1-(2-Carboxyethyl)-4-methylquinolinium bromide | 82551-23-3

• 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: 1-(2-Carboxyethyl)-4-methylquinolinium bromide
• 英文别名: 3-(4-methylquinolin-1-ium-1-yl)propanoic acid;bromide
• CAS: 82551-23-3
• 化学式: Br*C₁₃H₁₄NO₂
• 分子量: 296.164
• InChiKey: GXDRXHMZEOHKLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  41.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  C₇H₇O₃S^(1-)*C₁₅H₁₃N₂O₂S₂⁽¹⁺⁾ 、 1-(2-Carboxyethyl)-4-methylquinolinium bromide 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以92%的产率得到C₇H₇O₃S^(1-)*C₂₁H₁₈N₃O₄S⁽¹⁺⁾
  参考文献：
  名称：

  Thiazole Orange derivatives: Synthesis, fluorescence properties, and labeling cancer cells

  摘要：

  A series of Thiazole Orange (TO) derivatives were synthesized and modified by introducing different substitutional groups on benzothiazole and 4-methylquinoline All the TO derivatives were confirmed by (HNMR)-H-1 and MS. TO derivative bearing NH2- was modified by folic acid and used to label breast cancer cells. The phenomenon of fluorescence enhancement was shown by the fluorescence spectrums of TO derivatives and micrographs of the labeled breast cancer cells. It offered a new try in the aspect of labeling cells by the embedded dyes. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.083
• 作为产物：
  描述：

  3-溴丙酸 、 4-甲基喹啉 以 丙酮 为溶剂， 反应 8.0h， 生成 1-(2-Carboxyethyl)-4-methylquinolinium bromide
  参考文献：
  名称：

  Synthesis and Crystal Structure of Thiazole Orange Derivative

  摘要：

  由苯并噻唑鎓与4-甲基喹啉盐反应合成了标题化合物噻唑橙衍生物，并经1HNMR和MS鉴定。晶体形成后得到噻唑橙衍生物的结晶水合物，并通过单晶X射线衍射表征。该晶体属于三斜晶系，P-1空间群晶胞参数为a = 10.162(2) Å, b = 10.501(2) Å, c = 11.040(2) Å, α = 92.17(3)o , β = 117.10(3)o, γ = 92.28(3)o, V = 1045.9(4) Å3, Z = 2, Dc = 1.380 mg/m−3, μ = 0.2 mm−1, F(000) = 460，对于 3658 个观察到的反射，最终 R = 0.0625 和 wR = 0.1862 (I > 2σ(I))。由亚甲基桥链连接的两个芳香环是共面结构。合成了具有结晶水的噻唑橙衍生物的标题化合物，并通过 1HNMR、MS 和单晶 X 射线衍射对其进行了表征。

  DOI：

  10.1007/s10870-011-0080-0

文献信息

• Study on Synthesis and Spectrum of Novel Styryl Cyanine Dyes with a Carbazole Bridged Chain
  作者：Xuening Fei、Yingchun Gu、Chao Li、Xu Yang

  DOI：10.1007/s10895-011-1014-0

  日期：2012.5

  Based on the frequently-used cyanine dye probe thiazole orange (TO), a novel kind of cyanine dye was designed and synthesized. Carbazole was inserted into the methylidyne structure of TO as a bridge to afford a kind of novel styryl cyanine dye with carbazole bridged chain. The dyes were characterized by HNMR and MS. The spectra of the novel dyes were also studied and the results showed that the fluorescent wavelength of novel carbzole dye shifted red for 100 nm, stock shift increased by 70 nm and the fluorescent intensity enhanced by 70 times compared to that of TO. When the novel dye was labeled by BSA, its fluorescent wavelength changed little and the intensity enhanced. It is indicated that it can be used as an excellent fluorescent probe in biological labeling.

