pyrene-1,8-dicarboxylic acid dimethyl ester | 224825-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: pyrene-1,8-dicarboxylic acid dimethyl ester
• 英文别名: dimethylpyrene-1,8-dicarboxylate；Dimethyl pyrene-1,8-dicarboxylate
• CAS: 224825-64-3
• 化学式: C₂₀H₁₄O₄
• 分子量: 318.329
• InChiKey: HNDDVYSKRPMZJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  pyrene-1,8-dicarboxylic acid dimethyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 溴 、 三乙胺 作用下， 以 四氢呋喃 、 硝基苯 为溶剂， 反应 1.0h， 生成 3,6-bis[(triisopropylsilyl)ethynyl]pyrene-1,8-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  用于两点连接的具有调谐光谱特性的多取代芘的合成

  摘要：

  芘衍生物广泛用作修饰核酸中的标记和构建单元。为了增加光谱应用的多样性，开发了不同取代衍生物的合成。合成了在 3 位和 6 位具有不同取代基的 1,8-芘二羧酸酯。吸收和稳态荧光研究表明，芘发色团的光物理性质可以由取代基的性质控制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600256
• 作为产物：
  描述：

  1,8-pyrenedicarboxylic acid 、 碘甲烷 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到pyrene-1,8-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  用于两点连接的具有调谐光谱特性的多取代芘的合成

  摘要：

  芘衍生物广泛用作修饰核酸中的标记和构建单元。为了增加光谱应用的多样性，开发了不同取代衍生物的合成。合成了在 3 位和 6 位具有不同取代基的 1,8-芘二羧酸酯。吸收和稳态荧光研究表明，芘发色团的光物理性质可以由取代基的性质控制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600256

文献信息

• 1-, 3-, 6-, and 8-Tetrasubstituted Asymmetric Pyrene Derivatives with Electron Donors and Acceptors: High Photostability and Regioisomer-Specific Photophysical Properties
  作者：Yosuke Niko、Shunsuke Sasaki、Kaishi Narushima、Dharmendar Kumar Sharma、Martin Vacha、Gen-ichi Konishi

  DOI：10.1021/acs.joc.5b01987

  日期：2015.11.6

  The systematic synthesis of five 1-, 3-, 6-, and 8-tetrasubstituted asymmetric pyrenes with electron donor and acceptor moieties is presented, together with an examination of their photophysical properties. Pyrene derivative PA1, containing one formyl and three piperidyl groups, showed bright solvatochromic fluorescence from green (lambda(em) = 557 nm, Phi(FL) = 0.94 in hexane) to red (lambda(em) = 648 nm, Phi(FL) = 0.50 in methanol), suggesting potential applications for PA1 as an environmentally responsive probe. Although the synthesis of simple 1- and 3-disubstituted pyrene derivatives is considered difficult, PA13, with two formyl groups at the 1- and 3-positions and two piperidyl groups at the 6- and 8-positions, could be synthesized successfully. PA13 exhibited less pronounced solvatochromism, but displayed a narrow fluorescent band with high Phi(FL) in all solvents (Phi(FL) > 0.75). Moreover, its absorption band displayed an exceptional bathochromic shift compared to the other derivatives (e.g., lambda(abs) = 480 and 522 nm in ethanol for PA1 and PA13, respectively), suggesting that such modifications of pyrene may be quite important for the modulation of its energy gap. Additionally, all compounds exhibited exceptionally high photostability, which highlights the advantage of these new dyes and provides new insights on the design of photostable fluorophores.
• Synthesis of Polysubstituted Pyrenes with Tuned Spectroscopic Properties for Two-Point Attachment
  作者：Vladimir L. Malinovskii、Robert Häner

  DOI：10.1002/ejoc.200600256

  日期：2006.8

  Pyrene derivatives find widespread use as labels and building blocks in modified nucleic acids. To increase the variety of spectroscopic applications, a synthesis of differently substituted derivatives was developed. 1,8-Pyrenedicarboxylates bearing different substituents in the 3- and 6-position were synthesized. Absorption and steady-state fluorescence studies showed that the photophysical properties

  芘衍生物广泛用作修饰核酸中的标记和构建单元。为了增加光谱应用的多样性，开发了不同取代衍生物的合成。合成了在 3 位和 6 位具有不同取代基的 1,8-芘二羧酸酯。吸收和稳态荧光研究表明，芘发色团的光物理性质可以由取代基的性质控制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)