5-nitro-2-(4-fluorophenyl)benzoxazole | 1079992-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-nitro-2-(4-fluorophenyl)benzoxazole
• 英文别名: 2-(p-fluorophenyl)-6-nitrobenzoxazole；2-(4-Fluorophenyl)-6-nitro-1,3-benzoxazole
• CAS: 1079992-36-1
• 化学式: C₁₃H₇FN₂O₃
• mdl: MFCD22193588
• 分子量: 258.209
• InChiKey: HETXJBGOMDDJSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitro-2-(4-fluorophenyl)benzoxazole 在 nickel(II) chloride hexahydrate 、 锌 作用下， 以 甲醇 为溶剂， 以45%的产率得到6-amino-2-(p-fluorophenyl)benzoxazole
  参考文献：
  名称：

  Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents

  摘要：

  A new series of 5(or 6)-nitro/amino-2-(substituted phenyl/benzyl)benzoxazole derivatives (1a-1m, 2a-21) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans and their drug-resistant isolate. Microbiological results indicated that the synthesized compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between >400 and 12.5 mu g/ml. The results against B. subtilis, P. aeruginosa, drug-resistant B. subtilis, drug-resistant E. coli, and C. albicans isolate for these kinds of structures are quite encouraging. The 2D-QSAR analysis of a set of newly and previously synthesized benzoxazoles tested for growth inhibitory activity against B. subtilis ATCC 6633 was performed by using the multivariable regression analysis. The activity contributions for substituent effects of these compounds were determined from the correlation equation for predictions of the lead optimization. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.001
• 作为产物：
  描述：

  6-硝基苯并恶唑 、 对氟苯甲酰氯 在 hafnium-based metal-organic framework catalyst 作用下， 以 neat (no solvent) 为溶剂， 反应 7.0h， 以36%的产率得到5-nitro-2-(4-fluorophenyl)benzoxazole
  参考文献：
  名称：

  Zr和Hf-金属-有机构架：通过开环途径酰化反应合成2-芳基苯并恶唑的高效可循环异构催化剂

  摘要：

  由锆和ha组成的由12个配位簇和6个配位簇组成的金属有机骨架被证明是在无溶剂条件下将苯并恶唑开环酰化为2-芳基苯并恶唑的高效多相催化剂。拥有宽阔的开放空间结构和固有的甲酸酯位点，基于6个连接的Zr 6 / Hf 6节点的MOF能够识别出在常规加热和微波辐射下布朗斯台德酸催化的反应中产率的显着提高。此外，通过使用密度泛函理论（DFT）计算，证实了开环酰化反应活性位点的详细机理。

  DOI：

  10.1016/j.jcat.2019.04.023

文献信息

• Zr and Hf-metal-organic frameworks: Efficient and recyclable heterogeneous catalysts for the synthesis of 2-arylbenzoxazole via ring open pathway acylation reaction
  作者：Linh Ho Thuy Nguyen、Trang Thi Thu Nguyen、Phuong Hoang Tran、Yoshiyuki Kawazoe、Hung Minh Le、Tan Le Hoang Doan

  DOI：10.1016/j.jcat.2019.04.023

  日期：2019.6

  2-arylbenzoxazole under solvent free conditions. Owning the wide opening spaces structures and inherent formate sites, MOFs based on 6-connected Zr6/Hf6 node were able to identify a significantly enhanced yield in Brønsted acid catalyzed reactions under conventional heating and microwave irradiation. In addition, the detailed mechanism of active sites of the ring opening acylation reaction was confirmed

  由锆和ha组成的由12个配位簇和6个配位簇组成的金属有机骨架被证明是在无溶剂条件下将苯并恶唑开环酰化为2-芳基苯并恶唑的高效多相催化剂。拥有宽阔的开放空间结构和固有的甲酸酯位点，基于6个连接的Zr 6 / Hf 6节点的MOF能够识别出在常规加热和微波辐射下布朗斯台德酸催化的反应中产率的显着提高。此外，通过使用密度泛函理论（DFT）计算，证实了开环酰化反应活性位点的详细机理。
• Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents
  作者：Tugba Ertan、Ilkay Yildiz、Betul Tekiner-Gulbas、Kayhan Bolelli、Ozlem Temiz-Arpaci、Semiha Ozkan、Fatma Kaynak、Ismail Yalcin、Esin Aki

  DOI：10.1016/j.ejmech.2008.04.001

  日期：2009.2

  A new series of 5(or 6)-nitro/amino-2-(substituted phenyl/benzyl)benzoxazole derivatives (1a-1m, 2a-21) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans and their drug-resistant isolate. Microbiological results indicated that the synthesized compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between >400 and 12.5 mu g/ml. The results against B. subtilis, P. aeruginosa, drug-resistant B. subtilis, drug-resistant E. coli, and C. albicans isolate for these kinds of structures are quite encouraging. The 2D-QSAR analysis of a set of newly and previously synthesized benzoxazoles tested for growth inhibitory activity against B. subtilis ATCC 6633 was performed by using the multivariable regression analysis. The activity contributions for substituent effects of these compounds were determined from the correlation equation for predictions of the lead optimization. (C) 2008 Elsevier Masson SAS. All rights reserved.