2-formyl-5-(4'-ethoxyphenyl)thiophene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-formyl-5-(4'-ethoxyphenyl)thiophene
• 英文别名: 5-(4-ethoxyphenyl)thiophene-2-carbaldehyde
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: URQWPOJCBGRYKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-formyl-5-(4'-ethoxyphenyl)thiophene 、 N-Boc-3-amino-L-tyrosine methyl ester 以 乙醇 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  带有杂芳族侧链的新型丙氨酸：具有金属相关性的金属阳离子的荧光化学传感的合成和研究。

  摘要：

  合成了一个新的噻吩苯并恶唑-5-基-1-丙氨酸家族，该丙氨酸核心在侧链带有苯并恶唑，在2位具有噻吩环，并用不同的（杂）芳基取代基取代，以研究对苯并恶唑的调节作用。所得化合物的光物理和化学感应特性。这些新的杂环丙氨酸3a-f和一系列结构相关的双-噻吩基苯并恶唑基丙氨酸3g-j首次进行了评估，以识别具有环境，医学和分析意义的选定金属阳离子，例如Co 2 +，Cu 2+，Zn 2+和Ni 2+在乙腈溶液中，侧链的杂环通过荧光变化同时充当配位和报告单位。这种行为可以通过电子给体杂原子通过金属阳离子的络合参与识别事件来解释。荧光光谱滴定表明，噻吩苯并恶唑基丙氨酸3a–j和4a，b是上述阳离子的非选择性荧光化学传感器，其中Cu 2+与双-丙氨酸3j和脱保护的丙氨酸4a的相互作用获得了最佳结果。，b。这些噻吩基苯并恶唑基丙氨酸具有令人鼓舞的光物理和金属离子感测特性，表明它们可用于获得生物启发的金属离子荧

  DOI：

  10.1007/s00726-018-2549-z
• 作为产物：
  描述：

  氯乙醛 、 β-chloro-β-(4-ethoxyphenyl)propenal 在 sodiumsulfide nonahydrate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 5.17h， 以80%的产率得到2-formyl-5-(4'-ethoxyphenyl)thiophene
  参考文献：
  名称：

  Synthesis and characterization of novel, thermally stable 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5′-dicyanovinyl-2,2′-bithiophenes as potentially promising non-linear optical materials

  摘要：

  Two series of dicyanovinyl-substituted compounds namely 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5'-dicyanovinyl-2,2'-bithiophenes were synthesized through Knoevenagel condensation of the corresponding 2-aryl-5-formyl-thiophenes and 5-aryl-5'-formyl-2,2'-bithiophene precursors. In contrast, the 2-aryl-5-formyl-thiophenes precursor were prepared through the Vilsmeier Haack Arnold reaction starting from inexpensive and easily available precursors such as acetophenones; this method produced the title compounds in higher yield than that recently reported which involved the Suzuki coupling of functionalized aryl boronic acids with 5-bromo-2-formyl-thiophene. Electrochemical studies and characterization of both the linear and non-linear optical properties and thermal properties indicated that good non-linearity was complemented by exceptional thermal stability for some chromophores, making them potential candidates for several optoelectronic applications such as solvatochromic probes and non-linear optical materials. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.01.006

文献信息

• 2-Arylthienyl-Substituted 1,3-Benzothiazoles as New Nonlinear Optical Chromophores
  作者：Susana P. G. Costa、Rosa M. F. Batista、Paulo Cardoso、Michael Belsley、Maria Manuela M. Raposo

  DOI：10.1002/ejoc.200600059

  日期：2006.9

  A series of nonlinear optical chromophores 6 containing a substituted benzothiazole ring have been synthesized and characterized. 1,3-Benzothiazoles 6 were prepared by treating various formyl derivatives of thienyl compounds withortho-aminobenzenethiol in fair to excellent yields. These in turn were prepared by Suzuki coupling between aryl and thienyl precursors. The electronic interactions between

  一系列含有取代苯并噻唑环的非线性光学发色团 6 已被合成和表征。1,3-苯并噻唑 6 是通过用邻氨基苯硫醇处理噻吩基化合物的各种甲酰基衍生物制备的，产率一般到极好。这些又是通过芳基和噻吩基前体之间的 Suzuki 偶联制备的。共轭 1,3-苯并噻唑 6 中供体和受体端基之间的电子相互作用由强烈且显着的溶剂化变色 CT 跃迁揭示。化合物 6 的溶剂化变色行为是通过在几种溶剂中吸收最大值的线性回归分析确定的，其中苯并噻唑 6f 被发现是一种非常合适的指示染料，其在脂肪族和偶极非质子溶剂以及芳香族和氯化溶剂中的吸收波数 (Δmax = 1590 cm-1) 与 Kamlet 和 Taft 定义的 π* 值非常相关。超瑞利散射用于测量上述化合物的第一超极化率 β。热重分析（TGA）用于评估它们的热稳定性。实验结果表明，发色团 6 具有良好的非线性和热稳定性，使其成为器件应用的良好候选者。(© Wiley-VCH
• [EN] INHIBITORS TARGETING DRUG-RESISTANT INFLUENZA A<br/>[FR] INHIBITEURS CIBLANT LA GRIPPE A PHARMACORÉSISTANTE
  申请人：UNIV PENNSYLVANIA

  公开号：WO2013086131A1

  公开（公告）日：2013-06-13

  Provided are compounds according to formula (la) or (lb) as described herein, that are capable of modulating the activity of influenza viruses (e.g., influenza A virus), for example, via interaction with the M2 transmembrane protein, and other similar viroporins. Also provided are methods for treating an influenza A-affected disease state or infection comprising administering a composition comprising one or more compounds according to according to formulas (la') or (lb), as described herein.

