2-((4-bromophenyl)thio)naphthalene-1,4-dione | 89478-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((4-bromophenyl)thio)naphthalene-1,4-dione
• 英文别名: 2-(4-Bromo-phenylsulfanyl)-[1,4]naphthoquinone；2-[(4-Bromophenyl)sulfanyl]naphthalene-1,4-dione；2-(4-bromophenyl)sulfanylnaphthalene-1,4-dione
• CAS: 89478-02-4
• 化学式: C₁₆H₉BrO₂S
• 分子量: 345.216
• InChiKey: QPDSQLFAHOLRCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-溴苯硫酚 、 2-((4-bromophenyl)thio)naphthalene-1,4-dione 在 sodium dithionite 、 水 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.0h， 以96%的产率得到2,3-di-(4-bromophenyl)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-溴苯硫酚 、 1,4-萘醌 在 bismuth(III) chloride 作用下， 以 甲醇 为溶剂， 以73 %的产率得到2-((4-bromophenyl)thio)naphthalene-1,4-dione
  参考文献：
  名称：

  BiCl3 催化合成 2-amino-1,4-naphthoquinones 和 1,4-naphthoquinon-2-sulfides 和 1,4-naphthoquinone 的一锅顺序胺芳基化

  摘要：

  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。

  DOI：

  10.1039/d2ob01792j

文献信息

• 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.
• 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.
• 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。