N-methyl 4-(p-hydroxy styryl) pyridinium iodide | 20288-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl 4-(p-hydroxy styryl) pyridinium iodide
• 英文别名: (E)-4-(4-hydroxystyryl)-1-methylpyridin-1-ium iodide；(E)-4-(4-hydroxystyryl)-1-methylpyridinium iodide；HMII；4'-Hydroxy-4-stilbazol-methoiodid；4-(4-hydroxy-trans-styryl)-1-methyl-pyridinium; iodide；4-(4-Hydroxy-trans-styryl)-1-methyl-pyridinium; Jodid；4-[2-(1-Methylpyridin-4(1H)-ylidene)ethylidene]cyclohexa-2,5-dien-1-one--hydrogen iodide (1/1)；4-[2-(1-methylpyridin-4-ylidene)ethylidene]cyclohexa-2,5-dien-1-one;hydroiodide
• CAS: 20288-72-6
• 化学式: C₁₄H₁₄NO*I
• 分子量: 339.176
• InChiKey: PUVMUAOIOKUCRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  24.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl 4-(p-hydroxy styryl) pyridinium iodide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以98%的产率得到4-[(1-methyl-4(1H)-pyridinylidene)-ethylidene]-2,5-cyclohexadiene-1-one
  参考文献：
  名称：

  The aggregation of the merocyanine dyes, depending of the type of the counterions

  摘要：

  Counterions affect on the substructures formation in the case of the merocyanine dye, 1-methyl-4-[2-(4-hydroxyphenyl)ethenyl)]piridinium] hydrogensquarate both in gas and condense phase. Spectroscopically and structural elucidation of these aggregates have been performed, using solid-state conventional and linear-polarized IR-spectroscopy of oriented colloids as a nematic liquid crystal suspension, UV-vis spectroscopy. HPLC tandem ES1 mass spectrometry, H-1 and C-13 NMR, TGV and DSC. Quantum chemical DFT calculations have been carried out as well. Experimental and theoretical data are compared with analogous ones of corresponding iodide salt of dye studied. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2007.10.017
• 作为产物：
  描述：

  1,4-二甲基吡啶碘化物 在 四氢吡咯 作用下， 以 乙醇 、 乙二醇 为溶剂， 反应 0.05h， 生成 N-methyl 4-(p-hydroxy styryl) pyridinium iodide
  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

• 一种基于半花菁的铜离子比率荧光探针及其 制备与应用
  申请人：贺州学院

  公开号：CN107033072B

  公开（公告）日：2019-05-10

  本发明涉及一种基于半花菁的铜离子比率荧光探针及其制备与应用，所述荧光探针，分子式为C20H17IN2O2；所述荧光探针的制备包括步骤有：(1)4‑甲基吡啶与碘甲烷反应得到1,4‑二甲基吡啶碘盐，即化合物1，(2)将化合物1与4‑羟基苯甲醛反应得到4‑(4‑羟基苯乙烯基)‑1‑甲基吡啶碘盐，即化合物2，(3)将化合物2与2‑吡啶甲酸反应得到铜离子比率荧光探针1‑甲基‑4‑(4‑(2‑吡啶甲酰氧基)苯乙烯基)吡啶碘盐，即化合物3；所述荧光探针的应用，是在纯水溶液中将荧光探针与铜离子进行反应，利用两个不同发射波长处荧光强度的比率(F503nm/F448nm)变化来检测铜离子的存在与否。本发明探针制备处理过程简单，荧光探针分子在铜离子与其他阳离子共存体系中，表现出较高的选择性和灵敏度。
• Ultrasonic assisted synthesis of styrylpyridinium dyes: Optical properties and DFT calculations
  作者：Abed Saady、Pagidi Sudhakar、Molhm Nassir、Aharon Gedanken

  DOI：10.1016/j.ultsonch.2020.105182

  日期：2020.10

  technique has received considerable attention in several fields; in particular, it gained rapid momentum in organic synthesis due to the larger reaction rates, milder reaction conditions, and better yields. We report herein a facile synthesis of a series of styrylpyridinium based dyes under ultrasonic irradiation. Within short reaction time (15 min) under ultrasonic irradiation, compared to normal laboratory

  超声技术已在多个领域引起了广泛关注。特别是由于反应速率大，反应条件温和，收率高，有机合成迅速发展。我们在本文中报道了在超声辐射下一系列基于苯乙烯基吡啶鎓的染料的简便合成。与正常的实验室条件（4至16小时）相比，在超声波辐射下的短反应时间内（15分钟），我们可以获得良好的收率。缩短反应时间是因为超声可以加速吡啶鎓盐亲核试剂的生成，随后亲核添加醛，然后脱水得到苯乙烯基吡啶鎓染料（Knoevenagel缩合反应）。在不同溶剂中对所有化合物的光物理性质进行了全面研究。所有化合物在吸收和荧光发射光谱中均显示出负溶剂溶变色。这种行为是由于这些分子在基态上的偶极矩较高。进行DFT计算以了解分子的电子结构。我们的结果表明，声化学法比其他制备苯乙烯基吡啶鎓染料的方法具有更高的功效。
• Ratiometric Fluorescent Probes for Hydrogen Peroxide from a Focused Library
  作者：Sang Wook Lee、Hyun-Woo Rhee、Young-Tae Chang、Jong-In Hong

  DOI：10.1002/chem.201302523

  日期：2013.10.25

  Light shifting: Ratiometric fluorescent probes for hydrogen peroxide (H2O2) were developed through a focused library strategy. One of the probes in the library, showed a redshift of over 100 nm and an increase of over 30‐fold in the emission intensity ratio (see scheme). This probe was utilized to detect H2O2 generated during glucose oxidation.

