2-(2,6-dichlorophenyl)-1,3-benzoxazole | 1159516-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,6-dichlorophenyl)-1,3-benzoxazole
• CAS: 1159516-60-5
• 化学式: C₁₃H₇Cl₂NO
• 分子量: 264.111
• InChiKey: MGEISDILQNFVEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 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：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-<2,6-Dichlor-benzyliden>-2-hydroxy-anilin 在 氯化铵 作用下， 以 水 、 乙腈 为溶剂， 以82 %的产率得到2-(2,6-dichlorophenyl)-1,3-benzoxazole
  参考文献：
  名称：

  Introducing the Use of a Recyclable Solid Electrolyte for Waste Minimization in Electrosynthesis: Preparation of 2-aryl-benzoxazoles in flow

  摘要：

  The necessary use of large amounts of a homogeneous electrolyte represents a major issue and challenge for the whole sustainability of electrosynthetic procedures. Herein we report the use of a...

  DOI：

  10.1039/d4gc00930d

文献信息

• Catalyst-free microwave-promoted one pot synthesis of 2-aryl benzoxazoles using MnO2 nanoparticles as a convenient oxidant under mild condition
  作者：Hossein Naeimi、Zahra Rouzegar、Soraya Rahmatinejad

  DOI：10.1007/s11164-017-2909-4

  日期：2017.8

  An efficient and facile protocol for one pot synthesis of a series of 2-aryl benzoxazoles through coupling of o-aminophenol with aromatic aldehydes under microwave irradiation in the presence of MnO2 nanoparticles as oxidant reagent was demonstrated. The MnO2 nanoparticles were prepared via a solid-state chemical reaction technique. The structure of oxidant was assigned by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and scanning electron microscopy (SEM). The target molecules were obtained in good to high yields, high purity and short reaction times. The pure products were identified and characterized by physical and spectral data such as; melting point, IR, 1H NMR and 13C NMR. An efficient and facil protocol for one pot synthesis of a series of 2-aryl benzoxazoles through coupling of o-aminophenol with aromatic aldehydes under microwave irradiation in the precense of MnO2 nanoparticles as oxidant reagent was demonstrated.

  展示了一种高效、简便的一锅法合成一系列2-芳基苯并噁唑的协议，通过在微波辐射下将邻氨基酚与芳香醛偶联，使用二氧化锰纳米颗粒作为氧化剂。二氧化锰纳米颗粒采用固态化学反应技术制备。氧化剂的结构通过傅里叶变换红外光谱（FT-IR）、X射线衍射（XRD）和扫描电子显微镜（SEM）进行了表征。目标分子以良好到高的产率、高纯度和短反应时间获得。纯产品通过熔点、红外光谱、1H NMR和13C NMR等物理和光谱数据进行了鉴定和表征。
• Sonocatalyzed facile synthesis of 2-aryl benzoxazoles using MnO₂ nanoparticles as oxidant agent under mild conditions
  作者：Hossein Naeimi、Zahra Rouzegar、Soraya Rahmatinejad

  DOI：10.1080/00397911.2017.1365371

  日期：2017.11.17

  MnO2 was found to be an efficient oxidant agent for the synthesis of 2-substituted benzoxazoles through one-pot reaction of o-aminophenol and different aromatic aldehydes in acetonitrile under ultrasonic irradiation. This method was performed under mild conditions with high yields, inexpensive and readily available oxidant agent, facile and easy experimental procedure, simple purification of final products

  摘要纳米二氧化锰被发现是一种有效的氧化剂，通过超声波照射下邻氨基苯酚和不同芳香醛在乙腈中的一锅反应合成2-取代苯并恶唑。该方法在温和的条件下进行，收率高，氧化剂便宜且容易获得，实验程序简便易行，最终产物纯化简单，反应时间短。制备的纳米 MnO2 已通过 FTIR、XRD 和 SEM 技术进行表征。纯产品通过物理和光谱数据进行鉴定和表征，例如；熔点、IR、1H NMR 和 13C NMR。图形概要
• Synthesis, molecular simulation studies, in vitro biological assessment of 2-substituted benzoxazole derivatives as promising antimicrobial agents
  作者：GAJANAN S SHANBHAN、AMIT BHARGAVA、GIRIDHAR PAL SINGH、SHRINIVAS D. JOSHI、NARENDRA CHUNDAWAT

  DOI：10.55730/1300-0527.3535

  日期：——

  The 2-substituted benzoxazole derivatives are known to exhibit a wide spectrum of biological potential. Two series of novel benzoxazole derivatives containing 2-phenyl and 2-N-phenyl groups were synthesized, by following the green chemistry approach. All the newly synthesized derivatives were screened against gram-positive bacteria (Streptococcus pyogenes, Staphylococcus aureus), gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli) and the fungus (Aspergillus clavatus and Candida albicans). Most of these compounds have demonstrated potent antibacterial activities, especially against E. coli at 25 μg/mL, along with moderate antifungal activity. Among these, two compounds, 21 and 18, showed interesting antibacterial profile. Molecular docking studies suggested that the antibacterial activity can be linked to the inhibition of DNA gyrase. Overall, the study proposes that these biologically potent compounds can be considered for developing the next generation antimicrobial agents.

  众所周知，2-取代的苯并恶唑衍生物具有广泛的生物潜力。本研究采用绿色化学方法合成了含有 2-苯基和 2-N-苯基的两个系列的新型苯并恶唑衍生物。针对革兰氏阳性菌（化脓性链球菌、金黄色葡萄球菌）、革兰氏阴性菌（绿脓杆菌、大肠杆菌）和真菌（黄曲霉和白色念珠菌）对所有新合成的衍生物进行了筛选。这些化合物大多具有很强的抗菌活性，尤其是在 25 μg/mL 的浓度下对大肠杆菌具有很强的抗菌活性，同时还具有适度的抗真菌活性。其中，21 和 18 这两个化合物表现出了有趣的抗菌特性。分子对接研究表明，抗菌活性可能与抑制 DNA 回旋酶有关。总之，该研究认为这些具有生物效力的化合物可用于开发下一代抗菌剂。
• Khan, Khalid Mohammed; Karim, Aneela; Ambreen, Nida, Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 3, p. 894 - 900
  作者：Khan, Khalid Mohammed、Karim, Aneela、Ambreen, Nida、Amyn, Afroz、Saied, Sumayya、Ahmed, Aqeel、Perveen, Shahnaz

  DOI：——

  日期：——
• Samarium(III) Triflate as an Efficient and Reusable Catalyst for Facile Synthesis of Benzoxazoles and Benzothiazoles in Aqueous Medium
  作者：Vilas Ingle、Pratapsinha Gorepatil、Yogesh Mane

  DOI：10.1055/s-0033-1339758

  日期：——

  A simple, green, and efficient method is presented for the synthesis of benzoxazoles and benzothiazoles from reaction of o-aminophenols, o-aminothiophenols, and aliphatic or aromatic aldehydes using samarium triflate as a reusable acid catalyst under mild reaction conditions in aqueous medium.