6-(tert-butoxycarbonylamino)benzo[d]thiazole | 1192841-91-0

• 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-(tert-butoxycarbonylamino)benzo[d]thiazole
• 英文别名: 6-tert-butoxycarbonylaminobenzothiazole；tert-butyl N-(1,3-benzothiazol-6-yl)carbamate
• CAS: 1192841-91-0
• 化学式: C₁₂H₁₄N₂O₂S
• 分子量: 250.321
• InChiKey: VMNLVFZTBRRMNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(tert-butoxycarbonylamino)benzo[d]thiazole 在 [Cu(1,3-di-iso-propylimidazolin-2-ylidene)(Cl)] 、 potassium hydride 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 14.17h， 生成 2-tert-butoxycarbonylamino-6-(tert-butoxycarbonyl(methyl)amino)benzo[d]thiazole
  参考文献：
  名称：

  (NHC)Cu 催化的（杂）芳烃与可脱保护氨基甲酸酯的轻度 C-H 酰胺化：范围和机理研究

  摘要：

  芳基伯胺是合成、生物和材料科学中广泛存在的重要单元。在本文中，我们描述了 (NHC)Cu 系统的开发，该系统通过使用 N-氯代氨基甲酸酯或其钠衍生物作为实用的氨基源来介导（杂）芳烃的直接 CH 酰胺化。反应性铜-芳基中间体与酰胺化试剂的轻松化学计量反应使我们分离出关键的芳基氨基甲酸铜物种并形成 CN 键。(t)BuONa 碱的使用使这种转化在温和条件下具有催化作用。目前的 (NHC)Cu 催化的 CH 酰胺化在包括多氟苯、唑类和喹啉 N-氧化物在内的一系列芳烃上高效且选择性地大规模工作。

  DOI：

  10.1021/jacs.6b07486
• 作为产物：
  描述：

  6-氨基苯并噻唑 、 二碳酸二叔丁酯 在 zinc perchlorate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以93%的产率得到6-(tert-butoxycarbonylamino)benzo[d]thiazole
  参考文献：
  名称：

  Synthesis and Evaluation of Three ¹⁸F-Labeled Aminophenylbenzothiazoles as Amyloid Imaging Agents

  摘要：

  We have developed three fluorine-18 labeled 6-(methyl)amino-2-(4'-fluorophenyl)-1,3-benzothiazoles, which display high in vitro binding affinity For human amyloid beta plaques (K-i <= 10 nM). The radiolabeled F, robes were synthesized by aromatic nucleophilic Substitution of the corresponding nitro precursor with F-18-fluoride, followed by deprotection of the BOC group if required. Determination of the octanol/water partition coefficient, biodistribution studies In mice, and in vivo mu PET studies in rats and a rhesus monkey showed that initial brain uptake was high and brain washout was fast in normal animals. Radiometabolites were quantified in plasma and brain of mice and in monkey plasma using HPLC. Of the tested compounds, [F-18]2 (6-amino-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole) shows the most favorable brain kinetics in mice, rats, and a monkey. Its polar plasma radiometabolites do not cross the blood-brain barrier. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as a PET brain amyloid imaging agent.

  DOI：

  10.1021/jm900871v

文献信息

• (NHC)Cu-Catalyzed Mild C–H Amidation of (Hetero)arenes with Deprotectable Carbamates: Scope and Mechanistic Studies
  作者：Weilong Xie、Jung Hee Yoon、Sukbok Chang

  DOI：10.1021/jacs.6b07486

  日期：2016.9.28

  mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of (t)BuONa base made this transformation catalytic under mild conditions. The

  芳基伯胺是合成、生物和材料科学中广泛存在的重要单元。在本文中，我们描述了 (NHC)Cu 系统的开发，该系统通过使用 N-氯代氨基甲酸酯或其钠衍生物作为实用的氨基源来介导（杂）芳烃的直接 CH 酰胺化。反应性铜-芳基中间体与酰胺化试剂的轻松化学计量反应使我们分离出关键的芳基氨基甲酸铜物种并形成 CN 键。(t)BuONa 碱的使用使这种转化在温和条件下具有催化作用。目前的 (NHC)Cu 催化的 CH 酰胺化在包括多氟苯、唑类和喹啉 N-氧化物在内的一系列芳烃上高效且选择性地大规模工作。
• Synthesis and Evaluation of Three ¹⁸F-Labeled Aminophenylbenzothiazoles as Amyloid Imaging Agents
  作者：Kim Serdons、Koen Van Laere、Peter Janssen、Hank F. Kung、Guy Bormans、Alfons Verbruggen

  DOI：10.1021/jm900871v

  日期：2009.11.26

  We have developed three fluorine-18 labeled 6-(methyl)amino-2-(4'-fluorophenyl)-1,3-benzothiazoles, which display high in vitro binding affinity For human amyloid beta plaques (K-i <= 10 nM). The radiolabeled F, robes were synthesized by aromatic nucleophilic Substitution of the corresponding nitro precursor with F-18-fluoride, followed by deprotection of the BOC group if required. Determination of the octanol/water partition coefficient, biodistribution studies In mice, and in vivo mu PET studies in rats and a rhesus monkey showed that initial brain uptake was high and brain washout was fast in normal animals. Radiometabolites were quantified in plasma and brain of mice and in monkey plasma using HPLC. Of the tested compounds, [F-18]2 (6-amino-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole) shows the most favorable brain kinetics in mice, rats, and a monkey. Its polar plasma radiometabolites do not cross the blood-brain barrier. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as a PET brain amyloid imaging agent.