  光移：通过聚焦库策略开发了用于过氧化氢（H 2 O 2）的比例荧光探针。文库中的一种探针显示出超过100 nm的红移，并且发射强度比增加了30倍以上（请参阅方案）。该探针用于检测葡萄糖氧化过程中产生的H 2 O 2。
• Fluorescent neuroactive probes based on stilbazolium dyes
  作者：Adrienne S. Brown、Lisa-Marie Bernal、Teresa L. Micotto、Erika L. Smith、James N. Wilson

  DOI：10.1039/c0ob00849d

  日期：——

  A set of spectrally diverse stilbazolium dyes was identified in an uptake assay using cultured brainstem and cerebellum cells isolated from e19 chicks. Pretreatment of cells with indatraline, a monoamine reuptake inhibitor, allowed identification of dyes that may interact with monoamine transporters. Two structurally related, yet spectrally segregated, probes, (E)-1-methyl-4-[2-(2-naphthalenyl)ethenyl]-pyridinium iodide (NEP+, 3A) and (E)-4-[2-(6-hydroxy-2-naphthalenyl)ethenyl]-1-methyl-pyridinium iodide (HNEP+, 4A), were selected and further investigated using HEK-293 cells selectively expressing dopamine, norepinephrine or serotonin transporters. HNEP+ was selectively accumulated viacatecholamine transporters, with the norepinephrine transporter (NET) giving the highest response; NEP+ was not transported, though possible binding was observed. The alternate modes of interaction enable the use of NEP+ and HNEP+ to image distinct cell populations in live brain tissue explants. The preference for HNEP+ accumulation viaNET was confirmed by imaging uptake in the absence and presence of desipramine, a norepinephrine reuptake inhibitor.

  利用从 e19 雏鸡分离的脑干和小脑培养细胞进行摄取试验，鉴定了一组光谱多样的苯并唑鎓染料。用单胺再摄取抑制剂吲达曲林对细胞进行预处理，从而鉴定出可能与单胺转运体相互作用的染料。(E)-1-甲基-4-[2-(2-萘基)乙烯基]-吡啶鎓碘化物（NEP+，3A）和(E)-4-[2-(6-羟基-2-萘基)乙烯基]-1-甲基吡啶鎓碘化物（HNEP+、4A），并使用选择性表达多巴胺、去甲肾上腺素或血清素转运体的 HEK-293 细胞进行了进一步研究。HNEP+ 在乙酰胆碱转运体中选择性积累，去甲肾上腺素转运体（NET）的反应最高；NEP+ 没有转运，但观察到可能的结合。通过交替的相互作用模式，NEP+ 和 HNEP+ 可以对活体脑组织外植体中的不同细胞群进行成像。通过对去甲肾上腺素再摄取抑制剂地西帕明不存在和存在时的摄取成像，证实了 HNEP+ 通过 NET 聚集的偏好。
• Supramolecular host–guest coordination systems: [(G+)(Me3E)3MII(CN)6]∞ as ion exchangers, where (G+=Me3E, Et4N or stp), (E=Sn or Pb) and (M=Fe or Ru)
  作者：Amany M.A. Ibrahim

  DOI：10.1016/s0277-5387(99)00176-x

  日期：1999.9

  6 ] building blocks and (Me 3 E) connecting units, have been prepared and characterized by X-ray powder diffraction and different spectroscopic methods. 1-Methyl-4-(4′- R -styryl) or (2′- R -styryl) pyridinium cations (stp) have been successfully encapsulated within the expandable wide channels of the 3D-coordination polymers by tribochemical or ion exchange reactions producing novel molecular composites

  摘要制备了许多由[d M（CN）6]构件和（Me 3 E）连接单元构成的3D配位聚合物，并通过X射线粉末衍射和不同的光谱学方法对其进行了表征。1-甲基-4-（4'-R-苯乙烯基）或（2'-R-苯乙烯基）吡啶鎓阳离子（stp）已通过摩擦化学或离子交换反应成功地封装在3D配位聚合物的可扩展宽通道内新型分子复合材料。除具有热致变色行为的[6，[（4'-OCH 3 -stp）（Me 3 Sn）3 Fe II（CN）6 -MeOH]∞外，分子复合物[（stp）x（Me 3 E）3 Fe III 1– x Fe II x（CN）6]∞，1 – 12是混合价态材料，在混合价态铁之间表现出局部相互作用。结果表明客体stp-阳离子和主体基质之间存在离子电荷转移相互作用。分子复合物[（stp）（Me 3 E）3 M II（CN）6]∞，13 – 18是由于配位聚合物[（Me 3 E）4 M（CN）6]∞和[（Et