2-(4-fluorophenyl)-3-hydroxynaphthalene-1,4-dione | 436-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-fluorophenyl)-3-hydroxynaphthalene-1,4-dione
• 英文别名: 2-(4-fluoro-phenyl)-3-hydroxy-[1,4]naphthoquinone；2-(4-Fluor-phenyl)-3-hydroxy-[1,4]naphthochinon
• CAS: 436-95-3
• 化学式: C₁₆H₉FO₃
• 分子量: 268.244
• InChiKey: AGPOUOXBOMMBII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-3-hydroxynaphthalene-1,4-dione 在 4-二甲氨基吡啶 、 氢碘酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 2-(4-fluorophenyl)naphthalene-1,4-dione
  参考文献：
  名称：

  10.1039/d2ob00438k

  摘要：

  3-Aryllawsones are well known for their wide range of applications in medicinal chemistry, but their synthesis has always remained challenging as no comprehensive protocol has been outlined to date.

  DOI：

  10.1039/d2ob00438k
• 作为产物：
  描述：

  萘-1,2,4-三基三乙酸酯 在 盐酸 、 sodium hydroxide 、 溶剂黄146 、 copper dichloride 作用下， 生成 2-(4-fluorophenyl)-3-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3177

  摘要：

  DOI：

文献信息

• Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones – green palladium-catalysed Suzuki cross coupling
  作者：Aline da R. Louvis、Nayane A. A. Silva、Felipe S. Semaan、Fernando de C. da Silva、Gabriela Saramago、Laís C. S. V. de Souza、Bruno L. A. Ferreira、Helena C. Castro、Juliana P. Salles、André L. A. Souza、Robson X. Faria、Vitor F. Ferreira、Daniela de L. Martins

  DOI：10.1039/c6nj00872k

  日期：——

  2-hydroxy-3-iodo-1,4-naphthoquinone and boronic acids were employed to prepare several 2-hydroxy-3-aryl-1,4-naphthoquinones in aqueous conditions using microwave irradiation or conventional heating. Because of the biological activities of quinones, which are related to their ability to accept electrons to form semiquinones and hydroquinones, the electrochemical behaviour of the synthesized molecules was investigated

  醌是存在于多种天然产物或合成生物活性分子中的重要支架。芳基化是完成结构修饰的重要策略，从而导致新的潜在候选药物被用作药物。在目前的工作中，采用钯催化的2-羟基-3-碘-1,4-萘醌与硼酸之间的无钯，无膦的Suzuki偶联反应制备了几种2-羟基-3-芳基-1,4。 -萘醌在水性条件下使用微波辐射或常规加热。由于醌的生物活性与它们接受电子形成半醌和对苯二酚的能力有关，因此对合成分子的电化学行为进行了研究。Osiris和Molinspiration化学信息学计划，利用在计算机分析中，这意味着这些萘醌是候选药物，体外抗真菌和锥虫活性测试的结果进一步证实了这些萘醌。我们的体外数据表明，针对白色念珠菌ATCC 24433菌株的MIC值为8，微克mL -1，针对克氏锥虫锥虫病的锥虫杀虫活性，EC 50为0.67μM。
• Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction
  作者：Somadrita Borthakur、Swagata Baruah、Bipul Sarma、Sanjib Gogoi

  DOI：10.1021/acs.orglett.9b00726

  日期：2019.4.19

  An unprecedented Pd(II)-catalyzed decarbonylative C–H/C–C activation and annulation reaction, which proceeds via intramolecular cyclization, is reported. This reaction of hydroxynaphthoquinones with disubstituted alkynes provides good yields of substituted alkylidene phthalides, which are the key intermediates for the synthesis of bioactive natural products.

  据报道，空前的Pd（II）催化的脱羰CH-H / CC活化和环化反应是通过分子内环化进行的。羟基萘醌与二取代炔烃的这种反应提供了高收率的取代亚烷基苯酞，这是合成生物活性天然产物的关键中间体。
• Sc(OTf)3‐Catalyzed Synthesis of 3‐Substituted Lawsones through a Buchner‐Curtius‐Schlotterbeck Reaction
  作者：Sailam Sri Gogula、Dasari Vijaya Prasanna、B. Sridhar、Ch. Abraham Lincoln、P. Muralidhar Reddy、B. V. Subba Reddy

  DOI：10.1002/ejoc.202400362

  日期：2024.8.19

  An efficient method has been developed for the synthesis of 3-substituted lawsones using 10 mol % Sc(OTf)3 in toluene at −78 °C through a Buchner-Curtius-Schlotterbeck reaction. This method is simple and convenient to the synthesis of pharmaceutically relevant 3-substituted lawsones in high to excellent yields.

  开发了一种有效的方法，使用 10 mol% Sc(OTf) 3在甲苯中，在 -78 °C 下通过布赫纳-库尔蒂斯-施洛特贝克反应合成 3-取代的指甲花酮。该方法简单方便，可以高收率合成药学相关的3-取代指甲花酮。
• Suzuki-Miyaura Coupling between 3-Iodolawsone and Arylboronic Acids. Synthesis of Lapachol Analogues with Antineoplastic and Antileishmanial Activities
  作者：Sara Gomes、Gardenia Militão、Arinice Costa、Cláudia Pessoa、Letícia Costa-Lotufo、Edézio Cunha-Junior、Eduardo Torres-Santos、Paulo Costa、Alcides da Silva

  DOI：10.21577/0103-5053.20160326

  日期：——

  A series of 2-hydroxy-3-arylnaphthalene- 1,4-diones (3-aryllawsones) were synthesized by Suzuki-Miyaura cross coupling reaction of 3-iodolawsone with arylboronic acids/esters. The hydroxylated resulting products were transformed into their corresponding N, N-diethyl carbamates. The antineoplastic and antileishmanial activities of the compounds were evaluated and compared with lapachol and its carbamate, providing promising results.
• SHCHERBAN A. I.; ALEKSYUK M. P.; XARITONOV G. V., IZV. VUZOV. XIMIYA I XIM. TEXNOL.,
  作者：SHCHERBAN A. I.、 ALEKSYUK M. P.、 XARITONOV G. V.

  DOI：——

  日期：——