2,3-bis(p-tolylthio)naphthalene-1,4-dione | 88856-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-bis(p-tolylthio)naphthalene-1,4-dione
• 英文别名: 2,3-Bis[(4-methylphenyl)sulfanyl]naphthalene-1,4-dione
• CAS: 88856-15-9
• 化学式: C₂₄H₁₈O₂S₂
• 分子量: 402.538
• InChiKey: IUCYPRNFKHKSML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 三氯化铁 作用下， 生成 2,3-bis(p-tolylthio)naphthalene-1,4-dione
  参考文献：
  名称：

  Miyaki et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 961,963

  摘要：

  DOI：

文献信息

• Polymorphs of aromatic thiolato 1, 2 or 1,4-naphthoquinones
  作者：Bigyan R. Jali、Marjit W. Singh、J. B. Baruah

  DOI：10.1039/c0ce00591f

  日期：——

  Two polymorphs of 4-(phenylthio)naphthalene-1,2-dione have been shown to possess distinguishable C–H⋯O hydrogen bond interactions; on the other hand two polymorphs of 2,3-(bis-4-methylphenylsulfanyl)naphthalene-1,4-dione have different orientations of methylphenylsulfenyl groups.

  研究表明，4-（苯硫基）萘-1,2-二酮的两种多晶型具有不同的 C-H⋯O 氢键相互作用；另一方面，2,3-（双-4-甲基苯硫基）萘-1,4-二酮的两种多晶型的甲基苯硫基具有不同的取向。
• 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。
• Naphthoquinone Antimalarials. XXIII. Bz-Substituted Derivatives
  作者：Louis F. Fieser、Russell H. Brown

  DOI：10.1021/ja01179a010

  日期：1949.11.19
• Synthesis of Benzo[b]naphtho[2,3-d]thiophene-6,11-diones via Palladium(II) Acetate-mediated Cyclization of 3-Arylthio-1,4-naphthoquinone
  作者：Chung-Kyu Ryu、Ik Hwa Choi、Jung Yoon Lee、Seong Hee Jung

  DOI：10.3987/com-05-10341

  日期：——

  Palladium(II)-mediated oxidative cyclization of 3-arylthio1,4-naphthoquinone (4) giving biologically important benzo[b]naphtho[2,3-d]thiophene-6,11-diones (2) has been performed with a stoichiometric amount of palladium(II) acetate in distillated acetic acid.
• Synthesis of Mixed Aryl 2,3-Diarylsulphanyl-1,4-naphthoquinones
  作者：W. Marjit Singh、Jubaraj B. Baruah

  DOI：10.1080/00397910802528951

  日期：2009.3.25

  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.