2-acetoxymethyl-4-methyl-6-acetylresorcinol | 1446436-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetoxymethyl-4-methyl-6-acetylresorcinol
• 英文别名: (3-Acetyl-2,6-dihydroxy-5-methylphenyl)methyl acetate；(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl acetate
• CAS: 1446436-13-0
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: LHVGETIKTFFGSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetoxymethyl-4-methyl-6-acetylresorcinol 在 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 17.5h， 生成 peniphenone B
  参考文献：
  名称：

  通过邻甲基邻苯醌甲基甲酸酯中间体的仿生反应全合成苯乙酮AD

  摘要：

  苯甲酮A–D的总合成是通过适当的亲核试剂与常见的邻苯二甲酰甲基甲烷中间体之间的迈克尔反应实现的。基于生物合成假说的该策略最大程度地减少了保护基的使用，从而促进了天然产物的简洁合成。最复杂的靶标是苯并环的螺酮苯乙酮A，它是通过九个线性步骤由市售起始原料对映选择性合成的。

  DOI：

  10.1021/acs.orglett.5b02902
• 作为产物：
  描述：

  4-甲基间苯二酚 在 三氟化硼乙醚 、 溶剂黄146 作用下， 生成 2-acetoxymethyl-4-methyl-6-acetylresorcinol
  参考文献：
  名称：

  通过邻甲基邻苯醌甲基甲酸酯中间体的仿生反应全合成苯乙酮AD

  摘要：

  苯甲酮A–D的总合成是通过适当的亲核试剂与常见的邻苯二甲酰甲基甲烷中间体之间的迈克尔反应实现的。基于生物合成假说的该策略最大程度地减少了保护基的使用，从而促进了天然产物的简洁合成。最复杂的靶标是苯并环的螺酮苯乙酮A，它是通过九个线性步骤由市售起始原料对映选择性合成的。

  DOI：

  10.1021/acs.orglett.5b02902

文献信息

• Biomimetic Total Synthesis of <i>ent</i>-Penilactone A and Penilactone B
  作者：Justin T. J. Spence、Jonathan H. George

  DOI：10.1021/ol4017832

  日期：2013.8.2

  The total synthesis of ent-penilactone A and penilactone B has been achieved via biomimetic Michael reactions between tetronic acids and o-quinone methides. A five-component cascade reaction between a tetronic acid, formaldehyde, and a resorcinol derivative that generates four carbon–carbon bonds, one carbon–oxygen bond, and two stereocenters in a one-pot synthesis of penilactone A is also reported

  对苯二甲内酯A和半乳糖内酯B的全合成已经通过tetronic酸和邻醌甲基化物之间的仿生迈克尔反应得以实现。还报道了在一锅法合成戊内酯A中，四​​酸，甲醛和间苯二酚衍生物之间的五组分级联反应，该反应生成四个碳-碳键，一个碳-氧键和两个立体中心。
• Chemoreactive-Inspired Discovery of Influenza A Virus Dual Inhibitor to Block Hemagglutinin-Mediated Adsorption and Membrane Fusion
  作者：Guangwei Wu、Guihong Yu、Yunjia Yu、Shuang Yang、Zhongwei Duan、Wei Wang、Yankai Liu、Rilei Yu、Jing Li、Tianjiao Zhu、Qianqun Gu、Dehai Li

  DOI：10.1021/acs.jmedchem.0c00312

  日期：2020.7.9

  Owing to the emergence of drug resistance and high morbidity and mortality, the need for novel anti-influenza A virus (IAV) drugs with divergent targets is highly sought after. Herein, we reveal the discovery of an anti-IAV agent as a dual inhibitor to block hemagglutinin-mediated adsorption and membrane fusion using a chemoreactive ortho-quinone methide (o-QM) equivalent. Based on the o-QM equivalent nonenzymatically multipotent behavior, we created a series of clavatol-derived pseudonatural products and found that penindolone (PND), a new diclavatol indole adduct, exhibited potent and broad-spectrum anti-IAV activities with low risk of inducing drug resistance. Distinct from current anti-IAV drugs, PND possesses a novel scaffold and is the first IAV inhibitor targeting both HA1 and FIA2 subunits of virus hemagglutinin to dually block the IAV adsorption and membrane fusion process. More importantly, intranasal and oral administration of PND can protect mice against IAV-induced death and weight loss, superior to the effects of the clinical drug oseltamivir. Thus, the use of chemoreactive intermediates could expand our understanding of chemical diversity and aid in the development of anti-IAV drugs with novel targets.
• Total Synthesis of Peniphenones A–D via Biomimetic Reactions of a Common <i>o</i>-Quinone Methide Intermediate
  作者：Justin T. J. Spence、Jonathan H. George

  DOI：10.1021/acs.orglett.5b02902

  日期：2015.12.18

  The total synthesis of peniphenones A–D has been achieved via Michael reactions between appropriate nucleophiles and a common o-quinone methide intermediate. This strategy, which was based on a biosynthetic hypothesis, minimized the use of protecting groups and thus facilitated concise syntheses of the natural products. The most complex target, the benzannulated spiroketal peniphenone A, was synthesized

  苯甲酮A–D的总合成是通过适当的亲核试剂与常见的邻苯二甲酰甲基甲烷中间体之间的迈克尔反应实现的。基于生物合成假说的该策略最大程度地减少了保护基的使用，从而促进了天然产物的简洁合成。最复杂的靶标是苯并环的螺酮苯乙酮A，它是通过九个线性步骤由市售起始原料对映选择性合成的。