乙酮,1-(6-羟基-2,4-二甲氧基-3-甲基苯基)- | 14964-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙酮,1-(6-羟基-2,4-二甲氧基-3-甲基苯基)-
• 英文名称: 2',4'-dimethoxy-6'-hydroxy-3'-methylacetophenone
• 英文别名: Bancroftinone；1-(6-hydroxy-2,4-dimethoxy-3-methylphenyl)ethanone
• CAS: 14964-98-8
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: DUTVTRPNMVUOIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酮,1-(6-羟基-2,4-二甲氧基-3-甲基苯基)- 在 5%-palladium/activated carbon 、 碘 、 三溴化硼 、 sodium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 5,7-dihydroxy-3-(2-hydroxyphenyl)-6-methyl-4H-chromen-4-one
  参考文献：
  名称：

  Isolation, Synthesis, and Antisepsis Effects of a C-Methylcoumarinochromone Isolated from Abronia nana Cell Culture

  摘要：

  Only a few isoflavones have been isolated from plants of the genus Abronia. The biological properties of compounds isolated from Abronia species have not been well established, and their antisepsis effects have not been reported yet. In the present study, a new C-methylcoumarinochromone, was isolated from Abronia nana suspension cultures. Its structure was deduced as 9,11-dihydroxy-10-methylcoumarinochromone (boeravinone Y, 1) by spectroscopic data analysis and verified by chemical synthesis. The potential inhibitory effects of 1 against high mobility group box 1 (HMGB1)-mediated septic responses were investigated. Results showed that 1 effectively inhibited lipopolysaccharide-induced release of HMGB1 and suppressed HMGB1-mediated septic responses, in terms of reduction of hyperpermeability, leukocyte adhesion and migration, and cell adhesion molecule expression. In addition, 1 increased the phagocytic activity of macrophages and exhibited bacterial clearance effects in the peritoneal fluid and blood of mice with cecal ligation and puncture-induced sepsis. Collectively, these results suggested that 1 might have potential therapeutic activity against various severe vascular inflammatory diseases via inhibition of the HMGB1 signaling pathway.

  DOI：

  10.1021/acs.jnatprod.7b00826
• 作为产物：
  描述：

  4-羟基-2,6-二甲氧基苯甲醛 在 盐酸 、 三氯化铝 、 汞 、 锌 作用下， 生成 乙酮,1-(6-羟基-2,4-二甲氧基-3-甲基苯基)-
  参考文献：
  名称：

  Agil, Mohammad; Rahman, Wasiur; Hasaka, Noriko, Journal of the Chemical Society. Perkin transactions I, 1981, p. 1389 - 1392

  摘要：

  DOI：

文献信息

• Concise Synthesis and Cellular Evaluation of 3′-Formyl-4′,6′-dihydroxy-2′-methoxy-5′-methylchalcone (FMC) and Its Analogues
  作者：Xiang Zhuo、Li En-Zhen、Liang Hai、Guo Hong-Ju、Shi Ning、Zhang Xue-Hui、Qian Qi-Fang、Wu Jiu-Hong

  DOI：10.1080/00397911.2014.930492

  日期：2014.11.2

  (1b–1e) was first developed. All compounds were synthesized from commercially available 2,4,6-trihydroxyacetophenone; formylation at 3′ position under Vilsmeier–Haack conditions was followed by the introduction of a methyl group at 5′ position. The key step of selective methylation at 2′ position was achieved by trimethylsilyldiazomethane (TMSCHN2). Then substituted aromatic aldehydes were condensed

  摘要 3'-甲酰基-4',6'-二羟基-2'-甲氧基-5'-甲基查尔酮(FMC)是从Cleistocalyx operculatus中分离得到的天然产物。首先开发了针对 FMC 及其四种类似物 (1b-1e) 的四步合成策略。所有化合物均由市售的 2,4,6-三羟基苯乙酮合成；在 Vilsmeier-Haack 条件下在 3' 位置进行甲酰化，然后在 5' 位置引入甲基。2'位选择性甲基化的关键步骤是通过三甲基甲硅烷基重氮甲烷（TMSCHN2）实现的。然后在氢氧化钾存在下通过克莱森-施密特反应使取代的芳香醛缩合。所有结构均通过 1H NMR、13C NMR 和高分辨率质谱确认。筛选 FMC 和类似物的抗增殖活性。图形概要
• 61. Usnic acid. Part VI. The synthesis of O-dimethylpyrousnic acid
  作者：Harold F. Birch、Alexander Robertson

  DOI：10.1039/jr9380000306

  日期：——
• Matsuura, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 298,300
  作者：Matsuura

  DOI：——

  日期：——
• Anti-AIDS agents 68. The first total synthesis of a unique potent anti-HIV chalcone from genus Desmos
  作者：Kyoko Nakagawa-Goto、Kuo-Hsiung Lee

  DOI：10.1016/j.tetlet.2006.09.110

  日期：2006.11

  The first total synthesis of a unique highly functionalized and potent anti-HIV chalcone 1, isolated from genus Desmos, was achieved from commercially available 2,4,6-trihydroxytoluene (3) or 2,4,6-trihydroxybenzaldehyde (2) in five (from 3) or six steps (from 2). (c) 2006 Elsevier Ltd. All rights reserved.
• The benzoylation and benzylation of C-methylphloracetophenones
  作者：W. B. Whalley

  DOI：10.1039/jr9550000105

  日期：——