  根据本文描述的公式（la）或（lb），提供了一些化合物，这些化合物能够调节流感病毒（例如流感A病毒）的活性，例如通过与M2跨膜蛋白以及其他类似的病毒孔蛋白相互作用。还提供了一种治疗流感A感染疾病状态或感染的方法，包括通过给予包含根据本文描述的公式（la'）或（lb）的一个或多个化合物的组合物进行治疗。
• Fluorescence and two-photon absorption of push—pull aryl(bi)thiophenes: structure—property relationships
  作者：Emilie Genin、Vincent Hugues、Guillaume Clermont、Cyril Herbivo、M. Cidália R. Castro、Alain Comel、M. Manuela M. Raposo、Mireille Blanchard-Desce

  DOI：10.1039/c2pp25258a

  日期：2012.11

  Photophysical and TPA properties of series of push—pull aryl(bi)thiophene chromophores bearing electron-donating (D) and electron-withdrawing (A) end-groups of increasing strength are presented. All compounds show an intense intramolecular charge transfer (ICT) absorption band in the visible region. Increasing the D and/or A strength as well as the length of the conjugated path induces bathochromic and hyperchromic shifts of the absorption band as reported for analogous push—pull polyenes. Yet, in contrast with corresponding push—pull polyenes, a significant increase in fluorescence is observed. In particular, chromophores built from a phenyl—bithienyl conjugated path and bearing strong D and A end-groups were found to combine very large one and two-photon brightness as well as strong emission in the red/NIR region. These molecules hold promise as biphotonic fluorescent probes for bioimaging.

  本文介绍了一系列推拉芳基（双）噻吩发色团的光物理和 TPA 特性，这些发色团带有电子捐赠（D）和电子撤回（A）端基，其强度不断增加。所有化合物在可见光区域都显示出强烈的分子内电荷转移（ICT）吸收带。增加 D 和/或 A 的强度以及共轭路径的长度会引起吸收带的浴色和高色移，这与类似推挽多烯的情况相同。然而，与相应的推拉式多烯相比，荧光显著增加。特别是，由苯基-双噻吩共轭路径和带有强 D 和 A 端基的发色团被发现结合了非常大的单光子和双光子亮度，以及在红色/近红外区域的强发射。这些分子有望成为用于生物成像的双光子荧光探针。
• Non-canonical amino acids bearing thiophene and bithiophene: synthesis by an Ugi multicomponent reaction and studies on ion recognition ability
  作者：Cátia I. C. Esteves、M. Manuela M. Raposo、Susana P. G. Costa

  DOI：10.1007/s00726-017-2392-7

  日期：2017.5

  cations indicated that the bithienyl amino acid bearing a methoxy group is a selective colorimetric chemosensor for Cu2+, while the other (bi)thienyl amino acids act as fluorimetric chemosensors with high sensitivity towards Fe3+ and Cu2+ in a metal–ligand complex with 1:2 stoichiometry. The photophysical and ion sensing properties of these amino acids confirm their potential as fluorescent probes suitable

  通过杂环醛，胺，酸和异氰酸酯之间的多组分Ugi反应获得具有不同取代基的新的噻吩基和二噻吩基氨基酸。由于在侧链上存在硫杂环，这些非天然氨基酸具有很高的发射性，并带有额外的给电子原子，因此测试了它们在识别乙腈和乙腈中生物医学相关离子中作为荧光探针和化学传感器的能力。乙腈/水溶液。在有机和无机阴离子以及碱的存在下，通过分光光度法/分光荧光滴定法获得的结果；碱土金属和过渡金属阳离子表明，带有甲氧基的亚苄基氨基酸是Cu 2+的选择性比色化学传感器，而其他（联）噻吩基氨基酸充当荧光化学传感器，对化学配比为1：2的金属-配体络合物中的Fe 3+和Cu 2+具有高灵敏度。这些氨基酸的光物理和离子感测特性证实了它们作为适合掺入具有化学感应能力的肽构架的荧光探针的潜力。
• INHIBITORS TARGETING DRUG-RESISTANT INFLUENZA A
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：US20150191439A1

  公开（公告）日：2015-07-09

  Provided are compounds according to formula (Ia) or (Ib) as described herein, that are capable of modulating the activity of influenza viruses (e.g., influenza A virus), for example, via interaction with the M2 transmembrane protein, and other similar viroporins. Also provided are methods for treating an influenza A-affected disease state or infection comprising administering a composition comprising one or more compounds according to according to formulas (Ia′) or (Ib), as described herein.

  提供了符合公式（Ia）或（Ib）的化合物，可以通过与M2跨膜蛋白和其他类似的病毒孔蛋白相互作用，调节流感病毒（例如流感A病毒）的活性。还提供了一种治疗流感A受影响的疾病状态或感染的方法，包括给予含有一个或多个符合公式（Ia′）或（Ib）的化合物的组合物。