3-[(4-氟苯基)甲基]-1,3-苯并恶唑-2-酮 | 190074-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 3-[(4-氟苯基)甲基]-1,3-苯并恶唑-2-酮
• 英文名称: 3-(4-fluorobenzyl)benzoxazolin-2-one
• 英文别名: Benzoxazol-2(3H)-one, N-(4-fluorobenzyl)-；3-[(4-fluorophenyl)methyl]-1,3-benzoxazol-2-one
• CAS: 190074-23-8
• 化学式: C₁₄H₁₀FNO₂
• 分子量: 243.237
• InChiKey: QOLQGBVBGJVMLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四氯化碳 、 3-[(4-氟苯基)甲基]-1,3-苯并恶唑-2-酮 在 三氯化铝 、 N,N-二甲基甲酰胺 作用下， 生成 3-[(4-Fluorophenyl)methyl]-6-[3-[(4-fluorophenyl)methyl]-2-oxo-1,3-benzoxazole-6-carbonyl]-1,3-benzoxazol-2-one
  参考文献：
  名称：

  AICI3-DMF Reagent in the Friedel-Crafts Reaction. Application to the Synthesis of Symmetrical Benzophenones Derivatives

  摘要：

  Synthesis of series of symmetrical benzophenone derivatives by C-alkylation reaction of 2(3H)-benzoxazolone and 2 (3H)-benzothiazolone with carbon tetrachloride in presence of AlCl3-DMF reagent is reported.

  DOI：

  10.3987/com-96-7716
• 作为产物：
  描述：

  2-苯并唑啉酮 、 4-氟氯苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3-[(4-氟苯基)甲基]-1,3-苯并恶唑-2-酮
  参考文献：
  名称：

  Identification of 2-benzoxazolinone derivatives as lead against molecular targets of diabetic complications

  摘要：

  AbstractDiabetic complications follow multiple pathophysiological pathways involving aldose reductase (ALR2)‐mediated polyol pathway, advanced glycation end products (AGEs) and reactive oxygen species formation. Literature suggests ALR2 inhibitors such as epalrestat to possess significant potential in retinopathy and neuropathy. Thus, in this study, multiple pathophysiology directed molecules targeting ALR2, AGEs and free radicals formation were designed using in silico techniques. Initially, database was screened via in silico tools to obtain hits with affinity for the catalytic domain of ALR2. Additional focus was laid on the presence of structural attributes responsible for AGE's inhibitory and anti‐oxidant potential. Out of obtained hits, 2‐benzoxazolinone scaffold was selected and ten derivatives were synthesized accordingly. Finally, the synthesized molecules were evaluated for their ALR2 and AGEs inhibitory activities along with free radical scavenging potency.

  DOI：

  10.1111/cbdd.13369

文献信息

• 一种N-苄基苯并杂环酮化合物的制备方法
  申请人：湖南科技大学

  公开号：CN115043789B

  公开（公告）日：2023-07-14

  本发明公开了一种N‑苄基苯并杂环酮化合物的制备方法，苯甲醇衍生物与苯并杂环化合物在亚磷酸、碘、碱以及溶剂存在的条件下加热反应，制得N‑苄基苯并杂环酮化合物。本发明选用廉价易得的苯甲醇衍生物为苄基化试剂，以亚磷酸和单质碘为促进剂，在碱存在下，通过与苯并杂环化合物直接反应一锅一步高效实现了N‑苄基苯并杂环酮化合物的制备，具有无需过渡金属，原料廉价易得，底物范围广，绿色环保等优点，避免了使用危险试剂、过渡金属催化剂及多步反应的局限，有利于工业化生产。
• H3PO3/I2 mediated formation of N-benzyl benzo heterocyclic ketones from aromatic aldehydes and benzyl alcohol derivatives
  作者：Xiaoyi Wang、Junchun Xiang、Jie Wang、Zhilan Yu、Zi-Long Tang、Jing Xiao

  DOI：10.1016/j.tet.2022.133094

  日期：2022.11

  We report a H3PO3/I2 mediated formation of N-benzyl benzo heterocyclic ketones from the reaction of benzo heterocyclic compounds with aromatic aldehydes or benzyl alcohol derivatives under metal-free conditions in one-pot. For the first time, aromatic aldehydes were used as benzylated reagents to synthesize benzo heterocyclic ketones in the presence of K2CO3. Control experiments indicated that the

  我们报告了 H 3 PO 3 /I 2介导的N-苄基苯并杂环酮的形成，该反应由苯并杂环化合物与芳香醛或苯甲醇衍生物在无金属条件下在一锅中反应。首次以芳香醛为苄基化试剂在K 2 CO 3存在下合成苯并杂环酮。对照实验表明羰基氧最有可能来源于K 2 CO 3。H 3 PO 3还起到促进剂和氢源的双重作用。这种新方法具有底物范围广、成本低、条件简单等特点。
• AICI3-DMF Reagent in the Friedel-Crafts Reaction. Application to the Synthesis of Symmetrical Benzophenones Derivatives
  作者：Huseyin Ucar、Kim Van derpoorten、Jacques H. Poupaert

  DOI：10.3987/com-96-7716

  日期：——

  Synthesis of series of symmetrical benzophenone derivatives by C-alkylation reaction of 2(3H)-benzoxazolone and 2 (3H)-benzothiazolone with carbon tetrachloride in presence of AlCl3-DMF reagent is reported.
• Identification of 2-benzoxazolinone derivatives as lead against molecular targets of diabetic complications
  作者：Bhawna Vyas、Shalki Choudhary、Pankaj Kumar Singh、Baldev Singh、Renu Bahadur、Ashok Kumar Malik、Om Silakari

  DOI：10.1111/cbdd.13369

  日期：2018.12

  AbstractDiabetic complications follow multiple pathophysiological pathways involving aldose reductase (ALR2)‐mediated polyol pathway, advanced glycation end products (AGEs) and reactive oxygen species formation. Literature suggests ALR2 inhibitors such as epalrestat to possess significant potential in retinopathy and neuropathy. Thus, in this study, multiple pathophysiology directed molecules targeting ALR2, AGEs and free radicals formation were designed using in silico techniques. Initially, database was screened via in silico tools to obtain hits with affinity for the catalytic domain of ALR2. Additional focus was laid on the presence of structural attributes responsible for AGE's inhibitory and anti‐oxidant potential. Out of obtained hits, 2‐benzoxazolinone scaffold was selected and ten derivatives were synthesized accordingly. Finally, the synthesized molecules were evaluated for their ALR2 and AGEs inhibitory activities along with free radical scavenging potency.