2-[2-(α-pyridyl)methyl]imino-3-butanone oxime | 85777-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[2-(α-pyridyl)methyl]imino-3-butanone oxime
• 英文别名: 2-oximino-3-methyl-4-aza-5-(2-pyridyl)-3-pentene；3-(pyridin-2-ylmethylimino)butan-2-one oxime；3-[(2-pyridyl)methylimino]butan-2-one oxime；2-Butanone, 3-[(2-pyridinylmethyl)imino]-, oxime；N-[3-(pyridin-2-ylmethylimino)butan-2-ylidene]hydroxylamine
• CAS: 85777-07-7
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: PXTGQKIWRFRRHP-UHFFFAOYSA-N

物化性质

• 熔点：
  156.2-157.1 °C(Solv: ethanol (64-17-5))
• 沸点：
  335.6±44.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(α-pyridyl)methyl]imino-3-butanone oxime 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-((2-pyridyl)methylamino)-butan-2-one oxime
  参考文献：
  名称：

  Oximate metal complexes breaking the limiting esterolytic reactivity of oximate anions

  摘要：

  由于金属配位消除了亲核体的 "溶解失衡"，三叉氧配体的锌（II）和镉（II）络合物裂解 4-硝基苯乙酸酯的速率常数比高碱性游离氧阴离子的最大可能水平高出两个数量级。

  DOI：

  10.1039/c3cc43944e
• 作为产物：
  描述：

  2-氨甲基吡啶 、 二乙酰一肟 以 异丙醚 为溶剂， 反应 2.0h， 以88%的产率得到2-[2-(α-pyridyl)methyl]imino-3-butanone oxime
  参考文献：
  名称：

  Oximate metal complexes breaking the limiting esterolytic reactivity of oximate anions

  摘要：

  由于金属配位消除了亲核体的 "溶解失衡"，三叉氧配体的锌（II）和镉（II）络合物裂解 4-硝基苯乙酸酯的速率常数比高碱性游离氧阴离子的最大可能水平高出两个数量级。

  DOI：

  10.1039/c3cc43944e

文献信息

• Synthesis, structure and reactivity of cobalt(III) complexes with tridentate imino- and amino-oxime ligands
  作者：Laura Catalano、Renata Dreos、Giorgio Nardin、Lucio Randaccio、Giovanni Tauzher、Sara Vuano

  DOI：10.1039/dt9960004269

  日期：——

  produces a nucleophilic cobalt(I) species which, on reaction with MeI, gives a stable organocobalt dinuclear complex, previously reported. On the contrary, the reduction of [CoIIIL12]ClO4 involves hydrogenation of the ligand from imino- to amino-oxime, with the formation of a stable cobalt(II) species. Under these conditions, no reduction to CoI was observed. The different reactivity is attributed to the

  三齿亚氨基肟HL 2和HL 1是通过联乙酰一肟与2-（2-氨基乙基）吡啶和2-（氨基甲基）吡啶缩合制备的。它们在氧气存在下与钴（II）离子反应，生成配合物[Co III L 2 ] ClO 4（L = L 1或L 2）。亚氨基肟可在NaBH 4存在下氢化，得到相应的氨基肟HL 3和HL 4，它们在与Co II反应后形成配合物[Co III L（HL）] [ClO 4 ] 2。（L = L 3或L 4）。所有这些配合物都已通过单晶X射线衍射进行了结构表征。钴具有八面体环境，其中亚氨基肟配体为mer构型，而氨基肟配体为fac构型。用NaBH 4还原[Co III L 2 2 ] ClO 4产生亲核钴（I）物种，该物种在与MeI反应后可得到稳定的有机钴双核络合物，先前已有报道。相反，[Co III L 1 2 ] ClO 4的还原涉及将配体从亚氨基肟氢化为氨基肟，并形成稳定的钴（II）物种。在这些条件下，未观察到Co
• Structural, vibrational, NMR, quantum chemical, DNA binding and protein docking studies of two flexible imine oximes
  作者：YUNUS KAYA

