1,5-dimethyl-4-phenylimidazole 3-oxide | 215675-50-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,5-dimethyl-4-phenylimidazole 3-oxide
• 英文别名: 1,5-Dimethyl-3-oxido-4-phenylimidazol-3-ium
• CAS: 215675-50-6
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: ANBGIKMQKPYMAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1,5-dimethyl-4-phenylimidazole 3-oxide 在 1,1-双(三氟甲基)-2,2-二氰基乙烯 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以63%的产率得到1,3-二氢-1,5-二甲基-4-苯基-2H-咪唑-2-酮
  参考文献：
  名称：

  2-未取代的1 H-咪唑3-氧化物与2,2-双（三氟甲基）乙烯-1,1-二碳腈的反应：逐步1,3,2-偶极环加成

  摘要：

  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。

  DOI：

  10.1002/hlca.200690129
• 作为产物：
  描述：

  1,3,5-三甲基己羟基-1,3,5-三嗪 、 1-phenyl-propane-1,2-dione 1-oxime 以 乙醇 为溶剂， 生成 1,5-dimethyl-4-phenylimidazole 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

• First Examples of Reactions of AzoleN-Oxides with Thioketones: A Novel Type of Sulfur-Transfer Reaction
  作者：Grzegorz Mlostoń、Tomasz Gendek、Heinz Heimgartner

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

  日期：1998.9.9

  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).
• 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：——