(2-phenyl-5-benzoxazolyl)phenylmethanone | 82593-17-7

• 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: (2-phenyl-5-benzoxazolyl)phenylmethanone
• 英文别名: 2-phenyl-5-benzoylbenzoxazole；Phenyl(2-phenyl-1,3-benzoxazol-5-yl)methanone；phenyl-(2-phenyl-1,3-benzoxazol-5-yl)methanone
• CAS: 82593-17-7
• 化学式: C₂₀H₁₃NO₂
• 分子量: 299.329
• InChiKey: IUDZBZPEXHKRQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-苯甲酰基-2-羟基苯胺 在 对甲苯磺酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 6.0h， 生成 (2-phenyl-5-benzoxazolyl)phenylmethanone
  参考文献：
  名称：

  苯乙酮或二苯甲酮衍生的新型苯并恶唑及其合成前体的合成，蛋白酶抑制和抗衰老活性

  摘要：

  摘要这项工作报告了十种苯并恶唑衍生物的合成，蛋白酶抑制和抗衰老活性，这些衍生物是通过三步合成路线从4-羟基苯乙酮和4-羟基二苯甲酮获得的。评估了这些苯并恶唑，合成中间体和起始酮对半胱氨酸（木瓜蛋白酶，rCPB2.8和rCPB3.0）和丝氨酸（胰蛋白酶）蛋白酶的抑制作用。所有化合物对这些酶均显示出显着的IC 50值（木瓜蛋白酶为0.0086–0.7612 µM，胰蛋白酶为0.0075–0.5032 µM），比标准抑制剂（E64和TLCK分别为1.7821和7.2318 µM）更具活性。 ）。随后，在体外评估了所有化合物对前鞭毛形式的杀螨活性。亚马逊利什曼原虫。进一步评价了最具活性的化合物对抗烟毒气形式及其对鼠巨噬细胞的毒性。苯并恶唑4d（二苯甲酮衍生物）和中间体4-羟基-3-硝基苯乙酮2b表现出显着的抗霉菌活性（分别为IC 50  = 90.3 µM和IC 50  = 130.9 µM），其选择性指数分别为5

  DOI：

  10.1007/s00044-017-1824-y

文献信息

• 2-Arylbenzothiazoles and 2-Arylbenzoxazoles from α,α,α-Trihalomethyl Aromatic Compounds
  作者：Ying-Hung So、Richard Decaire

  DOI：10.1080/00397919809458691

  日期：1998.11

  Abstract α,α,α-Trichloromethyl and α,α,α-trifluoromethyl aromatic compounds react with o-aminothiophenol and o-aminophenol in polyphosphoric acid (PPA) to produce 2-arylbenzothiazoles and 2-arylbenzoxazoles in high yields.

  摘要 α,α,α-三氯甲基和α,α,α-三氟甲基芳香族化合物与邻氨基苯硫酚和邻氨基苯酚在多磷酸（PPA）中反应，以高收率生成2-芳基苯并噻唑和2-芳基苯并恶唑。
• Tseitlin, G.M.; Tokarev, B.V.; Kulagin, V.N., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 931 - 934
  作者：Tseitlin, G.M.、Tokarev, B.V.、Kulagin, V.N.

  DOI：——

  日期：——
• Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide−Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation
  作者：Ying-Hung So、Jerry P. Heeschen

  DOI：10.1021/jo960441u

  日期：1997.5.1

  The mechanism of 2-phenylbenzoxazole formation from benzoic acid and o-aminophenol in polyphosphoric acid (PPA) is studied by NMR spectroscopy and chemical analysis. Benzoic acid reacts with PPA to form benzoic-phosphoric anhydride and benzoic-polyphosphoric anhydride. The ratio of mixed anhydride to free carboxylic acid increases dramatically as the P2O5 content of PPA increases, but this ratio is independent of reaction temperature and time. When o-aminophenol dissolves in PPA, part of the hydroxyl group is converted to phosphate ester, and only protonated amine is detected. Benzoic acid, mixed anhydride, and PPA are in dynamic equilibrium, and so are PPA, o-aminophenol, and its phosphate ester. The mixed anhydride and o-aminophenol react to form 8-aminophenyl benzoate as the first reaction intermediate which undergoes rapid acyl migration to generate 2-hydroxybenzanilide. Ring closure of 2-hydroxybenzanilide to form 8-phenylbenzoxazole is acid catalyzed. The reactive components in phosphorus pentoxide-methanesulfonic acid (P2O5-MSA) which is a convenient alternative to PPA are very similar to those present in PPA. Benzoic acid is also converted into mixed anhydride in P2O5-MSA.
• TSEJTLIN, G. M.;TOKAREV, B. V.;KULAGIN, V. N., ZH. ORGAN. XIMII, 1982, 18, N 5, 1075-1079
  作者：TSEJTLIN, G. M.、TOKAREV, B. V.、KULAGIN, V. N.

  DOI：——

  日期：——
• [EN] ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME<br/>[FR] COMPOSÉ ORGANIQUE ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE COMPRENANT UN TEL COMPOSÉ<br/>[KO] 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
  申请人：DOOSAN CORP

  公开号：WO2018043913A1

  公开（公告）日：2018-03-08

  본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게는 발광층, 전자 수송층 또는 전자 수송 보조층에 사용됨에 따라 유기 전계 발광 소자의 발광 효율, 구동 전압, 수명 등을 향상시킬 수 있다.