2-(1,3-dioxolan-2-yl)-1,4-naphthoquinone | 75265-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1,3-dioxolan-2-yl)-1,4-naphthoquinone
• 英文别名: 2-(1,3-Dioxolan-2-yl)naphthalene-1,4-dione
• CAS: 75265-12-2
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: CIOCFGIIKTZYLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methyl-1-pyrrolidino-1-cyclohexene 、 2-(1,3-dioxolan-2-yl)-1,4-naphthoquinone 在 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 以16%的产率得到4-methyl-1,2,3,4-tetrahydrobenzo[j]phenanthridine-7,12-dione
  参考文献：
  名称：

  1,2,3,4,8,9,10,11-Octahydrobenzo[j]phenanthridine-7,12-diones as New Leads against Mycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) continues to be a worldwide health problem with over 1.4 million deaths each year. Despite efforts to develop more effective vaccines, more reliable diagnostics, and chemotherapeutics, tuberculosis remains a threat to global health, fueled by the HIV pandemic and the rapid generation of drug resistance. The exploration of novel drugs to serve as a companion drug for existing drugs is of paramount importance. As part of our program to design new 2-aza-anthraquinones with antimycobacterial activity, various tetrahydro- and octahydrobenzo[j]phenanthridinediones were synthesized. These compounds showed high in vitro potency against Mycobacterium tuberculosis, the etiological agent of TB and against other clinically relevant mycobacterial species at submicromolar concentrations. The susceptibility of a multidrug resistant strain toward these compounds and their ability to target intracellular replicating Mycobacterium tuberculosis was demonstrated. Next to the acute toxicity, the genotoxicity of these compounds was investigated. Often overlooked in studies, genotoxicity could be dismissed for the investigated compounds, making them a promising scaffold in TB drug research.

  DOI：

  10.1021/jm401735w
• 作为产物：
  描述：

  1,4-二羟基萘 在 potassium carbonate 、 对甲苯磺酸 、 silver nitrate 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 丙酮 、 苯 为溶剂， 反应 28.03h， 生成 2-(1,3-dioxolan-2-yl)-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of Quinones from Hydroquinone Dimethyl Ethers. Oxidative Demethylation with Cobalt(III) Fluoride

  摘要：

  用三氟化钴对1,4-二甲氧基萘和1,4-二甲氧基苯衍生物进行氧化脱甲基反应，能够获得良好至极佳的产率，从而得到相应的萘醌和苯醌衍生物。

  DOI：

  10.1055/s-1999-2875

文献信息

• Short synthesis of functionalized pentalongin derivatives using pyridinium ylid chemistry
  作者：Pieter Claes、Jan Jacobs、Sven Claessens、Norbert De Kimpe

  DOI：10.1016/j.tet.2010.07.012

  日期：2010.8

  of acylmethylnaphthoquinones. The latter naphthoquinones were prepared starting from 2-dioxolanylnaphthoquinone by means of both a stoichiometric and a catalytic method deploying various pyridinium ylids.

  通过酰基甲基萘醌的环化反应，合成了在C-1具有乙缩醛功能的3-取代的五聚体衍生物。后者的萘醌是从2-二氧戊环基萘醌开始，通过化学计量的和催化的方法，采用各种吡啶鎓碘化物来制备的。
• SYNTHESIS OF NOVEL QUINONES WITH SILVER (II) DIPICOLINATE AS A NEW SELECTIVE OXIDANT
  作者：Krystian Kloc、Jacek Mlochowski、Ludwik Syper

  DOI：10.1246/cl.1980.725

  日期：1980.6.5

  and naphthoquinones bearing oxiranyl or 1,3-dioxolan-2-yl substituents were prepared by oxidative demethylation of appropriate hydroquinone dimethyl ethers with silver (II) dipicolinate. A remarkable selectivity of this silver (II) complex as an oxidizing reagent was demonstrated.

  带有环氧乙烷基或 1,3-二氧戊环-2-基取代基的苯并和萘醌是通过适当的氢醌二甲醚与吡啶二羧酸银 (II) 的氧化去甲基化制备的。证明了这种银 (II) 络合物作为氧化剂的显着选择性。
• KLOC K.; MLOCHOWSKI J.; SYPER L., CHEM. LETT., 1980, NO 6, 725-728
  作者：KLOC K.、 MLOCHOWSKI J.、 SYPER L.

  DOI：——

  日期：——