8-methyl-2-phenyl-4H-3,1-benzoxazin-4-one | 72470-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 8-methyl-2-phenyl-4H-3,1-benzoxazin-4-one
• 英文别名: 8-methyl-2-phenyl-4H-benzo[d][1,3]oxazin-4-one；8-Methyl-2-phenyl-3,1-benzoxazin-4-one
• CAS: 72470-36-1
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: FWXYOFVGUPMCNT-UHFFFAOYSA-N

物化性质

• 沸点：
  373.2±12.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methyl-2-phenyl-4H-3,1-benzoxazin-4-one 在 hydrazine hydrate 作用下， 生成 3-amino-8-methyl-2-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  席夫碱衍生的 8-甲基-2-苯基喹唑啉-4(3H)-酮的合成：光谱特性、SAR、对接方法及其抗癌和抗菌活性

  摘要：

  以3-氨基喹唑啉酮中间体为原料，合成了一系列基于8-甲基-2-苯基喹唑啉酮席夫碱的新化合物。通过对接分析评估了这些化合物作为抗癌和抗菌剂的潜力。针对六十种不同的癌细胞系进行了抗癌评估。化合物7b和7h分别对黑色素瘤（MDA-MB-435细胞系）和非小细胞肺癌（NCI-H522）表现出强大的功效。发现化合物 7g 对乳腺癌 (HS-578T) 和中枢神经系统癌症 (SNB-19) 均有效。抗菌活性结果表明，新合成的含有卤素的化合物7d和7j对选定的细菌和真菌微生物表现出潜在的抑制作用。 SAR 研究表明，具有羟基和间位取代氯基等 EDG 的化合物在抗癌研究中更有效；而对位（7d 和 7j）EWG 取代的化合物表现出更高的抗菌活性。此外，抗菌对接分析表明，化合物7d和7j对细菌和真菌中的分子靶标具有高亲和力，负结合能范围为-8至-12.5 kcal/mol。我们支持对这些化合物与标准抗生素的组

  DOI：

  10.1016/j.molstruc.2024.138256
• 作为产物：
  描述：

  4-羟基-8-甲基-2-苯基喹啉 在 sodium hydroxide 、 乙酸酐 、 sode de l'acide trichloroisocyanurique 作用下， 生成 8-methyl-2-phenyl-4H-3,1-benzoxazin-4-one
  参考文献：
  名称：

  Production of 3- benzoyl-2,1-benzisoxazoles,2-phenyl-4H-3,1-benzoxazin-4-ones, and novel quinolinone derivatives from 2-phenylquinolin-4(1H)-ones and sodium dichloroisocyanurate

  摘要：

  A simple synthesis of certain 3-benzoyl-2,1 -benzisoxazoles 6 is accomplished via treatment of the corresponding 2-phenylquinolin-4(1H)-one 1 with sodium dichloroisocyanurate 2 in methanolic aq. alkali; the isomeric 2-phenyl-4H-3,1-benzoxazin-4-one 7 is also a product. Under different conditions the same reactants furnish two new types of quinolinone derivative, viz. 3,3-dichloro-2-phenylquinolin-4(3H)-one 4 and 2-alkoxy-3,3-dichloro-2,3-dihydro-2-phenylquinolin-4(1H)-one 5, as chief products; the former is an intermediate in the synthesis of products 6 and 7. Some of the chemical properties of the dichloro compounds 4 and 5 are described. Mechanistic pathways and proposals to explain the results and observations are presented.

  DOI：

  10.1039/p19930000511

文献信息

• Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
  作者：Xiao-Li Lian、Hao Lei、Xue-Jing Quan、Zhi-Hui Ren、Yao-Yu Wang、Zheng-Hui Guan

  DOI：10.1039/c3cc44215b

  日期：——

  A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.

