2-methoxy-3,4-bis(methoxymethoxy)benzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-3,4-bis(methoxymethoxy)benzaldehyde
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: UWHLPOHEZBCZMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methoxy-3,4-bis(methoxymethoxy)benzaldehyde 在 盐酸 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 生成 3,4-dihydroxy-2-methoxybenzonitrile
  参考文献：
  名称：

  Effects of electron-withdrawing substituents on DPPH radical scavenging reactions of protocatechuic acid and its analogues in alcoholic solvents

  摘要：

  The DPPH (2,2-diphenyl-l-picrylhydrazyl) radical scavenging activity of protocatechuic acid (3,4-dihydroxybenzoic acid) and its related catechols was examined. Compounds possessing strong electron-withdrawing substituents showed high activity. NMR analysis of the reaction mixtures of catechols and DPPH radical in methanol showed the formation of methanol adducts. The results suggest that high radical scavenging activity of catechols in alcohol is due to a nucleophilic addition of an alcohol molecule on o-quinones, which leads to a regeneration of a catechol structure. Furthermore, the radical scavenging activity in alcohols would largely depend on the electron-withdrawing/donating substituents, Since they affect the susceptibility toward nucleophilic attacks on o-quinone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.040
• 作为产物：
  描述：

  2,3,4-三羟基苯甲醛 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 2-methoxy-3,4-bis(methoxymethoxy)benzaldehyde
  参考文献：
  名称：

  Effects of electron-withdrawing substituents on DPPH radical scavenging reactions of protocatechuic acid and its analogues in alcoholic solvents

  摘要：

  The DPPH (2,2-diphenyl-l-picrylhydrazyl) radical scavenging activity of protocatechuic acid (3,4-dihydroxybenzoic acid) and its related catechols was examined. Compounds possessing strong electron-withdrawing substituents showed high activity. NMR analysis of the reaction mixtures of catechols and DPPH radical in methanol showed the formation of methanol adducts. The results suggest that high radical scavenging activity of catechols in alcohol is due to a nucleophilic addition of an alcohol molecule on o-quinones, which leads to a regeneration of a catechol structure. Furthermore, the radical scavenging activity in alcohols would largely depend on the electron-withdrawing/donating substituents, Since they affect the susceptibility toward nucleophilic attacks on o-quinone. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.040

文献信息

• First Total Synthesis of Highly Anti-Inflammatory Active Licochalcone D Through Water-Accelerated [3,3]-Sigmatropic Rearrangement
  作者：Si-Jun Kim、Jong-Gab Jun

  DOI：10.5012/bkcs.2013.34.1.54

  日期：2013.1.20

  mostother natural licochalcones possess the group on ring B. Total synthesis of licochalcone D has not been reportedeven possessing the strongest anti-inflammatory activity. Therefore, the first total synthesis of licochalcone Dhas been developed by using water-accelerated [3,3]-sigmatropic rearrangement method.Key Words : Licochalcone D, Anti-inflammatory activity, Glycyrrhiza inflata, Water-accelerated

  E-mail: [e-mail] September 14, 2012, Accepted October 4, 2012 甘草干燥根中提取的甘草查耳酮据报道具有多种生物活性，包括抗肿瘤、抗寄生虫、抗寄生虫、抗氧化、清除超氧化物、抗菌和 PTP1B 活性。甘草查耳酮D在A环上具有烯丙基而不是B环，然而，大多数其他天然甘草查耳酮在B环上具有烯丙基。甘草查耳酮D的全合成尚未见报道，甚至具有最强的抗炎活性。因此，利用水加速的[3,3]-sigmatropic重排方法开发了第一个甘草查耳酮全合成方法。关键词：甘草查耳酮D，抗炎活性，膨胀甘草，水加速的[3,3]-sigma -热带重排，
• Effects of electron-withdrawing substituents on DPPH radical scavenging reactions of protocatechuic acid and its analogues in alcoholic solvents
  作者：Shizuka Saito、Jun Kawabata

  DOI：10.1016/j.tet.2005.06.040

  日期：2005.8

  The DPPH (2,2-diphenyl-l-picrylhydrazyl) radical scavenging activity of protocatechuic acid (3,4-dihydroxybenzoic acid) and its related catechols was examined. Compounds possessing strong electron-withdrawing substituents showed high activity. NMR analysis of the reaction mixtures of catechols and DPPH radical in methanol showed the formation of methanol adducts. The results suggest that high radical scavenging activity of catechols in alcohol is due to a nucleophilic addition of an alcohol molecule on o-quinones, which leads to a regeneration of a catechol structure. Furthermore, the radical scavenging activity in alcohols would largely depend on the electron-withdrawing/donating substituents, Since they affect the susceptibility toward nucleophilic attacks on o-quinone. (c) 2005 Elsevier Ltd. All rights reserved.
• Short and Efficient Synthesis of Licochalcone B and D Through Acid-Mediated Claisen-Schmidt Condensation
  作者：Zengtao Wang、Zhiguo Liu、Yongkai Cao、Suresh Paudel、Goo Yoon、Seung Hoon Cheon

  DOI：10.5012/bkcs.2013.34.12.3906

  日期：2013.12.20