4-PAM | 2127-14-2

• 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: 4-PAM
• 英文别名: [(1-Methylpyridin-4(1H)-ylidene)methyl](oxo)ammonium iodide；N-[(1-methylpyridin-1-ium-4-yl)methylidene]hydroxylamine;iodide
• CAS: 2127-14-2
• 化学式: C₇H₉N₂O*I
• 分子量: 264.066
• InChiKey: AHCOTFCENMEKLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.68
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-PAM 在 盐酸 作用下， 以 甲醇 为溶剂， 以42%的产率得到N-methyl-4-pyridinealdoxime chloride
  参考文献：
  名称：

  Spectroscopic and structural insights into N-substituted pyridinium-4-aldoximes and their pentacyanoferrate(II) complexes

  摘要：

  Comparative kinetic and equilibrium studies on the formation and dissociation of three mono- and one bis-pyridinium-4-aldoxime pentacyanoferrate(II) complexes have been carried out in aqueous solutions at 25 degrees C and I = 0.1 M. The synthesis, spectroscopic and thermal characterization of a new N-methylpyridinium-4-aldoxime pentacyanoferrate(II) complex is presented. The obtained values for the equilibrium constants, identified as apparent formation constants (beta(f)/M-1) along with kinetic parameters, the formation (k(f)/M-1 s(-1)) and dissociation (k(d)/s(-1)) rate constants indicated the behaving of all protonated pyridinium-4-aldoximes as weak pi-acceptors. The pH-dependence of the dissociation rates has been analyzed in terms of ionization abilities of the coordinated ligands. The magnitude of the dissociation rates suggested that both protonated and deprotonated ligand forms are effective sigma-donors that bind to the [Fe(CN)(5)](3-) moiety through the nitrogen atom. The deprotonation of the coordinated aldoxime group leads to the reduced lability of the complexes due to increased sigma-donor capability of aldoximato nitrogen causing the strengthened of the iron(II)-nitrogen bond. The values of dissociation activation parameters, Delta H-double dagger and Delta S-double dagger, are found to be consistent with the S(N)1 dissociative type of mechanism. The spectroscopic data (FT-IR, NMR and UV-Vis) of the isolated coordinated pentacyanoferrates(II) conforms with the weak pi-acceptor properties of the pyridinium-4-aldoxime ligands. A detailed structural characterization of the iodide and chloride salt of N-methylpyridinium-4-aldoxime was also presented using NMR, FT-IR and UV-Vis spectroscopy, as well as X-ray diffraction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.07.077
• 作为产物：
  描述：

  4-吡啶甲醛 在 盐酸羟胺 、 水 、 丙酮 作用下， 生成 4-PAM
  参考文献：
  名称：

  Oximes of the Pyridine Series¹

  摘要：

  DOI：

  10.1021/ja01559a067

文献信息

• Revisiting the reactivity of oximate α-nucleophiles with electrophilic phosphorus centers. Relevance to detoxification of sarin, soman and DFP under mild conditions
  作者：François Terrier、Pedro Rodriguez-Dafonte、Eric Le Guével、Gilles Moutiers

  DOI：10.1039/b609658c

  日期：——

  results obtained for reactions at carbon centers, it can be concluded that the observed saturation effect is the reflection of an intrinsic property of the oximate functionality. An explanation of this behavior in terms of an especially strong requirement for desolvation of the oximates prior to nucleophilic attack which becomes more and more difficult with increasing basicity is suggested. This proposal

  电位计确定（R1R2）C = NOH官能度的相关pKa值后，使大量肟酸碱与两种模型有机磷酸酯即bis-（4 -硝基苯基）苯基膦酸酯（BNPPP）和双-（4-硝基苯基）甲基膦酸酯（BNPMP），以及三种有毒化合物，即沙林（GB），梭曼（GD）和氟磷酸二异丙酯（DFP），以及30：已测量到70（v / v）的H2O-Me2SO混合物。log k（Ox）vs的相应Bronsted型亲核图。pKa（Ox）揭示了明显的趋势，即肟酸的反应性会随着水溶液中碱度的增加而遭受饱和作用。对于BNPMP和三种有毒酯，这种行为反映在pKa约为9时趋于平稳，但在BNPPP系统中则存在更为戏剧化的情况，其中在pKa约为9时达到最大反应性，随后在较高pKa时速率明显下降。有趣的是，以前由沙林，梭曼和DFP系统的不同作者所报告的许多数据都非常符合我们的数据所建立的曲线布朗斯泰德相关性。根据在碳中心反应获得的该结果和先前的
• Microwave-assisted Quaternization of Various Pyridine Derivatives and their Antibacterial Activity
  作者：Valentina Bušić、Hrvoje Pavlović、Sunčica Roca、Dražen Vikić-Topić、Dajana Gašo-Sokač

  DOI：10.5562/cca2937

  日期：——

  ne, 2-amino-4-chloromethylthiazole hydrochloride, methyl iodide, 1, 3-diiodopropane and 1, 3-dibromopropane are reported. The synthesis yield by microwave dielectric heating is improved and reaction time shortened compared to conventional heating. Some of the synthesized compounds were tested regarding their potential antibacterial activity against two Gram-positive and two Gram-negative bacteria.

