N-(3,5-bis(trifluoromethyl)phenyl)benzo[d]thiazol-2-amine | 216985-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,5-bis(trifluoromethyl)phenyl)benzo[d]thiazol-2-amine
• 英文别名: N-(3,5-di(trifluoromethyl)phenyl)benzo[d]thiazol-2-amine；N-(3,5-ditrifluoromethylphenyl)benzo[d]thiazol-2-amine；N-[3,5-bis(trifluoromethyl)phenyl]-1,3-benzothiazol-2-amine
• CAS: 216985-57-8
• 化学式: C₁₅H₈F₆N₂S
• 分子量: 362.298
• InChiKey: BGAWJTUICRGKLP-UHFFFAOYSA-N

物化性质

• 熔点：
  150-155 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  349.4±52.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,5-双(三氟甲基)苯基异硫氰酯 、 2-硝基苯胺 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.5h， 以79%的产率得到N-(3,5-bis(trifluoromethyl)phenyl)benzo[d]thiazol-2-amine
  参考文献：
  名称：

  邻硝基苯胺高效合成2-氨基苯并噻唑衍生物

  摘要：

  报道了在 K2CO3 存在下，异硫氰酸芳基酯和邻硝基苯胺之间的无过渡金属反应合成 2-氨基苯并噻唑的新方法。新开发的方法是合成 2-氨基苯并噻唑的有效且具有成本效益的方法。

  DOI：

  10.3184/174751913x13848836801606

文献信息

• Merrifield resin supported phenanthroline–Cu(I): a highly efficient and recyclable catalyst for the synthesis of 2-aminobenzothiazoles via the reaction of 2-haloanilines with isothiocyanates
  作者：Jin Yang、Pinhua Li、Lei Wang

  DOI：10.1016/j.tet.2011.05.121

  日期：2011.8

  recyclable catalyst in the reaction of 2-halobenzenamines with isothiocyanates for the synthesis of 2-aminobenzothiazoles. The reactions were applicable to a variety of 2-halobenzenamines and isothiocyanates, and generated the corresponding 2-aminobenzothiazoles in good yields under mild reaction conditions. Moreover, the catalyst was quantitatively recovered from the reaction mixture by a simple filtration

  一种新型的Merrifield树脂负载的菲咯啉-Cu（I）络合物已被开发出来，并用作2-卤代苯胺与异硫氰酸酯反应合成2-氨基苯并噻唑的高效可循环催化剂。该反应适用于各种2-卤代苯甲胺和异硫氰酸酯，并在温和的反应条件下以高收率产生了相应的2-氨基苯并噻唑。此外，通过简单的过滤从反应混合物中定量回收催化剂，并以几乎恒定的活性重复使用十个循环。
• 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-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。
• Transition-Metal-Free <i>O</i>-, <i>S</i>-, and <i>N</i>-Arylation of Alcohols, Thiols, Amides, Amines, and Related Heterocycles
  作者：Rafael Cano、Diego J. Ramón、Miguel Yus

  DOI：10.1021/jo1022052

  日期：2011.1.21

  A new protocol for the Ullmann-type arylation process of different aromatic heterocycles without any transition-metal catalyst, implying the use of a combination of an excess of potassium hydroxide and dimethyl sulfoxide, is described. The reaction can be performed between a broad range of starting nucleophiles including phenol, alcohols, amines, nitrogen-containing five-membered systems such as pyrazoles, imidazoles, and indoles, and amides with haloarenes, iodide and bromide derivatives giving the best results, the possible pathway involving the in situ generation of the corresponding benzyne intermediate. When the reaction was performed with 2-iodoaniline and either carboxarnides or isothiocyanato derivatives, the corresponding benzoazole derivatives were obtained.
• A New and Efficient Synthesis of 2-Aminobenzothiazoles Derivatives from <i>O</i>-nitroaniline
  作者：Behrooz Mirza、Roghieh Mirzazadeh、Mohsen Zeeb

  DOI：10.3184/174751913x13848836801606

  日期：2013.12

  A novel synthesis of 2-aminobenzothiazoles from a transition-metal-free reaction between aryl isothiocyanates and o-nitroaniline in the presence of K2CO3 is reported. The newly developed method is an efficient and cost-effective approach to synthesise 2-aminobenzothiazoles.

  报道了在 K2CO3 存在下，异硫氰酸芳基酯和邻硝基苯胺之间的无过渡金属反应合成 2-氨基苯并噻唑的新方法。新开发的方法是合成 2-氨基苯并噻唑的有效且具有成本效益的方法。