  在常用的氰基染料探针噻唑橙（TO）的基础上，设计并合成了一种新型氰基染料。将咔唑作为桥插入 TO 的甲基idyne 结构中，得到了一种新型的咔唑桥链苯乙烯基氰基染料。这些染料通过 HNMR 和 MS 进行了表征。对新型染料的光谱也进行了研究，结果表明，新型咔唑染料的荧光波长红移了 100  nm，与 TO 相比，股移增加了 70  nm，荧光强度增强了 70 倍。当新型染料被 BSA 标记后，其荧光波长变化不大，荧光强度增强。这表明它可以作为一种优良的荧光探针用于生物标记。
• Synthesis and Crystal Structure of Thiazole Orange Derivative
  作者：Xuening Fei、Yingchun Gu、Yunquan Lan、Bin Shi、Baolian Zhang

  DOI：10.1007/s10870-011-0080-0

  日期：2011.8

  The title compound of Thiazole Orange derivative was synthesized by the reaction of benzothiazolium and 4-methyl quinoline salts, which was determined by 1HNMR and MS. A crystalline hydrate of thiazole orange derivative was obtained when the crystal formed and characterized by single-crystal X-ray diffraction. The crystal belongs to the Triclinic system, and the cell parameters of space group P-1 were a = 10.162(2) Å, b = 10.501(2) Å, c = 11.040(2) Å, α = 92.17(3)o, β = 117.10(3)o, γ = 92.28(3)o, V = 1045.9(4) Å3, Z = 2, Dc = 1.380 mg/m−3, μ = 0.2 mm−1, F(000) = 460, and the final R = 0.0625 and wR = 0.1862 for 3658 observed reflections (I > 2σ(I)). The two aromatic rings linked by the methylene bridged chain are a coplanar structure. The title compound of Thiazole Orange derivative with crystal water was synthesized and characterized by 1HNMR, MS, and single-crystal X-ray diffraction .

  由苯并噻唑鎓与4-甲基喹啉盐反应合成了标题化合物噻唑橙衍生物，并经1HNMR和MS鉴定。晶体形成后得到噻唑橙衍生物的结晶水合物，并通过单晶X射线衍射表征。该晶体属于三斜晶系，P-1空间群晶胞参数为a = 10.162(2) Å, b = 10.501(2) Å, c = 11.040(2) Å, α = 92.17(3)o , β = 117.10(3)o, γ = 92.28(3)o, V = 1045.9(4) Å3, Z = 2, Dc = 1.380 mg/m−3, μ = 0.2 mm−1, F(000) = 460，对于 3658 个观察到的反射，最终 R = 0.0625 和 wR = 0.1862 (I > 2σ(I))。由亚甲基桥链连接的两个芳香环是共面结构。合成了具有结晶水的噻唑橙衍生物的标题化合物，并通过 1HNMR、MS 和单晶 X 射线衍射对其进行了表征。
• Solid-phase synthesis of asymmetric cyanine dyes
  作者：Jennie Isacsson、Gunnar Westman

  DOI：10.1016/s0040-4039(01)00365-3

  日期：2001.4

  An efficient solid-phase synthesis of asymmetric cyanine dyes is described. Combinatorial synthesis and spectroscopic analysis of four dyes was carried out. The yields are quantitative after 20 h, but the reaction can be halted earlier, since it is shown that the starting material does not disturb the fluorescence measurements in these binding studies.

  描述了不对称花青染料的有效固相合成。进行了四种染料的组合合成和光谱分析。20小时后产量是定量的，但是反应可以更早地停止，因为在这些结合研究中显示出起始原料不会干扰荧光测量。
• US4386146A
  申请人：——

  公开号：US4386146A

  公开（公告）日：1983-05-31
• [EN] CHROMOGENIC SUBSTRATES FOR THE DETECTION OF SALMONELLA<br/>[FR] SUBSTRATS CHROMOGENES DE DETECTION DE Salmonella
  申请人：PRAILL PRICE RICHARDSON LTD.

  公开号：WO1999041409A1

  公开（公告）日：1999-08-19

  (EN) The invention relates to a method of detecting $i(salmonella) spp, comprising exposing a sample to a substrate containing a chromogenic compound that reacts with a cellular esterase/lipase present in $i(salmonella) spp and having an affinity for octanoate esters, the chromogenic compound comprising a 4-[2-(4-octanoyloxy-3,5-dimethoxyphenyl)-vinyl]-quinolinium-1-(propan-3-ylcarboxylic acid) cation and an anion. The invention further provides chromogenic compounds and media for such methods.(FR) L'invention concerne une méthode de détection de $i(Salmonella) spp., la méthode consistant à exposer un substrat contenant un composé chromogène entrant en réaction avec une estérase/lipase cellulaire présente dans $i(Salmonella) spp. et présentant une affinité avec des esters d'octanoate, le composé chromogène comprenant un cation 4-[2-(4-octanoyloxy-3,5-diméthoxyphényl)-vinyl]-quinolinium-1-(propan-3-yl acide carboxylique) et un anion. L'invention concerne également des composés chromogènes et des milieux d'application de ces méthodes.