乙酸1,4-二氧代-1,4-二氢萘-2-基酯 | 1785-65-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 乙酸1,4-二氧代-1,4-二氢萘-2-基酯
• 英文名称: 2-acetoxy-1,4-naphthoquinone
• 英文别名: (1,4-dioxonaphthalen-2-yl) acetate
• CAS: 1785-65-5
• 化学式: C₁₂H₈O₄
• mdl: MFCD00627070
• 分子量: 216.193
• InChiKey: QHISPATYFAPAKC-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  364.6±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  二氯甲烷；乙酸乙酯;甲醇
• 保留指数：
  1833

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  乙酸1,4-二氧代-1,4-二氢萘-2-基酯 在 sodium dithionite 、 sodium carbonate 作用下， 生成 4-acetoxy-naphthalene-1,3-diol
  参考文献：
  名称：

  Rideout,J.A. et al., Australian Journal of Chemistry, 1976, vol. 29, p. 1087 - 1098

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-萘醌 在 盐酸 、 乙醇 、 硫酸 、 甲基安非他命 、 联铬酸盐 、 zinc(II) chloride 作用下， 生成 乙酸1,4-二氧代-1,4-二氢萘-2-基酯
  参考文献：
  名称：

  Thiele; Winter, Justus Liebigs Annalen der Chemie, 1900, vol. 311, p. 355

  摘要：

  DOI：

文献信息

• Synthesis, biological evaluation, and correlation of cytotoxicity versus redox potential of 1,4-naphthoquinone derivatives
  作者：Chien-Chang Shen、Shakil N. Afraj、Chia-Cheng Hung、Balaji D. Barve、Li-Ming Yang Kuo、Zhi-Hu Lin、Hisu-O. Ho、Yao-Haur Kuo

  DOI：10.1016/j.bmcl.2021.127976

  日期：2021.6

  4-naphthoquinone derivatives of lawsone (1), 6-hydroxy-1,4-naphthoquinone (2), and juglone (3) were synthesized by alkylation, acylation, and sulfonylation reactions. The yields of lawsone derivatives 1a-1k (type A), 6-hydroxy-1,4-naphthoquinone derivatives 2a-2j (type B), and juglone derivatives 3a-3h (type C) were 52–99%, 53–96%, and 28–95%, respectively. All compounds were tested in vitro for the cytotoxicity

  通过烷基化、酰化和磺酰化反应合成了罗松酮 ( 1 )、6-羟基-1,4-萘醌 ( 2 ) 和胡桃酮 ( 3 )的一系列 1,4-萘醌衍生物。罗松酮衍生物1a-1k（A型）、6-羟基-1,4-萘醌衍生物2a-2j（B型）和胡桃酮衍生物3a-3h（C型）的产率为 52-99%、53-96 % 和 28-95%，分别。所有化合物都在体外测试了对人口腔表皮样癌 (KB) 和宫颈上皮样癌 (HeLa) 细胞的细胞毒性，并研究了它们的构效关系。化合物发现3c在 KB 细胞系中最有效（IC 50  = 1.39 µM）。评估了一些化合物对 DNA 拓扑异构酶 I 的抑制作用。化合物2C，3，图3a和图3d显示拓扑异构酶抑制活性与IC 50 8.3-91μM的值。通过循环伏安法检测 pH 7.2 磷酸盐缓冲液中所有萘醌的标准氧化还原电位 (E°)。已发现氧化还原电位与A型化合物的抑制作用之间存在明确的相关性。
• Highly Active Manganese-Mediated Acylation of Alcohols with Acid Chlorides or Anhydrides
  作者：Seung-Hoi Kim、Seong-Ryu Joo、Young-Jin Youn、Young-Ran Hwang

  DOI：10.1055/s-0036-1590973

  日期：2017.12

  To explore further the practical uses of highly active manganese (Mn*), a variety of alcohols were treated with Mn*, and the resulting complexes were coupled with acid chlorides and/or acetic anhydride in the absence of any extra catalyst. The subsequent reactions took place smoothly under mild conditions, providing the corresponding O-acylation products in good to excellent isolated yields.

  为了进一步探索高活性锰 (Mn*) 的实际用途，用 Mn* 处理各种醇，在没有任何额外催化剂的情况下，将所得配合物与酰氯和/或乙酸酐偶联。随后的反应在温和的条件下顺利进行，提供了相应的 O-酰化产物，分离产率良好至极好。
• Process for the preparation of trans-2,3-disubstituted naphthoquinones
  申请人：Nardi Antonio

  公开号：US20100137644A1

  公开（公告）日：2010-06-03

  The invention concerns a new process for the preparation of naphthoquinones, in particular an improved process for the preparation of 2,3-disubstituted 1,4-naphthoquinones, in the trans configuration.

  本发明涉及一种制备萘醌的新工艺，特别是改进了以反式构型制备2,3-二取代-1,4-萘醌的工艺。
• Iron-Catalyzed Radical Methylation of Activated Alkenes with tert-Butanol as the Methyl Source
  作者：Zhengbao Xu、Rui Jia、Zhiwei Ma、Shouhao Cao、Liang Shen、Hongfang Ji

  DOI：10.1055/s-0039-1690193

  日期：2019.10

  A free-radical-initiated methylation/addition/cyclization of N-arylacrylamides and a methylation/addition/elimination of quinines have been developed in which t-BuOH is used as a methyl source. These reactions provide effective and selective methods for the synthesis of various methylated oxindoles and quinones in moderate to good yields.

  已经开发了 N-芳基丙烯酰胺的自由基引发的甲基化/加成/环化和奎宁的甲基化/加成/消除，其中使用 t-BuOH 作为甲基源。这些反应为以中等至良好的产率合成各种甲基化羟吲哚和醌提供了有效和选择性的方法。
• Molecular anchors—mimicking metabolic processes in thiol analysis
  作者：Robert B. Smith、Claire Canton、Nathan S. Lawrence、Callum Livingstone、James Davis

  DOI：10.1039/b611471g

  日期：——

  The interaction between various novel naphthoquinones and glutathione was explored using a variety of electrochemical techniques. An adamantane derivatised quinone was found to adsorb strongly to carbon surfaces providing a robust film possessing a distinct and consistent voltammetric profile which is markedly different from solution based species. The anodic peak process was found to respond to increasing additions of glutathione and the analytical merits have been assessed. In contrast to conventional thiol–quinone electrochemistry, the detection pathway involves the solubilisation and removal of the hydrophobic quinone derivative through conjugation with glutathione. The peak potential (+0.2 V vs. Ag/AgCl) is such that an unambiguous response to glutathione can be achieved in the presence of a significant excess (1 mM) of common physiological components.

  利用多种电化学技术探讨了各种新型萘醌与谷胱甘肽之间的相互作用。发现金刚烷衍生化的醌能够强烈吸附在碳表面，形成具有独特且一致伏安图谱的坚固薄膜，这与溶解态的物种明显不同。研究发现，阳极峰值过程对谷胱甘肽的逐次添加有响应，并且其分析优点已得到评估。与传统的巯基-醌电化学不同，检测途径涉及通过与谷胱甘肽结合使疏水性醌衍生物溶解和去除。峰值电位（+0.2 V vs. Ag/AgCl）使得在存在大量（1 mM）常见生理组分时也能明确响应谷胱甘肽。

表征谱图