2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine | 38779-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine
• 英文别名: 1-hydroxy-4,5-dimethyl-2-(pyridin-2yl)imidazole；2-(1-Hydroxy-4,5-dimethyl-1h-imidazol-2-yl)pyridine；2-(1-hydroxy-4,5-dimethylimidazol-2-yl)pyridine
• CAS: 38779-79-2
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: ONLYTPYHBHQWGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine 、 zinc(II) acetate dihydrate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以75%的产率得到Bis[4,5-dimethyl-2-(pyridin-2-yl)-1Н-imidazol-1-olato]zinc dihydrate
  参考文献：
  名称：

  Luminescent zinc(II) and cadmium(II) complexes based on 2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine and 2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine

  摘要：

  Complexes (ZnLCl2)-Cl-1, (CdLCl2)-Cl-1, ZnL (2) (1) Cl-2 (center dot)1.5H(2)O, CdL (2) (1) Cl-2 (center dot)2H(2)O, CdL (2) (1) Cl-2 (MeOH)-Me-center dot center dot H2O [L-1 = 2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine] and inner-complex compounds ZnL (2) (2) center dot 2H(2)O, CdL (2) (2) [HL2 = 2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine] were synthesized. The complexes exhibit bright photoluminescence in the blue region of the spectrum, with the intensity exceeding this characteristic of the compounds L-1 and HL2. Compound L-1 in aqueous solution is a potential chemosensor for the determination of zinc and cadmium.

  DOI：

  10.1134/s1070363212110230
• 作为产物：
  描述：

  吡啶-2-甲醛 、 N-(2-hydroxyimino-1-methylpropyl)hydroxylamine acetate 以 溶剂黄146 为溶剂， 反应 18.0h， 以90%的产率得到2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine
  参考文献：
  名称：

  Luminescent zinc(II) and cadmium(II) complexes based on 2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine and 2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine

  摘要：

  Complexes (ZnLCl2)-Cl-1, (CdLCl2)-Cl-1, ZnL (2) (1) Cl-2 (center dot)1.5H(2)O, CdL (2) (1) Cl-2 (center dot)2H(2)O, CdL (2) (1) Cl-2 (MeOH)-Me-center dot center dot H2O [L-1 = 2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine] and inner-complex compounds ZnL (2) (2) center dot 2H(2)O, CdL (2) (2) [HL2 = 2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine] were synthesized. The complexes exhibit bright photoluminescence in the blue region of the spectrum, with the intensity exceeding this characteristic of the compounds L-1 and HL2. Compound L-1 in aqueous solution is a potential chemosensor for the determination of zinc and cadmium.

  DOI：

  10.1134/s1070363212110230

文献信息

• Synthesis of 2-aryl(hetaryl)-1-hydroxyimidazoles by the reaction of aliphatic 1,2-hydroxylamino oximes with aromatic and heteroaromatic aldehydes
  作者：B. A. Selivanov、A. Ya. Tikhonov

  DOI：10.1007/s11172-013-0169-z

  日期：2013.5

  A reaction of aliphatic 1,2-hydroxylamino oximes bearing the hydroxylamino group at the secondary carbon atom with aromatic and heteroaromatic aldehydes in acetic acid leads to the corresponding 1-hydroxy-2-aryl(hetaryl)-4,5-dialkylimidazoles in high yields. α-Aryl(hetaryl)-nitrones initially formed by the condensation of 1,2-hydroxylamino oximes with aldehydes are quantitatively converted to the corresponding imidazoles.

  脂肪族1,2-羟基氨基肟在乙酸中与芳香族和杂芳族醛反应，在仲碳原子上带有羟基氨基，从而高产量地生成相应的1-羟基-2-芳基（杂芳基）-4,5-二烷基咪唑。α-芳基（杂芳基）-腈酮最初由1,2-羟基氨基肟与醛缩合形成，然后定量转化为相应的咪唑。
• Synthesis and structure of metal complexes containing zwitterionic N-hydroxyimidazole ligands
  作者：Suaad Abuskhuna、Malachy McCann、John Briody、Michael Devereux、Kevin Kavanagh、Nijhuma Kayal、Vickie McKee

  DOI：10.1016/j.poly.2007.06.034

  日期：2007.9

  Cu(II) and Zn(II) complexes of N-hydroxyimidazoles were synthesised by reacting simple metal perchlorate salts with the imidazole ligand in alcohol and formulated with a metal:ligand ratio of 1:2. The X-ray crystal structures of five complexes (four Cu(II) and one Zn(II)) were obtained and each showed the two trans, N-hydroxyimidazole ligands forming six-membered, chelate rings with the metal. Both of the NO chelating, neutral N-hydroxyimidazole ligands are in the zwitterion form, with the uncoordinated imidazole imine N atom being protonated and the oxime O atom deprotonated. In the solid state the complexes form hydrogen-bonded supramolecular structures. (c) 2007 Elsevier Ltd. All rights reserved.
• Zinc(II) complexes with an imidazolylpyridine ligand: luminescence and hydrogen bonding
  作者：Mark B. Bushuev、Boris A. Selivanov、Natalia V. Pervukhina、Dmitrii Yu. Naumov、Lilia A. Sheludyakova、Marianna I. Rakhmanova、Alexsei Ya. Tikhonov、Stanislav V. Larionov

  DOI：10.1080/00958972.2014.892589

  日期：2014.2.16

  ZnLCl and [H2L](2)[ZnCl4], based on 2-(1-hydroxy-4,5-dimethyl-1H-imidazol-2-yl)pyridine (HL), have been synthesized. There is a short intraionic O-H center dot center dot center dot N hydrogen bond between the hydroxyimidazolyl and pyridyl of H2L+ cations (N center dot center dot center dot O 2.608(2) angstrom) in the structure of [H2L](2)[ZnCl4]. The formation of this rather strong hydrogen bond is confirmed by IR spectroscopy through a broad band at 3200-2200 cm(-1) and a band at 1655 cm(-1). HL crystallizes in the form of a hemihydrate, HL center dot 0.5H(2)O. HL assemble into infinite helical chains due to N-H center dot center dot center dot O intermolecular hydrogen bonds between the NH of imidazole and O of the N-oxide (O center dot center dot center dot N 2.623(2) angstrom). An unusual mid-IR pattern with three broad bands at 3373, 2530, and 1850 cm(-1) is typical for strong hydrogen bonds, explained by resonance-assisted hydrogen bonding occurring in the helical chains. On cooling to 5 K, noticeable changes in the IR spectra of [H2L](2)[ZnCl4] and HL center dot 0.5H(2)O were observed. ZnLCl and [H2L](2)[ZnCl4] exhibit bright photoluminescence with maxima of emission at 458 nm (for ZnLCl) and 490 nm (for [H2L](2)[ZnCl4]).