2-benzylsulfanyl-3-methyl-[1,4]naphthoquinone | 2593-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-benzylsulfanyl-3-methyl-[1,4]naphthoquinone
• 英文别名: 2-Benzylmercapto-3-methyl-[1,4]naphthochinon；2-Benzylsulfanyl-3-methylnaphthalene-1,4-dione
• CAS: 2593-59-1
• 化学式: C₁₈H₁₄O₂S
• 分子量: 294.374
• InChiKey: DVPALWYMAIMQJF-UHFFFAOYSA-N

物化性质

• 沸点：
  455.8±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苄基二硫 、 甲萘醌 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， 生成 2-benzylsulfanyl-3-methyl-[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

• Naphthoquinone Antimalarials. XXIII. Bz-Substituted Derivatives
  作者：Louis F. Fieser、Russell H. Brown

  DOI：10.1021/ja01179a010

  日期：1949.11.19
• CHEMICAL AGENTS FOR THE PREVENTION OF INHIBITION OR TUMOR METASTASIS
  申请人：Bresnick Anne R.

  公开号：US20130090355A1

  公开（公告）日：2013-04-11

  The present invention provides methods of preventing or inhibiting tumor metastasis in a subject by administering a therapeutically effective amount of (1) a compound from a group of enumerated compounds, or a pharmaceutically acceptable salt thereof; (2) an agent that covalently modifies at least one cysteine residue of S100A4 protein; or (3) an agent that inhibits the interaction between S100A4 and myosin-IIA.
• [EN] CHEMICAL AGENTS FOR THE PREVENTION OR INHIBITION OF TUMOR METASTASIS<br/>[FR] AGENTS CHIMIQUES POUR LA PRÉVENTION OU L'INHIBITION DE MÉTASTASES TUMORALES
  申请人：EINSTEIN COLL MED

  公开号：WO2011146101A1

  公开（公告）日：2011-11-24

  The present invention provides methods of preventing or inhibiting tumor metastasis in a subject by administering a therapeutically effective amount of (1) a compound from a group of enumerated compounds, or a pharmaceutically acceptable salt thereof; (2) an agent that covalently modifies at least one cysteine residue of S100A4 protein; or (3) an agent that inhibits the interaction between S100A4 and myosin-IIA.
• 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.