2,4,4,5,5-pentamethyl-1-hydroxy-2-imidazoline | 402520-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 2,4,4,5,5-pentamethyl-1-hydroxy-2-imidazoline
• 英文别名: 2,4,4,5,5-pentamethyl-4,5-dihydroimidazol-1-ol；2,4,4,5,5-pentamethyl-4,5-dihydro-1H-imidazol-1-ol；2,4,4,5,5-pentamethyl-4,5-dihydro-1H-imidazolyl-1-oxide；2,4,4,5,5-Pentamethyl-4,5-dihydro-1h-imidazole 3-oxide；1-hydroxy-2,4,4,5,5-pentamethylimidazole
• CAS: 402520-12-1
• 化学式: C₈H₁₆N₂O
• 分子量: 156.228
• InChiKey: RSZMPTDVFRCRLX-UHFFFAOYSA-N

物化性质

• 沸点：
  211.7±23.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,4,5,5-pentamethyl-1-hydroxy-2-imidazoline 在 N-氯代丁二酰亚胺 、 lithium diisopropyl amide 作用下， 以 乙醚 、 氯仿 、 二甲基亚砜 为溶剂， 生成 2-[1-Hydroxy-4,4,5,5-tetramethyl-imidazolidin-(2E)-ylidene]-3-oxo-3-phenyl-propionitrile
  参考文献：
  名称：

  Metal complex with the enaminoketone derivative of 2-imidazoline nitroxide

  摘要：

  DOI：

  10.1070/mc2001v011n05abeh001472
• 作为产物：
  描述：

  1,3-Dihydroxy-2,4,4,5,5-pentamethyl-imidazolidin 以 正庚烷 为溶剂， 反应 12.0h， 以85%的产率得到2,4,4,5,5-pentamethyl-1-hydroxy-2-imidazoline
  参考文献：
  名称：

  Metal complex with the enaminoketone derivative of 2-imidazoline nitroxide

  摘要：

  DOI：

  10.1070/mc2001v011n05abeh001472

文献信息

• A New Class of Enehydroxylamino Ketones− (R)-2-(1-Hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones: Synthesis and Reactions
  作者：Vladimir A. Reznikov、Galina I. Roshchupkina、Dmitrii G. Mazhukin、Pavel A. Petrov、Sergei A. Popov、Sergey V. Fokin、Galina V. Romanenko、Tatjana V. Rybalova、Yuri V. Gatilov、Yuri G. Shvedenkov、Irina G. Irtegova、Leonid A. Shundrin、Victor I. Ovcharenko

  DOI：10.1002/ejoc.200300536

  日期：2004.2

  Three approaches to the synthesis of (R)-2-(1-hydroxy-4,4,5,5-tetraalkylimidazolidin-2-ylidene)ethanones 1 are described: (a) condensation of 1,2-bishydroxylamines with β-ketoaldehyde synthons, (b) treatment of metallated 1-hydroxy-2-methyl-4,5-dihydroimidazoles with esters, and (c) 1,3-dipolar cycloaddition between 1-hydroxy-4,5-dihydroimidazole-3-oxide and DMAD. The reactivity of 1 with electrophiles

  描述了合成 (R)-2-(1-羟基-4,4,5,5-四烷基咪唑烷-2-亚基) 乙酮 1 的三种方法：(a) 1,2-双羟胺与 β-酮醛的缩合合成子，(b) 用酯处理金属化 1-羟基-2-甲基-4,5-二氢咪唑，和 (c) 1-羟基-4,5-二氢咪唑-3-氧化物和 DMAD 之间的 1,3-偶极环加成. 已经研究了 1 与亲电试剂的反应性。环外亚甲基（烯胺）碳原子被证明是亲电攻击的主要位点。合成的氯取代 1-羟基-2-乙炔咪唑烷与氰化钠反应形成相应的腈。这些腈的氧化伴随着持久性乙烯基氮氧化合物的形成而发生，它们作为潜在的顺磁性配体是令人感兴趣的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,
• 1,3-Dipolar cycloaddition or nucleophilic addition: Influence of solvents and nature of substituents in the reagent and substrate molecules on the reaction of 4,5-dihydro-1<i>H</i>-imidazole 3-oxides with alkynes
  作者：Sergey A. Popov、Vladimir A. Reznikov

  DOI：10.1002/jhet.5570430207

  日期：2006.3

  Two competitive processes - 1,3-dipolar cycloaddition and nucleophilic addition - in the reaction of 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole 3-oxides with asymmetrically substituted alkynes were shown to occur. The influence of solvents and the nature of substituents in the reagent and substrate molecules on the rate ratio of these competitive processes were studied.

  在4,4,5,5-四甲基-4,5-二氢-1 H-咪唑3-氧化物与不对称取代的炔烃的反应中，发生了两个竞争过程-1,3-偶极环加成和亲核加成。研究了溶剂以及试剂和底物分子中取代基的性质对这些竞争过程的速率比的影响。
• Aminonitrone-N-hydroxyaminoimine tautomeric equilibrium in the series of 1-hydroxy-2-imidazolines
  作者：Sergey A. Popov、Rodion V. Andreev、Galina V. Romanenko、Viktor I. Ovcharenko、Vladimir A. Reznikov

  DOI：10.1016/j.molstruc.2004.02.028

  日期：2004.7

  A series of 2-substituted 1-hydroxy-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazoles have been synthesized. Various effects on the state of the aminonitrone-N-hydroxyaminoimine tautomeric equilibrium, including solvent effects and substituent effect in the 2 position of heterocycle, have been studied. (C) 2004 Elsevier B.V. All rights reserved.
• Coordination chemistry of the nitronyl and imino nitroxides. Linear chain adducts with rhodium(II) trifluoroacetate dimer
  作者：Andre Cogne、Andre Grand、Paul Rey、Robert Subra

  DOI：10.1021/ja00191a020

  日期：1989.4
• BIRADICAL POLARIZING AGENTS FOR DYNAMIC NUCLEAR POLARIZATION
  申请人：Griffin Robert G.

  公开号：US20090302842A1

  公开（公告）日：2009-12-10

  The present invention provides methods for performing dynamic nuclear polarization using biradicals with a structure of formula (I) as described herein. In general, the methods involve (a) providing a frozen sample in a magnetic field, wherein the frozen sample includes a biradical of formula (I) and an analyte with at least one spin half nucleus; (b) polarizing the at least one spin half nucleus of the analyte by irradiating the frozen sample with radiation having a frequency that excites electron spin transitions in the biradical; (c) optionally melting the sample to produce a molten sample; and (d) detecting nuclear spin transitions in the at least one spin half nucleus of the analyte in the frozen or molten sample. The present invention also provides biradicals with a structure of formula (I) with the proviso that Q 1 and Q 2 are different when X 1 and X 2 are —O—. The present invention also provides methods for making biradicals with a structure of formula (IA) as described herein.