2-(3-hydroxy-1-phenylbut-2-enylideneamino)pyridine-3-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-hydroxy-1-phenylbut-2-enylideneamino)pyridine-3-ol
• 英文别名: 3-(3-hydroxypyridin-2-ylamino)-1-phenylbut-2-en-1-one；beacapyrH2；3-[(3-Hydroxypyridin-2-yl)amino]-1-phenylbut-2-en-1-one
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: IUYLTBRQEKRZDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  aluminium trinitrate 、 2-(3-hydroxy-1-phenylbut-2-enylideneamino)pyridine-3-ol 、 potassium nitrate 在 Et₃N 作用下， 以 甲醇 为溶剂， 以50%的产率得到potassium[bis(2-(3-hydroxy-1-phenyl-but-2-enylideneamino)pyridine-3-ol)aluminate(III)]
  参考文献：
  名称：

  某些新型2-氨基-3-羟基吡啶希夫碱化合物的合成，表征及其与13族金属离子的相互作用

  摘要：

  一系列新的铝（III），镓（III）和铟（III）与三个新的2-（3-羟基-1-甲基-丁-2-烯基亚氨基氨基）吡啶-3-醇三齿席夫碱配合物[ H 2 L 1 ]，2-（3-羟基-1-苯基-丁-2-烯叉基氨基）吡啶-3-醇[H 2 L 2 ]和2-（4-羟基-1,1,1-三氟-戊-2-烯基亚氨基）吡啶-3-醇[H 2 L 3 ]（衍生自2-氨基-3-羟基吡啶和乙酰丙酮，苯甲酰基丙酮和1,1,1-三氟-2,4-二酮通式[Y] [ML 2 ]（M = Al 3+，Ga 3+，In 3+和Y = K +合成并通过1 HNMR，FT-IR和UV-vis分光光度法表征。配合物的形成常数是在25°C在甲醇中分光光度法测定的。配合物的形成常数的趋势如下： Al 3+ H 2 L 2 > H 2 L 3

  DOI：

  10.1080/15533174.2011.610769
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 、 1-苯基-1,3-丁二酮 以 乙醇 为溶剂， 反应 8.0h， 以35%的产率得到2-(3-hydroxy-1-phenylbut-2-enylideneamino)pyridine-3-ol
  参考文献：
  名称：

  Synthesis, spectroscopic investigations, crystal structures and antibacterial activity of 3-(3-hydroxypyridin-2-ylamino)-1-phenylbut-2-en-1-one and its diorganotin(IV) complexes

  摘要：

  Two new organotin(IV) complexes, [SnPh2(L)] (1) and [SnMe2(L)] (2), have been synthesized from the reaction of SnPh2Cl2 and SnMe2Cl2 with a Schiff base, 3-(3-hydroxypyridin-2-ylamino)-1-phenylbut-2en-1-one (H2L), derived from 2-amino-3-hydroxypyridine and benzoylacetone. The new compounds have been characterized by elemental analysis, FT-IR, H-1 and Sn-119 NMR spectroscopy. The structures of H2L and 2 have been confirmed by X-ray crystallography. Crystals of H2L are orthorhombic with the space group P2(1)2(1)2(1). This compound forms a dimer in the solid state which is held together by two intermolecular hydrogen bonds. This Schiff base exists as the keto-amine tautomeric form with one intramolecular N-H center dot center dot center dot O hydrogen bond. In the two complexes the Schiff base is completely deprotonated and coordinates to tin as tridentate via the imine nitrogen and phenolic and enolic oxygen atoms, and the coordination number of the tin center is five. Complex 2 crystallizes in the monoclinic space group, P2(1)/n, and the structure is distorted square pyramidal, with the imine nitrogen in the apical position. The in vitro antibacterial activity of the Schiff base and its complexes has been evaluated against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria. H2L showed no activity, but the organotin(IV) complexes exhibited good activities along with the standard antibacterial drugs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.12.007

文献信息

• Synthesis and Characterization of Some New 2-Amino-3-Hydroxypyridine Schiff Base Compounds and Their Interactions with Group 13 Metal Ions
  作者：Khosro Mohammadi、Marzieh Abdeshah

  DOI：10.1080/15533174.2011.610769

  日期：2012.3.1

  A series of new aluminum(III), gallium(III), and indium(III) complexes with three new tridentate Schiff base of 2-(3-hydroxy-1-methyl-but-2-enylideneamino)pyridine-3-ol [H2L1], 2-(3-hydroxy-1-phenyl-but-2-enylideneamino)pyridine-3-ol [H2L2] and 2-(4-hydroxy-1,1,1-trifluoro-pent-2-enylideneamino)pyridine-3-ol [H2L3] (which have been derived from 2-amino-3-hydroxypyridine and diketones of acetylacetone

  一系列新的铝（III），镓（III）和铟（III）与三个新的2-（3-羟基-1-甲基-丁-2-烯基亚氨基氨基）吡啶-3-醇三齿席夫碱配合物[ H 2 L 1 ]，2-（3-羟基-1-苯基-丁-2-烯叉基氨基）吡啶-3-醇[H 2 L 2 ]和2-（4-羟基-1,1,1-三氟-戊-2-烯基亚氨基）吡啶-3-醇[H 2 L 3 ]（衍生自2-氨基-3-羟基吡啶和乙酰丙酮，苯甲酰基丙酮和1,1,1-三氟-2,4-二酮通式[Y] [ML 2 ]（M = Al 3+，Ga 3+，In 3+和Y = K +合成并通过1 HNMR，FT-IR和UV-vis分光光度法表征。配合物的形成常数是在25°C在甲醇中分光光度法测定的。配合物的形成常数的趋势如下： Al 3+ H 2 L 2 > H 2 L 3
• Synthesis, spectroscopic investigations, crystal structures and antibacterial activity of 3-(3-hydroxypyridin-2-ylamino)-1-phenylbut-2-en-1-one and its diorganotin(IV) complexes
  作者：Tahereh Sedaghat、Mohamad Naseh、Hamid Reza Khavasi、Hossein Motamedi

  DOI：10.1016/j.poly.2011.12.007

  日期：2012.2

  Two new organotin(IV) complexes, [SnPh2(L)] (1) and [SnMe2(L)] (2), have been synthesized from the reaction of SnPh2Cl2 and SnMe2Cl2 with a Schiff base, 3-(3-hydroxypyridin-2-ylamino)-1-phenylbut-2en-1-one (H2L), derived from 2-amino-3-hydroxypyridine and benzoylacetone. The new compounds have been characterized by elemental analysis, FT-IR, H-1 and Sn-119 NMR spectroscopy. The structures of H2L and 2 have been confirmed by X-ray crystallography. Crystals of H2L are orthorhombic with the space group P2(1)2(1)2(1). This compound forms a dimer in the solid state which is held together by two intermolecular hydrogen bonds. This Schiff base exists as the keto-amine tautomeric form with one intramolecular N-H center dot center dot center dot O hydrogen bond. In the two complexes the Schiff base is completely deprotonated and coordinates to tin as tridentate via the imine nitrogen and phenolic and enolic oxygen atoms, and the coordination number of the tin center is five. Complex 2 crystallizes in the monoclinic space group, P2(1)/n, and the structure is distorted square pyramidal, with the imine nitrogen in the apical position. The in vitro antibacterial activity of the Schiff base and its complexes has been evaluated against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria. H2L showed no activity, but the organotin(IV) complexes exhibited good activities along with the standard antibacterial drugs. (C) 2011 Elsevier Ltd. All rights reserved.