5-trifluoromethyl-2-(pyridin-4-yl)benzo[d]thiazole | 51643-59-5

• 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-trifluoromethyl-2-(pyridin-4-yl)benzo[d]thiazole
• 英文别名: 2-pyridin-4-yl-5-trifluoromethyl-benzothiazole；4-(5-Trifluoromethylbenzothiazol-2-yl)pyridine；5-Trifluoromethyl-2-(4-pyridyl)benzothiazol；2-pyridin-4-yl-5-(trifluoromethyl)-1,3-benzothiazole
• CAS: 51643-59-5
• 化学式: C₁₃H₇F₃N₂S
• 分子量: 280.273
• InChiKey: NQDGBYORSXLNBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-trifluoromethyl-2-(pyridin-4-yl)benzo[d]thiazole 、 溴甲苯 、 硼氢化钠 在 crude product 、 乙酸乙酯 、 petroleum ether 作用下， 以afforded the title compound as a pale yellow solid (7 g, 47%)的产率得到1-Benzyl-4-(5-trifluoromethylbenzothiazol-2-yl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Tetrahydropyridine derivatives as dopamine receptor subtype ligands

  摘要：

  一类1,2,3,6-四氢吡啶衍生物，其在4-位被融合的双环杂芳基团取代，在1-位被一个可选择取代的苄基团取代，是体内多巴胺受体亚型的配体，特别是D.sub.4亚型，因此在治疗和/或预防多巴胺系统疾病，特别是精神分裂症或抑郁症方面有用。

  公开号：

  US05849765A1
• 作为产物：
  描述：

  4-甲基吡啶 、 4-氯-3-硝基三氟甲苯 在 sulfur 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以85%的产率得到5-trifluoromethyl-2-(pyridin-4-yl)benzo[d]thiazole
  参考文献：
  名称：

  Nitro-Methyl Redox Coupling: Efficient Approach to 2-Hetarylbenzothiazoles from 2-Halonitroarene, Methylhetarene, and Elemental Sulfur

  摘要：

  A simple, straightforward, and atom economic approach to 2-hetarylbenzothiazoles starting from 2-halonitroarene, methylhetarene, and elemental sulfur under mild conditions is described. The method is highlighted by the direct redox nitro-methyl reaction for carbon-nitrogen bond formation without an added oxidizing or reducing agent.

  DOI：

  10.1021/ol401944a

文献信息

• Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities.
  作者：TAKUZO HISANO、MASATAKA ICHIKAWA、KONOSUKE TSUMOTO、MASANOBU TASAKI

  DOI：10.1248/cpb.30.2996

  日期：——

  Benzoxazoles, benzothiazoles and benzimidazoles having substituents on the azole and benzene nuclei were synthesized evaluated for antifungal, insecticidal and herbicidal activities. It was found that benzimidazoles tended to exhibit antifungal activity while benzothiazoles tended to show herbicidal activity. Chloro, trifluoromethyl, methoxy and ethoxy groups at the 5 position were potent substituents, and the 2-pyridyl group at the 2 position is a common structural unit. Among several active derivatives, 7-chloro-2-(2-pyridyl) benzimidazole and 2-(2-pyridyl)-5-trifluoromethylbenzothiazole exhibited significant activity against Panonycus citri.

  合成了在偶氮和苯环上具有取代基的苯并噁唑、苯并噻唑和苯并咪唑，并评估其抗真菌、杀虫和除草活性。研究发现，苯并咪唑倾向于表现出抗真菌活性，而苯并噻唑则倾向于显示除草活性。在5位位置上的氯、三氟甲基、甲氧基和乙氧基基团是有效的取代基，而在2位位置的吡啶基是一个常见的结构单元。在几种具有活性的衍生物中，7-氯-2-(2-吡啶基)苯并咪唑和2-(2-吡啶基)-5-三氟甲基苯并噻唑对柑橘红蜘蛛表现出显著活性。
• IMAGING AGENTS AND THEIR USE FOR THE DIAGNOSTIC IN VIVO OF NEURODEGENERATIVE DISEASES, NOTABLY ALZHEIMER'S DISEASE AND DERIVATIVE DISEASES
  申请人：Guerbet

  公开号：EP2501696B1

  公开（公告）日：2016-12-28
• US5849765A
  申请人：——

  公开号：US5849765A

  公开（公告）日：1998-12-15
• Nitro-Methyl Redox Coupling: Efficient Approach to 2-Hetarylbenzothiazoles from 2-Halonitroarene, Methylhetarene, and Elemental Sulfur
  作者：Thanh Binh Nguyen、Ludmila Ermolenko、Ali Al-Mourabit

  DOI：10.1021/ol401944a

  日期：2013.8.16

  A simple, straightforward, and atom economic approach to 2-hetarylbenzothiazoles starting from 2-halonitroarene, methylhetarene, and elemental sulfur under mild conditions is described. The method is highlighted by the direct redox nitro-methyl reaction for carbon-nitrogen bond formation without an added oxidizing or reducing agent.
• Tetrahydropyridine derivatives as dopamine receptor subtype ligands
  申请人：Merck Sharp & Dohme, Ltd.

  公开号：US05849765A1

  公开（公告）日：1998-12-15

  A class of 1,2,3,6-tetrahydropyridine derivatives, substituted in the 4-position by a fused bicyclic heteroaromatic moiety and in the 1-position by an optionally substituted benzyl moiety, are ligands for dopamine receptor subtypes within the body, in particular the D.sub.4 subtype, and are therefore useful in the treatment and/or prevention of disorders of the dopamine system, in particular schizophrenia or depression.

  一类1,2,3,6-四氢吡啶衍生物，其在4位被融合的双环杂芳基取代，并在1位被可选择取代的苄基取代，是体内多巴胺受体亚型的配体，特别是D.sub.4亚型，因此在治疗和/或预防多巴胺系统紊乱，特别是精神分裂症或抑郁症方面具有用处。