5-hydroxy-3-phenyl-1,4-naphthoquinone | 188031-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-hydroxy-3-phenyl-1,4-naphthoquinone
• 英文别名: 8-hydroxy-2-phenyl-1,4-naphthoquinone；3-phenyl-5-hydroxy-1,4-naphthoquinone；8-Hydroxy-2-phenylnaphthalene-1,4-dione
• CAS: 188031-61-0
• 化学式: C₁₆H₁₀O₃
• 分子量: 250.254
• InChiKey: JXLXHUTXJMZVGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-甲氧基-1,4-萘醌 在 aluminum (III) chloride 、 copper(II) tetrafluroborate hexahydrate 、 1,2-双(二苯基膦基)苯 、 palladium(II) acetylacetonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 5-hydroxy-3-phenyl-1,4-naphthoquinone
  参考文献：
  名称：

  通过末端二炔的金催化氧化环化生成内环乙烯基碳烯络合物：萘醌和咔唑醌

  摘要：

  在过去的几十年中，涉及卡宾/炔烃复分解的卡宾级联反应引起了人们的极大关注，因为这种化学方法具有巨大的潜力来构建复杂的环状分子。然而，在这些反应中形成的乙烯基金属类胡萝卜素仅限于环外碳烯，并且内环乙烯基卡宾配合物的产生仍未探索。在这里，我们报告了前所未有的金催化末端二炔的氧化环化反应。重要的是，这种氧化环化过程涉及内环乙烯基卡宾配合物的产生，这与以前的方案截然不同。该方法可以在非常温和的反应条件下轻松地从容易获得的二炔中轻松合成各种有价值的萘醌和咔唑醌，并且具有广泛的底物范围和宽泛的官能团耐受性。而且，理论计算为该环化反应的不同选择性提供了进一步的证据。

  DOI：

  10.1021/acscatal.8b04455

文献信息

• Palladium-catalyzed arylation of 1,4-naphthoquinones with aryl iodides and its synthetic application to the benzo[b]phenanthridine skeleton
  作者：Yusuke Akagi、Toshiya Komatsu

  DOI：10.1016/j.tetlet.2020.152446

  日期：2020.10

  We report a Pd-catalyzed arylation of 1,4-naphthoquinones with aryl iodides. This reaction shows excellent functional group tolerance and high regioselectivity when using nonsymmetric 1,4-naphthoquinone. Furthermore, the resulting 2-aryl-1,4-naphthoquinone could be successfully converted into benzo[b]phenanthridine-7,12-dione through treatment with aqueous ammonia, followed by oxidative cyclization

  我们报告钯与芳基碘化物催化的芳基化的芳基化。当使用非对称的1，4-萘醌时，该反应显示出优异的官能团耐受性和高的区域选择性。此外，通过用氨水处理，然后使用MnO 2进行氧化环化，可以将所得的2-芳基-1,4-萘醌成功地转化为苯并[ b ]菲啶-7,12-二酮。
• Arylation of Benzo-Fused 1,4-Quinones by the Addition of Boronic Acids under Dicationic Pd(II)-Catalysis
  作者：María Teresa Molina、Cristina Navarro、Ana Moreno、Aurelio G. Csákÿ

  DOI：10.1021/ol902084g

  日期：2009.11.5

  The first examples of the direct arylation of benzo-fused 1,4-quinones by the dicationic Pd(II)-catalyzed addition of arylboronic acids are reported. The addition reaction is carried out under very mild conditions (dioxane-H2O, rt, open air atmosphere) and is tolerant of free OH groups. In addition, the reaction shows high regioselectivity, when using nonsymmetrical quinones as starting materials.
• In vitro antiamyloidogenic properties of 1,4-naphthoquinones
  作者：Paloma Bermejo-Bescós、Sagrario Martín-Aragón、Karim L. Jiménez-Aliaga、Andrea Ortega、María Teresa Molina、Eduardo Buxaderas、Guillermo Orellana、Aurelio G. Csákÿ

  DOI：10.1016/j.bbrc.2010.08.038

  日期：2010.9

  The aim of this study is to find out whether several 1,4-naphthoquinones (1,4-NQ) can interact with the amyloidogenic pathway of the amyloid precursor protein processing, particularly targeting at beta-secretase (BACE), as well as at beta-amyloid peptide (A beta) aggregation and disaggregating preformed A beta fibrils. Compounds bearing hydroxyl groups at the quinoid (2) or benzenoid rings (5,6) as well as some 2- and 3-aryl derivatives (11-15) showed BACE inhibitory activity, without effect on amyloid aggregation or disaggregation. The halogenated compounds 8 and 10 were selective for the inhibition of amyloid aggregation. On the other hand, 1,4-naphthoquinone (1), 6-hydroxy-1,4-naphthoquinone (4) and 2-(3,4-dichlorophenyl)-1,4-naphthoquinone (26) did not show any BACE inhibitory activity but were active on amyloid aggregation and disaggregation preformed A beta fibrils. Juglone (5-hydroxy-1,4-naphthoquinone (3), and 3-(p-hydroxyphenyl)-5-methoxy-1,4-napththoquinone (19) were active on all the three targets. Therefore, we suggest that 1,4-NQ derivatives, specially 3 and 19, should be explored as possible drug candidates or lead compounds for the development of drugs to prevent amyloid aggregation and neurotoxicity in Alzheimer's disease. (C) 2010 Elsevier Inc. All rights reserved.
• Generation of Endocyclic Vinyl Carbene Complexes via Gold-Catalyzed Oxidative Cyclization of Terminal Diynes: Toward Naphthoquinones and Carbazolequinones
  作者：Chao Shu、Chong-Yang Shi、Qing Sun、Bo Zhou、Tian-You Li、Qiao He、Xin Lu、Rai-Shung Liu、Long-Wu Ye

  DOI：10.1021/acscatal.8b04455

  日期：2019.2.1

  generation of endocyclic vinyl carbene complexes was involved in this oxidative cyclization, which is distinctively different from previous protocols. This method allows the facile synthesis of various valuable naphthoquinones and carbazolequinones from readily available diynes under exceptionally mild reaction conditions and features a broad substrate scope and wide functional group tolerance. Moreover

  在过去的几十年中，涉及卡宾/炔烃复分解的卡宾级联反应引起了人们的极大关注，因为这种化学方法具有巨大的潜力来构建复杂的环状分子。然而，在这些反应中形成的乙烯基金属类胡萝卜素仅限于环外碳烯，并且内环乙烯基卡宾配合物的产生仍未探索。在这里，我们报告了前所未有的金催化末端二炔的氧化环化反应。重要的是，这种氧化环化过程涉及内环乙烯基卡宾配合物的产生，这与以前的方案截然不同。该方法可以在非常温和的反应条件下轻松地从容易获得的二炔中轻松合成各种有价值的萘醌和咔唑醌，并且具有广泛的底物范围和宽泛的官能团耐受性。而且，理论计算为该环化反应的不同选择性提供了进一步的证据。