2-(3-fluorophenyl)quinazolin-4(3H)-one | 138867-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3-fluorophenyl)quinazolin-4(3H)-one
• 英文别名: 2-(3-Fluorophenyl)quinazolin-4(3H)-one；2-(3-fluorophenyl)-3H-quinazolin-4-one
• CAS: 138867-17-1
• 化学式: C₁₄H₉FN₂O
• 分子量: 240.237
• InChiKey: SZXYHOIFTIWFNM-UHFFFAOYSA-N

物化性质

• 熔点：
  267 °C(Solv: ethanol (64-17-5))
• 沸点：
  402.5±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-fluorophenyl)quinazolin-4(3H)-one 在 氯化亚砜 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-anilino-2-(3-fluorophenyl)quinazoline
  参考文献：
  名称：

  The synthesized novel fluorinated compound (LJJ-10) induces death receptor- and mitochondria-dependent apoptotic cell death in the human osteogenic sarcoma U-2 OS cells

  摘要：

  We designed the 6-fluoro-2-(3-fluorophenyl)-4-substituted anilinoquinazoline derivatives as less toxic anti-cancer candidates. Our result demonstrated that LJJ-10 has greater cytotoxicity than that of the other compounds in human osteogenic sarcoma U-2 OS cells. LJJ-10-induced apoptosis was associated with enhancing ROS generation, DNA damage, and an increase of the protein levels of Fas, FasL, FADD, caspase-8, cytochrome c, Apaf-1, AIF, Endo G, caspase-9 and caspase-3 in U-2 OS cells. LJJ-10-triggered growth inhibition was significantly attenuated by N-acetylcysteine, cyclosporine A, anti-FasL monoclonal anti-body, and caspase-8, -9 and -3 specific inhibitors in U-2 OS cells. We suggest that LJJ-10-induced apoptotic cell death in U-2 OS cells through death receptor- and mitochondria-dependent apoptotic signaling pathways. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.059
• 作为产物：
  描述：

  2-硝基苯甲酰胺 在 palladium 10% on activated carbon 、 氢气 、 sodium hydrogensulfite 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 生成 2-(3-fluorophenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  The synthesized novel fluorinated compound (LJJ-10) induces death receptor- and mitochondria-dependent apoptotic cell death in the human osteogenic sarcoma U-2 OS cells

  摘要：

  We designed the 6-fluoro-2-(3-fluorophenyl)-4-substituted anilinoquinazoline derivatives as less toxic anti-cancer candidates. Our result demonstrated that LJJ-10 has greater cytotoxicity than that of the other compounds in human osteogenic sarcoma U-2 OS cells. LJJ-10-induced apoptosis was associated with enhancing ROS generation, DNA damage, and an increase of the protein levels of Fas, FasL, FADD, caspase-8, cytochrome c, Apaf-1, AIF, Endo G, caspase-9 and caspase-3 in U-2 OS cells. LJJ-10-triggered growth inhibition was significantly attenuated by N-acetylcysteine, cyclosporine A, anti-FasL monoclonal anti-body, and caspase-8, -9 and -3 specific inhibitors in U-2 OS cells. We suggest that LJJ-10-induced apoptotic cell death in U-2 OS cells through death receptor- and mitochondria-dependent apoptotic signaling pathways. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.059

文献信息

• Iridium-catalysed direct sulfamidation of quinazolinones
  作者：Yadong Feng、Yudong Li、Yunliang Yu、Lianhui Wang、Xiuling Cui

  DOI：10.1039/c8ra00524a

  日期：——

  An Ir-catalysed direct sulfamidation of quinazolinones has been achieved to construct a series of ortho-diamided quinazolinones in excellent yields, and nitrogen was released as the sole byproduct.

