: Scheme 1). As demonstrated in the case of 9d, a 'one-pot' procedure allows the preparation of 9 without isolation of the imidazole 3-oxides 1. The reaction of Ic with thioketene 12 leads to a mixture of four products (Scheme 4). The minor products, 9c and the ketene 15, result from an analogous sulfur-transfer reaction (Path a in Scheme 5), whereas the parent imidazole 14 and thiiranone 13 are the products of an oxygen-transfer reaction (Path b in Scheme 5).

  DOI：

  10.1002/(sici)1522-2675(19980909)81:9<1585::aid-hlca1585>3.0.co;2-n

文献信息

• Synthesis of Imidazole Derivatives Using 2-Unsubstituted 1H-Imidazole 3-Oxides
  作者：Grzegorz Mlostoń、Małgorzata Celeda、G. K. Surya Prakash、George A. Olah、Heinz Heimgartner

  DOI：10.1002/(sici)1522-2675(20000412)83:4<728::aid-hlca728>3.0.co;2-b

  日期：2000.4.12

  The reaction of 1,4,5-trisubstituted 1H-imidazole 3-oxides 1 with Ac2O in CH2Cl2 at 0-5 degrees leads to the corresponding 1,3-dihydro-2H-imidazol-2-ones 4 in good yields. In refluxing Ac2O, the N-oxides 1 are transformed to N-acetylated 1,3-dihydro-2H-imidazol-2-ones 5. The proposed mechanisms for these reactions are analogous to those for N-oxides of 6-membered heterocycles (Scheme 2). A smooth synthesis of 1H-imidazole-2-carbonitriles 2 starting with 1 is achieved by treatment with trimethylsilanecarbonitrile (Me2SiCN) in CH2Cl2 at 0-5 degrees (Scheme 3).
• BARTNIK R.; HAHN W. E.; MLOSTON G., ROCZ. CHEM. <ROCH-AC>, 1977, 51, NO 1, 49-57
  作者：BARTNIK R.、 HAHN W. E.、 MLOSTON G.

  DOI：——

  日期：——