2-methoxy-3,4,5,6-tetrafluorobenzoyl chloride | 358352-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-3,4,5,6-tetrafluorobenzoyl chloride
• 英文别名: 2,3,4,5-tetrafluoro-6-methoxybenzoyl chloride
• CAS: 358352-95-1
• 化学式: C₈H₃ClF₄O₂
• 分子量: 242.557
• InChiKey: FGZPFXIQVAUXNR-UHFFFAOYSA-N

物化性质

• 沸点：
  230.4±35.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methoxy-3,4,5,6-tetrafluorobenzoyl chloride 在 tetraphosphorus decasulfide 、 三溴化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 2-(3,4,5,6-tetrafluoro-2-hydroxyphenyl)-4,5,6,7-tetrafluorobenzothiazole
  参考文献：
  名称：

  Luminescent Zinc(II) Complexes of Fluorinated Benzothiazol-2-yl Substituted Phenoxide and Enolate Ligands

  摘要：

  Zn(II) complexes of the following new, fluorine-containing, benzothiazole-derived ligands have been synthesized and characterized crystallographically: 2-(3,3,3-trifluoro-2oxopropyl)benzothiazole (3), 4,5,6,7-tetrafluoro-2-(3,3,3-trifluoro-2-oxopropyl)benzothiazole (4), 4,5,6,7-tetrafluoro-2-(2hydroxyphenyl)benzothiazole (12), 2-(3,4,5,6-tetrafluoro-2-hydroxypheny1)-4,5,6,7-tetrafluorobenzothiazole (13), and 2(3,4,5,6-tetrafluoro-2-hydroxyphenyObenzothiazole (16); the Cu(II) complex of ligand 4 is also reported. These are analogs of the important photo- and electroluminescent material [Zn(BTZ)(2)](2), where H-BTZ = 2-(2-hydroxyphenyObenzothiazole. DFT calculations indicate that HOMO and LUMO energy levels in these materials are substantially lowered by fluorination. The fluorinated ZnL2 complexes are mononuclear (in contrast to the dinudear, nonfluorinated material [Zn(BTZ)(2)](2)). They easily sublime and show broad visible photoluminescence. A common crystallographic feature is the existence of pairs of fluorinated ZnL2 molecules related by inversion centers, with their pi systems facing one another.

  DOI：

  10.1021/ic302063u
• 作为产物：
  描述：

  2-methoxy-3,4,5,6-tetrafluorobenzoic acid 在 五氯化磷 作用下， 以85%的产率得到2-methoxy-3,4,5,6-tetrafluorobenzoyl chloride
  参考文献：
  名称：

  多氟水杨酸衍生物作为已知药物的类似物：合成，分子对接和生物学评估。

  摘要：

  我们已经开发了方便的合成多氟水杨酸及其衍生物的方法。首次在体外（通过生物膜的渗透性，COX-1抑制作用）和体内（抗炎，镇痛活性，急性毒性）研究了多氟水杨酸酯的生物学特性。在体外和体内实验中证实了多氟水杨酸酯的分子对接。

  DOI：

  10.1016/j.bmc.2016.10.014

文献信息

• A convenient and efficient approach to polyfluorosalicylic acids and their tuberculostatic activity
  作者：Evgeny V. Shchegol’kov、Irina V. Shchur、Yanina V. Burgart、Victor I. Saloutin、Sergey Yu. Solodnikov、Olga P. Krasnykh、Marionella A. Kravchenko

  DOI：10.1016/j.bmcl.2016.03.107

  日期：2016.5

  nucleophilic ortho-mono-substitution of fluorine atom with magnesium methoxide. We have managed to increase the yield of targeted polyfluorosalicylic acids from good to quantitative. We have studied the tuberculostatic activity of polyfluorosalicylic acids. It has been found that minimum inhibitory concentration (MIC) of compounds is from 0.7 to 6.5 μg/mL depending on the structure.

