3,4,5-三甲基-1,2-苯二酚 | 3938-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3,4,5-三甲基-1,2-苯二酚
• 英文名称: trimethylpyrocatechol
• 英文别名: 3,4,5-trimethyl-1,2-dihydroxybenzene；3,4,5-trimethyl-1,2-benzenediol；trimethylcatechol；TMBC；3,4,5-trimethylcatechol diester；3,4,5-Trimethyl-brenzcatechin；3,4,5-Trimethylbenzene-1,2-diol
• CAS: 3938-10-1
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: DEIKGXRMQUHZJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2907299090

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲基-1,2-苯二酚 、 乙酸酐 在 吡啶 作用下， 生成 3,4,5-trimethylcatechol diacetate
  参考文献：
  名称：

  Efficient <i>ortho</i>-Oxidation of Phenols with Diacyl Peroxides

  摘要：

  从间氯过苯甲酸出发，合成了稳定的对称二酰基过氧化物间氯苯甲酰过氧化物（mCBPO）和非对称二酰基过氧化物氯乙酰基间氯苯甲酰过氧化物（CAMCBPO）。这两种过氧化物主要选择性地在苯酚的邻位进行氧化。从某些苯酚出发，CAMCBPO得到了少量对位氧化产物。还报道了使用mCBPO提高苯酚邻位氧化产率的方法。

  DOI：

  10.1248/cpb.56.239
• 作为产物：
  描述：

  Lanierone 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以95%的产率得到3,4,5-三甲基-1,2-苯二酚
  参考文献：
  名称：

  Electronic and Steric Effects in the Dienone-Phenol Rearrangement of 2-Hydroxy- and 2-Alkoxycyclohexa-2,5-dien-1-ones

  摘要：

  A series of 4,4,6-trisubstituted-2-hydroxy- and -2-alkoxycyclohexa-2,5-dien-1-ones (7 and 8) were prepared, where the substituent at C-6 was H, CH3, Ph, tert-butyl, or Oft. In the acid-catalyzed dienone-phenol rearrangement of 7 and 8, the C-4 substituent migrates regioselectively to C-5, completely shunning the enol double bond, even though the substituents at C-6 are substantially larger than the OH or OMe groups situated at C-2. The C-5 regioselectivity in hydroxy dienones 7a-f and 8a,b, as well as the decreased rate of reaction in the case of dienone 7g, can be simply rationalized by considering the relative electron density at C-3 vs C-5 in the protonated form of ? or 8. Our results clearly indicate that the regioselectivity of the dienone-phenol rearrangement in these enolic systems is completely controlled by the electronic factors, which far outweigh any steric considerations.

  DOI：

  10.1021/jo00086a038

文献信息

• Process for preparing trimethylhydroquinone diacetate and trimethylhydroquinone
  申请人：Degussa AG

  公开号：US06350897B2

  公开（公告）日：2002-02-26

  A process for preparing trimethylhydroquinone diacetate, with subsequent hydrolysis to give trimethylhydroquinone, the process including reacting 2,2,6-trimethylcyclohexane-1,4-dione under oxidative conditions, in the presence of a sulfonating agent and a strong acid, and in the presence of an acylating agent.

  一种制备三乙酰基三甲基对苯二酚，并随后水解得到三甲基对苯二酚的过程，包括在氧化条件下，在磺化剂和强酸的存在下，以及在酰化剂的存在下，反应2,2,6-三甲基环己烷-1,4-二酮。
• HYDROQUINONE DIESTER DERIVATIVES AND THE METHOD FOR PRODUCING THE SAME
  申请人：——

  公开号：US20020007082A1

  公开（公告）日：2002-01-17

  A highly pure hydroquinone dietser derivative can be produced from the reaction product of ketoisophorone with an acylating agent in a high yield by a simple and easy operation. In the presence of an acid catalyst, a cyclohex-2-ene-1,4-dione derivative shown by the following formula (3) was allowed to react with an acylating agent (e.g., acetic anhydride), and the reaction product was purified by crystallization to obtain a hydroquinone diester derivative shown by the following formula (1). The compound (1) contains about 0 to 4% by weight of a catechol diester derivative represented by the following formula (2), being highly pure. As a solvent for crystallization, a mixed solvent of an organic carboxylic acid (e.g., acetic acid) corresponding to the acylating agent and water may be used. 1 In the formulae, R 1 and R 2 each represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group.

