1,2,4-triacetoxy-3-methylnaphthalene | 604-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,4-triacetoxy-3-methylnaphthalene
• 英文别名: 2-methyl-1,3,4-triacetoxynaphthalene；1,2,4-triacetoxy-3-methyl-naphthalene；1,2,4-Triacetoxy-3-methyl-naphthalin；(3-Methyl-naphthalintriyl-(1,2,4))-triacetat；(3,4-Diacetyloxy-2-methylnaphthalen-1-yl) acetate
• CAS: 604-86-4
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: XDQCHRLILMHGHT-UHFFFAOYSA-N

物化性质

• 沸点：
  445.5±45.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)
• 熔点：
  130 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,4-triacetoxy-3-methylnaphthalene 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以92%的产率得到2-羟基-3-甲基-1,4-萘醌
  参考文献：
  名称：

  Activated Zeolites and Heteropolyacids: An Efficient Catalysts for the Synthesis of Triacetoxyaromatic Precursors of Hydroxyquinones

  摘要：

  泰尔-温特反应在合成氢醌的前驱体三乙酸芳香化合物方面具有重要意义。氯磺酸等液态酸和杂多酸等固态酸作为高效催化剂，可以在室温下不使用有机溶剂的条件下，有效替代硫酸在醌类乙酰氧基化反应中的作用。

  DOI：

  10.14233/ajchem.2013.14276
• 作为产物：
  描述：

  2-甲基-3-(甲基氨基)-1,4-萘醌 在 硫酸 、 水 、 sodium acetate 、 溶剂黄146 、 锌 作用下， 生成 1,2,4-triacetoxy-3-methylnaphthalene
  参考文献：
  名称：

  Asano; Hase, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 59,60; dtsch. Ref. S. 55

  摘要：

  DOI：

文献信息

• Thiele acetylation of substituted benzoquinones
  作者：H. S. Wilgus、J. W. Gates,Jr

  DOI：10.1139/v67-314

  日期：1967.9.1

  The treatment of substituted quinones with acetic anhydride under acid catalysis gives substituted triacetoxybenzenes. Previous work on this reaction is summarized, and the reaction has been extended to include quinones having electron-withdrawing groups, and two quinones which had previously been reported as inactive.

  用醋酸酐在酸催化下处理取代醌可得到取代三乙酰氧基苯。对这种反应的先前研究进行了总结，并将该反应扩展到包括具有电子吸引基团的醌，以及之前被报道为不活跃的两种醌。
• Naphthalene anti-psoriatic agents
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0150831A2

  公开（公告）日：1985-08-07

  Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: wherein: R' is alkoxy of one to twelve carbon atoms, of one to twelve carbon atoms, alkylthio of one to twelve carbon atoms, optionally substituted phenoxy or optionally substituted phenylthio; R2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl; R3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2, or R3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O)nR wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms, optionally substituted phenyl or optionally substituted benzyl.

  哺乳动物的牛皮癣可通过局部施用式中的萘来缓解： 其中 R'是一至十二个碳原子的烷氧基、一至十二个碳原子的烷氧基、一至十二个碳原子的烷硫基、任选取代的苯氧基或任选取代的苯硫基； R2 是氢、低级烷基、任选取代的苯基或任选取代的苯基烷基； R3 是低级烷基、低级烷氧基或卤素，m 是 0、1 或 2，或者 R3 是任选取代的苯基、任选取代的苯基低级烷基、任选取代的苯基低级烷氧基、氨基、低级烷基氨基、低级二烷基氨基、氰基或 S(O)nR 其中 R 是低级烷基；任选取代的苯基；任选取代的苯基低级烷基；或任选取代的三至九个环原子的杂环芳基，含有一个或两个选自氮、氧和硫的杂原子，以及它们的药学上可接受的酸加成盐；且 m 为 1，n 为 0、1 或 2；以及 W 是一至七个碳原子的烷基、任选取代的苯基或任选取代的苄基。
• SUPPORTED METALATED PHTHALOCYANINE AS CATALYST FOR OXIDATION BY MOLECULAR OXYGEN. SYNTHESIS OF QUINONES AND CARBONYL COMPOUNDS
  作者：Didier Villemin、Mohamed Hammadi、Messaoud Hachemi

  DOI：10.1081/scc-120004139

  日期：2002.1

  Supported metalated phthalocyanine on K10 or on lamellar zirconium phosphate catalyses the oxidation of hydroquinones (and phenols) into quinones. Some interesting natural napthoquinones were also prepared (Juglone, Menadione, Lawsone, Phthiocol). Supported metalated phthalocyanine was also used in re-oxidation by oxygen of palladium and ruthenium, in the Wacker oxidation of olefins into ketones, in the oxidation of cyclohexadiene and in oxidation of benzylic alcohols in aldehydes.
• Bi(OTf)3-catalyzed acylation of p-quinones: a facile synthesis of acylated hydroquinones
  作者：J.S Yadav、B.V.Subba Reddy、T Swamy、K.Raghavender Rao

  DOI：10.1016/j.tetlet.2004.06.032

  日期：2004.7

  p-Quinones undergo smooth acylation with acetic anhydride in the presence of 2 mol% of bismuth triflate under mild conditions to afford the corresponding 1,4-diacylated-2-acetoxylated hydroquinones in excellent yields with high selectivity. (C) 2004 Elsevier Ltd. All rights reserved.
• 137. Acylation reactions catalysed by strong acids. Part VI. A comparison of zinc chloride and perchloric acid as catalysts for the thiele acetylation of quinones
  作者：H. Burton、P. F. G. Praill

  DOI：10.1039/jr9520000755

  日期：——