  已经研究了许多吡啶鎓衍生物的生物学和药理活性。它们的重要性在于其有效的抗微生物，抗病毒，抗高血压和免疫刺激活性。一些吡啶鎓醛肟衍生物是针对有机磷酸酯中毒的潜在解毒剂。在这项研究中，吡啶，α-甲基吡啶，吡啶-4-醛肟，吡啶-2-醛肟，烟酰胺，异烟酰胺和吡ot肟的微波加热下季铵化反应与不同的亲电试剂：2-溴-4'-硝基苯乙酮，2-据报道有氨基-4-氯甲基噻唑盐酸盐，甲基碘，1，3-二碘丙烷和1，3-二溴丙烷。与常规加热相比，微波介电加热可提高合成产率，并缩短反应时间。测试了一些合成的化合物对两种革兰氏阳性和两种革兰氏阴性细菌的潜在抗菌活性。抗菌评估显示1- [2-（4-硝基苯基）-2-氧代乙基]溴化吡啶鎓对G阳性和G阴性细菌的疗效相对较高。
• Synthesis of 1,2,5,6-/1,2,3,6-tetrahydropyridinyl-tetrahydro-cyclopentaisoxazole derivatives
  作者：Mija Ahn、Jung Mee Park、Ihl-Young Choi Lee、Myung Hee Jung

  DOI：10.1002/jhet.5570400602

  日期：2003.11

  Fused tetrahydrocyclopenta-isoxazoles were synthesized by 1,3-dipolar cycloaddition reactions with pyridinealdoxime or tetrahydropyridinealdoxime and cycloalkenes.

  通过与吡啶醛肟或四氢吡啶醛肟和环烯烃的1，3-偶极环加成反应合成了熔融的四氢环戊戊-异恶唑。
• Supramolecular inter-ionic charge-transfer complexes between derivatives of pyridinium-4-oxime cations and hexacyanoferrate(<scp>ii</scp>) anions
  作者：Blaženka Foretić、Robert Vianello、Dubravka Matković-Čalogović、Dijana Jadreško、Igor Picek

  DOI：10.1039/c8nj03066a

  日期：——

  charge-transfer band in the visible spectral region whose energy is closely related to the acceptor's electron affinity, LUMO orbital energy and one-electron reduction potential. Such influence of the acceptor's electrochemical nature is revealed through varying the group attached to the N atom of the pyridinium-4-oxime moiety. The color, composition and spectroscopic analysis of the complexes in the solid state

  单吡啶和双吡啶-4-肟化合物被引入作为新的电子受体，与六氰合铁酸酯形成有色，超分子，离子间电荷转移络合物（II）作为捐赠者。形成的复合物的结构和性质通过实验研究和计算研究相结合来表征。在水中，电子给体/受体二重体在可见光谱区域显示出特征性的电荷转移带，其能量与受体的电子亲和力，LUMO轨道能和单电子还原电势密切相关。通过改变连接到吡啶鎓-4-肟部分的N原子上的基团，揭示了受体的电化学性质的这种影响。固态配合物的颜色，组成和光谱分析为洞悉阳离子和阴离子对应物的结合以及晶格水的作用提供了见识。报道了两种4-吡啶肟/六氰基高铁酸盐的晶体结构（II）配合物，其溶液通过UV / Vis和1 H-NMR光谱表征。固态结构和水相二元化合物的比较揭示了涉及共轭吡啶鎓-4-肟作为电子受体的电荷转移相互作用的性质。
• Preparation and In Vitro Evaluation of Monoquaternary Inhibitors of Brain Cholinesterases
  作者：Daniel Jun、Martin Paar、Jiri Binder、Jan Marek、Miroslav Pohanka、Petr Stodulka、Kamil Kuca

  DOI：10.2174/157017809789124876

  日期：2009.9.1

  Acetylcholinesterase inhibitors are currently of high interest due to the many reasons. Among them, Alzheimers disease drugs are of great interest. In this study, eleven monoquaternary pyridinium salts substituted by different groups (electron donors and electron acceptors) in position four were prepared. Then, their anticholinesterase activity was tested. As observed, their IC50s ranged from 33 μM to 3981 μM. Moreover, probability of blood-brain barrier penetration was predicted.

  当前，乙酰胆碱酯酶抑制剂受到高度关注，原因有很多。其中，阿尔茨海默病药物尤为引人关注。在这项研究中，制备了十一种在第四位由不同基团（电子供体和电子受体）取代的单季铵吡啶盐。随后，测试了它们的抗胆碱酯酶活性。观察到它们的IC50范围从33 μM到3981 μM。此外，还预测了它们穿透血脑屏障的概率。