2,5-环己二烯-1,4-二酮,2-(苯基氨基)- | 16085-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-环己二烯-1,4-二酮,2-(苯基氨基)-
• 英文名称: 2-phenylamino-1,4-benzoquinone
• 英文别名: Anilinobenzochinon；2-Anilinocyclohexa-2,5-diene-1,4-dione
• CAS: 16085-14-6
• 化学式: C₁₂H₉NO₂
• mdl: MFCD00187688
• 分子量: 199.209
• InChiKey: RSRYAYQRBHJYCG-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  342.7±42.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-环己二烯-1,4-二酮,2-(苯基氨基)- 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 0.42h， 生成 6-Anilino-2-methyl-4,7(2H)-indazolchinon
  参考文献：
  名称：

  Zur Synthese und Struktur derp-Indazolchinone und ihrer Methylierungsprodukte Untersuchungen �ber Chinone, 8. Mitt.

  摘要：

  The p-benzoquinones 5 e-j react with diazomethane (after dehydrogenation) to 6-anilino- 2e, dimethylamino- 2h, phenylthio- 2i, and methylthioindazolquinone 2 j. Methylation with dimethylsulfate of these as well as of the already known indazolquinones 6-toluidino- 2 f, 6-methylanilino- 2 g, 5-tert.butyl- 2 m, 5,6-methyl- (isomer mixture) 2 l, n, and benz-indazolquinone 2 o yield the 1- and 2-N-methyl derivatives 3 and 4. The structure of the 2-methyl derivatives is established by reaction of the corresponding benzoquinones with 3-methylsydnon in the case of 4 e, 4 g. UV/VIS-, IR- and H-1-NMR-spectroscopy (in CDCl3 and DMSO) were used for structure determination. Comparison of the UV/VIS-spectra of 2 - 4 shows that the indazolquinones are existing as 2 H-4,7-diones. For the structure elucidation of the 1- rs. 2-methylderivatives (which can be attributed to the methylation products) NMR-spectroscopy is well suited even without knowing the second isomer (solvent-effect). The course of the reaction of quinones with diazomethane and of the methylation reactions of the indazolquinones is discussed.

  DOI：

  10.1007/bf00812321
• 作为产物：
  描述：

  2-anilino-hydroquinone 在 盐酸 、 三氯化铁 作用下， 生成 2,5-环己二烯-1,4-二酮,2-(苯基氨基)-
  参考文献：
  名称：

  Willstaetter; Majima, Chemische Berichte, 1910, vol. 43, p. 2592

  摘要：

  DOI：

文献信息

• ‘On water’: unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension
  作者：Vishnu K. Tandon、Hardesh K. Maurya

  DOI：10.1016/j.tetlet.2009.07.149

  日期：2009.10

  Unique nucleophilic substitution and addition reactions of 1,4-quinones in aqueous suspension with aromatic amines, primary aliphatic amines, amino acid, ester of amino acid, heterocyclic amines, hydrazine, amide, and thioethers are described in absence of catalyst against the traditional synthetic routes of these reactions in non-aqueous medium in presence of catalyst.

  在没有传统合成催化剂的催化剂的情况下，描述了水性悬浮液中1,4-醌与芳香胺，伯脂肪胺，氨基酸，氨基酸酯，杂环胺，肼，酰胺和硫醚的独特亲核取代和加成反应催化剂存在下在非水介质中进行这些反应的途径。
• Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C–H Iodination, Bromination, and Phenylselenation
  作者：Guilherme A. M. Jardim、John F. Bower、Eufrânio N. da Silva Júnior

  DOI：10.1021/acs.orglett.6b01586

  日期：2016.9.16

  4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C–H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C–H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative

  在Rh催化的条件下，典型的亲电子1,4-苯醌具有亲核反应性，因此暴露于适当的亲电子会产生CH碘化，溴化和苯硒化的产物。这为直接的卤代官能化提供了一种温和而通用的方法，并且是第一个可以实现此类化合物直接C–H苯基硒化的方法。概述了新协议的范围和局限性，并突出了代表性的衍生化。
• [EN] AMINO-QUINONE ANTIPOLYMERANTS AND METHODS OF USING<br/>[FR] AGENT D'ANTIPOLYMÉRISATION À BASE D'AMINO-QUINONE ET PROCÉDÉS D'UTILISATION
  申请人：ECOLAB USA INC

  公开号：WO2020068735A1

  公开（公告）日：2020-04-02

  Described are methods and composition for inhibiting polymerization of a monomer (e.g., styrene) composition using an aminated quinone antipolymerant, such as an aminated benzoquinone or aminated naphthoquinone antipolymerant having one or more secondary or tertiary amine group(s). The aminated quinone antipolymerant can be used with little or no nitroxyl group containing antipolymerant yet still provide excellent antipolymerant activity in a monomer-containing composition.

  描述了一种使用氨基喹诺烷抗聚合剂（例如，氨基苯醌或氨基萘醌抗聚合剂）来抑制单体（例如苯乙烯）组合物的聚合的方法和组合物，该氨基喹诺烷抗聚合剂具有一个或多个次级或三级胺基团。氨基喹诺烷抗聚合剂可以与几乎不含氮氧自由基的抗聚合剂一起使用，但仍然在含单体组合物中提供出色的抗聚合活性。
• Gem-disubstituted cyclohexadienones and their production
  申请人：ETHYL CORPORATION

  公开号：EP0336371A2

  公开（公告）日：1989-10-11

  Gem-disubstituted cyclohexadienone in which the gem substituents are a perfluoroalkyl group and a trihydrocar­bylsiloxy group are prepared by perfluoroalkylating a quinone with a perfluoroalkyltrihydrocarbylsilane in the presence of an active catalyst under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably in a dipolar aprotic solvent. These gem-disubstituted compounds are readily convertible to perfluoroalkyl-substituted aromatics and thus provide a means of circumventing the traditional need for photo-­chlorination followed by halogen exchange in the prepara­tion of such products.

  宝石二取代环己二烯酮（其中宝石取代基为全氟烷基和三氢羰基硅氧烷基）的制备方法是：在活性催化剂存在下，在基本上无水的条件下，最好是在合适的液相反应介质中，最理想的是在二极性无水溶剂中，用全氟烷基三氢羰基硅烷对醌进行全氟烷基化反应。这些 gem-二取代化合物很容易转化为全氟烷基取代的芳烃，因此提供了一种方法来避免在制备这类产品时需要先进行光氯化再进行卤素交换的传统做法。
• Acetic acid derivatives and their production
  申请人：ETHYL CORPORATION

  公开号：EP0426333A2

  公开（公告）日：1991-05-08

  Compounds of the formula where n is an integer from 1 to 12, R and R₁ are the same or different and are hydrogen or C₁ to C₆ linear or branched alkyl as well as their physiologically active salts and amides thereof and the enantiomers, mixtures and racemates are disclosed. Intermediates useful in preparing the above compounds are also disclosed as are processes for preparing these compounds.

  式中的化合物 其中 n 为 1 至 12 的整数，R 和 R₁ 相同或不同，且为氢或 C₁ 至 C₆ 直链或支链烷基，公开了它们的生理活性盐和酰胺及其对映体、混合物和外消旋体。此外，还公开了用于制备上述化合物的中间体以及制备这些化合物的工艺。