3-decyl-2-methylbenzothiazolium iodide | 445401-54-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-decyl-2-methylbenzothiazolium iodide
• 英文别名: 3-decyl-2-methyl-1,3-benzothiazol-3-ium;iodide
• CAS: 445401-54-7
• 化学式: C₁₈H₂₉NS*I
• 分子量: 418.405
• InChiKey: RDEQOQJYSNGJNR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-decyl-2-methylbenzothiazolium iodide 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-decyl-2-methylene-2,3-dihydrobenzothiazole
  参考文献：
  名称：

  NLO chromophores containing dihydrobenzothiazolylidene and dihydroquinolinylidene donors with an azo linker: Synthesis and optical properties

  摘要：

  We report the synthesis of a series of nonlinear optical chromophores containing either - a dihydrobenzothiazolylidene or dihydroquinolinylidene donor with an azo linker. The results demonstrate the versatility of coupling a diazonium salt to a donor-methylidene nucleus in order to access novel materials with good thermal stabilities and high nonlinear optical responses. From hyper-Raleigh scattering studies it was found that the use of the well-known TCF acceptor yields the best performing chromophores, one of which has a dynamic first hyperpolarizability of 1900 x 10(-30) esu at 800 nm. The results from this study suggest the use of pro-aromatic donors such as dihydrobenzothiazolylidene or dihydroquinolinylidene results in compounds with higher nonlinear optical responses than those containing donors based on either indoline or aniline. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.01.010
• 作为产物：
  描述：

  2-甲基苯并噻唑 、 1-碘癸烷 反应 72.0h， 以100%的产率得到3-decyl-2-methylbenzothiazolium iodide
  参考文献：
  名称：

  NLO chromophores containing dihydrobenzothiazolylidene and dihydroquinolinylidene donors with an azo linker: Synthesis and optical properties

  摘要：

  We report the synthesis of a series of nonlinear optical chromophores containing either - a dihydrobenzothiazolylidene or dihydroquinolinylidene donor with an azo linker. The results demonstrate the versatility of coupling a diazonium salt to a donor-methylidene nucleus in order to access novel materials with good thermal stabilities and high nonlinear optical responses. From hyper-Raleigh scattering studies it was found that the use of the well-known TCF acceptor yields the best performing chromophores, one of which has a dynamic first hyperpolarizability of 1900 x 10(-30) esu at 800 nm. The results from this study suggest the use of pro-aromatic donors such as dihydrobenzothiazolylidene or dihydroquinolinylidene results in compounds with higher nonlinear optical responses than those containing donors based on either indoline or aniline. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.01.010

文献信息

• Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines
  作者：A. Pardal、S. Ramos、P. Santos、L. Reis、P. Almeida

  DOI：10.3390/70300320

  日期：——

  The synthesis and spectroscopic characterisation of some representative N-alkyl-substituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzo-selenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated methyl group in the 2-position in relation to the nitrogen atom and N-methyl, -pentyl, -hexyl and -decyl chains, are typical precursors of cyanine

  描述了从苯并噻唑、苯并恶唑、苯并硒唑、吲哚和喹啉衍生的一些代表性 N-烷基取代季铵盐的合成和光谱表征。这些杂环盐在与氮原子和 N-甲基、-戊基、-己基和-癸基链相关的 2-位带有活化的甲基，是花青染料的典型前体。
• D-π-A-π-D Dyes with a 1,3,2-Dioxaborine Cycle in the Polymethine Chain: Efficient Long-Wavelength Fluorophores
  作者：Vladyslav Polishchuk、Mariia Stanko、Andrii Kulinich、Mykola Shandura

  DOI：10.1002/ejoc.201701466

  日期：2018.1.17

  nonsymmetric derivatives. The synthesis of dyes with various electron donor termini [indole, benzothiazole, pyran, 4-(dialkylamino)phenyl] and with different polymethine chain lengths is reported. The obtained compounds show intense absorption and fluorescence in the red and NIR region, their fluorescence brightness (the product of the molar extinction and the fluorescence quantum yield) attaining a value

