5-氟噻吩-2,3-二甲醛 | 1015071-22-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-氟噻吩-2,3-二甲醛
• 中文别名: 5-氟-2,3-噻吩二羧醛；5-氟代-2,3-噻吩二甲醛
• 英文名称: 5-fluorothiophene-2,3-dicarbaldehyde
• 英文别名: 5-Fluoro-2,3-thiophenedicarboxaldehyde
• CAS: 1015071-22-3
• 化学式: C₆H₃FO₂S
• mdl: MFCD15143649
• 分子量: 158.153
• InChiKey: UHZWVDHHMHBMDX-UHFFFAOYSA-N

物化性质

• 熔点：
  41-44°C
• 密度：
  1.485

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26
• 危险类别码：
  R22,R36
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-氟噻吩-2,3-二甲醛 在 sodium chlorite 、 水 作用下， 以 叔丁醇 为溶剂， 生成 5-fluorothiophene-2,3-dicarboxylic acid
  参考文献：
  名称：

  [EN] DHODH INHIBITORS CONTAINING A CARBOXYLIC ACID BIOISOSTERE
  [FR] INHIBITEURS DE DHODH CONTENANT UN BIOISOSTÈRE D'ACIDE CARBOXYLIQUE

  摘要：

  The invention relates to novel, optionally deuterated compounds of Formula (I) and their use as medicament.

  公开号：

  WO2023118576A1
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以3.6 g的产率得到5-氟噻吩-2,3-二甲醛
  参考文献：
  名称：

  Chromophore Fluorination Enhances Crystallization and Stability of Soluble Anthradithiophene Semiconductors

  摘要：

  We report dramatic improvements in the stability and crystallinity arising from partial fluorination of soluble anthradithiophene derivatives. These fluorinated materials still behave as p-type semiconductors but with dramatic increases in thermal and photostability compared to the non-fluorinated derivatives. The triethylsilyl-substituted material forms highly crystalline films even from spincast solutions, leading to devices with maximum hole mobility greater than 1.0 cm(2)N s. In contrast, the triisopropylsilyl derivative forms large, high-quality crystals that could serve as the substrate for transistor fabrication. For this compound, mobility as high as 0.1 cm(2)N S Was measured on the freestanding crystal.

  DOI：

  10.1021/ja073235k

文献信息

• Structural and Electronic Properties of Crystalline, Isomerically Pure Anthradithiophene Derivatives
  作者：Rawad K. Hallani、Karl J. Thorley、Yaochuan Mei、Sean R. Parkin、Oana D. Jurchescu、John E. Anthony

  DOI：10.1002/adfm.201502440

  日期：2016.4

  materials are typically synthesized as an inseparable mixture of syn and anti isomers. Recent syntheses of pure syn anthradithiophenes have shown no improvement in performance for the more homogeneous system, but similar studies on the pure anti isomer have not been reported. In this work, a simple protocol is described to prepare the pure anti isomer of fluorinated, functionalized anthradithiophenes, and perform

  蒽发色团在许多当前的高性能有机半导体发现，即使这些材料通常合成为一个不可分离的混合物顺式和反异构体。对于更均一的系统，最近合成的纯顺式蒽噻吩没有显示出性能上的改善，但是还没有关于纯抗异构体的类似研究的报道。在这项工作中，一个简单的协议描述，以制备纯的反氟化的，功能化的蒽噻吩的异构体，并对晶体中的分子间相互作用进行详细分析，从而产生增加的密度和更紧密的生色团接触。与同分异构体混合物相比，对这些纯异构体的电荷传输性质的研究表明，异构体纯度的益处并不一致。在顺式情况下，纯异构体和混合物之间的差异极小，而反异构体的迁移率则提高了近两倍。晶体中无序的分析表明了这种性能差异的原因。
• [EN] ANTIVIRAL AGENTS AND USES THEREOF<br/>[FR] AGENTS ANTIVIRAUX ET LEURS UTILISATIONS
  申请人：UNIV GRIFFITH

