2-(p-tolylthio)naphthalene-1,4-dione | 89478-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(p-tolylthio)naphthalene-1,4-dione
• 英文别名: 2-(4-methylphenylthio)-1,4-naphthoquinone；2-(4-methylphenyl)sulfanylnaphthalene-1,4-dione
• CAS: 89478-03-5
• 化学式: C₁₇H₁₂O₂S
• 分子量: 280.347
• InChiKey: IHRGUZGBIGODSC-UHFFFAOYSA-N

物化性质

• 沸点：
  442.6±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(p-tolylthio)naphthalene-1,4-dione 在 间氯过氧苯甲酸 作用下， 以 氘代氯仿 、 氯仿 为溶剂， 反应 48.0h， 生成 endo-<1R^*,4S^*,4aS^*,9aR^*,(S)S^*>-1,4-Methano-4a-(p-tolylsulfinyl)-1,4,4a,9a-tetrahydro-9,10-anthraquinone
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones

  摘要：

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.

  DOI：

  10.1021/jo00051a036
• 作为产物：
  描述：

  1,4-二甲氧基-2-((4-甲基苯基)硫代)萘 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以96%的产率得到2-(p-tolylthio)naphthalene-1,4-dione
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones

  摘要：

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.

  DOI：

  10.1021/jo00051a036

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。
• Light-Driven Carbon–Carbon Coupling of α-sp³–CH of Aliphatic Alcohols with sp²–CH Bond of 1,4-Naphthoquinones
  作者：Raushan Kumar Jha、Aditya Upadhyay、Kanika、Saket Jain、Neena K A、Sangit Kumar

  DOI：10.1021/acs.orglett.2c03066

  日期：2022.10.21

  Here, an α-selective Csp3–H bond functionalization of primary aliphatic alcohols with 1,4-naphthoquinones yielded Csp2–Csp2 coupled products driven by blue-LED light under catalyst, metal, base, and reagent-free conditions. In this transformation, cleavage of three C–H bonds (two sp3–C-H, one sp2–C–H, and one O–H) and four new bonds formed, leading to fluorescent 2-acylated-1,4-naphthohydroquinones

  在这里，在催化剂、金属、碱和无试剂条件下，脂肪伯醇与 1,4-萘醌的 α-选择性 C sp3 -H 键官能化产生了由蓝色 LED 光驱动的 C sp 2 -C sp 2偶联产物. 在该转化过程中，三个 C-H 键（两个 sp 3 -CH、一个 sp 2 -C-H 和一个 O-H）断裂并形成四个新键，从而产生荧光 2-acylated-1,4-naphthohydroquinones .
• Blue Light Irradiated Metal-, Oxidant-, and Base-Free Cross-Dehydrogenative Coupling of C(<i>sp</i>²)–H and N–H Bonds: Amination of Naphthoquinones with Amines
  作者：Raushan Kumar Jha、Monojit Batabyal、Sangit Kumar

  DOI：10.1021/acs.joc.3c00666

  日期：2023.6.2

  reaction proceeds by radical pathway in which naphthoquinone forms a highly oxidizing naphthoquinonyl biradical upon irradiation of blue light (457 nm). Consequently, electron transfer from electron-rich amine to an oxidizing naphthoquinonyl biradical leads to a naphthoquinonyl radical anion and aminyl radical cation, followed by proton transfer and delocalization leading to a carbon-centered naphthoquinonyl

  在此，我们报道了蓝光驱动的萘醌和醌的 C( sp 2 )–H 键与伯胺和仲胺的 N–H 键的胺化反应，用于合成 2-氨基萘醌和 2-氨基醌. 萘醌与各种具有给电子（-CH 3、-OCH 3、-SCH 3）、撤电子（-F、-Cl、-Br、-I）的脂肪族胺、芳香族胺、手性胺、伯胺和仲胺的偶联), 和 CO 2 H, -OH, -NH 2在蓝光照射下，无需使用任何额外的试剂、添加剂和氧化剂，选择性地发生具有酸性质子的基团，以 60-99% 的收率提供 C-N 偶联的 2-氨基-萘醌和氢气作为甲醇溶剂中的副产物。通过 DFT 计算、受控实验、动力学同位素效应和底物的替代效应的机理洞察表明，反应通过自由基途径进行，其中萘醌在蓝光 (457 nm) 照射下形成高度氧化的萘醌基双自由基。因此，从富电子胺到氧化性萘醌基双自由基的电子转移导致萘醌基阴离子和氨基自由基阳离子，随后质子转移和离域导致以碳为中心的萘醌基。
• 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 and biological evaluation of novel sulfonyl-naphthalene-1,4-diols as FabH inhibitors
  作者：Mamoun M. Alhamadsheh、Norman C. Waters、Sarbjot Sachdeva、Patricia Lee、Kevin A. Reynolds

  DOI：10.1016/j.bmcl.2008.10.097

  日期：2008.12

  A series of analogs of 2-tosylnaphthalene-1,4-diol were prepared and were found to be potent 10-20 nM reversible inhibitors of the Escherichia coli FabH enzyme. The inhibitors were also effective but to a lesser degree (30 nM-5 mu M), against the Mycobacterium tuberculosis and Plasmodium falciparum FabH enzymes. Preliminary SAR studies demonstrated that the sulfonyl group and naphthalene-1,4 diol were required for activity against all enzymes but the toluene portion could be significantly altered and leads to either modest increases or decreases in activity against the three enzymes. The in vitro activity of the analogs against E. coli FabH parallel the in vivo activity against E. coli TolC strain and many of the compounds were also shown to have antimalarial activity against P. falciparum. (C) 2008 Published by Elsevier Ltd.