5,6-difluoro-1,3-benzothiazole-2(3H)-thione | 786657-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5,6-difluoro-1,3-benzothiazole-2(3H)-thione
• 英文别名: 5,6-difluorobenzo[d]thiazole-2(3H)-thione；2(3H)-Benzothiazolethione, 5,6-difluoro-；5,6-difluoro-3H-1,3-benzothiazole-2-thione
• CAS: 786657-48-5
• 化学式: C₇H₃F₂NS₂
• 分子量: 203.236
• InChiKey: OGBDLZKYOMVRGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  296.7±50.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-difluoro-1,3-benzothiazole-2(3H)-thione 在 ammonium hydroxide 、 sodium hypochlorite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.75h， 生成 5,6-difluoro-2-(methylthio)benzothiazole
  参考文献：
  名称：

  Water Networks Contribute to Enthalpy/Entropy Compensation in Protein–Ligand Binding

  摘要：

  The mechanism (or mechanisms) of enthalpy-entropy (HIS) compensation in protein ligand binding remains controversial, and there are still no predictive models (theoretical or experimental) in which hypotheses of ligand binding can be readily tested. Here we describe a particularly well-defined system of protein and ligands-human carbonic anhydrase (HCA) and a series of benzothiazole sulfonamide ligands with different patterns of fluorination-that we use to define enthalpy/entropy (HIS) compensation in this system thermodynamically and structurally. The binding affinities of these ligands (with the exception of one ligand, in which the deviation is understood) to HCA are, despite differences in fluorination pattern, indistinguishable; they nonetheless reflect significant and compensating changes in enthalpy and entropy of binding. Analysis reveals that differences in the structure and thermodynamic properties of the waters surrounding the bound ligands are an important contributor to the observed H/S compensation. These results support the hypothesis that the molecules of water filling the active site of a protein, and surrounding the ligand, are as important as the contact interactions between the protein and the ligand for biomolecular recognition, and in determining the thermodynamics of binding.

  DOI：

  10.1021/ja4075776
• 作为产物：
  描述：

  2,4,5-三氟苯胺 、 potassium ethyl xanthogenate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以88%的产率得到5,6-difluoro-1,3-benzothiazole-2(3H)-thione
  参考文献：
  名称：

  聚卤代苯胺与钾/ O-乙基黄原酸钠的邻位选择性亲核芳香取代反应：方便地获得卤代的2（3 H）-苯并噻唑硫酮

  摘要：

  带有邻卤原子的聚卤苯胺在相对温和的温度下（95-120°C）与阴离子硫亲核试剂进行平滑的亲核芳族取代反应。这些反应非常有效且具有高邻位选择性。以O-乙基黄原酸钾/钠为亲核试剂，随后的环化反应以高收率提供卤代的2（3 H）-苯并噻唑硫酮（2-巯基苯并噻唑）。

  DOI：

  10.1021/jo049056s

文献信息

• Highly efficient synthesis of polyfluorinated 2-mercaptobenzothiazole derivatives
  作者：Larisa Politanskaya、Zequn Duan、Irina Bagryanskaya、Ilia Eltsov、Evgeny Tretyakov、Chanjuan Xi

  DOI：10.1016/j.jfluchem.2018.06.001

  日期：2018.8

  A convenient and efficient method for the synthesis of polyfluorinated 2-mercaptobenzothiazoles from the corresponding aniline derivatives and CS2, mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in toluene is described. The reaction proceeded via nucleophilic attack at the carbon atom of carbon disulfide by the nitrogen atom of NH2-group in arene followed by selective intramolecular fluorine

  描述了一种方便有效的方法，由甲苯中的1,8-二氮杂双环[5.4.0]十一烷基-7-烯（DBU）介导，由相应的苯胺衍生物和CS 2合成多氟2-巯基苯并噻唑。该反应通过芳烃中NH 2-的氮原子在二硫化碳的碳原子上的亲核攻击而进行，然后在邻位上选择性地将分子内氟原子取代为氨基。该合成方法可用于以良好或优异的产率制备含炔基的氟化2-巯基苯并噻唑。该反应在非常温和的反应条件（50℃）下进行，并使用容易获得的原料。
• Enantioselective Synthesis of Axially Chiral Biaryls via Copper-Catalyzed Thiolation of Cyclic Diaryliodonium Salts
  作者：Kai Zhu、Yi Wang、Qi Fang、Zongqiang Song、Fengzhi Zhang