  开发了一种新颖且高效的方法，利用单独的Oxone作为氧化剂，将2-芳基吲哚氧化合成2-芳基苯并噁唑酮。该反应对多种官能团具有良好的耐受性，并能快速且原子经济性地合成多种高产率的有价值2-芳基苯并噁唑酮。
• Palladium-Catalyzed C–H Bond Monofluorination of 2-Arylbenzo[d]oxazinone Using Nitrate as Crucial Promoter
  作者：Xu-Qin Li、Huu-Manh Vu、Fei-Wu Chen

  DOI：10.1055/s-0037-1611700

  日期：2019.4

  Abstract Monofluorination of 2-arylbenzo[d]oxazinones with N-fluorobenzenesulfonimide (NFSI) was achieved by palladium catalysis in moderate to good yields. Promoted by nitrate, the reaction provides an economic and environmentally friendly strategy. The synthesis of monofluorinated 2-arylbenzo[d]oxazinones has good compatibility with many common functional groups. The plausible mechanism of this monofluorination

  摘要 N-氟苯磺酰亚胺（NFSI）通过钯催化以中等到良好的产率实现了2-芳基苯并[ d ]恶嗪酮的单氟化。在硝酸盐的促进下，该反应提供了经济和环境友好的策略。单氟2-芳基苯并[ d ]恶嗪酮的合成与许多常见的官能团具有良好的相容性。讨论了这种单氟化的可能机理。 N-氟苯磺酰亚胺（NFSI）通过钯催化以中等到良好的产率实现了2-芳基苯并[ d ]恶嗪酮的单氟化。在硝酸盐的促进下，该反应提供了经济和环境友好的策略。单氟2-芳基苯并[ d ]恶嗪酮的合成与许多常见的官能团具有良好的相容性。讨论了这种单氟化的可能机理。
• Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
  作者：Subir Panja、Srabani Maity、Biju Majhi、Brindaban C. Ranu

  DOI：10.1002/ejoc.201900935

  日期：2019.9.8

  An efficient procedure for the Pd‐catalyzed olefination of 4H‐benzo[d][1,3]oxazin‐4‐ones with activated alkenes has been achieved via C‐H activation. The site selectivity of the reaction was explained by a DFT study.

  通过C-H活化，实现了有效的Pd催化4H-苯并[d] [1,3]恶嗪-4-烯与活化烯烃的烯化反应。DFT研究解释了反应的位点选择性。
• Palladium‐Catalyzed Reductive Double Carbonylation of Nitroarenes with Aryl Halides Using Mo(CO) ₆ as a Reductant and Carbonyl Source
  作者：Xueling Liu、Tongshun An、Zhiping Yin、Wenzhou Zhang

  DOI：10.1002/chem.202202880

  日期：2023.1.9

  The synthesis of benzoxazin-4-ones by palladium-catalyzed reductive double carbonylation of nitroarenes with aryl halides has been achieved. The key to success was the use of Mo(CO)6 as a reductant and bench-stable solid carbonyl source. Various aryl iodides, bromides, and trifluoromethanesulfonates are suitable reaction partners and produce corresponding nitrogen heterocycles in moderate to good yields

  通过钯催化的硝基芳烃与芳基卤化物的还原双羰基化反应合成了苯并恶嗪-4-酮。成功的关键是使用 Mo(CO) 6作为还原剂和实验室稳定的固体羰基源。各种芳基碘化物、溴化物和三氟甲磺酸酯是合适的反应伙伴，并以中等到良好的产率产生相应的氮杂环。值得注意的是，该方法避免了有毒CO气体的使用，并进一步应用于雌酮的后期修饰。
• Copper-mediated oxidative tandem reactions with molecular oxygen: synthesis of 2-arylbenzoxazinone derivatives from indoles
  作者：Mitsuaki Yamashita、Akira Iida

  DOI：10.1016/j.tetlet.2014.03.128

  日期：2014.4

  We developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl anthranilic acids and benzoxazinones. Our investigation revealed that the choice of solvent and additives is critical in these reactions. (C) 2014 Elsevier Ltd. All rights reserved.