  可以从ketoisophorone和酰化剂的反应产物中以高产率简单易操作的方式生产高纯度的羟基喹啉醚衍生物。在酸催化剂的存在下，通过以下公式（3）所示的环己-2-烯-1,4-二酮衍生物与酰化剂（例如醋酸酐）发生反应，反应产物经结晶纯化即可获得以下公式（1）所示的羟基喹啉醚衍生物。化合物（1）含有约0至4%重量的由以下公式（2）表示的间苯二酚酯衍生物，具有高纯度。作为结晶溶剂，可以使用与酰化剂对应的有机羧酸（例如醋酸）和水的混合溶剂。在上述公式中，R1和R2分别表示烷基、环烷基、芳基或杂环基。
• Late transition metal catalysts for olefin polymerization and oligomerization
  申请人：Cherkasov Kuzunich Vladimir

  公开号：US20060047094A1

  公开（公告）日：2006-03-02

  This invention relates to a transition metal compound represented by the formula LMX wherein M is a Group 3 to 11 metal L is a bulky bidentate or tridentate neutral ligand that is bonded to M by two or three heteroatoms and at least one heteroatom is nitrogen; X is a substituted or unsubstituted catecholate ligand provided that the substituted catecholate ligand does not contain a 1,2-diketone functionality.

  本发明涉及一种由式LMX所表示的过渡金属化合物，其中M是第3到11族金属，L是一种笨重的双或三齿中性配体，通过两个或三个杂原子与M结合，至少一个杂原子是氮；X是一种取代或未取代的邻二酚配体，但取代的邻二酚配体不含1,2-二酮官能团。
• Aromatic thermosetting resins and preparation thereof
  申请人：SUMIKIN CHEMICAL CO., LTD.

  公开号：EP0383995A2

  公开（公告）日：1990-08-29

  A condensed polycyclic, polynuclear aromatic thermosetting resin with improved moldability which is prevented from forming a cloud on a mold during molding is disclosed. The resin is a prepolymer derived by condensation polymerization of a condensed polycyclic aromatic compound or a mixture thereof with a monocyclic aromatic compounds and an aromatic compound having at least two hydroxymethyl groups as a crosslinking agent in the presence of an acid catalyst. The resin has a flow temperature of not higher than 150°C. The acid catalyst is water-insoluble or when it is water-soluble the resin has an insolubilized acid ratio of at least 50%. The resin is useful in the manufacture of thermoset molded articles having good heat resistance and good mechanical and electrical properties. It can be blended with a filler and/or reinforcing agent to form a molding compound.

  本发明公开了一种缩合多环、多核芳香族热固性树脂，它具有更好的成型性，在成型过程中不会在模具上形成云雾。该树脂是由缩合多环芳香族化合物或其混合物与单环芳香族化合物和至少有两个羟甲基的芳香族化合物作为交联剂在酸催化剂存在下缩合聚合而得的预聚物。树脂的流动温度不高于 150°C。酸催化剂不溶于水，或当它溶于水时，树脂的酸不溶比率至少为 50%。这种树脂可用于制造具有良好耐热性、机械和电气性能的热固性模塑制品。它可以与填料和/或增强剂混合形成模塑化合物。
• Trimethylcatechol diester and a method for producing the same
  申请人：DAICEL CHEMICAL INDUSTRIES, LTD.

  公开号：EP0850912A1

  公开（公告）日：1998-07-01

  This method provides a novel trimethylcatechol diester, i.e. 3,4,5-trimethylcatechol diester, at a high yield by reacting 2,6,6-trimethylcyclohexe-2-en-1,4-dione with an acylating agent in the presence of an acid catalyst. The acylating agent includes a C2-4 carboxylic acid anhydride (e.g. acetic anhydride) and a C2-4 carboxylic acid halide (e.g. acetyl chloride). The catalyst includes a protonic acid and a Lewis acid. Use of a polar solvent (e.g. halogenated hydrocarbon), as the reaction catalyst, results in an enhanced efficiency in the production of the object compound.

  该方法通过使 2,6,6-三甲基环己-2-烯-1,4-二酮与酰化剂在酸催化剂存在下发生反应，以高产 量提供新型三甲基邻苯二酚二酯，即 3,4,5-三甲基邻苯二酚二酯。酰化剂包括 C2-4 羧酸酐（如乙酸酐）和 C2-4 羧酸卤化物（如乙酰氯）。催化剂包括质子酸和路易斯酸。使用极性溶剂（如卤代烃）作为反应催化剂，可提高目标化合物的生产效率。