  公开号：WO2022160015A1

  公开（公告）日：2022-08-04

  The present invention relates to a compound of Formula (I), or a pharmaceutically acceptable salt thereof, and to pharmaceutical compositions comprising the compound. In Formula (I), rings W, X, Y and Z may relate to various heterocyclic, heteroaryl, cycloalkyl, cycloalkenyl, and/or aryl rings. The present invention also relates to uses of the compounds in treating a disease, disorder or condition caused by viral infection. (I) R3 is selected from the group consisting of:

  本发明涉及公式（I）的化合物或其药学上可接受的盐，以及包含该化合物的制药组合物。在公式（I）中，环W、X、Y和Z可能与各种杂环、杂芳基、环烷基、环烯基和/或芳香基相关。本发明还涉及使用该化合物治疗由病毒感染引起的疾病、障碍或病况。 (I) R3选自以下组中的一组：
• Novel Effective Fluorinated Benzothiophene-Indole Hybrid Antibacterials against S. aureus and MRSA Strains
  作者：Marius Seethaler、Tobias Hertlein、Elisa Hopke、Paul Köhling、Knut Ohlsen、Michael Lalk、Andreas Hilgeroth

  DOI：10.3390/ph15091138

  日期：——

  Increasing antibacterial drug resistance threatens global health, unfortunately, however, efforts to find novel antibacterial agents have been scaled back by the pharmaceutical industry due to concerns about a poor return on investment. Nevertheless, there is an urgent need to find novel antibacterial compounds to combat antibacterial drug resistance. The synthesis of novel drugs from natural sources is mostly cost-intensive due to those drugs’ complicated structures. Therefore, it is necessary to find novel antibacterials by simple synthesis to become more attractive for industrial production. We succeeded in the discovery of four antibacterial compound (sub)classes accessible in a simple one-pot reaction based on fluorinated benzothiophene-indole hybrids. They have been evaluated against various S. aureus and MRSA strains. Structure- and substituent-dependent activities have been found within the (sub)classes and promising lead compounds have been identified. In addition, bacterial pyruvate kinase was found to be the molecular target of the active compounds. In conclusion, simple one-pot synthesis of benzothiophene-indoles represents a promising strategy for the search of novel antimicrobial compounds.

  抗菌药耐药性的不断增加威胁着全球健康，但遗憾的是，由于担心投资回报率低，制药业已经缩减了寻找新型抗菌剂的努力。尽管如此，寻找新型抗菌化合物以对抗抗菌药耐药性的需求仍然十分迫切。由于天然药物结构复杂，从天然来源合成新型药物大多成本高昂。因此，有必要寻找简单合成的新型抗菌药物，以提高工业化生产的吸引力。我们以氟化苯并噻吩-吲哚杂化物为基础，通过简单的一锅反应成功发现了四种抗菌化合物（亚）类。我们对这些化合物进行了评估，以对抗各种金黄色葡萄球菌和 MRSA 菌株。在（亚）类化合物中发现了结构和取代基依赖性活性，并确定了有前景的先导化合物。此外，还发现细菌丙酮酸激酶是活性化合物的分子靶标。总之，苯并噻吩-吲哚的简单单锅合成是寻找新型抗菌化合物的一种有前途的策略。
• Tang, Ming L.; Reichardt, Anna D.; Wei, Peng, Journal of the American Chemical Society, 2009, vol. 131, p. 5264 - 5273
  作者：Tang, Ming L.、Reichardt, Anna D.、Wei, Peng、Bao, Zhenan

  DOI：——

  日期：——
• SILYLETHYNYLATED HETEROACENES AND ELECTRONIC DEVICES MADE THEREWITH
  申请人：University of Kentucky Research Foundation

  公开号：EP2132213B1

  公开（公告）日：2013-05-15