5-三氟甲基-1H-1,2,3-苯并噻唑 | 1548-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 5-三氟甲基-1H-1,2,3-苯并噻唑
• 英文名称: 6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazole
• 英文别名: 5-(Trifluoromethyl)-1H-1,2,3-Benzotriazole；5-(trifluoromethyl)-2H-benzotriazole
• CAS: 1548-67-0
• 化学式: C₇H₄F₃N₃
• mdl: MFCD00173974
• 分子量: 187.124
• InChiKey: GLSKMRNRRMNAQS-UHFFFAOYSA-N

物化性质

• 沸点：
  335.3±37.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-三氟甲基-1H-1,2,3-苯并噻唑 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.0h， 生成 (E)-2-(5-trifluoromethyl-2H-benzotriazol-2-yl)-3-(3-nitrophenyl)acrylonitrile
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 3-aryl-2-[1H(2H)-benzotriazol-1(2)-yl]acrylonitriles variously substituted: Part 4

  摘要：

  A new series of variously substituted 3-aryl-2-[1H(2H)-benzotriazol-1(2)-yl]acrylonitriles was synthesized and tested for antiproliferative and antitubercular activity as part of our continuing research program in the antimicrobial and antitumor fields. The most cytotoxic derivatives (5a,g,i,j,l and 7b) (CC50 < 3.0 microM against MT-4 cells) were evaluated against a panel of human cell lines derived from hematological and solid tumors, using 6-mercaptopurine (6-MP) and etoposide as reference drugs. In particular, E-2-(5,6-dimethyl-1H-benzotriazol-1-yl)-3-(3-nitrophenyl)acrylonitrile (5g) resulted more potent than 6-MP on all cell lines, even if 2-14-fold less potent than etoposide. In the antitubercular screening, the derivatives 5i,j and 7e showed moderate activity against some resistant strains of Mycobacterium tested.

  DOI：

  10.1016/j.farmac.2004.03.004
• 作为产物：
  描述：

  1-羟基-6-(三氟甲基)苯并三唑 在 频哪醇 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.25h， 以75%的产率得到5-三氟甲基-1H-1,2,3-苯并噻唑
  参考文献：
  名称：

  频哪醇为还原剂的钼催化杂芳族N-氧化物和氢氧化物的脱氧

  摘要：

  的吡啶甲钼催化脱氧Ñ -oxides和Ñ -hydroxybenzotriazoles，以及其它唑Ñ -oxides，使用频哪醇作为环保氧代受体已经研制成功。唯一的副产品是丙酮和水，使该工艺成为废物生成方面既定规程的便捷替代方案。该反应是高度化学选择性的，并且可以容忍各种官能团。该过程通常非常干净，在大多数情况下，经过简单的萃取即可分离出纯净的脱氧产物。

  DOI：

  10.1002/adsc.201700071

文献信息

• <i>tert</i>-Butyl nitrite mediated nitrogen transfer reactions: synthesis of benzotriazoles and azides at room temperature
  作者：Sadaf Azeez、Priyanka Chaudhary、Popuri Sureshbabu、Shahulhameed Sabiah、Jeyakumar Kandasamy

  DOI：10.1039/c8ob01950a

  日期：——

  A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

  的A转换ö苯二胺为苯并三唑类是用在室温下实现叔丁基亚硝酸盐。优化的条件也非常适合将磺酰基和酰基肼转化为相应的叠氮化物。该协议不需要任何催化剂或酸性介质。在短时间内以优异的产率获得了所需的产物。
• Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2‐Aryldiamines
  作者：Réka J. Faggyas、Nikki L. Sloan、Ned Buijs、Andrew Sutherland

  DOI：10.1002/ejoc.201900463

  日期：2019.9

  mild conditions, using a polymer‐supported nitrite reagent and p‐tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N‐alkyl, ‐aryl, and ‐acyl ortho‐aminoanilines leading to the synthesis of N1‐substituted benzotriazoles. The synthetic utility of this one‐pot heterocyclization process was exemplified with the preparation of a

  已经开发了一种操作简单的方法，通过使用聚合物负载的亚硝酸盐试剂和对甲苯磺酸在温和条件下通过重氮化和分子内环化多种 1,2-芳基二胺来制备 N-未取代的苯并三唑。通过有效活化和环化 N-烷基、-芳基和-酰基邻-氨基苯胺，合成 N1 取代的苯并三唑，进一步证明了该方法的官能团耐受性。这种单锅杂环化过程的合成效用可以通过制备许多具有生物学和医学意义的苯并三唑支架来举例说明，包括一种 α-氨基酸类似物。
• ARYLOAZOL-2-YL CYANOETHYLAMINO COMPOUNDS, METHOD OF MAKING AND METHOD OF USING THEREOF
  申请人：Soll Mark David

  公开号：US20140080862A1

  公开（公告）日：2014-03-20

  The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives of formula (I): wherein R 3 , R 4 , R 5 , R 6 , R 7 , P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.

  本发明涉及新颖的式(I)的芳基咪唑-2-基-氰基乙基氨基衍生物：其中R3、R4、R5、R6、R7、P、Q、V、W、X、Y、Z和a如描述中所定义，以及其组合物、制备方法以及它们作为杀虫剂的用途。
• ENANTIOMERICALLY ENRICHED ARYLOAZOL-2-YL CYANOETHYLAMINO COMPOUNDS, METHOD OF MAKING AND METHOD OF USING THEREOF
  申请人：Soll Mark David

  公开号：US20100125089A1

  公开（公告）日：2010-05-20

  The present invention relates to novel aryloazol-2-yl-cyanoethylamino derivatives substantially enriched in an enantiomer of formula (I): and compounds of formula (IH) wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 13a , R 13b , R 14a , R 14b , P, Q, V, W, X, Y, Z and a are as defined in the description, compositions thereof, processes for their preparation and their uses as pesticides.

  本发明涉及一种在式(I)的对映体方面显著富集的新颖芳基唑-2-基-氰基乙基氨基衍生物： 以及式(IH)的化合物 其中R3、R4、R5、R6、R7、R13a、R13b、R14a、R14b、P、Q、V、W、X、Y、Z和a如描述中所定义，以及它们的组合物、其制备方法以及它们作为杀虫剂的用途。
• Rhodium-catalyzed intermolecular hydroarylation of internal alkynes with N-1-phenylbenzotriazoles
  作者：Wang Zhou、Youqing Yang、Zhiwei Wang、Guo-Jun Deng

  DOI：10.1039/c3ob42007h

  日期：——

  A rhodium-catalyzed intermolecular hydroarylation of internal alkynes with N-1-phenylbenzotriazoles via C–H bond activation is described. This transformation offers an alternative method for the hydroarylation of internal alkynes with high stereoselectivity. The reaction mechanism was discussed according to the deuterium-labeling experiments.

  描述了一种铑催化的内炔与N-1-苯基苯并三嗪的分子间氢芳基化反应，采用C-H键活化。这一转化提供了一种高立体选择性的内炔氢芳基化的替代方法。根据氘标记实验讨论了反应机制。