3,5-Dimethoxy-4-hydroxyphenyl glyoxal | 199669-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-Dimethoxy-4-hydroxyphenyl glyoxal
• 英文别名: 2-(4-hydroxy-3,5-dimethoxyphenyl)-2-oxoacetaldehyde
• CAS: 199669-11-9
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: FMYLUQRSKAHEHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-Dimethoxy-4-hydroxyphenyl glyoxal 、 DL-色氨酸甲酯盐酸盐 以88%的产率得到methyl 1-(4-hydroxy-3,5-dimethoxybenzyl)-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Unexplored reactivity of 2-oxoaldehydes towards Pictet–Spengler conditions: concise approach to β-carboline based marine natural products

  摘要：

  在Pictet–Spengler条件下，开发了色氨酸甲酯/色胺与2-氧代醛之间的新型反应，并成功应用于Merinacarboline（A和B）、Eudistomin Y1、Pityriacitrin B、Pityriacitrin、Fascaplysin及其类似物的全合成。

  DOI：

  10.1039/c4ra01387e
• 作为产物：
  描述：

  乙酰丁香酮 在 碘 、 二甲基亚砜 作用下， 生成 3,5-Dimethoxy-4-hydroxyphenyl glyoxal
  参考文献：
  名称：

  Unexplored reactivity of 2-oxoaldehydes towards Pictet–Spengler conditions: concise approach to β-carboline based marine natural products

  摘要：

  在Pictet–Spengler条件下，开发了色氨酸甲酯/色胺与2-氧代醛之间的新型反应，并成功应用于Merinacarboline（A和B）、Eudistomin Y1、Pityriacitrin B、Pityriacitrin、Fascaplysin及其类似物的全合成。

  DOI：

  10.1039/c4ra01387e

文献信息

• Polycarboxylated compounds and compositions containing same
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US11028235B2

  公开（公告）日：2021-06-08

  Methods of selectively modifying lignin, polycarboxylated products thereof, and methods of deriving aromatic compounds therefrom. The methods comprise electrochemically oxidizing lignin using stable nitroxyl radicals to selectively oxidize primary hydroxyls on β-O-4 phenylpropanoid units to corresponding carboxylic acids while leaving the secondary hydroxyls unchanged. The oxidation results in polycarboxylated lignin in the form of a polymeric β-hydroxy acid. The polymeric β-hydroxy acid has a high loading of carboxylic acid and can be isolated in acid form, deprotonated, and/or converted to a salt. The β-hydroxy acid, anion, or salt can also be subjected to acidolysis to generate various aromatic monomers or oligomers. The initial oxidation of lignin to the polycarboxylated form renders the lignin more susceptible to acidolysis and thereby enhances the yield of aromatic monomers and oligomers obtained through acidolysis.

  选择性修改木质素的方法，其聚羧酸产物，以及从中获得芳香化合物的方法。该方法包括使用稳定的亚硝基自由基电化学氧化木质素，以选择性氧化β-O-4苯丙烯醇单元上的主要羟基为相应的羧酸，同时保持次要羟基不变。氧化结果形成聚羧酸木质素，以聚合物β-羟基酸的形式存在。聚合物β-羟基酸具有高负载的羧酸，可以以酸形式分离，去质子化和/或转化为盐。β-羟基酸，阴离子或盐也可以经过酸解来生成各种芳香单体或寡聚体。将木质素最初氧化为聚羧酸形式使木质素更易受到酸解的影响，从而增加通过酸解获得的芳香单体和寡聚体的产量。
• Process for preparing 1-(3,5-dimethoxy-4-hydroxy
  申请人：Dr. Lo. Zambeletti S.p.A.

  公开号：US04408074A1

  公开（公告）日：1983-10-04

  A process for preparing 1-(3,5-dimethoxy-4-hydroxy phenyl)-2-(N-methylamino) ethanol hydrochloride is described by reacting 2,6-dimethoxyphenol with anhydrous chloral in the presence of a catalyst, hydrolyzing 1-(3,5-dimethoxy-4-hydroxyphenyl)2,2,2-trichloro ethanol and subsequently isolating the 3,5-dimethoxy-4-hydroxyphenyl glyoxal thus obtained; finally, this compound, in the form of the bisulfite, is directly converted to the desired product by amination with methylamine in the presence of hydrogen with a hydrogenation catalyst and the final product is converted into the hydrochloride.

  本发明提供一种制备1-(3,5-二甲氧基-4-羟基苯基)-2-(N-甲基氨基)乙醇盐酸盐的方法，包括在催化剂存在下，将2,6-二甲氧基苯酚与无水氯醛反应，水解1-(3,5-二甲氧基-4-羟基苯基)2,2,2-三氯乙醇，随后分离所得的3,5-二甲氧基-4-羟基苯基乙二醛；最后，将该化合物以亚硫酸氢盐的形式，通过在氢气存在下，使用氢化催化剂和甲基胺进行氨基化反应，直接转化为所需的产物，并将最终产物转化为盐酸盐。
• NITROXYL-MEDIATED OXIDATION OF LIGNIN AND POLYCARBOXYLATED PRODUCTS
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20170342574A1

  公开（公告）日：2017-11-30

  Methods of selectively modifying lignin, polycarboxylated products thereof, and methods of deriving aromatic compounds therefrom. The methods comprise electrochemically oxidizing lignin using stable nitroxyl radicals to selectively oxidize primary hydroxyls on β-O-4 phenylpropanoid units to corresponding carboxylic acids while leaving the secondary hydroxyls unchanged. The oxidation results in polycarboxylated lignin in the form of a polymeric β-hydroxy acid. The polymeric β-hydroxy acid has a high loading of carboxylic acid and can be isolated in acid form, deprotonated, and/or converted to a salt. The β-hydroxy acid, anion, or salt can also be subjected to acidolysis to generate various aromatic monomers or oligomers. The initial oxidation of lignin to the polycarboxylated form renders the lignin more susceptible to acidolysis and thereby enhances the yield of aromatic monomers and oligomers obtained through acidolysis.
• POLYCARBOXYLATED COMPOUNDS AND COMPOSITIONS CONTAINING SAME
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20170342219A1

  公开（公告）日：2017-11-30

  Methods of selectively modifying lignin, polycarboxylated products thereof, and methods of deriving aromatic compounds therefrom. The methods comprise electrochemically oxidizing lignin using stable nitroxyl radicals to selectively oxidize primary hydroxyls on β-O-4 phenylpropanoid units to corresponding carboxylic acids while leaving the secondary hydroxyls unchanged. The oxidation results in polycarboxylated lignin in the form of a polymeric β-hydroxy acid. The polymeric β-hydroxy acid has a high loading of carboxylic acid and can be isolated in acid form, deprotonated, and/or converted to a salt. The β-hydroxy acid, anion, or salt can also be subjected to acidolysis to generate various aromatic monomers or oligomers. The initial oxidation of lignin to the polycarboxylated form renders the lignin more susceptible to acidolysis and thereby enhances the yield of aromatic monomers and oligomers obtained through acidolysis.
• US4408074A
  申请人：——

  公开号：US4408074A

  公开（公告）日：1983-10-04