3-dicyanomethylene-2-(N-methyl-2,3-dihydro-1,3-benzothiazol-2-ylidenemethyl)-4-oxo-1-cyclobutene-1-olate triethylammonium salt | 616232-60-1

• 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: 3-dicyanomethylene-2-(N-methyl-2,3-dihydro-1,3-benzothiazol-2-ylidenemethyl)-4-oxo-1-cyclobutene-1-olate triethylammonium salt
• CAS: 616232-60-1
• 化学式: C₆H₁₅N*C₁₆H₉N₃O₂S
• 分子量: 408.524
• InChiKey: DPHZYBINSUWWGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  91.36
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(6-iodohexyl)-2-methylbenzothiazolium iodide 、 3-dicyanomethylene-2-(N-methyl-2,3-dihydro-1,3-benzothiazol-2-ylidenemethyl)-4-oxo-1-cyclobutene-1-olate triethylammonium salt 以 乙醇 为溶剂， 反应 8.0h， 以15%的产率得到[2-Cyano-2-[2-[[3-(6-iodohexyl)-1,3-benzothiazol-2-ylidene]methyl]-4-[(3-methyl-1,3-benzothiazol-3-ium-2-yl)methylidene]-3-oxocyclobuten-1-yl]ethenylidene]azanide
  参考文献：
  名称：

  Fluorinated squaraine as near-IR label with improved properties for the labeling of oligonucleotides

  摘要：

  A new squaraine dye with fluorinated benzothiazole rings was synthesized. This new label possesses improved photophysical properties and chemical stability as compared to the corresponding non-fluorinated and the dicyanosquaraines. These squaraines were used for the labeling of a series of oligonucleotides with various sequences, lengths, and chemistries. The conjugates involving the fluorinated squaraine possess the best properties: emission wavelength >670 nm, high quantum yields (0.27-0.39). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.029
• 作为产物：
  描述：

  2-butoxy-3-dicyanomethylene-4-oxo-1-cyclobutene-1-olate triethylammonium salt 、 2,3-二甲基苯并噻唑鎓碘化物 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以50%的产率得到3-dicyanomethylene-2-(N-methyl-2,3-dihydro-1,3-benzothiazol-2-ylidenemethyl)-4-oxo-1-cyclobutene-1-olate triethylammonium salt
  参考文献：
  名称：

  Fluorinated squaraine as near-IR label with improved properties for the labeling of oligonucleotides

  摘要：

  A new squaraine dye with fluorinated benzothiazole rings was synthesized. This new label possesses improved photophysical properties and chemical stability as compared to the corresponding non-fluorinated and the dicyanosquaraines. These squaraines were used for the labeling of a series of oligonucleotides with various sequences, lengths, and chemistries. The conjugates involving the fluorinated squaraine possess the best properties: emission wavelength >670 nm, high quantum yields (0.27-0.39). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.029

文献信息

• VISCOSITY-SENSITIVE DYES AND METHOD
  申请人：SETA BioMedicals, LLC

  公开号：US20160091495A1

  公开（公告）日：2016-03-31

  Disclosed viscosity-sensitive reporter compounds and methods allow tracing the changes in viscosity in a biological sample/environment (e.g., in medical, biochemical, biological, and/or pharmaceutical applications). Compounds and methods of the present disclosure can be used to identify the localization and the rheological state of hydrogels, their degradation products and other biostructural materials, including surgical implants, as well as the effectiveness of drug delivery by hydrogel carriers.

  公开的粘度敏感报告化合物和方法可追踪生物样品/环境中粘度的变化（例如，在医学、生化、生物和/或制药应用中）。本公开的化合物和方法可用于确定水凝胶的定位和流变状态、它们的降解产物和其他生物结构材料（包括手术植入物）以及水凝胶载体的药物传递效果。
• Chiroptical Properties of Planar Benzobisthiazole-Bridged Squaraine Dimers
  作者：Emely Freytag、Lasse Kreimendahl、Marco Holzapfel、Jens Petersen、Heiko Lackinger、Matthias Stolte、Frank Würthner、Roland Mitric、Christoph Lambert

  DOI：10.1021/acs.joc.3c00821

  日期：2023.8.4

  the used squaraine chromophores. Sizable anisotropies gabs of up to 2.6 × 10–3 could be obtained. TD-DFT calculations were used to partition the rotational strength into the three Rosenfeld terms where the electric-magnetic coupling turned out to be the dominant contribution while the exciton chirality term is much smaller. This is because the chromophore dimers are essentially planar but the angle between

  通过将手性假吲哚半方酸菁与三种不同的苯并双噻唑桥融合，合成了五种手性方酸菁二聚体。由此产生的方酸二聚体表现出由激子耦合引起的最低能量吸收带的强烈分裂。两个激子跃迁和能量分裂的强度取决于发色团二聚体内两个方酸酸部分的角度。二聚体的电圆二色光谱显示出强烈的棉花效应，其符号取决于所使用的方酸菁发色团。可以获得高达 2.6 × 10 –3的相当大的各向异性gabs 。TD-DFT 计算用于将旋转强度划分为三个 Rosenfeld 项，其中电磁耦合是主要贡献，而激子手性项要小得多。这是因为发色团二聚体本质上是平面的，但一个方酸菁的电跃迁偶极矩与另一个方酸菁的磁跃迁偶极矩之间的角度严重偏离 90°，这使得两个矩向量之间的点积，从而，转动强度大。