5-氯-2-(吡啶-4-基)苯并[d]噻唑 | 51643-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 5-氯-2-(吡啶-4-基)苯并[d]噻唑
• 英文名称: 5-chloro-2-(pyridin-4-yl)benzo[d]thiazole
• 英文别名: 5-chloro-2-(pyridin-4-yl)benzothiazole；5-chloro-2-pyridin-4-yl-1,3-benzothiazole
• CAS: 51643-57-3
• 化学式: C₁₂H₇ClN₂S
• mdl: MFCD08234968
• 分子量: 246.72
• InChiKey: MSJOXDBWDRAALP-UHFFFAOYSA-N

物化性质

• 熔点：
  181 °C(Solv: ethanol (64-17-5))
• 沸点：
  423.7±51.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-氯-2-(吡啶-4-基)苯并[d]噻唑 在 甲醇 、 sodium tetrahydroborate 、 1-氯乙基氯甲酸酯 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(5-chlorobenzothiazol-2-yl)-1-(4-chlorobenzyl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  4-Heterocyclyl tetrahydropyridines as selective ligands for the human dopamine D4 receptor

  摘要：

  A series of 1,2,3,6-tetrahydropyridines 3 were synthesised, which resulted in selective high affinity dopamine Dq ligands. The SAR of heterocyclic replacements and aromatic substitution was investigated, leading to compounds of nanomolar binding affinity with excellent selectivity over both D-2 and D-3 receptors. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00402-2
• 作为产物：
  描述：

  4-甲氨基吡啶 、 2,5-二氯硝基苯 在 sulfur 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以70%的产率得到5-氯-2-(吡啶-4-基)苯并[d]噻唑
  参考文献：
  名称：

  A simple approach to benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine under solvent-free and catalyst-free conditions

  摘要：

  A novel solvent-free and catalyst-free synthesis of benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine has been developed. The reaction tolerated a wide range of functionalities, and various benzothiazoles were synthesized in moderate to good yields in the absence of external oxidant or reductant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.037

文献信息

• Transition-Metal-Free Synthesis of 2-Substituted Benzothiazoles from Nitrobenzenes, Methylheteroaryl Compounds, and Elemental Sulfur, Based on Nitro-Methyl Redox-Neutral Cyclization
  作者：Masahiro Teramoto、Mitsutaka Imoto、Motonori Takeda、Takumi Mizuno、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1021/acs.joc.0c02072

  日期：2020.12.4

  has been shown to promote the efficient synthesis of 2-substituted benzothiazoles from easily available nitrobenzenes, methyl-heteroaryl compounds, and elemental sulfur in the absence of transition-metal catalysts. The 2-substituted benzothiazoles were obtained in reasonable yields through the sulfuration of electron-deficient C–H bonds with elemental sulfur. This synthetic methodology also affords

  为了解决日益严重的环境污染和自然资源枯竭的问题，需要更绿色和更可持续的化学工艺。本文旨在利用氧化还原中性环化技术开发更绿色，更可持续的现代合成化学工艺。在没有过渡金属催化剂的情况下，氧化还原中性环化反应可促进由易得的硝基苯，甲基-杂芳基化合物和元素硫有效地合成2-取代的苯并噻唑。通过将缺电子的C–H键与元素硫进行硫化，可以以合理的收率获得2-取代的苯并噻唑。这种合成方法还无需使用任何外部氧化和/或还原试剂即可提供高原子经济性。
• Structure-property correlation of halogen substituted benzothiazole crystals
  作者：Nipun P. Thekkeppat、Labhini Singla、Srinu Tothadi、Priyadip Das、Angshuman Roy Choudhury、Soumyajit Ghosh

  DOI：10.1016/j.molstruc.2021.130765

  日期：2021.11

  We have synthesized 3 benzothiazole crystals (1–3) based on existing knowledge of combining flexibility and optical properties towards achieving applications for flexible optoelectronics. However, one crystal was found to be elastically bendable and was found to comply necessary packing features for elasticity. Other two crystals do not obey packing features for elasticity hence they are brittle in

  我们已经合成了 3 种苯并噻唑晶体 ( 1-3 )，基于现有知识，将柔韧性和光学特性相结合，以实现柔性光电子学的应用。然而，发现一种晶体是可弹性弯曲的，并且符合弹性所需的填充特征。其他两种晶体不服从弹性的堆积特征，因此它们本质上是脆的。此外，Hirshfeld 分析表明，与其他晶体相比，弹性晶体1具有更多的弱和色散相互作用。这些相互作用有助于产生弹性。此外，发现晶体1-3在特定激发波长下也发出荧光。因此，在这些晶体中，特别是晶体1被认为是柔性光电子学更有前途的候选者。
• 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。
• 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。
• 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.