2-methylimidazolone | 4915-81-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methylimidazolone
• 英文别名: 2-methyl-4(5H)-imidazolone；2-methyl-4,5-dihydro-1H-5-imidazolone；2-methyl-3,5-dihydroimidazol-4-one；Methyl-2-imidazolinon-4(5)；2-Methyl-Δ²-imidazolon-5；2-Methyl-3,5-dihydro-imidazol-4-on；2-methyl-1,4-dihydroimidazol-5-one
• CAS: 4915-81-5
• 化学式: C₄H₆N₂O
• 分子量: 98.1044
• InChiKey: BMXVNDCWQYPPAB-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylimidazolone 在 硫酸 、 硝酸 作用下， 以27%的产率得到2-(dinitromethylene)-5,5-dinitro-4-imidazolidinone
  参考文献：
  名称：

  Synthesis and reactions of 1,1-diamino-2,2-dinitroethylene

  摘要：

  Low temperature nitrations of 2-methylimidazole gave in addition to the known 2-methyl-5(4)-nitroimidazole (1), 2-(dinitromethylene)-5,5-dinitro-4-imidazolidinone (3) and parabanic acid (2). The tetranitro compound 3 was also obtained by nitration of 2-methyl-4,5-dihydro-( 1H)-5-imidazolone (:8). Thermal decomposition of 3 gave 2-(dinitromethylene)-4,5-imidazolidinedione (4) which also was the product from nitration of the new compound 2-methoxy-2-methyl-4,5-imidazolidinedione. Treatment of 4 with aqueous ammonia gave the previously unknown 1,1-diamino-2,2-dinitroethylene (5). The physical properties and chemical behaviour of (5) are described. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00673-5
• 作为产物：
  描述：

  2-甲基咪唑 在 高氯酸 、 chloramine-B 作用下， 以 水 为溶剂， 以91.6%的产率得到2-methylimidazolone
  参考文献：
  名称：

  氯胺-B将咪唑转化为咪唑酮的动力学和机理研究

  摘要：

  摘要1 H-咪唑（IzlH）和2-取代的咪唑，2-乙基-1 H-咪唑（2-EtIzlH），2-甲基-1 H-咪唑（2-MeIzlH）和1 H-咪唑的氧化转化建立了具有N-氯苯磺酰胺钠或氯胺-B（CAB）的-2-酯（2-EsIzlH）和1 H-咪唑-2-甲醛（2-CaIzH）形成相应的咪唑酮。在303 K的HClO 4介质中动力学研究了该反应。在可比较的实验条件下，所有五个咪唑的氧化反应动力学都相同，速率对[CAB] o的阶次依赖性和对[咪唑] o的分数阶依赖性和[H + ]。研究了添加苯磺酰胺，卤离子，NaClO 4和MeOH对反应速率的影响。通过GC-MS和NMR光谱分析鉴定并表征了反应产物。该速率是在不同温度下测量的，并且已根据Arrhenius图计算了复合活化参数。发现等速温度（β）为449 K，高于实验温度（303 K），表明该速率已处于焓控制下。这些咪唑的相对反应性依次为：2-EtIzlH>

  DOI：

  10.1007/s00706-016-1663-4

文献信息

• Biomimetic Oxidation of 2-Methylimidazole Derivative with a Chemical Model System for Cytochrome P-450.
  作者：Hiroyuki Miyachi、Yoshio Nagatsu

  DOI：10.1248/cpb.50.1137

  日期：——

  A chemical model system for cytochrome P-450, consisting of tetraphenylporphyrin manganese chloride (TPPMnCl) and iodosylbenzene, efficiently oxidized 2-methylimidazole to 2-methylimidazolone. This system was next applied to 4-(2-methyl-1-imidazolyl)-2,2-diphenylbutyramide, a muscarinic acetylcholine receptor antagonist under clinical trial, affording the previously unisolated imidazole ring 5-mono-oxidized

  一种由四苯基卟啉氯化锰（TPPMnCl）和碘基苯组成的细胞色素P-450的化学模型系统，将2-甲基咪唑有效地氧化为2-甲基咪唑酮。然后将该系统应用于临床试验中的毒蕈碱乙酰胆碱受体拮抗剂4-（2-甲基-1-咪唑基）-2,2-二苯基丁酰胺，提供了以前未被分离的咪唑环5-单氧化衍生物。主要代谢物的前体。该系统优于抗坏血酸铜系统，应适用于含有2-甲基咪唑部分的各种药物的体外研究。
• Retention Mechanism of Imidazoles in Connective Tissue. III. Aldehyde Adduct Formation of a 4(5H)(or 5(4H))-Imidazolone Product in Vitro.
  作者：Katsuji OHTA、Yoshiki FUKASAWA、Jun-ichi YAMAGUCHI、Masayuki AKIMOTO、Yoshiro KOHNO、Kiyomi FUKUSHIMA、Toshio SUWA、Shoji AWAZU

