benzotrifuranone | 1187398-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: benzotrifuranone
• 英文别名: 3,8,13-Trioxatetracyclo[10.3.0.02,6.07,11]pentadeca-1(12),2(6),7(11)-triene-4,9,14-trione；3,8,13-trioxatetracyclo[10.3.0.02,6.07,11]pentadeca-1(12),2(6),7(11)-triene-4,9,14-trione
• CAS: 1187398-54-4
• 化学式: C₁₂H₆O₆
• 分子量: 246.176
• InChiKey: IMAYREBYTPXIAV-UHFFFAOYSA-N

物化性质

• 沸点：
  521.3±50.0 °C(Predicted)
• 密度：
  1.766±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzotrifuranone 、 6-氨基-1,4-苯并二氧杂环 以 四氢呋喃 为溶剂， 以91%的产率得到2,2',2''-(2,4,6-trihydroxybenzene-1,3,5-triyl)tris(N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetamide)
  参考文献：
  名称：

  Rapid access to C ₃- and C _s-symmetric AAT organogelators via ring opening of a common benzotrifuranone precursor

  摘要：

  Presented is a rapid and general approach to functionalised 1-aza-adamantanetrione (AAT) donor-sigma-acceptor molecules from a phloroglucinol-derived trilactone, benzotrifuranone (BTF). Ten C3-symmetric AATs bearing diverse aryl amide substituents are accessed in two synthetic steps: (1) the exhaustive ring opening of BTF with aromatic amine nucleophiles (performed in up to 91% yield) and (2) cyclisation with hexamethylenetetramine (performed in up to 75% yield). Additionally, stepwise ring opening of BTF allows synthesis of phloroglucinol intermediates with two unique aryl amide substituents and ultimately Cs-symmetric AATs. Of the novel AATs prepared, three (including the Cs-symmetric hybrid) are effective gelators of chlorinated solvents (critical gelation concentration (CGC)=0.2-0.4 wt%) and one, with naphthyl substituents, forms translucent gels from aromatic solvents (CGC0.3 wt%). The combination of AATs with moderately electron-poor and electron-rich aromatic substituents results in functional complementarity and gelation at concentrations below what is required for the individual components. Electron microscopy of the gel morphologies shows high aspect ratio fibres underlying the gel network superstructures in most cases. Polarised optical microscopy has allowed imaging of representative native organogel phases, and reveals striking morphology differences between gels that also share different optical and/or thermal stability properties.

  DOI：

  10.1080/10610278.2010.500733
• 作为产物：
  描述：

  2,2',2''-(2,4,6-trihydroxybenzene-1,3,5-triyl)triacetic acid 在 PPA 作用下， 反应 16.0h， 以46%的产率得到benzotrifuranone
  参考文献：
  名称：

  Benzotrifuranone: Synthesis, Structure, and Access to Polycyclic Heteroaromatics

  摘要：

  Functionalized benzotrifurans can be accessed in one efficient acylation step from previously unreported benzotrifuranone. DFT calculations have confirmed the aromaticity of the heteroaromatic system and determined its electronic structure that is relevant to applications in materials and supramolecular chemistry.

  DOI：

  10.1021/ol901631n

文献信息

• Seven-Membered Intramolecular Hydrogen Bonding of Phenols: Database Analysis and Phloroglucinol Model Compounds
  作者：Ronald K. Castellano、Yan Li、Edwin A. Homan、Andrew J. Lampkins、Iris V. Marín、Khalil A. Abboud

  DOI：10.1002/ejoc.201200438

  日期：2012.8

  intramolecular hydrogen bonding (7MHB) arrangements involving phenolic hydroxyl group donors have been investigated through Cambridge Structural Database (CSD) and literature mining, and by the characterization of model compounds. The CSD reveals the numerous H-bond accepting functional groups that can participate in 7MHB when they are proximal to a phenolic OH, including alcohols, amides, amines, ethers, N-containing

