羟基苯-1,2,3,5-四羧酸 | 113678-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 羟基苯-1,2,3,5-四羧酸
• 英文名称: hydroxy-benzene-1,2,3,5-tetracarboxylic acid
• 英文别名: Hydroxy-benzol-1,2,3,5-tetracarbonsaeure；4-Hydroxybenzene-1,2,3,5-tetracarboxylic acid
• CAS: 113678-62-9
• 化学式: C₁₀H₆O₉
• 分子量: 270.152
• InChiKey: JCJIRSRINAZVAD-UHFFFAOYSA-N

物化性质

• 熔点：
  281-282 °C
• 沸点：
  594.1±50.0 °C(Predicted)
• 密度：
  1.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 羟基苯-1,2,3,5-四羧酸 生成 methoxy-benzene-1,2,3,5-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  Grove, Biochemical Journal, 1952, vol. 50, p. 648,661

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯-1,2,3,5-四羧酸 在 氢溴酸 作用下， 生成 羟基苯-1,2,3,5-四羧酸
  参考文献：
  名称：

  Grove, Biochemical Journal, 1952, vol. 50, p. 648,661

  摘要：

  DOI：

文献信息

• [EN] AROMATIC COMPOUNDS FROM FURANICS<br/>[FR] COMPOSÉS AROMATIQUES DÉRIVÉS DES FURANIQUES
  申请人：NEDERLANDSE ORGANISATIE VOOR TOEGEPAST-NATUURWETENSCHAPPELIJK ONDERZOEK TNO

  公开号：WO2017146581A1

  公开（公告）日：2017-08-31

  Described are methods for preparing phenols, benzene carboxylic acids, esters and anhydrides thereof from furanic compounds by reaction with a dienophile, wherein the furanic compounds are reacted with a hydrazine and/or oxime and then reacted with a dienophile.

  描述了一种从呋喃化合物通过与二烯醚反应制备酚、苯甲酸、酯和酐的方法，其中呋喃化合物与肼和/或肟反应，然后与二烯醚反应。
• PHTHALIDE FORMATION: III. CONDENSATIONS WITH 5-HYDROXY-2-METHYLBENZOIC ACID
  作者：E. H. Charlesworth、E. A. Dudley、E. E. Nishizawa、W. Radych

  DOI：10.1139/v54-119

  日期：1954.10.1

  The product obtained from the condensation of 5-hydroxy-2-methylbenzoic acid with aqueous formaldehyde and hydrochloric acid is dependent on the temperature. If the condensation is carried out at room temperature 3-hydroxy-6-methylphthalide results. This substance can also be obtained by the demethylation of 3-methoxy-6-methylphthalide. If the condensation is carried out at the boiling point the lactone of 8-hydroxymethyl-1,3-benzodioxane-6-methyl-7-carboxylic acid results. Proof of the presence of the m-dioxane and phthalide rings in this latter substance has been established by opening these rings in succession. In both cases this has led by a series of degradative steps to 4-methoxybenzene-1,2,3,5-tetracarboxylic acid. The structure of this acid has been confirmed by its synthesis in six unambiguous steps from mesitylene.

  通过5-羟基-2-甲基苯甲酸与水甲醛和盐酸缩合反应所得产物取决于温度。如果在室温下进行缩合反应，则会产生3-羟基-6-甲基邻苯二甲酸内酯。这种物质也可以通过3-甲氧基-6-甲基邻苯二甲酸内酯的去甲基化反应得到。如果在沸点下进行缩合反应，则会产生8-羟甲基-1,3-苯并二氧杂环-6-甲基-7-羧酸内酯。通过依次打开这些环来证明此后一种物质中存在m-二噁烷和邻苯二甲酸内酯环。在这两种情况下，通过一系列降解步骤，最终得到4-甲氧基苯-1,2,3,5-四羧酸。这种酸的结构已通过从甲苯中六步合成得到并得到确认。
• [EN] PRODUCTION OF AROMATIC ACIDS AND PHENOLICS<br/>[FR] PRODUCTION D'ACIDES AROMATIQUES ET DE COMPOSÉS PHÉNOLIQUES
  申请人：TNO

  公开号：WO2021080426A1

  公开（公告）日：2021-04-29

  The invention is directed to a process for the preparation of an aromatic acid or a phenolic compound, said process comprising reacting a dienophile and a furanic compound comprising an acetal moiety in a Diels-Alders reaction to obtain an aromatic compound comprising said acetal moiety, followed by hydrolysis and oxidation of said acetal moiety into a hydroxide or carboxylate moiety to form the aromatic acid or phenolic compound, wherein said dienophile is selected from the group consisting of alkylenes, acetylenes, acrylates, maleates, fumarates, maleimides, propiolates, acetylene dicarboxylates, and benzynes and wherein said acetal moiety is bound directly to the 2-position of the furanic compound.

  该发明涉及一种制备芳香酸或酚类化合物的方法，该方法包括将二烯酸酯和含有缩醛基团的呋喃化合物在Diels-Alder反应中反应，以获得含有该缩醛基团的芳香化合物，随后对该缩醛基团进行水解和氧化，将其转化为羟基或羧酸基团，形成芳香酸或酚类化合物。其中，所述二烯酸酯选自烯烃、乙炔、丙烯酸酯、马来酸酯、富马酸酯、马来酰亚胺、丙炔酸酯、乙炔二羧酸酯和苯炔，所述缩醛基团直接与呋喃化合物的2位结合。
• PRODUCTION OF AROMATIC ACIDS AND PHENOLICS
  申请人：Nederlandse Organisatie voor toegepast- natuurwetenschappelijk Onderzoek TNO

  公开号：EP3812361A1

  公开（公告）日：2021-04-28

  The invention is directed to a process for the preparation of an aromatic acid or a phenolic compound, said process comprising reacting a dienophile and a furanic compound comprising an acetal moiety in a Diels-Alders reaction to obtain an aromatic compound comprising said acetal moiety, followed by hydrolysis and oxidation of said acetal moiety into a hydroxide or carboxylate moiety to form the aromatic acid or phenolic compound, wherein said dienophile is selected from the group consisting of alkylenes, acetylenes, acrylates, maleates, fumarates, maleimides, propiolates, acetylene dicarboxylates, and benzynes and wherein said acetal moiety is bound directly to the 2-position of the furanic compound.

  本发明涉及一种制备芳香族酸或酚类化合物的工艺，所述工艺包括在 Diels-Alders 反应中使亲二烯化合物和包含缩醛分子的呋喃化合物反应，得到包含所述缩醛分子的芳香族化合物、随后将所述缩醛基团水解和氧化成氢氧化物或羧酸基团，形成芳香族酸或酚类化合物，其中所述亲二烯基团选自由烯烃、炔烃、丙烯酸酯、马来酸酯、富马酸酯、马来酰亚胺、丙醇酯、乙炔二羧酸酯和苄基化合物组成的组，且所述缩醛基团直接与呋喃化合物的 2-位结合。
• Aromatic compounds from furanics
  申请人：Nederlandse Organisatie voor toegepast-natuurwetenschappelijk onderzoek TNO

  公开号：US10562875B2

  公开（公告）日：2020-02-18

  Described are methods for preparing phenols, benzene carboxylic acids, esters and anhydrides thereof from furanic compounds by reaction with a dienophile, wherein the furanic compounds are reacted with a hydrazine and/or oxime and then reacted with a dienophile.

  描述了通过与亲二烯反应从呋喃化合物制备苯酚、苯羧酸、其酯和酸酐的方法，其中呋喃化合物与肼和/或肟反应，然后与亲二烯反应。