1,3,5-三甲基吡啶鎓碘化物 | 22739-24-8

• 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
• 中文名称: 1,3,5-三甲基吡啶鎓碘化物
• 英文名称: N-methyl-3,5-dimethylpyridinium iodide
• 英文别名: 1,3,5-trimethylpyridin-1-ium iodide；1,3,5-trimethyl-pyridinium; iodide；1,3,5-Trimethyl-pyridinium; Jodid；1,3,5-Trimethyl-pyridinium iodide；1,3,5-trimethylpyridin-1-ium;iodide
• CAS: 22739-24-8
• 化学式: C₈H₁₂N*I
• 分子量: 249.094
• InChiKey: RZPSTCJKPQNEBU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.87
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3,5-三甲基吡啶鎓碘化物 在 吡啶盐酸盐 作用下， 反应 10.0h， 以95%的产率得到3,5-二甲基吡啶
  参考文献：
  名称：

  Pyridinium Chloride: a New Reagent for N-Demethylation of N-Methylazinium Derivatives.

  摘要：

  A new N-demethylation reaction of N-methylazinium derivatives by using boiling pyridinium chloride is described. The reaction is quite clean, fast and yields are almost quantitatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01399-3
• 作为产物：
  描述：

  3,5-二甲基吡啶 、 碘甲烷 以 丙酮 为溶剂， 生成 1,3,5-三甲基吡啶鎓碘化物
  参考文献：
  名称：

  碘化物···π与有机碱共晶体中全卤化醌环的相互作用†

  摘要：

  在四溴醌和四氯醌与取代的N-甲基吡啶鎓阳离子的碘化物盐的新型共晶体中，已经描述了与醌型环的首次阴离子···π接触。在这些共晶体的七个晶体结构中，观察到一个中心对称单元I – ··醌··I –涉及碘化物阴离子与醌型环的电子贫化的碳骨架之间的紧密接触。然而，随着盐Ñ甲基-4- methylcarboxypyridinium碱结晶在两种多晶型，其特征在于O = C ... ...醌C = O相互作用代替我- ······醌我-一。固态的NMR和IR光谱探测了晶体黑色所暗示的可能的电荷转移，并通过DFT计算进行了分析。

  DOI：

  10.1021/acs.cgd.8b00634

文献信息

• Gear effect—10
  作者：Christian Roussel、Alexandru T. Balaban、Ulf Berg、Michel Chanon、Roger Gallo、Gerd Klatte、Joseph A. Memiaghe、Jacques Metzger、Daniela Oniciu、Johanna Pierrot-Sanders

  DOI：10.1016/s0040-4020(01)88642-7

  日期：1983.1

  The effect of the shape of a methyl group on reactivity, which cannot be accounted for by considering a methyl group as a spherical substituent with the appropriate van der Waals radius, was considered in kinetics of alkylalion of substituted pyridines and barriers to rotation and ground state conformations of an isopropyl group attached to a planar framework. The perturbation of a methyl group by an

  在取代吡啶的烷基化动力学以及旋转和基态壁垒中考虑了甲基形状对反应性的影响，这不能通过考虑将甲基作为具有适当范德华半径的球形取代基来解决。附着在平面骨架上的异丙基构象。甲基被邻甲基干扰是由独特的构象解释引起的，该构象解释涉及甲基的多面体形状。
• Bromo‐ and Polybromoantimonates(V): Structural and Theoretical Studies of Hybrid Halogen‐Rich Halometalate Frameworks
  作者：Sergey A. Adonin、Mikhail A. Bondarenko、Pavel A. Abramov、Alexander S. Novikov、Pavel E. Plyusnin、Maxim N. Sokolov、Vladimir P. Fedin

  DOI：10.1002/chem.201801338

  日期：2018.7.17

  Cation‐dependent reactions “[SbBr6]3−+Br2+HBr+CationBrx” result in the formation of bromide/polybromide complexes with zero‐, one‐, two‐, or three‐dimensional supramolecular frameworks and different Br/Sb ratios (up to 11). Seven new compounds representing six structural types were characterized by XRD and thermogravimetric analysis and DFT calculations enabled estimation of the energies of the Br⋅⋅⋅Br

  阳离子依赖性反应“[SbBr 6 ] 3− +Br 2 +HBr+CationBr x ”导致形成具有零、一、二维或三维超分子骨架和不同 Br/Sb 的溴化物/多溴化物复合物比率（最多 11）。代表六种结构类型的七种新化合物通过 XRD 和热重分析进行表征，DFT 计算能够估计 Br⋅⋅⋅Br 接触的能量 (1.1–4.6 kcal mol -1 )。
• Polybromides of pyridinium and quinolinium-type cations: Cation-induced structural diversity and theoretical analysis of Br⋯Br interactions
  作者：Igor D. Gorokh、Sergey A. Adonin、Alexander S. Novikov、Maxim N. Sokolov、Denis G. Samsonenko、Vladimir P. Fedin

  DOI：10.1016/j.molstruc.2018.11.070

  日期：2019.3

  Abstract Four novel polybromide salts containing pyridinium-type and quinolinium-type cations – (2-Br-5-MePy)2H}Br3 (1), (1,3,5-MePy)(Br3) (Br2)} (2), (1-Et-2,6-MePy)(Br3) (Br2)0.5} (3) and (N-MeIsoquin)(Br3) (Br2)0.5} (4) were isolated from HBr/Br2 solutions. Hirshfeld surface analysis for the organic parts of X-ray structures of 1–4 and a set of related compounds reported earlier reveals that

  摘要 四种含有吡啶鎓型和喹啉鎓型阳离子的新型多溴化物盐 - (2-Br-5-MePy)2H}Br3 (1), (1,3,5-MePy)(Br3) (Br2)} ( 2), (1-Et-2,6-MePy)(Br3) (Br2)0.5} (3) 和 (N-MeIsoquin)(Br3) (Br2)0.5} (4) 从 HBr/Br2 中分离解决方案。对 1-4 的 X 射线结构的有机部分和早先报道的一组相关化合物的 Hirshfeld 表面分析表明，在所有情况下，晶体堆积主要由分子间接触 Br H、HH、С-H、Br Br 和Br C. DFT 计算允许估计 Br⋯Br 卤素键能 (0.9–7.5 kcal/mol)。
• Correlation of nonadditive kinetic effects with MINDO/3-derived molecular geometries
  作者：Jeffrey I. Seeman、Roseanne Galzerano、Keith Curtis、John C. Schug、Jimmy W. Viers

  DOI：10.1021/ja00409a089

  日期：1981.9
• Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels
  作者：Günter Tovar、Heike Boehm、Sabine Laschat、Markus Mateescu、Isabell Nuss、Alexander Southan、Hayley Messenger、Seraphine Wegner、Julia Kupka、Monika Bach

  DOI：10.1055/s-0033-1338614

  日期：——

  A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the N-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.