3-(3-hydroxypyridin-2-ylimino)-1-phenylbutan-1-one | 949933-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-hydroxypyridin-2-ylimino)-1-phenylbutan-1-one
• 英文别名: 3-(3-hydroxypyridin-2-ylamino)-1-phenylbut-2-en-1-one；3-[(3-Hydroxy-2-pyridinyl)imino]-1-phenyl-1-butanone；3-(3-hydroxypyridin-2-yl)imino-1-phenylbutan-1-one
• CAS: 949933-71-5
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: DBXSUJSFOZVMHY-UHFFFAOYSA-N

物化性质

• 沸点：
  493.0±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxypyridin-2-ylimino)-1-phenylbutan-1-one 、 二苯基二氯化锡 在 triethylamine 作用下， 以 乙醇 为溶剂， 以71%的产率得到[tin(diphenyl)(3-(3-hydroxypyridin-2-ylamino)-1-phenylbut-2-en-1-one(-H))]
  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
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 、 1-苯基-1,3-丁二酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以78%的产率得到3-(3-hydroxypyridin-2-ylimino)-1-phenylbutan-1-one
  参考文献：
  名称：

  4-（3-羟基吡啶-2-亚胺基）-4-苯基丁烷-2-一的解离和金属络合的电位和热力学研究

  摘要：

  合成了席夫碱3-（3-羟基吡啶-2-ylimino）-1-苯基丁-2-（HPIB），并通过元素分析和红外光谱对其进行了表征。在40％（v / v）乙醇-水混合物中用电位计确定HPIB的质子-配体解离常数及其与Cu 2 +，Ni 2 +，Co 2+和Mn 2+的金属配合物的逐步稳定常数。在氮气下在0.100 M KCl存在下。配合物的稳定性遵循Cu 2+ > Ni 2+ > Co 2+ > Mn 2+的顺序。HPIB的解离常数和稳定性常数，log K在不同温度下测定其金属配合物，并推导和讨论了相应的热力学参数。发现质子-配体解离是非自发的，吸热的，并且在熵上是不利的。伴随复合物形成的ΔG 0和ΔH 0的值与金属离子的离子半径，电负性，电离焓和水合焓有关。-Δ的顺序ģ 0和- Δ ħ 0被发现服从的Mn 2+ <钴2+ <镍2+ <铜2+，与Irving-Williams订单一致。不同的热力学

  DOI：

  10.1021/je600586e

文献信息

• 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.
• Potentiometric and Thermodynamic Studies of Dissociation and Metal Complexation of 4-(3-Hydroxypyridin-2-ylimino)-4-phenylbutan-2-one
  作者：Bakir Jeragh、Dhuha Al-Wahaib、Ahmed A. El-Sherif、Ali El-Dissouky

  DOI：10.1021/je600586e

  日期：2007.9.1

  proton−ligand dissociation constant of HPIB and the stepwise stability constants of its metal complexes with Cu2+, Ni2+, Co2+, and Mn2+ were determined potentiometrically in a 40 % (v/v) ethanol−water mixture in the presence of 0.100 M KCl under nitrogen. The stabilities of the complexes follow the order Cu2+ > Ni2+ > Co2+ > Mn2+. The dissociation constants of HPIB and the stability constants, log K, of its metal

  合成了席夫碱3-（3-羟基吡啶-2-ylimino）-1-苯基丁-2-（HPIB），并通过元素分析和红外光谱对其进行了表征。在40％（v / v）乙醇-水混合物中用电位计确定HPIB的质子-配体解离常数及其与Cu 2 +，Ni 2 +，Co 2+和Mn 2+的金属配合物的逐步稳定常数。在氮气下在0.100 M KCl存在下。配合物的稳定性遵循Cu 2+ > Ni 2+ > Co 2+ > Mn 2+的顺序。HPIB的解离常数和稳定性常数，log K在不同温度下测定其金属配合物，并推导和讨论了相应的热力学参数。发现质子-配体解离是非自发的，吸热的，并且在熵上是不利的。伴随复合物形成的ΔG 0和ΔH 0的值与金属离子的离子半径，电负性，电离焓和水合焓有关。-Δ的顺序ģ 0和- Δ ħ 0被发现服从的Mn 2+ <钴2+ <镍2+ <铜2+，与Irving-Williams订单一致。不同的热力学