2-[4-(二甲基氨基)苯乙烯基]-1-甲基吡啶鎓碘化物 | 2156-29-8

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[4-(二甲基氨基)苯乙烯基]-1-甲基吡啶鎓碘化物
• 中文别名: 2-[4-(二甲氨基)苯乙烯基]-1-甲基吡啶碘；2-[4-(二甲基氨基)苯乙烯基]-1-甲基吡啶碘化物；2-[4-(二甲氨基)苯乙烯基]-1-甲基吡啶盐碘化物
• 英文名称: (E)-2-[4-(dimethylamino)phenyl]vinyl-1-methylpyridinium iodide
• 英文别名: NSC 10517；2-<4-(dimethylamino)styryl>-1-ethylpyridinium iodide；2-{2-[4-(dimethylamino)phenyl]ethenyl}-1-methylpyridinium iodide；trans-2-[4-(dimethylamino)styryl]-1-methylpyridinium iodide；2-4-(dimethylamino)phenylethenyl-1-methylpyridinium iodide；(E)-2-(4-(dimethylamino)styryl)-1-methylpyridinium iodide；N,N-dimethyl-4-[2-(1-methylpyridin-1-ium-2-yl)ethenyl]aniline;iodide
• CAS: 2156-29-8
• 化学式: C₁₆H₁₉N₂*I
• 分子量: 366.245
• InChiKey: XPOIQAIBZGSIDD-UHFFFAOYSA-M

物化性质

• 熔点：
  280 °C (dec.)(lit.)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  7.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

2-Di-1-ASP (DASPI, 2M2PM, D 308, Compound 18a) 是一种单苯乙烯基染料，可用作线粒体染色剂和G-quadruplex (G4) DNA的凹槽结合型荧光探针。

体外研究

2-Di-1-ASP (Compound 18a) displays significant fluorescence enhancements in the presence of G-quadruplex (G4) structures (up to 300-fold), and good selectivity with respect to double-stranded DNA. 2-Di-1-ASP shows fluorimetric selectivity for parallel G4-DNA forms ( c-kit2 , c-kit87up , c-myc ).

反应信息

• 作为反应物：
  描述：

  2-[4-(二甲基氨基)苯乙烯基]-1-甲基吡啶鎓碘化物 在 氘代盐酸 作用下， 以 重水 为溶剂， 生成
  参考文献：
  名称：

  A stimuli-responsive supramolecular assembly between inverted cucurbit[7]uril and hemicyanine dye

  摘要：

  在这项研究中，确定了倒置的葫芦[7]葡萄糖苷（iQ[7]）对2-（4-（二甲氨基）苯乙烯基）-1-甲基吡啶（DASPMI）结合模式的影响。

  DOI：

  10.1039/c8nj03344g
• 作为产物：
  描述：

  碘化1,2-二甲基吡啶鎓 在 四氢吡咯 作用下， 以 乙醇 、 乙二醇 为溶剂， 反应 0.05h， 生成 2-[4-(二甲基氨基)苯乙烯基]-1-甲基吡啶鎓碘化物
  参考文献：
  名称：

  Combinatorial Approach to Organelle-Targeted Fluorescent Library Based on the Styryl Scaffold

  摘要：

  The first fluorescent styryl dye library with a broad color range was synthesized by combinatorial condensation of various aldehydes and methyl pyridinium compounds, and their applications as organelle specific staining probes were demonstrated.

  DOI：

  10.1021/ja027587x

文献信息

• Development of fluorescence probes based on stilbazolium salts for monitoring free radical polymerization processes
  作者：Stanisław Wróblewski、Katarzyna Trzebiatowska、Beata Jędrzejewska、Marek Pietrzak、Ryszard Gawinecki、Jerzy Pączkowski

  DOI：10.1039/a902904d

  日期：——

  A series of 1-methyl-2-(4-aminostyryl)pyridinium perchlorates and iodides were investigated as fluorescent probes for the monitoring of the progress of free radical polymerization. The study on the changes in the fluorescence intensity and spectroscopic shifts of studied compounds were carried out during thermally initiated polymerization of methyl methacrylate and during photoinitiated polymerization of a 2-ethyl-2-(hydroxymethyl)propane-1,3-diol triacrylate (TMPTA)–1-methylpyrrolidin-2-one (MP) mixture. The purpose of these studies was to find a relationship between the changes in the shape and intensity of probe fluorescence and degree of monomer conversion into polymer. The polymer formation was estimated gravimetrically or by the measurement of the degree of monomer double bond disappearance using FTIR spectroscopy.

