1,5-Dihydroxy-2,6-dimethylnaphthalin | 123979-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-Dihydroxy-2,6-dimethylnaphthalin
• 英文别名: 2,6-Dimethylnaphthalene-1,5-diol；2,6-dimethyl-1,5-dihydroxynaphthalene
• CAS: 123979-29-3
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: GOQCGUCUHMZECD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-Dihydroxy-2,6-dimethylnaphthalin 在 甲烷磺酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,4,5,7,9,10-Hexamethyl-1,6-dioxapyrene
  参考文献：
  名称：

  Synthesis and properties of substituted 1,6-dioxapyrene donors

  摘要：

  The synthesis of substituted 1,6-dioxapyrenes, 2b-g, from 2,6-dipropyl-1,5-naphthalenediol (7a) or 2,6-dimethyl-1,5-naphthalenediol (7b) is described. Diol 7a was prepared by Claisen allylic rearrangement followed by reduction, and 7b was prepared by Mannich reaction of 1,5-naphthalenediol followed by base-promoted hydrogenolysis. The 1,6-dioxapyrenes can be oxidized to stable cation radicals at +0.2-0.35 V vs SCE and to dications at +0.8-1.20 V. The preparation of some tetracyanoquinodimethane salts and binary cation radical salts of the 1,6-dioxapyrenes is reported.

  DOI：

  10.1021/jo00025a020
• 作为产物：
  描述：

  1,5-二羟基萘 在 palladium on activated charcoal 甲醇 、 氢气 、 三乙胺 、 乙酰氯 作用下， 以 乙醇 、 水 为溶剂， 反应 8.75h， 生成 1,5-Dihydroxy-2,6-dimethylnaphthalin
  参考文献：
  名称：

  Synthesis and properties of substituted 1,6-dioxapyrene donors

  摘要：

  The synthesis of substituted 1,6-dioxapyrenes, 2b-g, from 2,6-dipropyl-1,5-naphthalenediol (7a) or 2,6-dimethyl-1,5-naphthalenediol (7b) is described. Diol 7a was prepared by Claisen allylic rearrangement followed by reduction, and 7b was prepared by Mannich reaction of 1,5-naphthalenediol followed by base-promoted hydrogenolysis. The 1,6-dioxapyrenes can be oxidized to stable cation radicals at +0.2-0.35 V vs SCE and to dications at +0.8-1.20 V. The preparation of some tetracyanoquinodimethane salts and binary cation radical salts of the 1,6-dioxapyrenes is reported.

  DOI：

  10.1021/jo00025a020

文献信息

• 2,4,5-TRIAMINOPHENOLS AND RELATED COMPOUNDS
  申请人：Dhawan Rajjiv

  公开号：US20130012741A1

  公开（公告）日：2013-01-10

  New triaminophenol compositions and related compounds are disclosed, as are processes for their preparation and for the preparation of novel salts and diacid complexes from such compounds. Polymers prepared from these compositions can be made into high strength fiber, film, and tape and are useful in applications such as protective apparel, aircraft, automotive components, personal electronics, and sports equipment.

  本文披露了新的三氨酚组合物和相关化合物，以及用于它们制备的工艺和从这些化合物制备新的盐和二酸复合物的工艺。从这些组合物中制备的聚合物可以制成高强度纤维、薄膜和胶带，并可用于防护服装、飞机、汽车零部件、个人电子产品和运动器材等应用。
• [EN] 2,4,5-TRIAMINOTHIOPHENOLS AND RELATED COMPOUNDS<br/>[FR] 2,4,5-TRIAMINOTHIOPHÉNOLS ET COMPOSÉS ASSOCIÉS
  申请人：DU PONT

  公开号：WO2012088190A1

  公开（公告）日：2012-06-28

  New triaminothiophenol compositions and related compounds are disclosed, as are processes for their preparation and for the preparation of novel salts, diacid complexes, and polymers from such compounds. Polymers prepared from these compositions can be made into high strength fiber, film, and tape and are useful in applications such as protective apparel, aircraft, automotive components, personal electronics, and sports equipment.

