1,4,5-trimethyl-1H-imidazole 3-oxide | 63455-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4,5-trimethyl-1H-imidazole 3-oxide
• 英文别名: 1,4,5-Trimethylimidazole 3-oxide；1,4,5-trimethyl-3-oxidoimidazol-3-ium
• CAS: 63455-73-2
• 化学式: C₆H₁₀N₂O
• 分子量: 126.158
• InChiKey: BVAJAORTUJLZSR-UHFFFAOYSA-N

物化性质

• 熔点：
  68 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  263.0±43.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1,4,5-trimethyl-1H-imidazole 3-oxide 在 Raney nickel 作用下， 以 甲醇 为溶剂， 以68%的产率得到1,4,5-三甲基-1H-咪唑
  参考文献：
  名称：

  Synthesis of optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole rings

  摘要：

  Optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole units were obtained via a multistep synthesis with the [3+2] cycloaddition of Boc-protected (S)-(pyrrolidin-2-yl) methyl azide with 2-ethynylimidazoles in the presence of CuI (CuAAC reaction) as the key step. Typical for terminal alkynes, the reactions occurred regioselectively and 1,4-disubstituted 1,2,3-triazoles were formed exclusively. The deprotection of the pyrrolidine N-atom was performed by treatment with TFA under standard conditions. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.019
• 作为产物：
  描述：

  1,4,5-Trimethyl-imidazol-2-carbonsaeure-3-oxid 生成 1,4,5-trimethyl-1H-imidazole 3-oxide
  参考文献：
  名称：

  FERGUSON I. J.; SCHOFIELD K.; BARNETT J. W.; GRIMMETT M. R., J. CHEM. SOC. PERKIN TRANS., PART 1 , 1977, NO 6, 672-675

  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。
• Unexpected Aldehyde-Catalyzed Reaction of Imidazole N-Oxides with Ethyl Cyanoacetate
  作者：Anton V. Kutasevich、Anna S. Efimova、Marina N. Sizonenko、Valery P. Perevalov、Ludmila G. Kuz’mina、Vitaly S. Mityanov

  DOI：10.1055/s-0039-1691527

  日期：2020.1

  The reaction of 2-unsubstituted imidazole N-oxides with ethyl cyanoacetate and aromatic aldehydes leads to the formation of ethyl 2-cyano-2-(1,3-dihydro-2H-imidazole-2-ylidene)acetates. The reaction proceeds through an initial [3+2] cycloaddition, followed by cleavage of the cycloadduct and regeneration of the aldehyde, which essentially plays a catalytic role.

  2-未取代咪唑N-氧化物与氰基乙酸乙酯和芳香醛的反应导致形成2-氰基-2-(1,3-二氢-2H-咪唑-2-亚基)乙酸乙酯。该反应通过最初的 [3+2] 环加成反应进行，然后是环加合物的裂解和醛的再生，这基本上起催化作用。
• Multicomponent assembling of imidazole N -oxides, aldehydes and CH-acids: A simple and efficient approach to newly functionalized imidazole derivatives
  作者：Vitaly S. Mityanov、Anton V. Kutasevich、Michail M. Krayushkin、Boris V. Lichitsky、Arkady A. Dudinov、Andrey N. Komogortsev、Tatyana Yu. Koldaeva、Valery P. Perevalov

  DOI：10.1016/j.tet.2017.10.026

  日期：2017.11

  An efficient and simple method for C2-functionalization of 2-unsubstituted imidazole N-oxides has been developed. It consists at the condensation of 2-unsubstituted imidazole N-oxides with aldehydes and CH-acids. This method permits broad variations in the structure of starting materials.

  已经开发了一种有效且简单的方法用于2-未取代的咪唑N-氧化物的C2-官能化。它由2-未取代的咪唑N-氧化物与醛和CH-酸的缩合组成。该方法允许起始材料结构的广泛变化。
• Synthesis of highly functional imidazole derivatives via assembly of 2-unsubstituted imidazole N-oxides with CH-acids and arylglyoxals
  作者：Valery P. Perevalov、Vitaly S. Mityanov、Boris V. Lichitsky、Andrey N. Komogortsev、Ludmila G. Kuz’mina、Tatyana Yu. Koldaeva、Vladimir S. Miroshnikov、Anton V. Kutasevich

  DOI：10.1016/j.tet.2020.130947

  日期：2020.2

  A novel and convenient method for the synthesis of a wide range of polyfunctional imidazole derivatives based on the three-component condensation of imidazole N-oxides with CH-acids and arylglyoxals has been developed. This reaction proceeds smoothly in moderate-to-good yields with a wide range of starting materials.

  基于咪唑N-氧化物与CH-酸和芳基乙二醛的三组分缩合反应，已开发出一种新颖，方便的合成多种多官能咪唑衍生物的方法。该反应在多种起始原料下以中等至良好的收率顺利进行。
• Assembly of isoxazol-5-one with 2-unsubstituted imidazole <i>N</i>-oxides and aldehydes
  作者：Ekaterina S. Uvarova、Anton V. Kutasevich、Egor S. Lipatov、Vitaly S. Mityanov

  DOI：10.1039/d2ob02157a

  日期：——

  A new synthetic protocol has been developed to construct polyfunctional isoxazol-5-one derivatives with imidazole moiety. It is based on the Knoevenagel condensation of isoxazol-5-one with aldehydes and subsequent Michael addition of imidazole N-oxides as part of a tandem three-component process. This reaction proceeds smoothly in moderate-to-good yield under catalyst-free conditions.

  已经开发了一种新的合成方案来构建具有咪唑部分的多功能异恶唑-5-酮衍生物。它基于 isoxazol-5-one 与醛的 Knoevenagel 缩合以及随后的咪唑 N-氧化物的迈克尔加成，作为串联三组分工艺的一部分。该反应在无催化剂条件下以中等到良好的收率顺利进行