6-fluoro-N-para-tolylbenzo[d]thiazol-2-amine | 1213706-17-2

• 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-fluoro-N-para-tolylbenzo[d]thiazol-2-amine
• 英文别名: 6-fluoro-N-(p-tolyl)benzo[d]thiazol-2-amine；6-fluoro-N-p-tolylbenzo[d]thiazol-2-amine；6-fluoro-N-(4-methylphenyl)-1,3-benzothiazol-2-amine
• CAS: 1213706-17-2
• 化学式: C₁₄H₁₁FN₂S
• mdl: MFCD23260514
• 分子量: 258.319
• InChiKey: RSRSEIDJLCBLES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以80%的产率得到6-fluoro-N-para-tolylbenzo[d]thiazol-2-amine
  参考文献：
  名称：

  DDQ-Promoted C-S Bond Formation: Synthesis of 2-Aminobenzothiazole Derivatives under Transition-Metal-, Ligand-, and Base-Free Conditions

  摘要：

  A transition-metal-free method for the intramolecular S-arylation of o-halobenzothiaoureas via DDQ-mediated leading to the 2-aminobenzothiazole derivatives is reported. The reactions are performed at room temperature under ligand-and base-free conditions with good to excellent yields.

  DOI：

  10.1055/s-0031-1291159

文献信息

• Iron-Catalyzed Tandem Reactions of 2-Halobenzenamines with Isothiocyanates Leading to 2-Aminobenzothiazoles
  作者：Jing-Wen Qiu、Xing-Guo Zhang、Ri-Yuan Tang、Ping Zhong、Jin-Heng Li

  DOI：10.1002/adsc.200900450

  日期：2009.10

  A highly practical method for the synthesis of 2-aminobenzothiazoles has been developed through an iron-catalyzed tandem reaction. The present tandem process allows the assembly of a wide range of 2-aminobenzothiazoles by the reactions of 2-halobenzenamines with isothiocyanates.

  通过铁催化的串联反应，已经开发出一种非常实用的合成2-氨基苯并噻唑的方法。本发明的串联方法允许通过2-卤代苯甲胺与异硫氰酸酯的反应组装各种2-氨基苯并噻唑。
• Direct transition metal-free C–S bond formation: synthesis of 2-aminobenzothiazole derivatives via base-mediated approach
  作者：Rui Wang、Zhi Chen、Liang Yue、Wei Pan、Jun-Jie Zhao

  DOI：10.1016/j.tetlet.2012.06.034

  日期：2012.8

  A general, efficient, and more practical protocol for the base-mediated intermolecular or intramolecular S-arylation leading to the 2-aminobenzothiazole derivatives is reported. Remarkably, all reactions were carried out under transition-metal-free conditions with good to excellent yields, rendering the methodology presented herein highly valuable from both environmental and economic points of view

  据报道，通用的，有效的和更实用的方案用于碱基介导的分子间或分子内S-芳基化反应，产生2-氨基苯并噻唑衍生物。值得注意的是，所有反应都是在无过渡金属的条件下以良好至极好的收率进行的，因此从环境和经济角度来看，本文提出的方法都具有很高的价值。
• Postsynthetic modification of IRMOF-3 with a copper iminopyridine complex as heterogeneous catalyst for the synthesis of 2-aminobenzothiazoles
  作者：Jie Liu、Xiaobin Zhang、Jin Yang、Lei Wang

  DOI：10.1002/aoc.3109

  日期：2014.3

  A copper iminopyridine complex has been immobilized on to a metal–organic framework (MOF) through postsynthetic modification of IRMOF‐3. The modified MOFs were fully demonstrated by using a variety of methods, and the structural integrity of the modified MOFs has been confirmed by powder X‐ray diffraction (XRD). Furthermore, it was shown that the modified IRMOF‐3 can act as an efficient solid catalyst

  通过IRMOF-3的后期合成修饰，已将亚氨基吡啶铜络合物固定在金属-有机骨架（MOF）上。改性MOF可以通过多种方法得到充分证明，并且改性MOF的结构完整性已通过粉末X射线衍射（XRD）得以证实。此外，研究表明，经修饰的IRMOF-3可通过2-碘苯胺与异硫氰酸酯的异质反应，作为合成2-氨基苯并噻唑的有效固体催化剂。而且，催化剂可以容易地从反应混合物中分离出来，并连续使用六个连续循环而不会明显降低催化活性。版权所有©2014 John Wiley＆Sons，Ltd.
• Synthesis of 2-aminobenzothiazole via FeCl3-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water
  作者：Qiuping Ding、Banpeng Cao、Xianjin Liu、Zhenzhen Zong、Yi-Yuan Peng

  DOI：10.1039/c0gc00123f

  日期：——

  An FeCl3-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water is described, which provides an environmentally benign, efficient, and practical route for the generation of 2-aminobenzothiazole. This present tandem process shows broad substrate scope in the presence of octadecyltrimethylammonium chloride as a phase-transfer catalyst. In addition, the reaction media can be recovered

  一个 的FeCl 3催化的串联反应 2-碘苯胺 和 异硫氰酸酯 在 水 描述，它提供了一种环境友好，高效且实用的途径来生成 2-氨基苯并噻唑。目前的串列工艺显示，在存在十八烷基三甲基氯化铵 作为相转移 催化剂。另外，反应介质可以被回收和再循环而不损失效率。
• Synthesis of 2-Aminobenzothiazoles via Copper(I)-Catalyzed Cross-Coupling with Part-Per-Million Catalyst Loadings
  作者：Ya-Lei Sun、Yuan Zhang、Xiao-Hui Cui、Wei Wang

  DOI：10.1002/adsc.201100054

  日期：2011.5.9

  An efficient protocol has been developed for the preparation of 2‐aminobenzothiazoles via a copper(I)‐catalyzed tandem reaction of 2‐iodoanilines with isothiocyanates at very low catalyst loadings [typically 50 ppm of copper(I) iodide (CuI)]. A variety of 2‐iodoanilines could be cross‐coupled with isothiocyanates, affording 2‐aminobenzothiazoles in moderate to good yields (49–93%) under the given conditions

  已经开发了一种有效的方案，用于在极低的催化剂负载量（通常为50 ppm的碘化铜（CuI））下，通过铜（I）催化的2-碘苯胺与异硫氰酸酯的串联反应制备2-氨基苯并噻唑。各种2-碘苯胺可与异硫氰酸酯交叉偶联，在给定条件下可提供中等至良好产率（49-93％）的2-氨基苯并噻唑。该反应的周转数（TON）达到67,000，并且该反应至少可以放大至克级。