3-oxo-4-[(1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]cyclobut-1-enolate, inner salt | 12243-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-oxo-4-[(1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]cyclobut-1-enolate, inner salt
• 英文别名: Bis-(1,3,3-trimethyl-indolenyl-(2))-dioxotetracyclo-pentamethin；Bis-(1,3,3-trimethyl-indolenyl-(2))-dioxotetracyclo-pentamethin, 1,5-Bis-(1,3,3-trimethyl-indolinyl-(2))-dioxo-tetrangulo-pentamethin；Bis-<1.3.3-trimethyl-indolenyl-(2)>-dioxo-tetracyclopentamethin；[2,4-dioxo-3-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidenemethyl)-cyclobutylidenemethyl]-1,3,3-trimethyl-3H-indolium betaine；2,4-bis[1,3,3-trimethyl-2-indolinylidenemethyl]cyclobutenediylium-1,3-dioxolate；3-oxo-4-((1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene)-2-((1,3,3-trimethylindolin-2-ylidene)methyl)cyclobut-1-en-1-olate；3-oxo-4-[(1,3,3-trimethylindol-1-ium-2-yl)methylidene]-2-[(1,3,3-trimethylindol-2-ylidene)methyl]cyclobuten-1-olate
• CAS: 12243-46-8
• 化学式: C₂₈H₂₈N₂O₂
• 分子量: 424.543
• InChiKey: YOYCQJDHFJMODW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-4-[(1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]cyclobut-1-enolate, inner salt 在 劳森试剂 作用下， 以 氯苯 为溶剂， 以68 %的产率得到2,4-bis(1,3,3-trimethyl-2-indolinylidenemethyl)-1,4-dithiosquaraine
  参考文献：
  名称：

  双-二氰基亚甲基取代的靛红：合成、光谱性质、分子和晶体结构

  摘要：

  这项工作的目的是合成两种在四元环中含有一个或两个丙二腈残基的新型吲哚宁方酸，并研究它们的光谱特性、分子和晶体结构。通过 DFT/CAM-B3LYP 方法对取代的方晶进行几何优化。用X射线方法研究了新型染料的分子和晶体结构。已经表明这些分子以双顺构象存在。

  DOI：

  10.1016/j.molstruc.2022.134038
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 以 甲苯 、 乙腈 、 正丁醇 为溶剂， 反应 0.5h， 生成 3-oxo-4-[(1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]cyclobut-1-enolate, inner salt
  参考文献：
  名称：

  Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria

  摘要：

  The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.

  DOI：

  10.1021/acs.orglett.0c01922

文献信息

• Luminescent compounds
  申请人：——

  公开号：US20030235846A1

  公开（公告）日：2003-12-25

  Luminescent compounds, reactive intermediates used to synthesize luminescent compounds, and methods of synthesizing and using luminescent compounds. These compounds may be based on squaric, croconic, and rhodizonic acid, and their analogs, among others, and relate generally to the structure: 1 where Z is a four, five, or six-member aromatic ring, and A, B, C, D, E, and F are substituents of Z, in any order, that may include O, S, Se, Te, C(R a )(R b ), N-R c , N(R d )(R e ), W 1 , and W 2 . Generally, each compound includes at least one of W 1 or W 2 , where W 1 and W 2 have the structures: 2 respectively. The compounds may include a reactive group and/or a carrier. The luminescent compounds may be useful in both free and conjugated forms as probes, labels, and/or indicators.

  发光化合物，用于合成发光化合物的反应中间体，以及合成和使用发光化合物的方法。这些化合物可能基于方酰、克罗酰和罗地酮酸及其类似物等，通常与结构相关：其中Z是一个四、五或六元芳香环，而A、B、C、D、E和F是Z的取代基，可以包括O、S、Se、Te、C(Ra)(Rb)、N-Rc、N(Rd)(Re)、W1和W2，顺序任意。通常，每种化合物至少包括W1或W2中的一种，其中W1和W2的结构分别为：。这些化合物可能包括一个反应基团和/或一个载体。这些发光化合物可能在自由和共轭形式下作为探针、标记物和/或指示剂而有用。
• Synthesis of squaraine dyes under mild conditions: applications for labelling and sensing of biomolecules
  作者：Mazen Haj Sleiman、Sylvain Ladame

  DOI：10.1039/c3cc47894g

  日期：——

  We report the synthesis of squaraine dyes under mild conditions by carbodiimide activation of squaric acid or semi-squaraine dyes. Despite low yields when the reaction was carried out in solution, these conditions were successfully applied to efficient peptide labelling on resin and nucleic acid sensing in solution.

