6-fluoro-N-ethylbenzo[d]thiazol-2-amine | 1225736-77-5

• 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: 6-fluoro-N-ethylbenzo[d]thiazol-2-amine
• 英文别名: N-ethyl-6-fluorobenzo[d]thiazol-2-amine；N-ethyl-6-fluoro-1,3-benzothiazol-2-amine
• CAS: 1225736-77-5
• 化学式: C₉H₉FN₂S
• 分子量: 196.248
• InChiKey: RQJSGSZEROKGGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  异硫氰酸乙酯 、 2-碘-4-氟苯胺 在 三乙烯二胺 、 iron(III) chloride 、 1,10-菲罗啉 、 十八烷基三甲基氯化铵 作用下， 以 水 为溶剂， 以77%的产率得到6-fluoro-N-ethylbenzo[d]thiazol-2-amine
  参考文献：
  名称：

  合成 2-氨基苯并噻唑 通过 的FeCl 3催化的串联反应 2-碘苯胺 和 异硫氰酸酯 在 水

  摘要：

  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。

  DOI：

  10.1039/c0gc00123f

文献信息

• Laccase-Catalysed Homocoupling of Primary Aromatic Amines towards the Biosynthesis of Dyes
  作者：Ana Catarina Sousa、Lígia O. Martins、M. Paula Robalo

  DOI：10.1002/adsc.201300501

  日期：2013.10.11

  AbstractColoured disubstituted benzoquinonimine trimeric structures are obtained as main reaction products of the oxidation of p‐electron donor primary aromatic amines using two different laccases, CotA‐laccase from Baccilus subtilus and TvL from Trametes versicolor. These orange‐red to purple products, presenting high molar extinction coefficients, presumably result from oxidative homocoupling reactions, through the formation of NC bonds at positions 2 and 5, of the laccase oxidised intermediate as showed in the proposed oxidative pathway. The product of 1,4‐phenylenediamine is shown to be the trimer known as Bandrowski’s base which has an established role in hair and fur dyeing. Our results also show that the occurrence and/or rates of oxidation of aromatic amines are strongly dependent on the presence of p‐electron releasing substituents in the aromatic ring and are independent on the properties of the enzyme used. Overall our data contribute for (i) understanding key features of laccase reactivity with p‐substituted aromatic amines and (ii) establishing enzymatic processes that lead to the synthesis of coloured bio‐products under mild conditions with potential impact in the cosmetic and dye industries.magnified image
• Convenient and Reliable Routes Towards 2-Aminothiazoles: Palladium-Catalyzed<i>versus</i>Copper-Catalyzed Aminations of Halothiazoles
  作者：Stéphanie Toulot、Timo Heinrich、Frédéric R. Leroux

  DOI：10.1002/adsc.201300591

  日期：2013.11.11

  AbstractTwo efficient methods for the amination of 2‐halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2‐aminothiazoles were synthesized under optimized conditions and isolated in good yields. The first palladium‐catalyzed CN coupling reactions between 2‐halothiazoles and primary alkylamines are presented. In a second part, ligand‐free copper‐catalyzed aminations of 2‐halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2‐halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2‐aminothiazoles, key molecules in pharmaceutical research.magnified image
• 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。