2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-fluorophenyl)ethanone | 163729-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-fluorophenyl)ethanone
• 英文别名: 2-(Benzotriazol-1-yl)-1-(4-fluorophenyl)ethanone
• CAS: 163729-25-7
• 化学式: C₁₄H₁₀FN₃O
• mdl: MFCD12937676
• 分子量: 255.251
• InChiKey: KNZPMBOERVRNJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-fluorophenyl)ethanone 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 1-(2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-fluorophenyl)ethylidene)-2-(4-(3,5-bis(trifluoromethyl)phenyl)thiazol-2-yl)hydrazine
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel thiazole substituted benzotriazole derivatives

  摘要：

  A series of novel hybrid molecules 4a-y containing thiazole and benzotriazole templates were designed and synthesized. The structures of the synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR and mass spectral data. All the synthesized compounds were tested for their antimicrobial activity (zone of inhibition) against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. After that minimum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs) and minimum fungicidal concentrations (MFCs) of all the synthesized compounds were determined. The investigation of antimicrobial screening data revealed that most of the tested compounds showed moderate to good microbial inhibitions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.094
• 作为产物：
  描述：

  T406石油添加剂 在 4-二甲氨基吡啶 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.0h， 生成 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-fluorophenyl)ethanone
  参考文献：
  名称：

  Exploration of the SAR of anti-invasive chalcones: Synthesis and biological evaluation of conformationally restricted analogues

  摘要：

  In order to get a clearer view on the active geometry of anti-invasive chalcones, we have prepared a number of isoxazoles and related substances as conformationally restrained mimics of 1,3-diarylpropenones, and also of (Z)-stilbenes. In vitro anti-invasive activity data for 3,5-isoxazoles and 4,5-isoxazoles, together with an in silico geometrical comparison, point towards an active conformation for chalcones more resembling their s-trans geometry than the s-cis counterpart. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.069

文献信息

• Energy Transfer Photolysis of <i>N</i>-Enoxybenzotriazoles into Benzotriazolyl and α-Carbonyl Radicals
  作者：Quynh H. Nguyen、Ho Seong Hwang、Eun Jin Cho、Seunghoon Shin

  DOI：10.1021/acscatal.2c02862

  日期：2022.8.5

  triplet state energy transfer and the presence of a very long-lived radical chain (Φ = 210 and 131, respectively, for [1,3]-shift and carboamination), which was initiated by the addition of electrophilic benzotriazolyl radicals to the olefin moieties. The N–O homolysis was further characterized by electrochemical and photophysical studies, as well as density functional theory computation.

  N的辐照在光敏剂存在下，具有蓝色 LED 的 -enoxybenzotriazoles 可有效地呈现两种反应性自由基中间体，即苯并三唑基和 α-羰基自由基。在交叉实验中提出了这些自由基作为离散物种的形成，并且这种 N-O 断裂引发了综合有用的转化，例如原子经济的 [1,3]-转移和基团转移自由基加成，导致生物学有趣的苯并三唑基衍生物。这些转化的便利（<5 分钟）通过三重态能量转移和非常长寿命的自由基链的存在（对于 [1,3] 位移和碳胺化，分别为 Φ = 210 和 131）合理化，这是通过向烯烃部分添加亲电子苯并三唑基自由基引发的。
• Visible-Light-Induced Regioselective Radical Oxo-Amination of Alkenes with O₂ as the Oxygen Source
  作者：Jiayang Wang、Baoer Shao、Haixia Ge、Yongjin Li、Huan Qi、Li Xiao

  DOI：10.1021/acs.orglett.3c01910

  日期：2023.7.21

  accessible and green O2 as the oxygen source has been developed. The transformation possesses the advantages of operational simplicity, a broad substrate scope, high atom economy, and mild reaction conditions. The mechanistic studies reveal that an energy transfer process probably occurs in the initial stage, and the reaction proceeds via β-scission of the alkoxyl radical species.

  开发了一种有效且新颖的可见光诱导末端烯烃氧化胺化，用于以易于获得的绿色O 2作为氧源构建α-氨基酮。该转化具有操作简单、底物范围广、原子经济性高、反应条件温和等优点。机理研究表明，能量转移过程可能发生在初始阶段，反应通过烷氧基自由基的β-断裂进行。
• Synthesis and biological evaluation of some novel thiazole substituted benzotriazole derivatives
  作者：Nitin D. Gaikwad、Sachin V. Patil、Vivek D. Bobade

  DOI：10.1016/j.bmcl.2012.03.094

  日期：2012.5

  A series of novel hybrid molecules 4a-y containing thiazole and benzotriazole templates were designed and synthesized. The structures of the synthesized compounds were elucidated by IR, H-1 NMR, C-13 NMR and mass spectral data. All the synthesized compounds were tested for their antimicrobial activity (zone of inhibition) against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. After that minimum inhibitory concentrations (MICs), minimum bactericidal concentrations (MBCs) and minimum fungicidal concentrations (MFCs) of all the synthesized compounds were determined. The investigation of antimicrobial screening data revealed that most of the tested compounds showed moderate to good microbial inhibitions. (C) 2012 Elsevier Ltd. All rights reserved.
• Exploration of the SAR of anti-invasive chalcones: Synthesis and biological evaluation of conformationally restricted analogues
  作者：Bart I. Roman、Tine De Ryck、Laura Dierickx、Barbara W.A. Vanhoecke、Alan R. Katritzky、Marc Bracke、Christian V. Stevens

  DOI：10.1016/j.bmc.2012.05.069

  日期：2012.8

  In order to get a clearer view on the active geometry of anti-invasive chalcones, we have prepared a number of isoxazoles and related substances as conformationally restrained mimics of 1,3-diarylpropenones, and also of (Z)-stilbenes. In vitro anti-invasive activity data for 3,5-isoxazoles and 4,5-isoxazoles, together with an in silico geometrical comparison, point towards an active conformation for chalcones more resembling their s-trans geometry than the s-cis counterpart. (C) 2012 Elsevier Ltd. All rights reserved.