2-[(E)-2-(4-hydroxy-3-methoxystyryl)-1-methyl]quinolinium iodide | 5418-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[(E)-2-(4-hydroxy-3-methoxystyryl)-1-methyl]quinolinium iodide
• 英文别名: (E)-2-(4-hydroxy-3-methoxystyryl)-1-methylquinolin-1-ium iodide；2-(4-hydroxy-3-methoxy-styryl)-1-methyl-quinolinium; iodide；2-(4-Hydroxy-3-methoxy-styryl)-1-methyl-chinolinium; Jodid；2-Methoxy-4-[2-(1-methylquinolin-1-ium-2-yl)ethenyl]phenol;iodide
• CAS: 5418-80-4
• 化学式: C₁₉H₁₈NO₂*I
• 分子量: 419.262
• InChiKey: XYGBZINVXDIAPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  33.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-(4-hydroxy-3-methoxystyryl)-1-methyl]quinolinium iodide 、 sodium p-hydroxybenzenesulfonate 以 甲醇 为溶剂， 以45%的产率得到2-(4-hydroxy-3-methoxystyryl)-1-methylquinolinium 4-hydroxybenzenesulfonate
  参考文献：
  名称：

  Crystal Engineering of Acentric Styryl Quinolinium Crystals with Strongly Hydrogen-Bonded Phenolic Anions

  摘要：

  We report on new acentric styryl quinolinium crystals with phenolic sulfonate counteranions and investigate their supramolecular interactions that affect their quadratic non-linear optical properties. The phenolic group acting as an electron-donor as well as hydrogen-bond donor site is located at one end of the anion, while the sulfonate group acting as an electron-acceptor as well as hydrogen-bond acceptor site is located at the opposite end of the anion. New styryl quinolinium crystals with 4-hydroxybenzenesulfonate and 6-hydroxynaphthalene-2-sulfonate counteranions exhibit a large macroscopic optical nonlinearity with very efficient second harmonic generation (SHG) efficiency. In styryl quinolinium 4-hydroxybenzenesulfonate crystals, the styryl quinolinium cation chromophores exhibit an acentric ordering with a high order parameter close to 1.0, which is optimal for electro-optic applications or THz-wave generation. The 4-hydroxybenzenesulfonate counteranions form strong head-to-tail hydrogen bonds, and they are also packed in acentric layers. The direction of the polar axes in cation and anion layers is practically identical. Therefore, the introducing phenolic group acting as an electron-donor as well as hydrogen-bond donor to the sulfonate counteranion is a potential technique for crystal engineering to tailor molecular ordering as well as the physical properties of salt-type quinolinium derivatives.

  DOI：

  10.1021/cg401261z
• 作为产物：
  描述：

  2-甲基喹啉 以 环丁砜 、 甲醇 为溶剂， 生成 2-[(E)-2-(4-hydroxy-3-methoxystyryl)-1-methyl]quinolinium iodide
  参考文献：
  名称：

  作为细菌生物膜抑制剂的新型 c-di-GMP G-四联体诱导剂的设计和合成

  摘要：

  临床病原体形成的生物膜通常会导致慢性和复发性抗生素耐药性感染。高细胞水平的环二鸟苷酸 (c-di-GMP) 是一种无处不在的细菌二级信使，已被证明与病原体的固着生物膜生活方式有关。本研究提出了一种有前景的抗生物膜策略，包括诱导 c-di-GMP 形成功能失调的 G-四链体，从而阻断 c-di-GMP 介导的生物膜调节途径。在这一新策略中，设计并合成了一系列新型 c-di-GMP G-四联体诱导剂，用于开发治疗性生物膜抑制剂。复合5h在 1.25 μM 下表现出良好的 c-di-GMP G-四链体诱导活性和 62.18 ± 6.76% 的生物膜抑制活性，没有任何 DNA 嵌入效应。此外，5h在干扰 c-di-GMP 相关生物学功能方面的良好表现，包括细菌运动和细菌胞外多糖分泌，结合报告菌株和转录组分析结果证实了 c-di-GMP 信号相关的作用机制的5H。

