4-[(1-methyl-4(1H)-pyridinylidene)-ethylidene]-2,5-cyclohexadiene-1-one | 148904-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(1-methyl-4(1H)-pyridinylidene)-ethylidene]-2,5-cyclohexadiene-1-one
• 英文别名: 4-[(1-methyl-4(1H)-pyridinylidene)ethylidene]-2,5-cyclohexadien-1-one；Brooker's merocyanine；4-[2-(1-methylpyridin-4-ylidene)ethylidene]cyclohexa-2,5-dien-1-one
• CAS: 148904-15-8
• 化学式: C₁₄H₁₃NO
• mdl: MFCD00010099
• 分子量: 211.263
• InChiKey: DBOHWMPKJCJANT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(1-methyl-4(1H)-pyridinylidene)-ethylidene]-2,5-cyclohexadiene-1-one 在 氢溴酸 作用下， 以 乙醇 为溶剂， 以75%的产率得到1-methyl-4-<2-(4-hydroxyphenyl)-vinyl>-pyridinium bromide
  参考文献：
  名称：

  Wolff; Klaussner; Nees, Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics, 1993, vol. 97, # 10, p. 1407 - 1410

  摘要：

  DOI：
• 作为产物：
  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

文献信息

• TWISTED PI-ELECTRON SYSTEM CHROMOPHORE COMPOUNDS WITH VERY LARGE MOLECULAR HYPERPOLARIZABILITIES AND RELATED COMPOSITIONS AND DEVICES
  申请人：Marks Tobin J.

  公开号：US20100273919A1

  公开（公告）日：2010-10-28

  Unconventional twisted π-electron system electro-optic (EO) chromophores/compounds, compositions and related device structures. Crystallographic analysis of several non-limiting chromophores reveals, for instance, large ring-ring dihedral twist angles and a highly charge-separated zwitterionic structure in the ground state, in both solution phase and solid-state.

  非传统扭曲的π-电子体系电光（EO）色团/化合物，组成和相关器件结构。对几种非限制性色团的晶体学分析显示，例如在溶液相和固态中，存在大的环-环二面角扭转角和高度电荷分离的带电离子结构。
• Structural characterization of the Brooker’s merocyanine/β-cyclodextrin complex using NMR spectroscopy and molecular modeling
  作者：Jennifer S. Holt

  DOI：10.1016/j.molstruc.2009.11.034

  日期：2010.2

  molecule and the complex, the molecular structures of the cis and trans isomers of Brooker’s merocyanine in β-cyclodextrin were optimized using the semi-empirical PM3 method as well as the hybrid ONIOM method which models the cyclodextrin at the PM3 level and the dye molecule using B3LYP/6-31g(d). The most stable complexes were similar in binding energy, although the molecular structures were quite different

  摘要 Brooker 的部花青 (4-[(1-methyl-4(1H)-pyridinylidene)ethylidene]-2,5-cyclohexadien-1-one) 是一种染料分子，具有独特的光化学/质子分解异构化循环。中性分子的顺反异构化仅在一个方向发生，并加入光化学能。然而，当染料分子与 β-环糊精复合时，异构化会自发发生，不需要进一步的能量。为了理解天然染料分子和复合物之间的区别，使用半经验 PM3 方法以及模拟环糊精的混合 ONIOM 方法优化了 β-环糊精中布鲁克氏部花青的顺式和反式异构体的分子结构。 PM3 水平和染料分子使用 B3LYP/6-31g(d)。最稳定的复合物的结合能相似，虽然分子结构大不相同。与 PM3 模型相比，ONIOM 优化的结构导致共轭染料分子的平面度增加。β-环糊精腔中的反式异构体也使用 1 H-NMR 络合诱导的位移进行了实验表征，发现结果与
• Complexes of carboxylato pillar[6]arene with Brooker-type merocyanines: Spectral properties, pKa shifts and the design of a displacement assay for trimethyl lysine
  作者：Dóra Hessz、Stella Bádogos、Márton Bojtár、István Bitter、László Drahos、Miklós Kubinyi

  DOI：10.1016/j.saa.2021.119455

  日期：2021.5

  dye-WP6 mixtures were described in terms of four equilibrium reactions: the acidic dissociations of the pyridinium phenols into the zwitterionic phenolates, the acidic dissociations of the complexed phenols, the bindings of the phenol form dyes to WP6 and the bindings of the phenolates to WP6. The equilibrium constants were determined by an analysis of the absorption spectra. It was found that the acidity

  在水溶液中研究了三种强溶剂化染料的超分子配合物，布鲁克的花菁（M1）及其两个衍生物（M2，M3）与羧基支柱[6]芳烃（WP6）。染料-WP6混合物是通过四个平衡反应来描述的：吡啶鎓酚的酸性分解成两性离子酚盐，络合酚的酸性分解，酚形式染料与WP6的结合以及酚盐与WP6的结合。 WP6。通过分析吸收光谱确定平衡常数。发现在络合时，酚形式的花菁的酸度大大降低，p K a观察到1.1-1.6单位的变化。在中性溶液中，M1和M2的酚形式的配合物占主导地位，而酸性更高的M3（一种二溴衍生物）则相反，酚盐配合物更稳定。比较染料-WP6配合物的光谱性质，结合常数和p K a -s，选择配合物M3·WP6作为置换试验。证明了该络合物可作为比色指示剂置换试验，将三甲基赖氨酸与其他赖氨酸衍生物区分开。
• METHODS TO INCREASE THE PHOTOSTABILITY OF DYES
  申请人：Hahn Klaus

  公开号：US20110046000A1

  公开（公告）日：2011-02-24

  The presently disclosed subject matter provides dyes having an improved photostability, biosensors comprising such dyes, and methods of use thereof, including methods for detecting target molecules in a sample under test and for live-cell imaging. The dyes can include a binding member, including a biomolecule or fragments thereof, which can interact with target molecules of interest and can be specific to a given conformational state or covalent modification, e.g., phosphorylation, of the target molecule. The presently disclosed dyes can be used for detecting changes in the binding, conformational change, or posttranslational modification of the target molecule.

  所述主题提供了具有改善光稳定性的染料、包括此类染料的生物传感器以及其使用方法，包括用于检测样品中的靶分子和用于活细胞成像的方法。该染料可以包括结合成员，包括生物分子或其片段，其可以与感兴趣的靶分子相互作用，并且可以特定于给定的构象状态或靶分子的共价修饰，例如磷酸化。目前披露的染料可用于检测靶分子的结合、构象变化或后翻译修饰的变化。
• Twisted Pi-Electron System Chromophore Compounds with Very Large Molecular Hyperpolarizabilities and Related Compositions and Devices
  申请人：Marks Tobin J.

  公开号：US20110278512A1

  公开（公告）日：2011-11-17

  Unconventional twisted π-electron system electro-optic (EO) chromophores/compounds, compositions and related device structures. Crystallographic analysis of several non-limiting chromophores reveals, for instance, large ring-ring dihedral twist angles and a highly charge-separated zwitterionic structure in the ground state, in both solution phase and solid-state.

  非传统的扭曲π电子体系的电光（EO）色团/化合物、组成和相关器件结构。对几种非限制性的色团进行晶体学分析，例如大的环-环二面角扭曲角度以及在溶液相和固态中均表现出高度带电离子结构的基态。

表征谱图