5-methoxy-2,3-dimethylbenzothiazol-3-ium iodide | 42474-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-methoxy-2,3-dimethylbenzothiazol-3-ium iodide
• 英文别名: 5-methoxy-2,3-dimethylbenzo[d]thiazol-3-ium iodide；5-Methoxy-2,3-dimethyl-benzthiazoliumiodid；5-methoxy-2,3-dimethyl-benzothiazolium; iodide；5-Methoxy-2,3-dimethyl-benzothiazolium; Jodid；5-methoxy-2,3-dimethyl-1,3-benzothiazol-3-ium;iodide
• CAS: 42474-74-8
• 化学式: C₁₀H₁₂NOS*I
• 分子量: 321.182
• InChiKey: CCYQXLMQIMFANU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.95
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-2,3-dimethylbenzothiazol-3-ium iodide 在 氢溴酸 作用下， 生成 5-hydroxy-2,3-dimethyl-benzothiazolium; iodide
  参考文献：
  名称：

  Preparation of hydroxy cyclammonium quaternary salts

  摘要：

  公开号：

  US02541015A1
• 作为产物：
  描述：

  2-甲基-5-甲氧基苯并噻唑 、 碘甲烷 反应 0.58h， 以60%的产率得到5-methoxy-2,3-dimethylbenzothiazol-3-ium iodide
  参考文献：
  名称：

  Spectral fine tuning of cyanine dyes: electron donor—acceptor substituted analogues of thiazole orange

  摘要：

  在荧光花青染料的战略位置引入电子供体和受体基团可以微调吸收和发射光谱，同时保留染料与生物分子主体（例如双链 DNA 和单链抗体）结合的能力最初选择用于与母体未取代染料噻唑橙 (TO) 结合的片段。观察到的光谱位移与计算的 HOMO-LUMO 能隙一致，反映了 LUMO 中 TO 的喹啉一半上的电子密度局域化。苯并噻唑环和喹啉环上分别带有供甲氧基和撤回三氟甲基的染料将吸收光谱移动到足够长的波长，以允许在绿色波长下激发，而不是母体染料，母体染料在蓝色中最佳激发。

  DOI：

  10.1039/c5pp00117j

文献信息

• Spectral fine tuning of cyanine dyes: electron donor—acceptor substituted analogues of thiazole orange
  作者：Elizabeth E. Rastede、Matteus Tanha、David Yaron、Simon C. Watkins、Alan S. Waggoner、Bruce A. Armitage

  DOI：10.1039/c5pp00117j

  日期：2015.9

  The introduction of electron donor and acceptor groups at strategic locations on a fluorogenic cyanine dye allows fine-tuning of the absorption and emission spectra while preserving the ability of the dye to bind to biomolecular hosts such as double-stranded DNA and a single-chain antibody fragment originally selected for binding to the parent unsubstituted dye, thiazole orange (TO). The observed spectral shifts are consistent with calculated HOMO-LUMO energy gaps and reflect electron density localization on the quinoline half of TO in the LUMO. A dye bearing donating methoxy and withdrawing trifluoromethyl groups on the benzothiazole and quinoline rings, respectively, shifts the absorption spectrum to sufficiently longer wavelengths to allow excitation at green wavelengths as opposed to the parent dye, which is optimally excited in the blue.

  在荧光花青染料的战略位置引入电子供体和受体基团可以微调吸收和发射光谱，同时保留染料与生物分子主体（例如双链 DNA 和单链抗体）结合的能力最初选择用于与母体未取代染料噻唑橙 (TO) 结合的片段。观察到的光谱位移与计算的 HOMO-LUMO 能隙一致，反映了 LUMO 中 TO 的喹啉一半上的电子密度局域化。苯并噻唑环和喹啉环上分别带有供甲氧基和撤回三氟甲基的染料将吸收光谱移动到足够长的波长，以允许在绿色波长下激发，而不是母体染料，母体染料在蓝色中最佳激发。
• Reactions of quinazolinium salts with quaternary heterocyclic salts yielding 3-hetarylquinolines
  作者：S. P. Gromov、M. A. Razinkin、V. S. Drach、S. A. Sergeev

  DOI：10.1007/bf02503494

  日期：1998.6

  from quinazoline derivatives and quaternary heterocyclic salts. An independent synthesis was carried out and transformations of one of the probable intermediates were studied. By-products were isolated. The effects of the nature of the heterocycle and substituents on the course of the ring transformation reaction were found, and the mechanism of the reaction was suggested.

  发现了一种新型的嘧啶环在 C-亲核试剂作用下的转化，并开发了一种由喹唑啉衍生物和季杂环盐合成 3-杂芳基喹啉的新方法。进行了独立的合成并研究了可能的中间体之一的转化。分离出副产物。发现了杂环和取代基的性质对环转化反应过程的影响，并提出了反应机理。
• [EN] INHIBITORS OF CDC2-LIKE KINASES (CLKS) AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DES KINASES DE TYPE CDC2 (CLK) ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SIRTRIS PHARMACEUTICALS INC

  公开号：WO2009085226A3

  公开（公告）日：2009-11-05
• Lugovkin,B.P., Journal of general chemistry of the USSR, 1963, vol. 33, p. 3132 - 3134
  作者：Lugovkin,B.P.

  DOI：——

  日期：——
• Nucleic Acid‐Templated Synthesis of Cationic Styryl Dyes <i>in Vitro</i> and in Living Cells
  作者：Kriangsak Faikhruea、Kotchakorn Supabowornsathit、Kitipong Angsujinda、Chanat Aonbangkhen、Vorrapon Chaikeeratisak、Tanapat Palaga、Wanchai Assavalapsakul、Hans‐Achim Wagenknecht、Tirayut Vilaivan

  DOI：10.1002/chem.202400913

  日期：——

  A novel method for synthesizing cationic styryl dyes through a nucleic acid‐templated reaction has been developed. This approach overcomes issues associated with traditional synthesis methods, such as harsh conditions, low throughput, and wasteful chemicals. The presence of a nucleic acid template accelerated the styryl dye formation from quaternized heteroaromatic and cationic aldehyde substrates. These styryl dyes show remarkable optical properties change when bound to nucleic acids, hence the success of the synthesis could be readily monitored in situ by UV‐Vis and fluorescence spectroscopy and the optical properties data were also observable at the same time. This method provides the desired products from a broad range of coupling partners. By employing different substrates and templates, it is possible to identify new dyes that can bind to a specific type of nucleic acid such as a G‐quadruplex. The templated dye synthesis is also successfully demonstrated in live HeLa cells. This approach is a powerful tool for the rapid synthesis and screening of dyes specific for diverse types of nucleic acids or cellular organelles, facilitating new biological discoveries.