3-benzyl-4-hydroxynaphthalene-1,2-dione | 15451-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-benzyl-4-hydroxynaphthalene-1,2-dione
• 英文别名: 2-hydroxy-3-benzyl-1,4-naphthoquinone；2-benzyl-3-hydroxynaphthalene-1,4-dione；2-benzyl-3-hydroxy-[1,4]naphthoquinone；2-benzyl-3-hydroxy-1,4-naphthoquinone；2-benzyl-3-hydroxy[1,4]naphthoquinone；3-benzyllawsone；2-Benzyl-3-hydroxy-[1,4]naphthochinon
• CAS: 15451-41-9
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: DAFZNKDZHABMQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-benzyl-4-hydroxynaphthalene-1,2-dione 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 异丙醇 、 甲苯 为溶剂， 反应 0.25h， 生成 2-benzyl-3-((6-bromohexyl)oxy)naphthalene-1,4-dione
  参考文献：
  名称：

  1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues

  摘要：

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.

  DOI：

  10.1021/ml300242v
• 作为产物：
  描述：

  2-benzyloxy-3-chloro-1,4-naphthoquinone 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以47%的产率得到3-benzyl-4-hydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  1,4-Naphthoquinone Cations as Antiplasmodial Agents: Hydroxy-, Acyloxy-, and Alkoxy-Substituted Analogues

  摘要：

  Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4 49.5 nM against heteroresistant P. falciparum W2.

  DOI：

  10.1021/ml300242v

文献信息

• A New Method to Prepare 3-Alkyl-2-hydroxy-1,4-naphthoquinones: [nl]Synthesis of Lapachol and Phthiocol
  作者：[nl]Vitor Ferreira、Sabrina Ferreira、David Rodrigues da Rocha、José Carneiro、Wilson Santos

  DOI：10.1055/s-0030-1260771

  日期：2011.7

  In this article a mild, simple, safe, and chemoselective synthesis and reduction of o-quinone methides to the corresponding 3-alkyl-2-hydroxy-1,4-naphthoquinones, compounds with interesting biological activity, mediated by the formic acid-water system is described. This new one-pot methodology was applied to the synthesis of lapachol and constitutes an efficient and inexpensive alternative for the preparation of this natural bioactive compound

  本文介绍了一种温和、简单、安全且化学选择性强的合成与还原邻醌甲烷为相应的3-烷基-2-羟基-1,4-萘醌的方法，这些化合物具有有趣的生物活性，通过甲酸-水体系介导。这种新的一锅法方法应用于合成拉帕醇，为制备这种天然生物活性化合物提供了一种高效且经济的替代方案。
• Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C
  作者：Tokutaro Ogata、Tomoyo Yoshida、Maki Shimizu、Manami Tanaka、Chie Fukuhara、Junko Ishii、Arisa Nishiuchi、Kiyofumi Inamoto、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2016.01.040

  日期：2016.3

  A novel etherification of 2-hydroxy-1,4-naphthoquinone derivatives with alkoxyalkyl chlorides and hydride bases is described. Precise study of the conditions and substrate scope suggested that the reaction occurs specifically in the molecule having a 2-hydroxy-1,4-benzoquinone skeleton. A chemoselective O-methylation reaction was achieved to afford a synthetically important intermediate, which offered

  描述了2-羟基-1，4-萘醌衍生物与烷氧基烷基氯化物和氢化物碱的新型醚化。对条件和底物范围的精确研究表明，该反应特别发生在具有2-羟基-1,4-苯醌骨架的分子中。实现了化学选择性的O-甲基化反应，以提供合成上重要的中间体，该中间体可轻松获得具有抗肿瘤活性的天然产物。
• Dimere Naphthochinone, VIII. Synthese 3,3′-dihydroxylierter 2,2′-Bi-1,4-naphthochinone
  作者：Hartmut Laatsch

  DOI：10.1002/jlac.198319831104

  日期：1983.11.15

  Zur Synthese 3,3′-dihydroxylierter 2,2′-Bi-1,4-naphthochinone oder ihrer Dimethylether ist die Phenoloxidation entsprechender Naphthole nicht geeignet. Die Titelverbindungen sind jedoch durch Hydroxylierung von 3,3′-unsubstituierten 2,2′-Binaphthochinonen oder durch Halogen Hydroxy-Austausch leicht zugänglich.

