2-[(4-methoxyl)phenylthio]-1,4-naphthoquinone | 89478-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[(4-methoxyl)phenylthio]-1,4-naphthoquinone
• 英文别名: 2-(4-Methoxy-phenylmercapto)-α-naphthochinon；2-[(4-Methoxyphenyl)sulfanyl]naphthalene-1,4-dione；2-(4-methoxyphenyl)sulfanylnaphthalene-1,4-dione
• CAS: 89478-04-6
• 化学式: C₁₇H₁₂O₃S
• 分子量: 296.346
• InChiKey: LYUWJSZAWOWBCN-UHFFFAOYSA-N

物化性质

• 沸点：
  465.3±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯硫酚 、 2-[(4-methoxyl)phenylthio]-1,4-naphthoquinone 在 sodium dithionite 、 水 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.0h， 以94%的产率得到2,3-di-(4-methoxyphenyl)sulphanyl-1,4-naphthalenediol
  参考文献：
  名称：

  Synthesis of Mixed Aryl 2,3-Diarylsulphanyl-1,4-naphthoquinones

  摘要：

  The reaction of 2-arylsulphanyl-1,4-napththoquinone with aromatic thiols and sodium dithionate leads to bis-2,3-(arylsulphanyl)naphthalene-1,4-diols in high yield. Corresponding oxidized products, namely 2,3-diarylsulphanyl-1,4-naphthoquinones, are prepared in near quantitative yield by a copper(II)-catalyzed aerial oxidation reaction of bis-2,3-(arylsulphanyl)naphthalene-1,4-diols under mild condition.

  DOI：

  10.1080/00397910802528951
• 作为产物：
  描述：

  4,4'-二甲氧基二苯二硫 在 1,3-双(二苯基膦)丙烷 、 H₃N*C₂H₆O₆S₂ 、 tetrabutylammonium tetrafluoroborate 、 silver(I) acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 生成 2-[(4-methoxyl)phenylthio]-1,4-naphthoquinone 、 2-(4-chlorophenylthio)-1,4-naphthoquinone
  参考文献：
  名称：

  Silver-Catalyzed Direct Thiolation of Quinones by Activation of Aryl Disulfides to Synthesize Quinonyl Aryl Thioethers

  摘要：

  A silver-catalyzed coupling reaction of quinones with aryl disulfides for the synthesis of quinonyl aryl thio ethers is described. In the presence of AgOAc (0.2 equiv)/dppp (0.24 equiv) as the catalyst, (NH4)(2)S2O8 (3.0 equiv) as the oxidant, and Bu4NBF4 (1.0 equiv) as the additive, the reaction is simple, provides high yield (up to 88% yield), and possesses a broad substrate scope. The reaction is believed to proceed via direct activation of disulfides evidenced by observation of a metathesis reaction between two different disulfides placed together under the reaction conditions and C-13 NMR spectroscopy analysis.

  DOI：

  10.1021/acs.joc.5b00247

文献信息

• 一种醌芳基硫醚类化合物的合成方法
  申请人：深圳拒马科技有限公司

  公开号：CN105418468B

  公开（公告）日：2017-03-22

  本发明涉及一种下式(III)所示醌芳基硫醚类化合物的合成方法，所述方法包括：在有机溶剂中，于催化剂、氧化剂、有机配体和促进剂存在下，下式(I)化合物和下式(II)化合物于50‑70℃下反应6‑10小时，反应结束后经后处理，从而得到所述式(III)化合物，其中，R选自H、C1‑C6烷基、C1‑C6烷氧基、卤素或硝基。所述方法通过催化剂、氧化剂、有机配体、促进剂以及有机溶剂的综合筛选和协同作用，从而可以高产率得到目的产物，为该类化合物提供了全新的合成方法，具有良好的应用价值和工业生产潜力。
• Visible Light-Mediated Thiolation of Substituted 1,4-Naphthoquinones Using Eosin Y as a Photoredox Catalyst
  作者：Bhawana Nagar、Basab Bijayi Dhar

  DOI：10.1021/acs.joc.1c02924

  日期：2022.3.4

  (isolated yield of ≥75%) for thiolation of substituted 1,4-naphthoquinones using various aromatic and aliphatic thiols at room temperature is described herein. The rate-determining step of the reaction is thiyl radical generation, and the radical was characterized by high-resolution mass spectrometry. Cost effectiveness, operational simplicity, a short reaction time, high atom economy, and a very good yield

  在伊红 Y 存在下，本文描述了在室温下使用各种芳香族和脂肪族硫醇对取代的 1,4-萘醌进行硫醇化的可见光诱导的一步程序（分离产率≥75%）。该反应的限速步骤是硫自由基的产生，该自由基通过高分辨质谱进行表征。成本效益、操作简单、反应时间短、原子经济性高和非常好的产率使得这种光氧化还原介导的过程成为过渡金属（例如，Cu、Ag 和 Pd）催化的醌与硫醇或二硫化物。
• BiCl₃ catalyzed synthesis of 2-amino-1,4-naphthoquinones and 1,4-naphthoquinon-2-sulfides and one-pot sequential amine-arylation of 1,4-naphthoquinone
  作者：Mayurakhi Bhuyan、Gakul Baishya

  DOI：10.1039/d2ob01792j

  日期：——

  Using the Lewis acid catalyst BiCl3, a new method for the synthesis of 2-amino-1,4-naphthoquinones and 1,4-naphthoquinon-2-sulfides from 1,4-naphthoquinone has been devised. This method has a broad substrate scope and product extraction is easy. It is low-cost, requires mild and sustainable reaction conditions and results in superior product yields. Additionally, this study presents the first technique

  使用路易斯酸催化剂BiCl 3，设计了一种从1,4-萘醌合成2-氨基-1,4-萘醌和1,4-萘醌-2-硫化物的新方法。该方法底物适用范围广，产物提取容易。它成本低廉，需要温和且可持续的反应条件，并可提高产品收率。此外，本研究提出了第一种用胺和芳基肼/K 2 S 2 O 8进行单锅顺序胺芳基化的技术直接从 1,4-萘醌生产芳基化 2-氨基-1,4-萘醌。这种从经历自由基偶联反应的芳基肼产生芳基自由基的操作上直接的通过自由基捕获控制实验得到了很好的证明。
• OERIU, Pharmazie, 1961, vol. 16, p. 320 - 327
  作者：OERIU

  DOI：——

  日期：——
• Oxidative Free Radical Reaction of 2-Phenylthio-1,4-naphthoquinones Initiated by Manganese(III) Acetate
  作者：Che-Ping Chuang、Sheow-Fong Wang

  DOI：10.3987/com-96-7553

  日期：——

  A free radical reaction between 2-phenylthio-1,4-naphothoquinines and diethyl malonate initiated by manganese(III) acetate is described. This free radical reaction provides a new method for the synthesis of 6,11-dihydro-6,11-dioxo-12H-5-thianaphthacenes. This reaction was performed in various solvents, the best results were obtained in DMSO. With meta substituent on phenylthio ring, this reaction shows unusual high regioselectivity.