  公开了新的三氨基硫代苯酚组合物和相关化合物，以及其制备的工艺和从这些化合物制备新型盐、二酸复合物和聚合物的工艺。从这些组合物制备的聚合物可制成高强度纤维、薄膜和胶带，并可用于防护服装、飞机、汽车零部件、个人电子产品和体育器材等应用。
• [EN] INTEGRATED PROCESSES FOR THE PREPARATION OF HETEROCYCLIC AROMATIC POLYMER PRECURSORS<br/>[FR] PROCESSUS INTÉGRÉS DE PRÉPARATION DE PRÉCURSEURS DE POLYMÈRES AROMATIQUES HÉTÉROCYCLIQUES
  申请人：DU PONT

  公开号：WO2012088184A1

  公开（公告）日：2012-06-28

  An integrated process is provided for efficiently preparing 2, 4, 5-triaminothiophenol, starting; high purity salts thereof; and complexes of 2, 4, 5-triaminothiophenol with aromatic diacids, which are precursors for making polymer for high performance fibers. The process design eliminates several costly intermediate drying and recrystallization steps. The handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.

  提供了一种集成工艺，用于高效制备2,4,5-三氨基噻吩酚，起始；其高纯度盐；以及2,4,5-三氨基噻吩酚与芳香族二酸的络合物，这些是制备高性能纤维聚合物的前体。该工艺设计消除了几个昂贵的中间干燥和重结晶步骤。避免了固体材料的处理，这些材料可能具有皮肤致敏性和毒性，从而消除了人类和环境的暴露。
• The chemistry of 1,6-dioxapyrenes part 3 : Scope and limitations of an acid catalyzed ring-closing reaction
  作者：Jørn B. Christensen、Klaus Bechgaard

  DOI：10.1002/jhet.5570400503

  日期：2003.9

  One of the few methods for synthesis of 1,6-dioxapyrenes is the acid catalyzed cyclization of 2,6-disubstituted 1,5-bis(2-oxoalkoxy)naphthalenes. The scope and limitations of this reaction has been investigated and 11 new 2,7-disubstituted 1,6-dioxapyrenes have been prepared and characterized. Most of the compounds undergo two reversible oxidations to give the corresponding radical as well as di- cations

  合成1，6-二氧杂戊二烯的几种方法之一是2，6-二取代的1，5-双（2-氧代烷氧基）萘的酸催化环化。已经研究了该反应的范围和局限性，并且已经制备和表征了11种新的2，7-二取代的1，6-二氧杂戊二烯。大多数化合物经历两个可逆的氧化反应，生成相应的自由基和阳离子。
• Untersuchung an 1,4-Naphthochinonen, 18. Mitt.: 6-Methyl- und 3,6-Dimethylplumbagin
  作者：Gotthard Wurm、Bernd Goeßler

  DOI：10.1002/ardp.19893220807

  日期：——

  radikalische Methylierung von 6‐Methylplumbagin (9). Als Vorstufe für 9 dient 1,5‐Dihydroxy‐2,6‐dimethylnaphthalin (7), die Schlüsselreaktion zur Synthese ist die Bis‐ortho‐Lithiierung von 1,5‐Bis‐methoxy‐methoxynaphthalin (3). Bei der Oxidation von 7 ← 9 mit durch Cosalen® aktiviertem O2 entsteht das Dimethylderivat 10 des Naturstoffs Maritinon als Nebenprodukt.

  3,6-Dimethylplumbagine (12) 是通过 6-methylplumbagine (9) 的自由基甲基化产生的。1,5-二羟基-2,6-二甲基萘 (7) 用作 9 的前体；关键合成反应是 1,5-双-甲氧基-甲氧基萘 (3) 的双邻位锂化反应。在 Cosalen® 激活的 O2 氧化 7 ← 9 期间，天然产物 maritinon 的二甲基衍生物 10 作为副产物形成。