  DOI：10.1021/acs.orglett.9b04555

  日期：2020.3.6

  Here, we report a chiral copper(II)-bisoxazoline-catalyzed enantioselective ring opening of cyclic diaryliodonium salts with heteroaryl thiols. The readily available 2-mercaptobenzoxazole and 2-mercaptobenzothiazole derivatives reacted efficiently with cyclic diaryliodonium salts and afforded various axially chiral biaryls bearing iodine and sulfur functional groups in excellent yields and enantioselectivities

  在这里，我们报告的手性铜（II）-双恶唑啉催化的环状二芳基碘鎓盐与杂芳基硫醇的对映选择性开环。容易获得的2-巯基苯并恶唑和2-巯基苯并噻唑衍生物与环状二芳基碘鎓盐有效反应，并以优异的产率和对映选择性提供了各种带有碘和硫官能团的轴向手性联芳基。将产物进一步转化为多种对映体纯的烷基联芳基硫醚，其可用作手性配体。
• HETEROARYL DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
  申请人：Knust Henner

  公开号：US20090163485A1

  公开（公告）日：2009-06-25

  The present invention relates to compounds of formula wherein Ar, Het, R 1 and n are as defined herein and to pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixtures thereof. Compounds of formula I are orexin receptor antagonists and are useful in the treatment of sleep apnea, narcolepsy, insomnia, parasomnia, jet lag syndrome, circadian rhythms disorder and sleep disorders associated with neurological diseases.

  本发明涉及以下公式的化合物，其中Ar，Het，R1和n的定义如本文所述，并且涉及适用于药物的酸盐、光学纯对映体、拉氏体或其二对映异构体混合物。公式I的化合物是促进睡眠激素受体拮抗剂，可用于治疗睡眠呼吸暂停症、嗜睡症、失眠、睡眠障碍、时差综合症、昼夜节律紊乱和与神经系统疾病相关的睡眠障碍。
• Heteroaryl derivatives as orexin receptor antagonists
  申请人：Hoffmann-La Roche Inc.

  公开号：US07897627B2

  公开（公告）日：2011-03-01

  The present invention relates to compounds of formula wherein Ar, Het, R1 and n are as defined herein and to pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixtures thereof. Compounds of formula I are orexin receptor antagonists and are useful in the treatment of sleep apnea, narcolepsy, insomnia, parasomnia, jet lag syndrome, circadian rhythms disorder and sleep disorders associated with neurological diseases.

  本发明涉及式I的化合物，其中Ar，Het，R1和n的定义如本文所述，以及药学上适宜的酸盐加成物，光学纯对映体，外消旋体或其间异构体混合物。式I的化合物是促进睡眠的受体拮抗剂，可用于治疗睡眠呼吸暂停症，嗜睡症，失眠症，睡眠障碍，时差综合症，昼夜节律紊乱和与神经系统疾病相关的睡眠障碍。
• Neue 2-Mercaptothiazolderivate, Verfarhen zu deren Herstellung sowie die Verwendung von 2-Mercaptothiazolderivaten in Arzneimitteln
  申请人：BAYER AG

  公开号：EP0137426A2

  公开（公告）日：1985-04-17

  Die vorliegende Erfindung betrifft neue 2-Mercaptothiazolderivate, Verfahren zu ihrer Herstellung sowie die Verwendung von 2-Mercaptothiazolderivaten in Arzneimitteln, insbesondere in thromboembolischen Mitteln.

  本发明涉及新的 2-巯基噻唑衍生物、其制备工艺以及 2-巯基噻唑衍生物在药物中的用途，特别是在血栓栓塞剂中的用途。