6-bromo-N-methyl-2-quinaldinium iodide | 59105-86-1

• 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: 6-bromo-N-methyl-2-quinaldinium iodide
• 英文别名: 6-bromo-1,2-dimethyl-quinolinium; iodide；6-Brom-1,2-dimethyl-chinolinium; Jodid；1,2-Dimethyl-6-brom-chinolinium-iodid；Quinolinium, 6-bromo-1,2-dimethyl-, iodide；6-bromo-1,2-dimethylquinolin-1-ium;iodide
• CAS: 59105-86-1
• 化学式: C₁₁H₁₁BrN*I
• 分子量: 364.024
• InChiKey: IPHQJLDZDIFJEN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  巴豆酸 、 6-bromo-N-methyl-2-quinaldinium iodide 在 喹啉 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以85%的产率得到5-[(6-Bromo-1-methylquinolin-1-ium-2-yl)methylidene]-2-[(6-bromo-1-methylquinolin-2-ylidene)methyl]-3,4-dioxocyclopenten-1-olate
  参考文献：
  名称：

  Infrared Absorbing Croconaine Dyes:  Synthesis and Metal Ion Binding Properties

  摘要：

  [GRAPHICS]Quinaldine-based croconaine dyes synthesized by the condensation reaction between croconic acid and the respective quinaldinium salts are described. These dyes exhibit absorption maximum in the infrared region (840-870 nm) with high molar extinction coefficients (1-5 x 10(5) M-1 cm(-1)) and have very low fluorescence quantum yields. Upon binding to divalent metal ions, these dyes were found to form complexes with a 2:1 stoichiometry having high association constants of the order of 10(11)-10(14) M-2, while the monovalent metal ions showed negligible affinity. The binding of the croconaine dye 3d with divalent metal ions especially Zn2+, Pb2+, and Cd2+ led to significant chelation-enhanced fluorescence emission. The broadening of the aromatic signals, vinylic and N-methyl protons and the negligible changes at the aliphatic region of the dye 3d in the H-1 NMR spectrum in the presence of Zn2+, indicate that the binding occurs at the carbonyl groups of the croconyl ring. The shift in the croconyl carbonyl stretching frequency in the [3d-Zn2+] complex analyzed through FT-IR analysis further confirms the involvement of two electron-rich carbonyl groups of the croconyl moiety in the complexation. These results demonstrate that the binding of the divalent metal ions at the carbonyl oxygens of these infrared absorbing dyes can be favorably utilized for the development of potential sensors for the detection of metal ions and further can be exploited as sensitizers for photodynamic therapeutic applications.

  DOI：

  10.1021/jo702209a
• 作为产物：
  描述：

  4-溴苯胺 在 盐酸 作用下， 反应 18.0h， 生成 6-bromo-N-methyl-2-quinaldinium iodide
  参考文献：
  名称：

  Synthesis of Novel Quinaldine-Based Squaraine Dyes:  Effect of Substituents and Role of Electronic Factors

  摘要：

  [GRAPHICS]Condensation of squaric acid with quinaldinium salts containing electron-donating substituents gave only the semisquaraines. However, with salts possessing electronegative and electron-withdrawing groups, the squaraine dyes were isolated in quantitative yields. The semisquaraines formed undergo condensation with highly nucleophilic salts yielding the unsymmetrical squaraine dyes. These results demonstrate the role of electronic factors and provide valuable information for the design of efficient squaraine-based sensitizers that can have potential applications in photodynamic therapy.

  DOI：

  10.1021/ol048411y

文献信息

• 一种一甲川菁染料的合成方法
  申请人：付义乐

  公开号：CN105885466A

  公开（公告）日：2016-08-24

  本发明涉及一种一甲川菁染料的合成方法，其包括以下步骤：(1)将N-甲基喹啉-2-硫酮、对甲苯磺酸甲酯、含有活性甲基的杂环季铵盐以及无水乙醇加入圆底烧瓶中，滴入三乙胺，回流；(2)将上述步骤(1)回流后的溶液经减压蒸出部分溶剂，冷却，待有固体析出，再进行抽滤，干燥，重结晶，以最终得到一甲川菁染料成品。本发明操作简单，合成产率高、步骤少且时间短，能有效避免中间产物的纯化处理，合成效率高，合成成本较低。
• Efficient One-Pot Three-Component Synthesis of Monomethine Cyanine Dyes with Quinoline Nucleus and Their Spectral Properties
  作者：Y.L. Fu、B.R. Zhang、S. Wang、X.X. Gao、L.Y. Wang

  DOI：10.5012/bkcs.2013.34.2.489

  日期：2013.2.20

  An improved method for the preparation of monomethine cyanine dyes with quinoline nucleus by one-pot three-component using 1-methyl-2-quinolinethione, quaternized 2- or 4-methylheterocyclic compounds and methyl p-toluenesulfonate as starting materials was described. Compared with the traditional methods, the new synthetic method reduced the reaction steps, shortened the reaction time, avoided the separation

  介绍了以1-甲基-2-喹啉硫酮、季铵化2-或4-甲基杂环化合物和对甲苯磺酸甲酯为起始原料的一锅三组分制备具有喹啉核的单甲炔花青染料的改进方法。与传统方法相比，新的合成方法减少了反应步骤，缩短了反应时间，避免了中间体的分离纯化，降低了成本。染料在478.0-563.0 nm范围内吸收，摩尔消光系数为1.3 × 10 4 -9 .4 × 10 4 L mol ×1 cm ×1 。它们在不同溶剂中的荧光最大值和斯托克斯位移分别在 525.2-594.4 nm 和 16.2-80.6 nm 范围内。从染料在不同溶剂中的光谱性质来看，
• Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry
  作者：X.H. Zhang、Q. Liu、H.J. Shi、L.Y. Wang、Y.L. Fu、X.C. Wei、L.F. Yang

  DOI：10.1016/j.dyepig.2013.09.011

  日期：2014.1

  A series of dimethine cyanine dyes, used as fluorescent probes, were synthesized under microwave irradiation, and identified by H-1 NMR, IR, elemental analysis and HRMS. The investigation of their spectral properties in phosphate-buffer saline (PBS) showed that the absorption and emission maxima of the dyes were in the region 370-480 nm and 471-569 nm, respectively. The properties of the dyes as fluorescent probes for living cells imaging and flow cytometry were investigated. The results showed that dyes 1, 2, 8 or 9 could penetrate an intact cell membrane, stained the cell nuclear and exhibited bright fluorescence. Little background interference, low cell cytotoxicity and little photobleaching were showed during the imaging tests. The dyes 1, 8 and 9 could be applied in flow cytometry and dye 1/PI, dye 8/PI or dye 9/PI couple could be proposed as double staining agents to measure sperm cell viability. Thus the dyes represented the cell-permeant fluorescent probes. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and antimicrobial properties of some quinoline derivatives
  作者：P. V. Prisyazhnyuk、V. K. Patratii、N. G. Prodanchuk、K. G. Tashchuk、S. D. Fedoryak

  DOI：10.1007/bf00760705

  日期：1984.4
• CHERNYUK I. N.; SHELEST V. V.; ALBOTA L. A.; PILYUGIN G. T.; BIBIK L. I., ZH. ORGAN. XIMII <ZORK-AE>, 1976, 12, HO 2, 452-455
  作者：CHERNYUK I. N.、 SHELEST V. V.、 ALBOTA L. A.、 PILYUGIN G. T.、 BIBIK L. I.

  DOI：——

  日期：——