6-hydroxy-2-(4'-fluorophenyl)-1,3-benzothiazole | 142647-84-5

• 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: 6-hydroxy-2-(4'-fluorophenyl)-1,3-benzothiazole
• 英文别名: 2-(4-Fluorophenyl)-6-hydroxybenzothiazole；2-(4-fluorophenyl)-1,3-benzothiazol-6-ol
• CAS: 142647-84-5
• 化学式: C₁₃H₈FNOS
• 分子量: 245.277
• InChiKey: AMGGIBWEIGCKRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-methoxy-2-(4'-fluorophenyl)-1,3-benzothiazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到6-hydroxy-2-(4'-fluorophenyl)-1,3-benzothiazole
  参考文献：
  名称：

  Synthesis and Evaluation of ¹⁸F-Labeled 2-Phenylbenzothiazoles as Positron Emission Tomography Imaging Agents for Amyloid Plaques in Alzheimer’s Disease

  摘要：

  Imaging agents targeting amyloid beta(A beta) may be useful for early diagnosis and follow-up of treatment of patients with Alzheimer's disease (AD). Three of five tested 2-(4'-fluorophenyl)-1,3-benzothiazoles displayed high binding affinities for A beta plaques in AD human brain homogenates (K-i between 2.2 and 22.5 nM). They all contained the F-18-label directly attached to the aromatic ring and were synthesized starting from the nitro precursor. Determination of the partition coefficient, biodistribution studies in normal mice, and in vivo mu PET studies in normal rats showed that their initial brain uptake was high and brain washout was fast. The most promising compound [F-18]5, or 6- methyl-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole, seemed to be metabolically stable in the brain, and its plasma radiometabolites, which do not cross the blood-brain barrier, were determined. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as an A beta plaque imaging agent for the study of patients with AD.

  DOI：

  10.1021/jm8013376

文献信息

• Nucleophilic displacement method for synthesis of non-rigid PBZ polymers
  申请人：The Dow Chemical Company

  公开号：US05194562A1

  公开（公告）日：1993-03-16

  Azole rings, such as oxazole and thiazole rings, can activate an aromatic ring bonded to a leaving group such as a halogen atom so that the aromatic ring will undergo aromatic nucleophilic substitution. The reaction is useful for making ethers, thioethers and amines containing azole rings. In particular, monomers having azole rings, activated aromatic rings with leaving groups and nucleophilic moieties can react under conditions of aromatic nucleophilic displacement to form non-rigid rob PBZ polymers. The non-rigid rod PBZ polymers can be used to form molecular composites with rigid rod PBZ polymers which molecular composites are not substantially phase separated.

  唑环，如噁唑和噻唑环，可以激活与含卤原子等离子基团相结合的芳香环，从而使芳香环经历芳香亲核取代反应。该反应对于制备含有唑环的醚、硫醚和胺很有用。特别是，具有唑环、激活的含有离去基团的芳香环和亲核基团的单体可以在芳香亲核取代条件下反应，形成非刚性杆PBZ聚合物。非刚性杆PBZ聚合物可用于与刚性杆PBZ聚合物形成分子复合材料，这些分子复合材料基本上不会相分离。
• Monomers useful in nucleophilic displacement synthesis of polybenzazole
  申请人：The Dow Chemical Company

  公开号：US05216110A1

  公开（公告）日：1993-06-01

  Azole rings, such as oxazole and thiazole rings, can activate an aromatic ring bonded to a leaving group such as a halogen atom so that the aromatic ring will undergo aromatic nucleophilic substitution. The reaction is useful for making ethers, thioethers and amines containing azole rings. In particular, monomers having azole rings, activated aromatic rings with leaving groups and nucleophilic moieties can react under conditions of aromatic nucleophilic displacement to form non-rigid rod PBZ polymers. The non-rigid rod PBZ polymers can be used to form molecular composites with rigid rod PBZ polymers which molecular composites are not substantially phase separated.

  氮杂环类化合物，例如噁唑环和噻唑环，可以激活与卤素原子等离子基相连的芳香环，使得芳香环会经历芳香性亲核取代反应。该反应对于制备含有氮杂环的醚、硫醚和胺类化合物很有用。特别是，在芳香性亲核取代条件下，具有氮杂环、活化的含离去基的芳香环和亲核性官能团的单体可以反应，形成非刚性杆状PBZ聚合物。非刚性杆状PBZ聚合物可以用于与刚性杆状PBZ聚合物形成分子复合材料，这些分子复合材料没有明显的相分离。
• ISOTOYPICALLY-LABELED BENZOTHIAZOLE COMPOUNDS AS IMAGING AGENTS FOR AMYLOIDOGENIC PROTEINS
  申请人：Klunk William E.

  公开号：US20090142269A1

  公开（公告）日：2009-06-04

  The present invention provides an isolated linezolid impurity, desfluoro linezolid, the preparation thereof and its use as a reference standard.

  本发明提供了一种分离的利奈唑酮杂质，去氟利奈唑酮，其制备方法及其用作参考标准的用途。
• NUCLEOPHILIC DISPLACEMENT METHOD FOR SYNTHESIS OF NON-RIGID PBZ POLYMERS
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0623115A1

  公开（公告）日：1994-11-09
• EP0623115A4
  申请人：——

  公开号：EP0623115A4

  公开（公告）日：1995-01-11