  研究人员将一系列 1-甲基-2-(4-氨基苯乙烯基)吡啶高氯酸盐和碘化物作为监测自由基聚合过程的荧光探针。在甲基丙烯酸甲酯的热引发聚合和 2-乙基-2-（羟甲基）丙烷-1,3-二醇三丙烯酸酯（TMPTA）-1-甲基吡咯烷-2-酮（MP）混合物的光引发聚合过程中，对所研究化合物的荧光强度变化和光谱偏移进行了研究。这些研究的目的是找出探针荧光的形状和强度变化与单体转化为聚合物的程度之间的关系。聚合物的形成可用重力法或傅立叶变换红外光谱法测量单体双键消失的程度来估算。
• Synthesis, structure and in vitro antibacterial activities of new hybrid disinfectants quaternary ammonium compounds: Pyridinium and quinolinium stilbene benzenesulfonates
  作者：Kullapa Chanawanno、Suchada Chantrapromma、Theerasak Anantapong、Akkharawit Kanjana-Opas、Hoong-Kun Fun

  DOI：10.1016/j.ejmech.2010.06.014

  日期：2010.9

  The series of pyridinium (1–10) and quinolinium (11–20) stilbene benzenesulfonates have been synthesized and their structures were investigated by UV–vis, FT-IR and 1H NMR spectroscopy. In addition, compound 5 was also determined by single crystal X-ray diffraction technique. The antibacterial activity of the synthesized compounds against both Gram-positive and Gram-negative bacteria has been determined

  已合成了一系列吡啶鎓（1-10）和喹啉鎓（11-20）1,2-二苯乙烯苯磺酸盐，并通过UV-vis，FT-IR和1 H NMR光谱研究了它们的结构。另外，化合物5也通过单晶X射线衍射技术测定。已经确定了合成化合物对革兰氏阳性和革兰氏阴性细菌的抗菌活性。喹啉鎓衍生物表现出两种非常有效的特征活性，即（i）对耐甲氧西林的金黄色葡萄球菌的比活性和（ii）具有宽带光谱活性。化合物11，13和14是对革兰氏阳性菌（耐甲氧西林金黄色葡萄球菌，金黄色葡萄球菌，枯草芽孢杆菌，耐万古霉素的粪肠球菌和粪肠球菌）和革兰氏阴性细菌（志贺氏菌）表现出最广谱抗菌活性的活性。发现这些化合物的MIC优于市售消毒剂苯扎氯铵（BZK）。
• Solvent-Free Condensation of Methyl Pyridinium and Quinolinium Salts with Aldehydes Catalyzed by DBU
  作者：Linda Loucif Seiad、Didier Villemin、Nathalie Bar、Messaoud Hachemi

  DOI：10.1080/00397911.2010.528573

  日期：2012.3.1

  Abstract Methylpyridinium and methylquinolinium salts were condensed under solvent-free conditions with aromatic aldehydes in the presence of 1,8-diazabicyclo[5.4.]undec-7-ene (DBU) as catalyst, by grinding at room temperature. The products are dyes or useful intermediates. The DBU can be easily recycled and reused. GRAPHICAL ABSTRACT

  摘要 在1,8-二氮杂双环[5.4.]十一碳-7-烯（DBU）催化剂存在下，在无溶剂条件下，将甲基吡啶鎓和甲基喹啉鎓盐与芳香醛缩合，在室温下研磨。产品为染料或有用的中间体。DBU 可以轻松回收和再利用。图形概要
• Synthesis and Characterization of Mono-, Bis-, and Trissubstituted Pyridinium and Pyrylium Dyes
  作者：Masaki Matsui、Shigeo Kawamura、Katsuyoshi Shibata、Hiroshige Muramatsu

  DOI：10.1246/bcsj.65.71

  日期：1992.1

  A series of mono-, bis-, and trissubstituted pyridinium and pyrylium dyes have been synthesized by the condensation of methylpyridinium and methylpyrylium salts with aldehydes or nitroso compound. Large bathochromic shifts were observed in the following order, both in substituted azomethine pyridinium and pyrylium dyes, mono < bis < tris. The magnitude of the shift appeared in the order of multiple

  通过甲基吡啶鎓和甲基吡啶鎓盐与醛或亚硝基化合物缩合合成了一系列单、双和三取代的吡啶鎓和吡咯鎓染料。在取代的偶氮甲碱吡啶鎓和吡咯鎓染料中，按以下顺序观察到大的红移，单<双<三。位移的大小以多重键的顺序出现，–CH=CH– < –CH=CH–CH=CH– < –CH=N–。
• Solvation studies of some tailor made α-N,N-dimethylaminostyryl-N-alkyl pyridinium dyes in binary solvent mixtures containing alcohols, hexane, 1,4-dioxane, DCM and acetone
  作者：Sarita Tripathy、Sukalyan Dash

  DOI：10.1016/j.molliq.2015.01.046

  日期：2015.6

  Solvation of some α-N,N-dimethylaminostyryl-N-alkyl pyridinium dyes has been studied in binary solvent mixtures of alcohol–hexane, alcohol–1,4-dioxane, acetone–hexane, acetone–1,4-dioxane, DCM–hexane, DCM–1,4-dioxane and 1,4-dioxane–hexane to analyze the preferential solvation of any of the solvent in the binary mixture. Due to solvent–solvent interaction, hyper and hypo-polarity in the solvent complex

  已经研究了一些α-N，N-N-二甲基氨基苯乙烯基-N-烷基吡啶鎓染料在醇-己烷，醇-1,4-二恶烷，丙酮-己烷，丙酮–1,4-二恶烷，DCM-己烷，DCM–1,4-二恶烷和1,4-二恶烷–己烷分析二元混合物中任何溶剂的优先溶剂化。由于溶剂之间的相互作用，在溶剂配合物中观察到了超极性和低极性，这从染料分子的吸收最大值的红移和蓝移反映出来。染料周围的溶剂笼受到极性-极性和非极性-非极性相互作用以及两种相互作用类型之间适当平衡的影响。

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