  DOI：10.1248/bpb.21.958

  日期：——

  2-Methylimidazole (2MI), as well as imidazole, has been though to undergo cupro-ascorbate (Cu-VC)-catalyzed oxidative transformation in vitro to become a reactive species capable of combining with aldehydes intrinsic to connective-tissue proteins. We attempted to seize the essence of the above reaction through obtaining the structural information of an aldehyde-bonding species. As major products from 2MI in the in vitro Cu-VC system, 2-hydroxymethylimidazole (2(OH)MI) and 2-methyl-4-(5H)(or 5(4H))-imidazolone (2MIone) were identified by mass-spectral and chromatographic comparison with the corresponding authentic standards synthesized. The in situ addition of acetaldehyde or propionaldehyde as a simple protein-aldehyde model to the system resulted in the deducible formation of an aldol condensate, 2-methyl-4(or 5)-ethylidene-4(5H)(or 5(4H))-imidazolone (2MEIone) or its possible analogue with a propylidene moiety, respectively. The authentic compound of 2MIone directly reacted with acetaldehyde and easily afforded the products assignable to the isomers of 2MEIone through the ethylidfene moiety at physiological pH and temperature, whereas neither 2MI or 2(OH)MI reacted at all. These results suggest that a 4(5H)(or 5(4H))-imidazolone product, although simply a monooxygenated form, is sufficiently reactive to give aldol condensation-typed covalent adducts with aldehydes, even under physiological conditions, probably having an activated methylene moiety in the ring strucuture. Based on the present results, we discussed the mechanism of the retention of imidazole-containing drugs in connective tissue.

  2-甲基咪唑（2MI）和咪唑一样，在体外通过铜-抗坏血酸盐（Cu-VC）催化氧化反应，成为能与结缔组织蛋白固有的醛结合的反应性物质。我们试图通过获得醛结合物质的结构信息来抓住上述反应的本质。作为2MI在体外Cu-VC系统中的主要产物，2-羟甲基咪唑（2（OH）MI）和2-甲基-4-（5H）（或5（4H））-咪唑酮（2MIone）通过与相应合成标准品的质量谱和色谱比较来鉴定。将乙醛或丙醛作为简单的蛋白质-醛模型原位添加到系统中，可分别推断出醛缩合物的形成，即2-甲基-4（或5）-亚乙基-4（5H）（或5（4H））-咪唑酮（2MEIone）或其可能的类似物，带有丙亚基。2MIone的正宗化合物与乙醛直接反应，在生理pH值和温度下，通过乙亚基部分很容易得到可归因于2MEIone异构体的产物，而2MI或2（OH）MI则完全没有反应。这些结果表明，4（5H）（或5（4H））-咪唑酮产物虽然只是单加氧形式，但具有足够的反应性，即使在生理条件下，也能与醛发生醛缩合
• Finger, Journal fur praktische Chemie (Leipzig 1954), 1907, vol. <2> 76, p. 97
  作者：Finger

  DOI：——

  日期：——
• Brunken; Bach, Chemische Berichte, 1956, vol. 89, p. 1363,1370
  作者：Brunken、Bach

  DOI：——

  日期：——
• Photochromic DNA having fluorescent protein-inspired nucleosides
  作者：Akio Kobori、Taichiro Arai、Yuya Sakata、Takayuki Sugita、Asako Yamayoshi、Akira Murakami

  DOI：10.1016/j.tetlet.2018.08.064

  日期：2018.10

  Molecular switches controlled by light stimuli can be applicable to the variety of the biological application. In this study, skeletal structures of a chromophore of fluorescent protein were applied as aglycones of newly designed photochromic nucleosides, "Fluorescent protein-inspired nuceloside: FIN". Phosphoramidite units of the photochromic nucleosides having imidazolinone derivatives with benzylidene or 3-pyridilidene groups were successfully synthesized for FIN-containing ODNs. Thermodynamic studies of the FIN-containing ODNs revealed that photo-irradiation with specific wavelength induced stability change of the duplexes. (C) 2018 Elsevier Ltd. All rights reserved.