  我们报告了在温和条件下通过碳二亚胺活化方酸或半方酸染料合成方酸染料的方法。尽管在溶液中进行反应时收率低，但这些条件已成功应用于树脂上有效的肽标记和溶液中的核酸检测。
• Molecular structure and spectral properties of indolenine based norsquaraines versus squaraines
  作者：Olga S. Kolosova、Svitlana V. Shishkina、Vered Marks、Gary Gellerman、Iryna V. Hovor、Anatoliy L. Tatarets、Ewald A. Terpetschnig、Leonid D. Patsenker

  DOI：10.1016/j.dyepig.2018.12.007

  日期：2019.4

  dyes, wherein the oxygen of the squaric acid bridge was substituted with a barbituric or a dicyanomethylene group, were synthesized and their molecular structure, spectral and luminescent properties were compared to those of analogous squaraine dyes. The molecular structure was investigated using X-ray analysis, NMR spectroscopy and ab initio DFT B3LYP/6-311G (d, p) simulations. The calculated populations

  合成了新的基于吲哚烯胺的去甲鸟嘌呤染料，其中方酸桥的氧被巴比妥基或二氰基亚甲基取代，并且将它们的分子结构，光谱和发光性质与类似的方酸方块染料进行了比较。使用X射线分析，NMR光谱和从头算DFT B3LYP / 6-311G（d，p）模拟研究了分子结构。发现可能的构象体总数和内部旋转的障碍与实验数据高度吻合。Norsquarain吸收和发射与相应的quaqua相同的长波长光谱范围内的光，但归因于分子内H-键和增加的构象刚度，它们对溶剂极性和蛋白质（BSA）的敏感性较低。
• A novel fast green method for the preparation of the squaraine dye 3-oxo-4[(1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]cyclobut-1-enolate, inner salt
  作者：Stela Minkovska、Nikola Burdzhiev、Alexi Alexiev、Todor Deligeorgiev

  DOI：10.1007/s11696-018-0398-6

  日期：2018.6

  A novel green method was developed for the preparation of a squaraine dye, on an 8-mmol scale, by microwave irradiation of two equivalents of 1,3,3-trimethyl-2-methyleneindoline with one equivalent squaric acid in the green solvent, ethyl l-lactate. The time required for this green synthesis is only 4 min. The target squaraine dye was isolated in excellent yield (81%) and with high purity.

  一种新型绿色方法被开发用于制备一种8mmol规模的squaraine染料，通过微波辐射将等量的1,3,3-三甲基-2-亚甲基吲哚啉与等量的squaric acid在绿色溶剂乙基l-乳酸中混合。这种绿色合成所需的时间仅为4分钟。目标squaraine染料以高纯度和高产率（81%）被分离出来。
• Macrophage identification agent, and identification method, sorting method, evaluation method, screening method and kit using the macrophage identifier agent
  申请人：CANON KABUSHIKI KAISHA

  公开号：US10041937B2

  公开（公告）日：2018-08-07

  An object of the present invention is to provide an identification method for a macrophage subtype using an organic compound. Another object of the present invention is to provide a macrophage identification agent containing an organic compound in which a spectral characteristic obtained when the organic compound is added is different depending on a macrophage subtype. Still another object of the present invention is to provide an evaluation method for a macrophage subtype using a macrophage identification agent, an analysis method for correlation between a macrophage subtype and a test substance, a screening method for correlation between a macrophage subtype and a test substance, and a kit. An identification method for a macrophage subtype utilizing that a spectral characteristic obtained with an organic compound added is different depending on a macrophage subtype is provided.

  本发明的一个目的是提供一种利用有机化合物识别巨噬细胞亚型的方法。本发明的另一个目的是提供一种含有有机化合物的巨噬细胞识别剂，其中添加有机化合物时获得的光谱特性因巨噬细胞亚型的不同而不同。本发明的另一个目的是提供一种使用巨噬细胞鉴定剂的巨噬细胞亚型的评估方法、巨噬细胞亚型与测试物质之间相关性的分析方法、巨噬细胞亚型与测试物质之间相关性的筛选方法和试剂盒。本发明提供了一种巨噬细胞亚型的鉴别方法，该方法利用了添加有机化合物后获得的光谱特性随巨噬细胞亚型的不同而不同的特点。