3,6-二甲酰基-1,2-二羟基-4,5-二甲基苯 | 1192600-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,6-二甲酰基-1,2-二羟基-4,5-二甲基苯
• 英文名称: 2,3-dihydroxy-5,6-dimethylterephthalaldehyde
• 英文别名: 2,3-dimethyl-5,6-dihydroxybenzene-1,4-dialdehyde；3,6-diformyl-1,2-dihydroxy-4,5-dimethylbenzene；2,3-Dihydroxy-5,6-dimethylterephthalaldehyde
• CAS: 1192600-96-6
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: YVPHVIKLOKXPJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-二甲酰基-1,2-二羟基-4,5-二甲基苯 、 4,5-二乙氧基苯-1,2-二胺 以 氯仿 、 乙腈 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Highly substituted Schiff base macrocycles via hexasubstituted benzene: a convenient double Duff formylation of catechol derivatives

  摘要：

  The synthesis of soluble, shape-persistent macrocycles is important for developing new materials. Double Duff formylation of 4,5-dialkylcatechol derivatives yields 3,6-diformyl-4,5-dialkylcatechols in moderate yields. These hexasubstituted aromatics are useful precursors to highly substituted Schiff base macrocycles. We illustrate convenient routes to these compounds as well as structural studies of two new macrocycles with alkyl substituents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.094
• 作为产物：
  描述：

  2,3-dimethoxy-5,6-dimethylterephthalaldehyde 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到3,6-二甲酰基-1,2-二羟基-4,5-二甲基苯
  参考文献：
  名称：

  Highly substituted Schiff base macrocycles via hexasubstituted benzene: a convenient double Duff formylation of catechol derivatives

  摘要：

  The synthesis of soluble, shape-persistent macrocycles is important for developing new materials. Double Duff formylation of 4,5-dialkylcatechol derivatives yields 3,6-diformyl-4,5-dialkylcatechols in moderate yields. These hexasubstituted aromatics are useful precursors to highly substituted Schiff base macrocycles. We illustrate convenient routes to these compounds as well as structural studies of two new macrocycles with alkyl substituents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.094

文献信息

• Formylation of phenols using formamidine acetate
  作者：S. Hessam M. Mehr、Hannah Depmeier、Katsuya Fukuyama、Mahboobeh Maghami、Mark J. MacLachlan

  DOI：10.1039/c6ob02727j

  日期：——

  We report a new method to formylate phenol derivatives using formamidine acetate and acetic anhydride. This general-purpose transformation is a significant improvement over many other methods and does not require high temperatures or the addition of strong acid or base. Mono-, di-, and tri-formylated product can be obtained, depending on the substrate and conditions used.

  我们报告了一种使用乙酸form和乙酸酐对苯酚衍生物进行甲酰化的新方法。这种通用转化是对许多其他方法的重大改进，不需要高温或添加强酸或强碱。根据所用的底物和条件，可以获得单，二和三甲酰化产物。
• Regioisomerism in Symmetric Dimethyl Dialdehydes Dictates their Photochemical Reactivity
  作者：Florian Feist、Leona L. Rodrigues、Sarah L. Walden、Christopher Barner-Kowollik

  DOI：10.1021/acs.joc.2c01020

  日期：2022.7.15

  exhibiting near-quantitative endo-selectivity (>99%) and provide excellent yields (96–98%). The influence of the regioisomerism of the dialdehydes on their photochemical behavior is profound, evidenced by an in-depth investigation of their photochemical performance. We exemplify the capability of the photosystems via the synthesis of complex Diels–Alder adducts with various dienophiles, including alkynes

  我们在此报告了单个生色团中两个化学等价羰基的第一次光驱动选择性单衍生化（去对称化）。通过比较具有两个等效邻甲基苯甲醛单元的四种对称区域异构体，我们确定了可以以双波长选择性方式激活的二甲基对苯二甲醛 (DMTA)。在可见光和紫外光照射下，DMTA 经历了两个连续的 Diels-Alder 反应，呈现出近定量的内切-选择性 (>99%) 并提供出色的收率 (96–98%)。二醛的区域异构对其光化学行为的影响是深远的，对其光化学性能的深入研究证明了这一点。我们通过与各种亲双烯体（包括炔烃）合成复杂的 Diels-Alder 加合物来举例说明光系统的能力。
• Highly substituted Schiff base macrocycles via hexasubstituted benzene: a convenient double Duff formylation of catechol derivatives
  作者：Kevin E. Shopsowitz、David Edwards、Amanda J. Gallant、Mark J. MacLachlan

  DOI：10.1016/j.tet.2009.07.094

  日期：2009.9

  The synthesis of soluble, shape-persistent macrocycles is important for developing new materials. Double Duff formylation of 4,5-dialkylcatechol derivatives yields 3,6-diformyl-4,5-dialkylcatechols in moderate yields. These hexasubstituted aromatics are useful precursors to highly substituted Schiff base macrocycles. We illustrate convenient routes to these compounds as well as structural studies of two new macrocycles with alkyl substituents. (C) 2009 Elsevier Ltd. All rights reserved.