  已实现对喹唑酮的直接磺胺化反应，以构建一系列产率极高的邻二酰胺基喹唑酮，并且氮作为唯一副产物释放。
• Palladium(II) N^O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3<i>H</i>)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide
  作者：Sundarraman Balaji、Gunasekaran Balamurugan、Rengan Ramesh、David Semeril

  DOI：10.1021/acs.organomet.0c00814

  日期：2021.3.22

  A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of readily available benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N^O chelating complexes of general configuration [Pd(L)Cl(PPh3)] (where L = dimethylamino benzoylhydrazone ligands) have been designed and synthesized. The formation

  已经描述了一种方便的方案，该方案通过容易获得的苄醇和2-氨基苯甲酰胺的脱氢偶联使用钯（II）配合物一锅合成喹唑啉-4（3 H）-酮。新型[Pd（L）Cl（PPh 3）与结构相关的Pd（II）N ^ O螯合物）]（其中L =二甲基氨基苯甲酰hydr配体）已设计并合成。络合物的形成已通过分析和光谱方法（FT-IR，NMR，HR-MS）得到认可。通过单晶X射线衍射研究证实了钯（II）离子周围存在正方形平面的几何形状。在有氧条件下，使用1.0 mol％的催化剂负载量，可以从各种各样的苄醇中成功地成功获得各种各样的取代的喹唑啉酮类化合物，产率高至优异。此外，对照实验表明，脱氢偶联反应首先涉及醛中间体的形成，然后涉及环状氨基中间体的形成。
• N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols
  作者：Pennamuthiriyan Anandaraj、Rengan Ramesh、Thangavel Sathiya Kamatchi

  DOI：10.1016/j.inoche.2021.109190

  日期：2022.3

  New Pincer type Pd(II) complex [Pd(NNO)(PPh3)] (1) prompted synthesis of quinazolinones via dehydrogenative coupling of readily accessible alcohols, and o-aminobenzamide is described. A diverse range of quinazolinones has been synthesized efficiently with good to excellent yields employing low catalyst loading (0.5 mol%) under the aerobic condition without any additives/oxidants. A plausible mechanism

  新的 Pincer 型 Pd(II) 复合物 [Pd(NNO)(PPh 3 )] ( 1 ) 通过容易获得的醇的脱氢偶联促进了喹唑啉酮的合成，并描述了邻氨基苯甲酰胺。在好氧条件下，使用低催化剂负载量（0.5 mol%），无需任何添加剂/氧化剂，即可有效合成多种喹唑啉酮类化合物，产率从良好到优异。已经通过环状缩醛胺中间体提出了构建喹唑啉酮的合理机制。大规模合成证明了当前策略的生产力。
• Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions
  作者：Nadia Ghorashi、Zahra Shokri、Reza Moradi、Amira Abdelrasoul、Amin Rostami

  DOI：10.1039/c9ra10303a

  日期：——

  study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80–95% yield) and benzothiazoles (65–98% yield) using air or O2 as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient

  目前的研究将漆酶/DDQ 作为一种受生物启发的协同催化系统，在环境温度下使用空气或 O 2作为水介质中的理想氧化剂合成喹唑啉酮（80-95% 产率）和苯并噻唑（65-98% 产率）。好氧氧化环化反应分两个步骤进行： (i) 化学环化；(ii) 化学酶氧化。由于使用O 2作为氧化剂，漆酶作为生态友好的生物催化剂，水性介质作为溶剂，并且不含任何有毒的过渡金属和卤化物，这些方法比其他报道的方法更环保、高效、简单和实用。催化剂。因此，这些方法可以应用于制药和其他敏感的合成过程。
• α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
  作者：Jian Huang、Wei Chen、Jiazhi Liang、Qin Yang、Yan Fan、Mu-Wang Chen、Yiyuan Peng

  DOI：10.1021/acs.joc.1c01497

  日期：2021.11.5

  the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil

  由 α-酮酸分别与 2-氨基苯甲酰胺、苯-1,2-二胺、2-氨基苯酚和 2-氨基苯硫醇反应合成喹唑啉酮、喹喔啉酮、苯并恶嗪酮和苯并噻唑的通用有效方法是描述。该反应在无催化剂条件下进行，以水为唯一溶剂，无需任何添加剂，成功应用于西地那非的合成。更重要的是，这些反应可以大规模进行，产物可以很容易地通过过滤和乙醇洗涤（或结晶）进行纯化。