  已经通过剑桥结构数据库 (CSD) 和文献挖掘以及模型化合物的表征研究了涉及酚羟基供体的七元分子内氢键 (7MHB) 排列。CSD 揭示了在接近酚 OH 时可以参与 7MHB 的众多 H 键接受官能团，包括醇、酰胺、胺、醚、含氮杂环、酮、N-氧化物、磷酸盐和磷烷氧化物. HB 接触定义为 Ophenol...N 和 Ophenol...O 距离约。2.7 A，以及落在典型肽γ-转角范围内的两个二面角。已鉴定的 7MHB 基序中的两个已很容易映射到间苯三酚（1,3,5-三羟基苯）支架上，以提供八种模型化合物；涉及所有三个羟基的分子内氢键显示在溶液中和化合物的固态中持续存在。分子内 7MHB 强制执行非平面构象，这在设计分子主体和催化剂时应该很有用。
• A small molecule multi-FRET platform from benzotrifuranone
  作者：Ashton N. Bartley、Sadie F. DePeter、Ronald K. Castellano

  DOI：10.1016/j.dyepig.2023.111732

  日期：2023.12

  investigation of the first molecular multi-FRET system from the benzotrifuranone (BTF) scaffold. The step-conservative synthetic approach to the representative target exploits the sequential aminolysis reactivity of BTF, together with CuAAC, for installation of three optically complementary chromophores, naphthalene, pyrene, and coumarin (1). Studied in parallel are two sets of three single- and double-dye comparator

  报道了第一个基于苯并三呋喃酮 (BTF) 支架的分子多 FRET 系统的制备和光物理研究。针对代表性靶标的逐步保守合成方法利用BTF 与 CuAAC 的连续氨解反应性，安装三种光学互补的发色团：萘、芘和香豆素 (1)。并行研究的是两组三个单染料和双染料比较分子。目标的荧光发射的特征在于~80%的能量转移效率和~170 nm的伪斯托克斯位移。该设计应适应其他发色团组和将染料三联体共价连接到表面和/或基材上，用于材料或生命科学中的应用。
• Rapid access to <i>C</i> ₃- and <i>C</i> _s-symmetric AAT organogelators via ring opening of a common benzotrifuranone precursor
  作者：Matthew B. Baker、Ling Yuan、Christopher J. Marth、Yan Li、Ronald K. Castellano

  DOI：10.1080/10610278.2010.500733

  日期：2010.11.1

  Presented is a rapid and general approach to functionalised 1-aza-adamantanetrione (AAT) donor-sigma-acceptor molecules from a phloroglucinol-derived trilactone, benzotrifuranone (BTF). Ten C3-symmetric AATs bearing diverse aryl amide substituents are accessed in two synthetic steps: (1) the exhaustive ring opening of BTF with aromatic amine nucleophiles (performed in up to 91% yield) and (2) cyclisation with hexamethylenetetramine (performed in up to 75% yield). Additionally, stepwise ring opening of BTF allows synthesis of phloroglucinol intermediates with two unique aryl amide substituents and ultimately Cs-symmetric AATs. Of the novel AATs prepared, three (including the Cs-symmetric hybrid) are effective gelators of chlorinated solvents (critical gelation concentration (CGC)=0.2-0.4 wt%) and one, with naphthyl substituents, forms translucent gels from aromatic solvents (CGC0.3 wt%). The combination of AATs with moderately electron-poor and electron-rich aromatic substituents results in functional complementarity and gelation at concentrations below what is required for the individual components. Electron microscopy of the gel morphologies shows high aspect ratio fibres underlying the gel network superstructures in most cases. Polarised optical microscopy has allowed imaging of representative native organogel phases, and reveals striking morphology differences between gels that also share different optical and/or thermal stability properties.
• Benzotrifuranone: Synthesis, Structure, and Access to Polycyclic Heteroaromatics
  作者：Yan Li、Andrew J. Lampkins、Matthew B. Baker、Bobby G. Sumpter、Jingsong Huang、Khalil A. Abboud、Ronald K. Castellano

  DOI：10.1021/ol901631n

  日期：2009.10.1

  Functionalized benzotrifurans can be accessed in one efficient acylation step from previously unreported benzotrifuranone. DFT calculations have confirmed the aromaticity of the heteroaromatic system and determined its electronic structure that is relevant to applications in materials and supramolecular chemistry.