  相应萘酚的苯酚氧化不适合合成3,3'-二羟基化的2,2'-bi-1,4-萘醌或它们的二甲醚。然而，通过3，3′-未取代的2，2′-联萘醌的羟基化或通过卤素羟基交换，容易获得标题化合物。
• Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions
  作者：Dhevalapally B. Ramachary、Mamillapalli Kishor

  DOI：10.1039/c003588b

  日期：——

  A practical and sustainable chemical process for the synthesis of highly substituted tetrahydro-isobenzofuran-1,5-diones was achieved for the first time through asymmetric cascade Michael-aldol reaction of 4-hydroxy-3-alkyl-5H-furan-2-ones with alkyl vinyl ketones in the presence of a catalytic amount of L-proline or 9-amino-9-deoxyepiquinine/TCA. In this article, we discovered for the first time the

  通过4-羟基-3-烷基-5 H-呋喃-2-的不对称级联迈克尔-醛醇反应，首次实现了一种实用且可持续的化学方法，用于合成高度取代的四氢-异苯并呋喃-1,5-二酮具有烷基乙烯基酮的催化剂，在催化量的大号脯氨酸 或者 9-氨基-9-脱氧表醌/三氯乙酸。在本文中，我们首次通过动力学拆分发现了特权双环内酯的不对称合成，并展示了其在药物和天然产物合成中的合成应用。
• Synthesis and Biological Screening of New Lawson Derivatives as Selective Substrate‐Based Inhibitors of Cytochrome<i>bo₃</i>Ubiquinol Oxidase from<i>Escherichia coli</i>
  作者：Isam Elamri、Melanie Radloff、Katharina F. Hohmann、Vijaykumar D. Nimbarte、Hamid R. Nasiri、Michael Bolte、Schara Safarian、Hartmut Michel、Harald Schwalbe

  DOI：10.1002/cmdc.201900707

  日期：2020.7.20

  Moreover, two inhibitors for both cyt bo 3 and cyt bd‐I oxidase could be identified. Based on molecular‐docking simulations, we propose binding modes of the new Lawson inhibitors. The molecular fragment benzyl enhances the inhibitory potential and selectivity for cyt bo 3, whereas heterocycles reduce this effect. This work extends the library of 3‐alkylated Lawson derivatives as selective inhibitors for respiratory

  大肠杆菌的呼吸链含有两种不同类型的末端氧化酶，它们根据不断变化的环境条件而受到不同的调节。这些氧化还原酶催化分子氧还原成水并提供质子动力。细胞色素bo 3氧化酶 (cyt bo 3 ) 在大气氧水平下充当主要末端氧化酶，而bd型氧化酶在微氧条件下最为丰富。在大肠杆菌中，两种类型的呼吸末端氧化酶（HCO 和bd型）均使用 ubiquinol-8 作为电子供体。在这里，我们通过 L-脯氨酸催化的三组分还原烷基化 (TCRA) 评估了新设计和合成的 3-烷基化 Lawson 衍生物的抑制潜力。通过电位测试测试了这些 Lawson 衍生物对大肠杆菌末端氧化酶（cyt bo 3和 cyt bd ‐I）的抑制作用。四种化合物能够将 cyt bo 3的氧化还原酶活性降低 50% 以上，而不影响 cyt bd- I 活性。此外，还可以鉴定出 cyt bo 3和 cyt bd ‐I 氧化酶的两种抑制剂。基于