1-methyl-1H-imidazole-3-oxide

• 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-methyl-1H-imidazole-3-oxide
• 英文别名: 1-methylimidazole-3-N-oxide；1-methylimidazole-3N-oxide；1-methylimidazole 3-oxide；1-methylimidazole-N-oxide；NMI-O；1-methyl-3-oxidoimidazol-3-ium
• 化学式: C₄H₆N₂O
• 分子量: 98.1044
• InChiKey: ZYRXXCQGMOUOOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  硫酸二甲酯 、 1-methyl-1H-imidazole-3-oxide 以 neat (no solvent) 为溶剂， 反应 4.0h， 以99%的产率得到3-methoxy-1-methyl-1H-imidazol-3-ium methylsulfate
  参考文献：
  名称：

  使用 N-甲氧基杂芳鎓盐对未活化烯烃进行氢杂芳基化

  摘要：

  我们报告了在氢原子转移 (HAT) 条件下未活化的烯烃与 N-甲氧基哒嗪鎓、咪唑鎓、喹啉鎓和异喹啉鎓盐的首次还原偶联，并扩大了烯烃与 N-甲氧基吡啶鎓盐的偶联范围。N-甲氧基哒嗪鎓、咪唑鎓、喹啉鎓和异喹啉鎓盐可通过 1-2 个步骤从商业芳烃或芳烃 N-氧化物 (25-99%) 中获得。N-甲氧基咪唑鎓盐可通过三个步骤从商业胺（50-85%）中获得。总共制备了 36 种带有给电子、吸电子、烷基、芳基、卤素和卤代烷基取代基的离散甲氧基杂芳鎓盐（数种为数克），并与 38 种不同的烯烃偶联。转变在环境温度和中性条件下进行，专门提供单烷基化产物，并形成单一的烯烃加成区域异构体。将仲和叔自由基加成到吡啶鎓盐中的制备性有用和互补位点选择性已被记录：较硬的仲自由基有利于 C-2 加成 (2->10:1)，而较软的叔自由基有利于与 C-4 的键形成 (4.7 -> 29:1）。具有 1,2-二取代和 2,2-二取代烯烃的二烯仅在后者

  DOI：

  10.1021/jacs.7b02388
• 作为产物：
  描述：

  N-甲基咪唑 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到1-methyl-1H-imidazole-3-oxide
  参考文献：
  名称：

  1-Methylimidazole 3-N-oxide as a new promoter for the Morita–Baylis–Hillman reaction

  摘要：

  The Morita-Baylis-Hillman reaction of aldehydes with alpha,beta-unsaturated ketones can be affected by the Lewis bases. We have found that 1-methylimidazole 3-N-oxide promoted the Morita-Baylis-Hiliman reaction of various activated aldehyde compounds in non-solvent system. This is a mild reaction condition and requires no special equipment to give the Morita-BaylisHillman adducts. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.099
• 作为试剂：
  描述：

  芳樟醇 、 三乙基氯硅烷 在 1-methyl-1H-imidazole-3-oxide 作用下， 反应 8.0h， 以97%的产率得到3-(triethylsiloxy)-3,7-dimethyl-1,6-octadiene
  参考文献：
  名称：

  Preparation of 1-methylimidazole-N-oxide (NMI-O)

  摘要：

  DOI：

  10.15227/orgsyn.093.0331

文献信息

• Amines<i>vs. N</i>-Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1-Methylimidazole<i>N</i>-Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols
  作者：James I. Murray、Alan C. Spivey

  DOI：10.1002/adsc.201500773

  日期：2015.12.14

  efficiencies of Lewis-basic amines vs. N-oxides for the acylation, sulfonylation and silylation of primary, secondary and tertiary alcohols is reported. Whilst the amines are generally superior to the N-oxides for acylation, the N-oxides are superior for sulfonylation and silylation. In particular, 1-methylimidazole N-oxide (NMI-O) is found to be a highly efficient catalyst for sulfonylation and silylation reactions

  报道了路易斯-伯胺和N-氧化物对伯，仲和叔醇的酰化，磺酰化和甲硅烷基化的相对催化效率的比较。虽然胺通常是优于Ñ -oxides为酰化，所述Ñ -oxides优于用于磺酰化和甲硅烷基化。特别地，发现1-甲基咪唑N-氧化物（NMI-O）是用于磺酰化和甲硅烷基化反应的高效催化剂。据我们所知，NMI-O是第一种胺或N-氧化物路易斯碱性有机催化剂，能够在温和的反应条件下以较低的催化剂负载量高产率地促进叔醇的高效甲硅烷基化。
• Isoamyl acetate synthesis in imidazolium-based ionic liquids using packed bed enzyme microreactor
  作者：Marina Cvjetko、Jasna Vorkapić-Furač、Polona Žnidaršič-Plazl

  DOI：10.1016/j.procbio.2012.04.028

  日期：2012.9

  The acylation of isoamyl alcohol with acetic anhydride catalyzed by immobilized Candida antarctica lipase B was studied in ionic liquids (ILs) based on quaternary imidazolium cations with alkyl, alkenyl, alkynyl, benzyl, alkoxyl or N-aminopropyl side chains. Among the tested ILs, the highest enzyme activity together with the highest isoamyl acetate yield were obtained in [C(7)mmim][Tf2N].No loss of lipase B activity was observed during one-month incubation in this hydrophobic IL without the presence of substrates. Isoamyl acetate synthesis using [C(7)mmim][Tf2N] as solvent was further studied in a continuously operated miniaturized enzymatic packed bed reactor at various flow rates and temperatures. Up to 92% isoamyl acetate yield could be obtained within 15 min by using 0.5 M acetic anhydride and 1.5 M isoamyl alcohol inlet concentrations at 55 degrees C, corresponding to the volumetric productivity of 61 mmol l(-1) min(-1), which to the best of our knowledge is the highest reported so far for this reaction. No decrease in productivity was experienced during the subsequent runs of continuous microbioreactor operation performed within 14 consecutive days. The benefits of reactor miniaturization along with the green solvent application were therefore successfully exploited for the development of a sustainable flavour ester production. (C) 2012 Elsevier Ltd. All rights reserved.
• Laus, Gerhard; Schwaerzler, Alexander; Bentivoglio, Gino, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2008, vol. 63, # 4, p. 447 - 464
  作者：Laus, Gerhard、Schwaerzler, Alexander、Bentivoglio, Gino、Hummel, Michael、Kahlenberg, Volker、Wurst, Klaus、Kristeva, Elka、Schuetz, Johannes、Kopacka, Holger、Kreutz, Christoph、Bonn, Guenther、Andriyko, Yuriy、Nauer, Gerhard、Schottenberger, Herwig

  DOI：——

  日期：——