2,3,4,5-tetrafluorobenzoyl isothiocyanate | 950725-15-2

• 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: 2,3,4,5-tetrafluorobenzoyl isothiocyanate
• 英文别名: Tetrafluorobenzoyl isothiocyanate
• CAS: 950725-15-2
• 化学式: C₈HF₄NOS
• 分子量: 235.162
• InChiKey: LUOJVMTUBQAGSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetrafluorobenzoyl isothiocyanate 在 三乙胺 作用下， 以 二甲基亚砜 、 甲苯 、 乙腈 为溶剂， 反应 11.0h， 生成 6,8-difluoro-2,7-dimorpholino-1,3-benzothiazin-4-one
  参考文献：
  名称：

  氟代2-环烷基亚胺基取代的1,3-苯并噻嗪-4-酮的合成及前庭评价

  摘要：

  通过将N-亲核试剂加到邻氟苯甲酰基异硫氰酸酯中，然后环化氟苯甲酰基-硫脲，获得了新型的氟化2-取代的1,3-苯并噻嗪-4-酮。已经发现了合成原始的2-环烷基亚氨基-和2-羰基哌嗪基取代的苯并噻嗪酮的合成方法，所述苯环中带有不同数目的氟原子。2-乙氧基羰基哌嗪子基-5-氟-1,3-苯并噻嗪-4-酮在体外具有较高的抗结核活性（MIC 0.7微克/毫升），因此表明在该杂环族中对生物活性化合物的搜寻似乎是一个合理的方法。

  DOI：

  10.1016/j.jfluchem.2019.02.009
• 作为产物：
  描述：

  ammonium thiocyanate 、 四氟苯甲酰氯 以 乙腈 为溶剂， 反应 0.08h， 生成 2,3,4,5-tetrafluorobenzoyl isothiocyanate
  参考文献：
  名称：

  Fluorinated 1,3-benzothiazin-4-ones containing fluoroquinolone fragment

  摘要：

  We have developed an efficient synthetic approach to potential antibacterial agents with double mechanism of action through the combination of antibacterial fluoroquinolones with 1,3-benzothiazin-4-ones.

  DOI：

  10.1007/s10593-019-02499-1

文献信息

• Polyfluorobenzoyl chlorides and isothiocyanates in reactions with CH-reactive benzimidazoles
  作者：E. V. Nosova、G. N. Lipunova、A. A. Laeva、V. N. Charushin

  DOI：10.1007/s11172-005-0312-6

  日期：2005.3

  Reactions of 2-benzoylmethylbenzimidazole with tetra- and pentafluorobenzoyl chlorides afford fluorine-containing 6-benzoyl-7H-benzimidazo[3,2-a]quinolones. 2-Cyanomethyl- or 2-benzoylmethylbenzimidazole reacts with tetra(penta) fluorobenzoyl isothiocyanates to give fluorine containing 1,3-benzothiazinones, which differently behave in reactions with cycloalkylimines.

  2-苯甲酰基甲基苯并咪唑与四氟和五氟苯甲酰氯反应得到含氟的 6-苯甲酰基-7H-苯并咪唑并[3,2-a]喹诺酮。2-氰基甲基或 2-苯甲酰基甲基苯并咪唑与四（五）氟苯甲酰基异硫氰酸酯反应生成含氟的 1,3-苯并噻嗪酮，其在与环烷基亚胺的反应中表现不同。
• BENZOTHIAZINETHIONE DERIVATIVES AND PREPARATION METHODS AND USES THEREOF
  申请人：Yu Luoting

  公开号：US20140303152A1

  公开（公告）日：2014-10-09

  Benzothiazinethione derivatives of formula (I), their preparative methods and uses are provided. Benzothiazinethione derivatives of the invention have significant effect of inhibiting Mycobacterium tuberculosis .

  本发明提供了式（I）的苯并噻唑硫酮衍生物，其制备方法和用途。该发明的苯并噻唑硫酮衍生物具有显著抑制结核分枝杆菌的作用。
• BENZOTHIAZINETHIONE DERIVATIVES AND THEIR PREPARATIVE METHODS AND USES
  申请人：Si Chuan University

  公开号：EP2719691A1

  公开（公告）日：2014-04-16

  The invention belongs to the medicine field, and particularly relates to benzothiazinethione derivatives and preparation methods and uses thereof. In the aspect of the present invention, novel benzothiazinethione derivatives of formula I are provided, the benzothiazinethione derivatives of the invention are new compounds obtained based on extensive screening. Experimental results show that the benzothiazinethione derivatives of formula I have obvious inhibitory effects on mycobacterium tuberculosis, with effects equivalent to or even better than that of isoniazide (MIC90=0.8µM). The benzothiazinethione derivatives of formula I have anti-mycobacterium tuberculosis activities, and provide new choices for the development and application of antitubercular agents.

  该发明属于医学领域，特别涉及苯并噻唑硫酮衍生物及其制备方法和用途。根据本发明的方面，提供了新型的化学式I的苯并噻唑硫酮衍生物，该发明的苯并噻唑硫酮衍生物是基于广泛筛选获得的新化合物。实验结果表明，化学式I的苯并噻唑硫酮衍生物对结核分枝杆菌具有明显的抑制作用，其效果相当于甚至优于异烟肼（MIC90=0.8µM）。化学式I的苯并噻唑硫酮衍生物具有抗结核分枝杆菌活性，并为抗结核药物的开发和应用提供了新选择。
• Synthesis of Fluorine-Containing 2-Pyrrolyl- and 2-Indolyl-Substituted 1,3-Benzothiazin-4-ones
  作者：E. V. Nosova、A. D. Poteeva、G. N. Lipunova、P. A. Slepukhin、V. N. Charushin

  DOI：10.1134/s1070428019030205

  日期：2019.3

  New 2-(1-methyl-1H-pyrrol-2-yl)- and 2-(1-methyl-1H-indol-3-yl)-5-fluoro- and -6,7,8-trifluoro-1,3-benzothiazin-4-ones have been synthesized in high yields by reaction of o-fluorobenzoyl isothiocyanates with C-nucleophilic 1-methyl-1H-pyrrole and 1-methyl-1H-indole, followed by base-catalyzed cyclization. The products were characterized by 1H, 13C, and 19F NMR and mass spectra and X-ray diffraction

  新的2-（1-甲基-1 H-吡咯-2-基）-和2-（1-甲基-1 H-吲哚-3-基）-5-氟-和-6,7,8-三氟-通过邻氟苯甲酰基异硫氰酸酯与C-亲核性1-甲基-1 H-吡咯和1-甲基-1 H-吲哚反应，然后进行碱催化的环化反应，已高收率合成了1,3-苯并噻嗪-4-酮。产物通过1 H，13 C和19 F NMR以及质谱和X射线衍射数据表征。
• Fluorine-containing heterocycles: XV. Reactions of polyfluorobenzoyl isothiocyanates with aminoazines and aminoazoles
  作者：E. V. Nosova、G. N. Lipunova、A. A. Laeva、V. N. Charushin

  DOI：10.1134/s1070428006100253

  日期：2006.10

  Reactions of tetra- and pentafluorobenzoyl isothiocyanates with aminoazoles and aminoazines led to the formation of fluorinated 1,3-benzothiazin-4-ones which reacted with cyclic amines in different ways. Replacement of the N=C=S fragment was observed in some reactions of polyfluorobenzoyl isothiocyanates with nucleophiles.