6-(3-Fluoro-benzoyl)-3H-benzooxazol-2-one | 144220-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3-Fluoro-benzoyl)-3H-benzooxazol-2-one
• 英文别名: 6-(3-fluorobenzoyl)-3H-1,3-benzoxazol-2-one
• CAS: 144220-94-0
• 化学式: C₁₄H₈FNO₃
• mdl: MFCD12541947
• 分子量: 257.221
• InChiKey: UWHMEZXELKNMFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(3-Fluoro-benzoyl)-3H-benzooxazol-2-one 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2(3H)-Benzoxazolone, 3-[(4,5-dihydro-2-thiazolyl)methyl]-6-(3-fluorobenzoyl)-
  参考文献：
  名称：

  Synthesis and antimicrobial activity of thiazolinomethyl-2(3H)-benzoxazolone derivatives (I)

  摘要：

  A number of thiazolinoalkyl-2(3H)-benzoxazolones have been synthesized by using cyano derivatives of 6-acyl-2(3H)-benzoxazolones with cysteamine HCl. Their antibacterial and antifungal activities have been evaluated. The chemical structures have been proved by means of their IR, H-1-NMR and mass spectroscopic data and by elemental analysis. The antimicrobial activity of compounds was investigated by tube dilution and disk techniques using bacteria (Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853, Streptococcus faecalis RSKK 10541) and yeast-like fungi (Candida parapsilosis, C albicans, C pseudotropicalis, C stellatoidea). Inhibitory effects were observed for many compounds against C albicans, eg, compounds 3b and 3c MIC = 25 mu g/ml, C pseudotropicalis, eg, compound 3b MIC = 12.5 mu g/ml, and P aeruginosa and S faecalis, eg, compound 3c, MIC = 25 mu g/ml.

  DOI：

  10.1016/0223-5234(96)88264-x
• 作为产物：
  描述：

  2-苯并唑啉酮 在 三氯化铝 、 TEA 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 6-(3-Fluoro-benzoyl)-3H-benzooxazol-2-one
  参考文献：
  名称：

  “像炸薯条”重排：一种合成6-酰基-2（3 H）-苯并恶唑酮和6-酰基-2（3 H）-苯并噻唑酮的新颖有效的方法

  摘要：

  6-酰基-2（3 H）-苯并恶唑酮和6-酰基-2（3 H）-苯并噻唑酮衍生物具有特别令人感兴趣的抗炎，抗癫痫，镇痛和抗病毒特性。在这项研究中，我们对第2 6-位酰化报告的原始方法（3 ħ） -苯并恶唑酮和2-（3 ħ）苯并噻唑酮，其包括涉及从酰基迁移的两步骤程序中ñ -在165℃下由AlCl 3催化到杂环的6-位。与以前描述的其他酰化方法相比，发现这种新方法在AlCl 3的消耗和收率（76-90％）方面更为有效。

  DOI：

  10.1016/s0040-4020(97)10400-8

文献信息

• Synthesis and antibacterial and antifungal properties of thiazolinoethyl-2(3H)-benzoxazolone derivatives. II
  作者：DD Erol、MD Aytemir、N Yuluĝ

  DOI：10.1016/0223-5234(96)85883-1

  日期：1996.1

  Cyano derivatives of 6-acyl-2(3H)-benzoxazolones were reacted with cysteamine HCl in ethanol to give the corresponding 6-acyl-3-thiazolinoethyl-2(3H)-benzoxazolones and their antibacterial and antifungal activities were investigated. The chemical structures were proved by means of their IR and H-1-NMR spectra and elemental analysis. Investigation of antimicrobial activity of the compounds was carried out by tube dilution and disc techniques using bacteria (Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853 and Streptococcus faecalis ATCC 29212) and yeast-like fungi (Candida parapsilosis, C albicans, C pseudotropicalis and C stellatoidea). Inhibitory effects were observed for many compounds against S aureus and Bacillus subtilis. Compounds 13 and 15 had minimum inhibitory concentrations (MIG) of 8.4 and 4.2 mu g/mL respectively. The antifungal studies against C albicans (10 and 16, MIC = 67.5 mu g/mL), C parapsilosis (15, MIC = 67.5 mu g/mL) and C stellaatoidea (9, MIC = 67.5 mu g/mL) were more successful in comparison.
• Palaska; Unlu; Ozkanli, Arzneimittel-Forschung/Drug Research, 1995, vol. 45, # 6, p. 693 - 696
  作者：Palaska、Unlu、Ozkanli、Pilli、Erdogan、Safak、Demirdamar、Gumusel、Duru

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• SomeN-Mannich Bases of 2-Benzoxazolinones and Their Analgesic Activities
  作者：Gülhan Pilli、Hakki Erdogan、Cihat Şafak、Ünsal Çaliş、Rümeysa Sunal

  DOI：10.1002/ardp.19923250815

  日期：——
• Pilli; Erdogan; Sunal, Arzneimittel-Forschung/Drug Research, 1993, vol. 43, # 12, p. 1351 - 1354
  作者：Pilli、Erdogan、Sunal

  DOI：——

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