5-氯-2-(4-硝基苯基)苯并恶唑 | 893-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氯-2-(4-硝基苯基)苯并恶唑
• 英文名称: 5-chloro-2-(4-nitrophenyl)-1,3-benzoxazole
• 英文别名: 5-chloro-2-(4-nitrophenyl)benzoxazole；5-chloro-2-(4-nitro-phenyl)-benzooxazole；2-(4-Nitro-phenyl)-5-chlor-benzoxazol；5-Chlor-2-(4-nitro-phenyl)-benzoxazol
• CAS: 893-18-5
• 化学式: C₁₃H₇ClN₂O₃
• mdl: MFCD01159450
• 分子量: 274.663
• InChiKey: CTBHCEMIKHAGFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  4

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 在 碘苯二乙酸 作用下， 以 甲醇 为溶剂， 生成 5-氯-2-(4-硝基苯基)苯并恶唑
  参考文献：
  名称：

  Prakash, Om; Batra, Anita; Sharma, Vijay, Journal of the Indian Chemical Society, 2003, vol. 80, # 11, p. 1031 - 1034

  摘要：

  DOI：

文献信息

• Iron(III) Chloride Mediated <i>para</i> ‐Selective C‐H Functionalization: Access to C5‐Chloro and C5,C7‐Dichloro/Dianisyl Substituted 2‐Arylbenzoxazoles
  作者：Kanchanbala Sahoo、Niranjan Panda

  DOI：10.1002/adsc.202101359

  日期：2022.3

  Iron(III) chloride mediated para-selective C−H chlorination and subsequent annulation of 2-amidophenol to synthesize C5- and C5, C7-chlorinated benzoxazoles was developed. Further, the oxidative cross-dehydrogenative coupling of amidophenol with anisole by ferric chloride was explored to achieve the remotely anisylated benzoxazoles.

  开发了氯化铁 (III) 介导的对位选择性 C-H 氯化和随后的 2-氨基苯酚环化以合成 C5-和 C5、C7-氯化苯并恶唑。此外，还探索了三氯化铁对氨基苯酚与苯甲醚的氧化交叉脱氢偶联，以实现远程苯甲酰化苯并恶唑。
• KMnO4/HOAc system promoted one-pot synthesis of benzoxazoles from o-aminophenols or oxidative cyclization of o-hydroxyarylidene anilines at room temperature
  作者：B. F. Mirjalili、A. Bamoniri、E. Bagheri

  DOI：10.1007/s13738-015-0795-5

  日期：2016.5

  1,3-Benzoxazoles via oxidative cyclization of corresponding o-hydroxyarylidene anilines was synthesized in the presence of KMnO4/HOAc system. This system also was applied for the one-pot synthesis of 1,3-benzoxazoles from o-amino phenols and aldehydes. The both protocols were processed at room temperature under solvent-free conditions with good to excellent yields.

  在KMnO4/HOAc体系的存在下，通过相应的o-羟基芳基亚胺的氧化环化合成了1,3-苯并恶唑。这一体系还用于从o-氨基酚和醛的一锅法合成1,3-苯并恶唑。这两种方法均在室温下无溶剂条件下进行，产率良好至优秀。
• Efficient Aerobic Oxidative Synthesis of 2‐Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4‐Methoxy‐TEMPO
  作者：Yong‐Xing Chen、Ling‐Feng Qian、Wei Zhang、Bing Han

  DOI：10.1002/anie.200803381

  日期：2008.11.17
• Iodine (III)-mediated synthesis of some 2-aryl/hetarylbenzoxazoles as antibacterial/antifungal agents
  作者：Ravi Kumar、Reshmi R. Nair、Saurabh Sudha Dhiman、Jitender Sharma、Om Prakash

  DOI：10.1007/s00044-009-9211-y

  日期：2010.7

  Ten 2-aryl/hetarylbenzoxazoles (5a, 5b, and 6a-h) were synthesized via oxidative cyclization of Schiff bases (3a, 3b, and 4a-h) with 1.1 equivalent of iodobenzene diacetate (IBD) in methanol. All of these 2-aryl/hetarylbenzoxazoles (5a, 5b, and 6a-h) were tested in vitro for their antibacterial and antifungal activities against Bacillus subtilis, Bacillus stearothermophilus, Escherichia coli, and Pseudomonas putida. These compounds also were screened for their antifungal activity against Aspergillus flavus and Aspergillus niger. Biological activity of these compounds was compared with those of commercially available antibiotics, chloramphenicol and antifungal agent cycloheximide. Most of these compounds, 5a, 5b, 6a, 6b, 6d, 6e, 6g, 6h, were equipotent or more potent than these commercial drugs at concentration 100 mu g/ml.
• Thermal cyclization of ? -nit ros o-?-naphthol, o-nitronaphthols, and o-nitrophenols with aromatic aldehydes
  作者：E. Yu. Belyaev、L. E. Kondrat'eva、N. A. Shakhov

  DOI：10.1007/bf00478478

  日期：1972.1