2-methoxy-1,4-anthracenedione | 31619-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-methoxy-1,4-anthracenedione
• 英文别名: 2-methoxyanthracene-1,4-dione；2-methoxy-1,4-anthraquinone；2-methoxy-anthracene-1,4-dione；2-Methoxy-anthracen-1,4-dion；2-Methoxy-anthrachinon-1,4
• CAS: 31619-41-7
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: BQKKYANHXFRHLT-UHFFFAOYSA-N

物化性质

• 熔点：
  217 °C
• 沸点：
  440.7±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-1,4-anthracenedione 生成 2-Chloro-3-methoxyanthracene-1,4-dione
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-蒽醌 在 硫酸 、 sodium hydrogensulfite 作用下， 生成 2-methoxy-1,4-anthracenedione
  参考文献：
  名称：

  Fieser, Journal of the American Chemical Society, 1928, vol. 50, p. 467

  摘要：

  DOI：

文献信息

• Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C
  作者：Tokutaro Ogata、Tomoyo Yoshida、Maki Shimizu、Manami Tanaka、Chie Fukuhara、Junko Ishii、Arisa Nishiuchi、Kiyofumi Inamoto、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2016.01.040

  日期：2016.3

  A novel etherification of 2-hydroxy-1,4-naphthoquinone derivatives with alkoxyalkyl chlorides and hydride bases is described. Precise study of the conditions and substrate scope suggested that the reaction occurs specifically in the molecule having a 2-hydroxy-1,4-benzoquinone skeleton. A chemoselective O-methylation reaction was achieved to afford a synthetically important intermediate, which offered

  描述了2-羟基-1，4-萘醌衍生物与烷氧基烷基氯化物和氢化物碱的新型醚化。对条件和底物范围的精确研究表明，该反应特别发生在具有2-羟基-1,4-苯醌骨架的分子中。实现了化学选择性的O-甲基化反应，以提供合成上重要的中间体，该中间体可轻松获得具有抗肿瘤活性的天然产物。
• Synthesis method for reductant precursor
  申请人：Energy Conversion Devices, Inc.

  公开号：US04592867A1

  公开（公告）日：1986-06-03

  A synthesis method is provided for the synthesis of quinone compounds of the formula ##STR1## where n is 0-3, Y.sup.1 is alkoxy, Y.sup.2 is alkoxy, chloro, bromo or hydrogen and R' and R" each and independently are hydrogen, alkyl or phenyl. These compounds are useful as reductant precursors in tellurium imaging compositions.

  提供了一种合成方法，用于合成式为##STR1##的醌化合物，其中n为0-3，Y.sup.1为烷氧基，Y.sup.2为烷氧基、氯、溴或氢，R'和R"各自独立地为氢、烷基或苯基。这些化合物可用作硒镉成像组合物中的还原剂前体。
• Obtention of Anthraquinones by Selective Oxidation of the Corresponding Anthracenes and 9,10-Dimethoxyanthracenes with Copper or Zinc Nitrate supported on Silica Gel
  作者：Mario Anastasia、Pietro Allevi、Cristina Bettini、Alberto Fiecchi、Anna Maria Sanvito

  DOI：10.1055/s-1990-27101

  日期：——

  Anthracene, 9,10-dimethoxyanthracene and substituted analogues are selectively oxidized to the corresponding anthraquinones in good yields by copper(II) or zinc(II) nitrate supported on silica gel; the ether groups at different position from 9 and 10 are unaffected.

  蒽、9,10-二甲氧基蒽和取代的类似物可被硅胶上的硝酸铜（II）或硝酸锌（II）选择性地氧化成相应的蒽醌类化合物，且收率良好；位于 9 和 10 不同位置的醚基不受影响。
• Quinone synthesis
  申请人：ENERGY CONVERSION DEVICES, INC.

  公开号：EP0178904A2

  公开（公告）日：1986-04-23

  A process for producing a quinone of the formula wherein n is zero, 1 or 2; Y' is alkoxy; Y2 is H, C1, Br or alkoxy; and R' and R" are independently selected from H, alkyl and phenyl, which comprises the steps of: (a) reacting a tetrabromide of the formula with potassium iodide; (b) reacting the product of step (a) with a 2-alkoxy-1,4-benzoquinone, to give the desired quinone when Y2 is H; (c) if desired, reacting the quinone in which Y2 is H with C12 or Br2, to give the desired quinone in which Y2 is C1 or Br; and (d) if desired, reacting the quinone in which Y2 is C1 or Br with a lithium, sodium or potassium alkoxide, to give the desired quinone in which Y2 is alkoxy.

  一种生产式醌的工艺 其中n为零、1或2；Y'为烷氧基；Y2为H、C1、Br或烷氧基；R'和R "独立地选自H、烷基和苯基，该工艺包括以下步骤 (a) 式中的四溴化物与碘化钾反应 与碘化钾反应 (b) 当 Y2 为 H 时，将步骤（a）的产物与 2-烷氧基-1,4-苯醌反应，得到所需的醌； (c) 如果需要，将 Y2 为 H 的醌与 C12 或 Br2 反应，得到 Y2 为 C1 或 Br 的所需醌；以及 (d) 如果需要，将 Y2 为 C1 或 Br 的醌与锂、钠或钾氧化碱反应，得到 Y2 为烷氧基的所需醌。
• Syntheses, electrochemistry and molecular modeling of N,N′-dicyanoquinonediimine (DCNQI) derivatives of substituted 1,4-anthracenediones: precursors for organic metals.
  作者：Elena Barranco、Nazario Martín、José L. Segura、Carlos Seoane、Pilar de la Cruz、Fernando Langa、Araceli Gonzalez、José M. Pingarrón

  DOI：10.1016/s0040-4020(01)80405-1

  日期：1993.5

  The title compounds (10) have been obtained from the corresponding 1,4-anthracenedione derivatives (3), prepared by different synthetic routes, by reaction with bis(trimethylsilyl)carbodiimide (BTC). The cyclic voltammetry of these compounds (3 and 10) reveals the presence of two reduction waves to the corresponding anion-radical and dianion. The acceptor ability of compounds 10 can be modulated by the presence of substituents on the DCNQI ring. The syn/anti isomers have been studied by molecular mechanics and the results are in good agreement with the H-1-NMR high resolution spectral data.