  DOI：10.1007/s12039-016-1136-7

  日期：2016.9

  Two flexible imine oxime molecules, namely, 3-(pyridin-2-ylmethylimino)-butan-2-one oxime (HL 1) and 3-(pyridin-2-ylmethylimino)-pentan-2-one oxime (HL 2) have been synthesized and characterized by elemental analysis, IR and NMR techniques. The conformational behavior was investigated using the density functional theory (DFT) with the B3LYP method combined with the 6-311 ++G(d,p) basis set. As a result

  两个灵活的亚胺肟分子，即3-（吡啶-2-基甲基亚氨基）-丁-2-酮肟（HL 1）和3-（吡啶-2-基甲基亚氨基）-戊-2-酮肟（HL 2）具有通过元素分析，IR和NMR技术合成并表征。使用密度泛函理论（DFT）将B3LYP方法与6-311 ++ G（d，p）基组结合使用，研究构象行为。构象研究的结果，确定了两个亚胺肟的三个稳定分子和最稳定的构象异构体。计算出了HL 1和HL 2最稳定构象的光谱性质（如振动和NMR）。计算结果用于模拟标题化合物的红外光谱，与观察到的光谱具有很好的一致性。此外，两个亚胺肟的稳定的三个分子已被用于使用Discovery Studio 3.5进行具有DNA和蛋白质结构的DNA结合和蛋白质对接研究（从Protein Data Bank下载），以找到最优选的配体结合方式在DNA和蛋白质腔内。 柔性亚胺肟具有有趣的结构特征，尤其是在分子之间的相互作用中。对于研究人员而言，它们是潜在的生物活性分子。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Co: SVol.B2, 32, page 379 - 381
  作者：

  DOI：——

  日期：——
• Tridentate Chelate Compounds. I
  作者：Francis Lions、Kenneth V. Martin

  DOI：10.1021/ja01568a018

  日期：1957.6
• Syntheses, crystal structures and autoreduction behavior of antiferromagnetically coupled dicopper(II) oximato complexes
  作者：Masahiko Maekawa、Susumu Kitagawa、Yasuo Nakao、Sachiyo Sakamoto、Akihiro Yatani、Wasuke Mori、Setsuo Kashino、Megumu Munakata

  DOI：10.1016/s0020-1693(99)00215-7

  日期：1999.10

  Four dicopper(II) oximato complexes of 2-[2-(alpha-pyridyl)methyl]imino-3-butanone oxime (pmiboH) and 2-[2-(alpha-pyridyl)ethyl]imino-3-butanone oxime (peiboH), [Cu-2(pmibo)(2)](ClO4)(2) (1), [Cu-2(pmibo)(2)](NO3)(2). CH3OH, (2), [Cu-2(peibo)(2)](ClO4)(2). CH3OH (3) and [Cu-2(peibo)(2)(H2O)(2)](ClO4)(2) (4), were prepared and characterized structurally and magnetically. All the dicopper(II) oximato complexes have a common cationic structure in which the two Cu atoms are bridged through two N-O bridges of the oximato ligand to afford a dinuclear structure. The cation moieties of 1 and 2 consist of one six-membered Cu2N2O2 chelate ring and four five-membered (CuN2C2 and CuNC2N) chelate rings, providing a planar configuration. The cation moieties of 3 and 4 are also composed of three six-membered (Cu2N2O2 and CuNC3N) chelate rings and two five-membered CuN2C2 chelate rings, giving a twisted-boat configuration. The -2J values (H = -2JS(1)S(2)) are 835, 825, 550 and 510 cm(-1) for 1, 2, 3 and 4, respectively, indicative of a strong antiferromagnetic interaction in the solid state. All the dicopper(II) oximato complexes show seven H-1 NMR signals at 23 degrees C in the range of -0.5 to 30 ppm with the linewidths at half-height, Delta v(1/2) of 60-1500 Hz, which is characteristic of antiferromagnetic species and indicates that the dinuclear structure is kept in solution. The -2J values reflect the degree of distortion from the planarity of the Cu-2 framework. The -2J values roughly correlate with the H-1 NMR parameters; the larger the -2J values, the smaller the chemical shifts and linewidths. Complexes 1 and 2 were found to undergo an autoreduction reaction in dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF) and N,N-dimethylacetamide (DMA), and their behaviors were first monitored by UV-Vis and H-1 NMR methods. (C) 1999 Elsevier Science S.A. All rights reserved.