2-hydroxy-3,4-bis(methoxymethoxy)benzaldehyde | 85698-99-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3,4-bis(methoxymethoxy)benzaldehyde
• CAS: 85698-99-3
• 化学式: C₁₁H₁₄O₆
• 分子量: 242.229
• InChiKey: YUJAPZZPFLQVMU-UHFFFAOYSA-N

物化性质

• 沸点：
  368.8±42.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3,4-bis(methoxymethoxy)benzaldehyde 在 盐酸 、 N,N-二异丙基乙胺 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 、 正己烷 、 水 、 乙腈 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 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以29%的产率得到2-hydroxy-3,4-bis(methoxymethoxy)benzaldehyde
  参考文献：
  名称：

  基于3,3'-双香豆素的c-Met抑制剂的设计与合成†

  摘要：

  基于3,3'-biscoumarin hit 3的优化，合成了基于双香豆素的c-Met抑制剂库，该库从多种香豆素衍生物库中被鉴定为c-Met的非ATP竞争性抑制剂。在这些化合物中，38和40不仅显示出强大的酶活性，IC 50值分别为107 nM和30 nM，而且还抑制了BaF3 / TPR-Met和EBC-1细胞中的c-Met磷酸化。

  DOI：

  10.1039/c4ob00364k

文献信息

• 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
• Islam, Azizul; Khan, Saeed Ahmad; Krishnamurti, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 10, p. 965 - 966
  作者：Islam, Azizul、Khan, Saeed Ahmad、Krishnamurti, M.

  DOI：——

  日期：——
• 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.
• Design and synthesis of 3,3′-biscoumarin-based c-Met inhibitors
  作者：Jimin Xu、Jing Ai、Sheng Liu、Xia Peng、Linqian Yu、Meiyu Geng、Fajun Nan

  DOI：10.1039/c4ob00364k

  日期：——

  A library of biscoumarin-based c-Met inhibitors was synthesized, based on optimization of 3,3′-biscoumarin hit 3, which was identified as a non-ATP competitive inhibitor of c-Met from a diverse library of coumarin derivatives. Among these compounds, 38 and 40 not only showed potent enzyme activities with IC50 values of 107 nM and 30 nM, respectively, but also inhibited c-Met phosphorylation in BaF3/TPR-Met

  基于3,3'-biscoumarin hit 3的优化，合成了基于双香豆素的c-Met抑制剂库，该库从多种香豆素衍生物库中被鉴定为c-Met的非ATP竞争性抑制剂。在这些化合物中，38和40不仅显示出强大的酶活性，IC 50值分别为107 nM和30 nM，而且还抑制了BaF3 / TPR-Met和EBC-1细胞中的c-Met磷酸化。