  新合成的 5-cyano-2,2-difluoro-4,6-dimethyl-1,3,2-dioxaborine 中的腈基显示出显着增加甲基的酸度。这使得花青与两个甲基基团缩合形成 D–π–A–π–D 染料，其中二恶硼啉循环是聚甲炔链的一部分。在那里，半产物中剩余甲基的反应性降低到足以逐步进行反应，从而获得非对称衍生物。报告了具有各种电子供体末端 [吲哚、苯并噻唑、吡喃、4-(二烷基氨基)苯基] 和具有不同聚次甲基链长的染料的合成。所得化合物在红色和近红外区域显示出强烈的吸收和荧光，它们的荧光亮度（摩尔消光和荧光量子产率的乘积）达到 200,000 m–1 cm–1 的值。它们的特点是小规模的正溶剂化变色，但它们的荧光量子产率对环境极性更敏感。已经进行了时间相关 (TD)DFT 计算来研究新二氧杂环戊二烯的电子结构并揭示这些分子中长波长电子跃迁的性质。
• An Insight into Symmetrical Cyanine Dyes as Promising Selective Antiproliferative Agents in Caco-2 Colorectal Cancer Cells
  作者：João L. Serrano、Ana Maia、Adriana O. Santos、Eurico Lima、Lucinda V. Reis、Maria J. Nunes、Renato E. F. Boto、Samuel Silvestre、Paulo Almeida

  DOI：10.3390/molecules27185779

  日期：——

  Several cytotoxic approaches have been used over the years to overcome this public health threat, such as chemotherapy, radiotherapy, and photodynamic therapy (PDT). Cyanine dyes are a class of compounds that have been extensively studied as PDT sensitisers; nevertheless, their antiproliferative potential in the absence of a light source has been scarcely explored. Herein, the synthesis of eighteen symmetric

  癌症仍然是全球发病率最高的疾病之一。多年来，已经使用了几种细胞毒性方法来克服这种公共卫生威胁，例如化学疗法、放射疗法和光动力疗法 (PDT)。花青染料是一类作为PDT增感剂已被广泛研究的化合物；然而，它们在没有光源的情况下的抗增殖潜力几乎没有被探索过。本文描述了 18 种对称单、三和七次甲基花青染料的合成及其作为潜在抗癌剂的评估。分析了杂环性质、抗衡离子和次甲基链长对抗增殖作用和选择性的影响，并收集了相关的构效关系数据。还评估和讨论了光对最有希望的染料的细胞毒活性的影响。研究中的大多数单甲碱和三甲碱花青染料在初始筛选（10 µM ）。然而，浓度-活力曲线显示 Caco-2 细胞系的效力和选择性更高。苯并恶唑衍生的单次甲基花青染料是最有前途的化合物（IC 浓度-活力曲线显示 Caco-2 细胞系具有更高的效力和选择性。苯并恶唑衍生的单次甲基花青染料是最有前途的化合物（IC 浓度-活力曲线显示
• NMR spectroscopy study of 2-methylbenzoxazolium salts hydroxylation in DMSO-d6 solution
  作者：Ricardo Santos、Luís M. Fernandes、Renato F. Boto、Rogério Simões、Paulo Almeida

  DOI：10.1016/j.tetlet.2006.07.091

  日期：2006.9

  2-Methylbenzoxazolium salts showed an unexpected transformation at room temperature, promoted by residual water present in dimethyl sulfoxide. This transformation was followed up inside of an NMR sample tube using DMSO-d(6) as solvent, in a series of representative quaternary ammonium salts with carboxymethyl, ethyl, pentyl and decyl N-alkyl chains, resulting in an exclusive product. The corresponding benzothiazolium and benzoselenazolium salts presented a si similar behavior after heating at a temperature of 50 degrees C with the addition of one drop of D2O for the first of these two salts. This reaction could play a very important role in explaining certain secondary reactions occurring in the preparation of compounds where these salts are precursors, classically in cyanine dye synthesis. Four new benzoxazolols were characterized by NMR spectroscopy and HR FAB-MS. (c) 2006 Elsevier Ltd. All rights reserved.