  DOI：

  10.1021/acs.jmedchem.1c00465

文献信息

• Organic styryl quinolinium crystal with aromatic anion bearing electron-rich vinyl group
  作者：Seung-Heon Lee、Ba-Wool Yoo、Hoseop Yun、Mojca Jazbinsek、O-Pil Kwon

  DOI：10.1016/j.molstruc.2015.07.071

  日期：2015.11

  Abstract A new organic π-conjugated quinolinium derivative was designed and synthesized in order to investigate the influence of the anion structure on characteristics of the crystal. The quinolinium derivative consists of a 2-(4-hydroxy-3-methoxystyryl)-1-methylquinolinium (HMQ) cation and a 4-vinylbenzenesulfonate (VBS) counter anion, which contains an electron-rich vinyl group. Single HMQ-VBS crystals

  摘要 为研究阴离子结构对晶体特性的影响，设计合成了一种新型有机π共轭喹啉衍生物。喹啉衍生物由 2-(4-羟基-3-甲氧基苯乙烯基)-1-甲基喹啉 (HMQ) 阳离子和 4-乙烯基苯磺酸盐 (VBS) 抗衡阴离子组成，其中含有富电子乙烯基。通过在甲醇中的溶液生长方法生长的单个 HMQ-VBS 晶体表现出单斜 P21/c 空间群对称性。与先前报道的带有 4-甲基苯磺酸盐抗衡阴离子的 HMQ 类似晶体 (HMQ-T) 相比，HMQ-VBS 晶体通常具有相似的分子排列特征，但显示出与阴离子 - 阴离子和阴离子 - 阳离子相互作用，以及与阳离子-阳离子相互作用相关的 π-π 堆积。因此，HMQ-VBS 表现出显着不同的物理特性，包括结晶状态下的线性吸收和荧光，即使这些特性与溶液状态下的 HMQ-T 相同。
• Conformational polymorphism on styrl quinolinium salts of 2-[(E)-2-(4-hydroxy-3-methoxystyrl)-1-methyl]-quinolinium 4-chlorobenzenesulfonate (HMQ-CBS): Potential nonlinear optical crystals for terahertz application
  作者：Maruthappan Manikandan、Tianliang Chen、Zhihua Sun、Shuquan Zhang、Junhua Luo

  DOI：10.1016/j.inoche.2015.09.017

  日期：2015.11

  Polymorphism is an important phenomenon to investigate the relationship between the chemical structures and properties of functional materials. Here, we demonstrate the existence of conformational polymorphism in the terahertz (THz) compounds of 2-[(E)-2-(4-hydroxy-3-methoxystyr1)-1-methyl]quinolinium 4-chlorobenzenesulfonate (abbreviated as HMQ-CBS). There are two different crystalline phases (I and II, respectively). X-ray structural analyses reveal that HMQ-CBS crystallizes in the monoclinic crystallographic system with the non-centrosymmetric space group Pc for phase-I, and centrosymmetric space group ofP2i/n for phase-II. These two different crystalline phases exhibit the distinct anionic orientations and crystal packings, leading to significantly different nonlinear optical (NW) properties. Second harmonic generation (SHG) measurements reveal that crystals in phase4 possess the SHG efficiency of about 0.5 times that of N, N-dimethylamino-N-methylstilbazolium p-toluenesulphonate (DAST), which indicates that HMQ-CBS in phase4 might be a potential NW crystal forTHz application. In contrast, crystals in the phase-II show no SHG responses. Comparison of their crystal structures and NLO properties enables us to understand the correlation between molecular conformational changes and bulk NW properties, and sheds light on the design of organic THz materials. (C) 2015 Elsevier B.V. All rights reserved.
• Werner, Journal of the American Chemical Society, 1920, vol. 42, p. 2311
  作者：Werner

  DOI：——

  日期：——
• SUBSTRATES FOR THE ASSAY OF ENZYMES
  申请人：KING'S COLLEGE LONDON

  公开号：EP0375723A1

  公开（公告）日：1990-07-04
• US5221606A
  申请人：——

  公开号：US5221606A

  公开（公告）日：1993-06-22