  我们已经开发了用于polyfluorosalicylic酸合成通过亲核的实际方法邻-单用甲醇镁氟原子的3'-取代。我们设法将目标多氟水杨酸的收率从良好提高到定量。我们已经研究了多氟水杨酸的抗结核活性。已经发现化合物的最小抑制浓度（MIC）为0.7至6.5μg/ mL，这取决于结构。
• Luminescent, highly halogenated 2-(2-hydroxyphenyl)benzothiazole derivatives and their zinc complexes
  作者：Lana Chawishli、Aya Ibrahim、Svitlana Karamshuk、Hana Khan、Majid Motevalli、Saltanat Toiganbayeva、Isaac Abrahams、William P Gillin、Peter B Wyatt

  DOI：10.1016/j.jfluchem.2023.110165

  日期：2023.8

  We have developed synthetic routes to new luminescent materials which are fully halogenated analogues of the zinc(II) complex of 2-(2-hydroxyphenyl)benzothiazole. 2,4-Difluoro-6-methoxybenzoyl chloride is a useful intermediate in this approach, which involves condensation with fluorinated arylamines to form the arylamide, cyclisation using P2S5, demethylation with BBr3 and halogenation to replace hydrogen

  我们开发了新型发光材料的合成路线，这些材料是 2-(2-羟基苯基)苯并噻唑锌 (II) 络合物的完全卤化类似物。2,4-二氟-6-甲氧基苯甲酰氯是该方法中有用的中间体，该方法涉及与氟化芳胺缩合形成芳酰胺，使用 P 2 S 5环化，使用 BBr 3脱甲基化以及卤化以取代酚环上存在的氢原子。当 2-氨基-1,3,4,5,6,7,8-七氟萘用作胺组分时，环化步骤导致 F-1 优先于 F-3 损失，从而形成角萘并[2,1- d]噻唑环系（通过X射线衍射和NMR证实）。与类似的全氟化材料相比，在特定位置引入氯和溴原子可以微调发射性能。
• Fluoroaryl containing β,β′-dioxoesters in the synthesis of fluorobenzopyran-4(2)-ones
  作者：S.P Kisil’、Ya.V Burgart、V.I Saloutin、O.N Chupakhin

  DOI：10.1016/s0022-1139(01)00346-3

  日期：2001.5

  Fluoroaryl containing beta, beta'-dioxoesters and their copper(II) chelates have been prepared by acylation of ethyl acetoacetate with 2,6-dimethoxy-3,4,5-trifluorobenzoyl, 2-methoxy-3,4,5,6-tetrafluorobenzoyl and pentafluorobenzoyl chlorides. Cyclization of these beta,beta'-dioxoesters leads to formation of substituted fluorochromones. Depending on conditions, 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzed to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. The same chromone reacts with morpholine to form a seven-substituted product and ammonium hydroxide to give 3-iminoacetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter affords 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin Ethyl-2-(2,6-dimethoxy-3,4,5-trifluorobenzoyl)-3-oxobutanoates undergoes ketone-splitting to 1-(2,6-dimethoxy-3,4,5-trifluorophenyl)-1.3-butandione. (C) 2001 Elsevier Science B.V. All rights reserved.
• ——
  作者：S. P. Kisil'、Ya. V. Burgart、V. I. Saloutin

  DOI：10.1023/a:1013479323203

  日期：——

  For the first time were obtained ethyl 2-(2-methoxy-3,4,5,6-tetrafluorobenzoyl)-3-oxobutanoate and ethyl 2-pentafluorobenzoyl-3-oxobutanoate and their copper chelates. The compounds were prepared by acylation of ethyl acetoacetate with 2-methoxy-3,4,5,6-tetrafluoro- and pentafluorobenzoyl chlorides. Cyclization of these beta,beta(1)-dioxoesters afforded substituted chromones. 2-Methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzes depending on reaction conditions either to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or to 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. Reaction with morpholine provided 7-substituted product, and with aqueous ammonia as a result of rearrangement forms 3-acetimidoyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter yields 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin.
• Polyfluorinated salicylic acid derivatives as analogs of known drugs: Synthesis, molecular docking and biological evaluation
  作者：E.V. Shchegol'kov、I.V. Shchur、Ya.V. Burgart、V.I. Saloutin、A.N. Trefilova、G.A. Ljushina、S.Yu. Solodnikov、L.N. Markova、V.V. Maslova、O.P. Krasnykh、S.S. Borisevich、S.L. Khursan

  DOI：10.1016/j.bmc.2016.10.014

  日期：2017.1

  We have developed the convenient methods for synthesis of polyfluorosalicylic acids and their derivatives. For the first time the biological properties of polyfluorosalicylates were investigated in vitro (permeability through the biological membranes, COX-1 inhibitory action) and in vivo (anti-inflammatory, analgesic activities, acute toxicity). Molecular docking of polyfluorinated salicylates confirmed

  我们已经开发了方便的合成多氟水杨酸及其衍生物的方法。首次在体外（通过生物膜的渗透性，COX-1抑制作用）和体内（抗炎，镇痛活性，急性毒性）研究了多氟水杨酸酯的生物学特性。在体外和体内实验中证实了多氟水杨酸酯的分子对接。