2-(4-chlorophenylthio)-1,4-naphthoquinone | 89478-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-chlorophenylthio)-1,4-naphthoquinone
• 英文别名: 2-[(4-Chlorophenyl)sulfanyl]naphthalene-1,4-dione；2-(4-chlorophenyl)sulfanylnaphthalene-1,4-dione
• CAS: 89478-01-3
• 化学式: C₁₆H₉ClO₂S
• 分子量: 300.765
• InChiKey: IBZFWLSPSPIOKD-UHFFFAOYSA-N

物化性质

• 沸点：
  456.1±45.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：

  2-(4-chlorophenylthio)-1,4-naphthoquinone 在 palladium diacetate 、 溶剂黄146 作用下， 反应 40.0h， 以26%的产率得到2-chlorobenzo[b]naphtho[2,3-d]thiophene-6,11-dione
  参考文献：
  名称：

  Synthesis of Benzo[b]naphtho[2,3-d]thiophene-6,11-diones via Palladium(II) Acetate-mediated Cyclization of 3-Arylthio-1,4-naphthoquinone

  摘要：

  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.

  DOI：

  10.3987/com-05-10341
• 作为产物：
  描述：

  4,4'-二氯二苯二硫醚 、 1,4-萘醌 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 48.0h， 以64%的产率得到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。
• 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。
• Silver-Catalyzed Direct Thiolation of Quinones by Activation of Aryl Disulfides to Synthesize Quinonyl Aryl Thioethers
  作者：Cheng Zhang、Jesse McClure、C. James Chou

  DOI：10.1021/acs.joc.5b00247

  日期：2015.5.15

  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.
• 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.