3-butoxy-4-(1,3,3-trimethyl-3H-indol-2-ylidenemethyl)-3-cyclobutene-1,2-dione | 357657-11-5

• 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-butoxy-4-(1,3,3-trimethyl-3H-indol-2-ylidenemethyl)-3-cyclobutene-1,2-dione
• 英文别名: 3-butoxy-4-(1,3,3-trimethyl-2,3-dihydro-1H-2-indolylidenmethyl)-3-cyclobutene-1,2-dione；3-butoxy-4-((1,3,3-trimethylindolin-2-ylidene)methyl)cyclobut-3-ene-1,2-dione；3-butoxy-4-[(1,3,3-trimethylindol-2-ylidene)methyl]cyclobut-3-ene-1,2-dione
• CAS: 357657-11-5
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: HMLJUYSDGQANOP-UHFFFAOYSA-N

物化性质

• 沸点：
  433.2±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-butoxy-4-(1,3,3-trimethyl-3H-indol-2-ylidenemethyl)-3-cyclobutene-1,2-dione 以 乙醇 、 甲苯 、 正丁醇 为溶剂， 反应 20.0h， 生成 3-dicyanomethylene-4-[((1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylidene)]-2-[(3-(4-oxo(butoxy)butyl)benzotiazol-2-ylidene)methyl]-cyclobut-1-en-1-olate
  参考文献：
  名称：

  Synthesis, characterization and protein-association of dicyanomethylene squaraine dyes

  摘要：

  We prepared several new dicyanomethylene squaraine dyes derived from indolenine, benzothiazole and benzoselenazole, with different substituent groups. All the obtained dyes display intense and narrow absorption bands and bright fluorescence emission in the Vis/NIR region (665-716 nm) when dissolved in organic solvents, especially for the unsymmetrical dyes containing sulphur and selenium atoms.The use of synthesized squaraine dyes as fluorescent probes for detection of bovine serum albumin (BSA) and human serum albumin (HSA) was explored in Tris-HCI buffer solutions. We observed that all the dyes are non-emissive in buffer solution but become fluorescent in the presence of BSA or HSA proteins, with the emission intensity increasing proportionally to the protein concentration (0.00-1.22 mu M). The most pronounced effect was observed for the symmetrical squaraine having two moieties of indolenine. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2017.07.070
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 三乙胺 作用下， 以 乙腈 、 正丁醇 为溶剂， 反应 24.3h， 生成 3-butoxy-4-(1,3,3-trimethyl-3H-indol-2-ylidenemethyl)-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Fluorescence properties of indolenine semi-squarylium dyes

  摘要：

  3-Butoxy-4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-cyclobut-1,2-dione exhibited the most intense florescence at fluorescence maxima 536 and 563 nm with fluorescence quantum yield 0.21 among any indolenine semi-squarylium dyes in the crystalline form due to the isolated dimer-type molecular packing and its suitable melting point. This compound showed aggregation-induced emission enhancement. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.089

文献信息

• Luminescent compounds
  申请人：——

  公开号：US20040166515A1

  公开（公告）日：2004-08-26

  The invention provides reporter compounds based on squaric, croconic, and/or rhodizonic acid, among others, reactive intermediates used to synthesize the reporter compounds, and methods of synthesizing and using the reporter compounds, among others. The reporter compounds relate generally to the following structure: 1 Here, Z is a four, five, or six-member aromatic ring, and A, B, C, D, E, and F are substituents of Z, where F is absent when Z is a five-member ring, and where E and F are absent when Z is a four-member ring. A, B, C, D, E, and F are selected from a variety of elements and groups, including but not necessarily limited to O, S, Se, Te, C(R a )(R b ), N—R c , N(R d )(R e ), W 1 , and W 2 . 2

  该发明提供了基于方酸、紫红酸和/或罗地酸等反应中间体的记者化合物，用于合成记者化合物的反应中间体以及合成和使用记者化合物的方法等。记者化合物通常与以下结构相关：1在这里，Z是一个四、五或六元芳香环，A、B、C、D、E和F是Z的取代基，当Z为五元环时，F不存在，当Z为四元环时，E和F不存在。A、B、C、D、E和F是从多种元素和基团中选择的，包括但不限于O、S、Se、Te、C（Ra）（Rb）、N-Rc、N（Rd）（Re）、W1和W2。2
• 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。
• Environment-sensitive indolenine-based hemisquaraine dyes: Synthesis, molecular structure, and spectral properties
  作者：Rostyslav P. Svoiakov、Olesia G. Kulyk、Iryna V. Hovor、Svitlana V. Shishkina、Anatoliy L. Tatarets

  DOI：10.1016/j.dyepig.2023.111612

  日期：2023.11

  Environment-sensitive fluorescent dyes are widely used in biomedical research, clinical diagnostics, molecular and cellular biology, analytical and bioanalytical chemistry. Many sensing dyes in the series of cyanines, styryls, BODIPY, squaraines, fluoresceins, and rhodamines among others have been developed and employed for these applications. Meanwhile, push-pull hemisquaraine dyes have been only moderately

  环境敏感荧光染料广泛应用于生物医学研究、临床诊断、分子和细胞生物学、分析和生物分析化学。花青、苯乙烯基、BODIPY、方酸菁、荧光素和罗丹明等系列的许多传感染料已被开发并用于这些应用。与此同时，推拉式半方酸染料作为环境传感器仅得到了适度的探索。在此，我们开发了一系列含有甲氨基（MeH）、二甲氨基（MeMe）、苯氨基（PhH）、苯甲氨基（PhMe）和二苯氨基（PhPh）基团的半方菁染料。发现这些取代基强烈影响染料对H键形成、极性、pH、粘度以及牛血清白蛋白 (BSA) 的存在，有助于开发特定应用的传感器。
• Fluorescence properties of indolenine semi-squarylium dyes
  作者：Masaki Matsui、Toshihiro Shibata、Masato Fukushima、Yasuhiro Kubota、Kazumasa Funabiki

  DOI：10.1016/j.tet.2012.09.089

  日期：2012.12

  3-Butoxy-4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-cyclobut-1,2-dione exhibited the most intense florescence at fluorescence maxima 536 and 563 nm with fluorescence quantum yield 0.21 among any indolenine semi-squarylium dyes in the crystalline form due to the isolated dimer-type molecular packing and its suitable melting point. This compound showed aggregation-induced emission enhancement. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis, characterization and protein-association of dicyanomethylene squaraine dyes
  作者：Tiago D. Martins、Marlene L. Pacheco、Renato E. Boto、Paulo Almeida、José Paulo S. Farinha、Lucinda V. Reis

  DOI：10.1016/j.dyepig.2017.07.070

  日期：2017.12

  We prepared several new dicyanomethylene squaraine dyes derived from indolenine, benzothiazole and benzoselenazole, with different substituent groups. All the obtained dyes display intense and narrow absorption bands and bright fluorescence emission in the Vis/NIR region (665-716 nm) when dissolved in organic solvents, especially for the unsymmetrical dyes containing sulphur and selenium atoms.The use of synthesized squaraine dyes as fluorescent probes for detection of bovine serum albumin (BSA) and human serum albumin (HSA) was explored in Tris-HCI buffer solutions. We observed that all the dyes are non-emissive in buffer solution but become fluorescent in the presence of BSA or HSA proteins, with the emission intensity increasing proportionally to the protein concentration (0.00-1.22 mu M). The most pronounced effect was observed for the symmetrical squaraine having two moieties of indolenine. (C) 2017 Elsevier Ltd. All rights reserved.