2-(4-nitrophenyl)-5-(trifluoromethyl)benzothiazole | 1564084-31-6

• 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: 2-(4-nitrophenyl)-5-(trifluoromethyl)benzothiazole
• 英文别名: 2-(4-nitrophenyl)-5-(trifluoromethyl)benzo[d]thiazole；2-(4-Nitrophenyl)-5-(trifluoromethyl)-1,3-benzothiazole；2-(4-nitrophenyl)-5-(trifluoromethyl)-1,3-benzothiazole
• CAS: 1564084-31-6
• 化学式: C₁₄H₇F₃N₂O₂S
• 分子量: 324.283
• InChiKey: NOWQHDRUEYRYJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-5-(trifluoromethyl)benzothiazole 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到4-[5-(三氟甲基)-1,3-苯并噻唑-2-基]苯胺
  参考文献：
  名称：

  Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection

  摘要：

  A series of 2-arylbenzothiazole derivatives have been prepared as fluorogenic enzyme substrates in order to detect aminopeptidase, esterase, phosphatase and beta-galactosidase activity in clinically important Gram-negative and Gram-positive bacteria. Substrates were incorporated into an agar-based culture medium and this allowed growth of intensely fluorescent bacterial colonies based on hydrolysis by specific enzymes. Substrate 20 targeted L-alanine aminopeptidase activity and was hydrolysed exclusively by a range of Gram-negative bacteria and inhibited the growth of a range of Gram-positive bacteria. Substrate 19a targeted beta-alanyl aminopeptidase activity and generated fluorescent colonies of selected Gram-negative species including Pseudomonas aeruginosa. Substrate 21b targeted C8-esterase activity and resulted in strongly fluorescent colonies of selected species known to harbour such enzyme activity (e. g., Salmonella and Pseudomonas). Most Gram-negative species produced colonies with an intense blue fluorescence due to hydrolysis of phosphatase substrates 24a-c and substrate 24c was also hydrolysed by strains of Staphylococcus aureus. Compounds 26b and 26c targeted beta-galactosidase activity and generated strongly fluorescent colonies with coliform bacteria that produced this enzyme (e. g., Escherichia coli). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.013
• 作为产物：
  描述：

  2-氨基-4-(三氟甲基)苯硫酚盐酸盐 在 四氯苯醌 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 2-(4-nitrophenyl)-5-(trifluoromethyl)benzothiazole
  参考文献：
  名称：

  Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection

  摘要：

  A series of 2-arylbenzothiazole derivatives have been prepared as fluorogenic enzyme substrates in order to detect aminopeptidase, esterase, phosphatase and beta-galactosidase activity in clinically important Gram-negative and Gram-positive bacteria. Substrates were incorporated into an agar-based culture medium and this allowed growth of intensely fluorescent bacterial colonies based on hydrolysis by specific enzymes. Substrate 20 targeted L-alanine aminopeptidase activity and was hydrolysed exclusively by a range of Gram-negative bacteria and inhibited the growth of a range of Gram-positive bacteria. Substrate 19a targeted beta-alanyl aminopeptidase activity and generated fluorescent colonies of selected Gram-negative species including Pseudomonas aeruginosa. Substrate 21b targeted C8-esterase activity and resulted in strongly fluorescent colonies of selected species known to harbour such enzyme activity (e. g., Salmonella and Pseudomonas). Most Gram-negative species produced colonies with an intense blue fluorescence due to hydrolysis of phosphatase substrates 24a-c and substrate 24c was also hydrolysed by strains of Staphylococcus aureus. Compounds 26b and 26c targeted beta-galactosidase activity and generated strongly fluorescent colonies with coliform bacteria that produced this enzyme (e. g., Escherichia coli). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.013

文献信息

• Synthesis of Quinazolinones and Benzothiazoles Using α-Keto Acids under Ball Milling
  作者：Anoop Sharma、Jitender Singh、Anuj Sharma

  DOI：10.1021/acs.joc.3c02435

  日期：2024.4.19

  (23 derivatives) and benzothiazoles (23 derivatives) has been developed through stainless-steel-driven decarboxylative acyl radical generation from α-keto acids. A library of 2-arylquinazolinones and 2-arylbenzothiazoles has been prepared in moderate to good yields at room temperature. Moreover, control experiments and XPS studies supported the reduction (by zerovalent iron) of molecular oxygen through

  机械化学是指通过机械力（例如铣削、研磨或剪切）引发化学反应以实现化学转变。作为机械催化的体现，本文通过不锈钢驱动的 α-酮酸脱羧酰基自由基生成，开发了一种无氧化剂和无溶剂的喹唑啉酮（23 种衍生物）和苯并噻唑（23 种衍生物）的合成方法。 2-芳基喹唑啉酮和2-芳基苯并噻唑库已在室温下以中等至良好的产率制备。此外，控制实验和 XPS 研究支持通过球的适度磨损来还原分子氧（通过零价铁），从而通过 SET 过程促进超氧自由基阴离子的生成。
• Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection
  作者：Marie Cellier、Elizabeth Fazackerley、Arthur L. James、Sylvain Orenga、John D. Perry、Graeme Turnbull、Stephen P. Stanforth

  DOI：10.1016/j.bmc.2014.01.013

  日期：2014.2

  A series of 2-arylbenzothiazole derivatives have been prepared as fluorogenic enzyme substrates in order to detect aminopeptidase, esterase, phosphatase and beta-galactosidase activity in clinically important Gram-negative and Gram-positive bacteria. Substrates were incorporated into an agar-based culture medium and this allowed growth of intensely fluorescent bacterial colonies based on hydrolysis by specific enzymes. Substrate 20 targeted L-alanine aminopeptidase activity and was hydrolysed exclusively by a range of Gram-negative bacteria and inhibited the growth of a range of Gram-positive bacteria. Substrate 19a targeted beta-alanyl aminopeptidase activity and generated fluorescent colonies of selected Gram-negative species including Pseudomonas aeruginosa. Substrate 21b targeted C8-esterase activity and resulted in strongly fluorescent colonies of selected species known to harbour such enzyme activity (e. g., Salmonella and Pseudomonas). Most Gram-negative species produced colonies with an intense blue fluorescence due to hydrolysis of phosphatase substrates 24a-c and substrate 24c was also hydrolysed by strains of Staphylococcus aureus. Compounds 26b and 26c targeted beta-galactosidase activity and generated strongly fluorescent colonies with coliform bacteria that produced this enzyme (e. g., Escherichia coli). (C) 2014 Elsevier Ltd. All rights reserved.