1-cyclohexyl-4,5-diphenylimidazole 3-oxide | 215675-49-3

• 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-cyclohexyl-4,5-diphenylimidazole 3-oxide
• 英文别名: 1-Cyclohexyl-3-oxido-4,5-diphenylimidazol-3-ium
• CAS: 215675-49-3
• 化学式: C₂₁H₂₂N₂O
• 分子量: 318.418
• InChiKey: QTYGEMKNKSQCML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1-cyclohexyl-4,5-diphenylimidazole 3-oxide 在 2,2,4,4-tetramethyl-3-thioxocyclobutanone 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以95%的产率得到3-cyclohexyl-4,5-diphenyl-1H-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 、 六氢-1,3,5-三环己基-S-三嗪 以 乙醇 为溶剂， 生成 1-cyclohexyl-4,5-diphenylimidazole 3-oxide
  参考文献：
  名称：

  Mloston, Grzegorz; Jasinski, Marcin, ARKIVOC, 2011, vol. 2011, # 6, p. 162 - 175

  摘要：

  DOI：

文献信息

• Reactions of 2-Unsubstituted 1 H -Imidazole 3-Oxides with Heterocumulenes and Dimethyl Acetylenedicarboxylate
  作者：Grzegorz Mlostoń、Tomasz Gendek、Heinz Heimgartner

  DOI：10.1016/s0040-4020(00)00449-x

  日期：2000.7

  Reaction of 2-unsubstituted 1H-imidazole 3-oxides with isocyanates, isothiocyanates, and dimethyl acetylenedicarboxylate led to the formation of 2-functionalized imidazole derivatives. Stepwise reaction mechanisms via zwitterionic intermediates are proposed. The intermediate [3+2] cycloadducts stabilize via extrusion of COX or ring opening.

  2-未取代的1 H-咪唑3-氧化物与异氰酸酯，异硫氰酸酯和乙炔二甲酸二甲酯的反应导致形成2-官能化的咪唑衍生物。提出了通过两性离子中间体的逐步反应机理。中间的[3 + 2]环加合物可通过挤出COX或开环来稳定。
• Reactions of 2-Unsubstituted 1H-Imidazole 3-Oxides with 2,2-Bis(trifluoromethyl)ethene-1,1-dicarbonitrile: A Stepwise 1,3-Dipolar Cycloaddition
  作者：Grzegorz Mlostoń、Marcin Jasiński、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/hlca.200690129

  日期：2006.7

  The reaction of 1,4,5-trisubstituted 1H-imidazole-3-oxides 1 with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile (7, BTF) yielded the corresponding 1,3-dihydro-2H-imidazol-2-ones 10 and 2-(1,3-dihydro-2H-imidazol-2-ylidene)malononitriles 11, respectively, depending on the solvent used. In one example, a 1 : 1 complex, 12, of the 1H-imidazole 3-oxide and hexafluoroacetone hydrate was isolated as

  1,4,5-三取代的1 H-咪唑-3-氧化物1与2,2-双（三氟甲基）乙烯-1,1-二碳腈（7，BTF）的反应生成相应的1,3-二氢-2 H-咪唑-2-酮10和2-（1,3-二氢-2 H-咪唑-2-亚烷基）丙二腈11，这取决于所使用的溶剂。在一个实施例中，分离出1 H-咪唑3-氧化物和六氟丙酮水合物的1：1络合物12作为第二产物。产物的形成通过逐步的1，3-偶极环加成和随后的断裂来解释。11d和12的结构 通过X射线晶体学确定。
• 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).
• Mloston; Gendek; Linden, Polish Journal of Chemistry, 2008, vol. 82, # 8, p. 1561 - 1569
  作者：Mloston、Gendek、Linden、Heimgartner

  DOI：——

  日期：——