3-methoxy-4-[(methyl-sulfonyl)oxy]-benzoic acid methyl ester

• 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: 3-methoxy-4-[(methyl-sulfonyl)oxy]-benzoic acid methyl ester
• 英文别名: methyl 3-methoxy-4-[(methylsulfonyl)oxy]benzoate；methyl 4-mesylvanillate；Methyl 3-methoxy-4-methylsulfonyloxybenzoate
• 化学式: C₁₀H₁₂O₆S
• 分子量: 260.268
• InChiKey: PWYJSFIRRFKHGV-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：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-[(methyl-sulfonyl)oxy]-benzoic acid methyl ester 在 2,2'-联吡啶 、 1,10-菲罗啉 、 氯化镍二甲氧基乙烷 、 palladium chloride*2MeCN 、 三乙胺 、 1,4-双(二苯基膦)丁烷 、 sodium bromide 、 lithium bromide 、 锌 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 dimethyl 2,2',6-trimethoxy-[1,1'-biphenyl]-4,4'-dicarboxylate
  参考文献：
  名称：

  [EN] ELECTROCHEMICAL REDUCTIVE COUPLING OF PHENOL DERIVATIVES
  [FR] COUPLAGE RÉDUCTEUR ÉLECTROCHIMIQUE DE DÉRIVÉS DE PHÉNOL

  摘要：

  A scalable Ni- or Ni/Pd-catalyzed electrochemical reductive coupling method is disclosed, affording biaryls in good to excellent yield via the electrolysis of lignin-derived aryl sulfonate esters. This method features the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry and the high selectivity for desired biaryls over other side products. The biaryls find applications in building blocks for high-performance polyesters or PVC plasticizers.

  公开号：

  WO2023278766A1
• 作为产物：
  描述：

  香草酸甲酯 、 甲基磺酰氯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以71%的产率得到3-methoxy-4-[(methyl-sulfonyl)oxy]-benzoic acid methyl ester
  参考文献：
  名称：

  Mechanism of Drug Resistance of Hemagglutinin of Influenza Virus and Potent Scaffolds Inhibiting Its Function

  摘要：

  Highly pathogenic influenza viruses have become a global threat to humans. It is important to select an affective therapeutic option suitable for the subtypes in an epidemics or pandemic. To increase the options, the development of novel antiviral agents acting on targets different from those of the currently approved drugs is required. In this study. we performed molecular dynamics simulations on a spike protein on the viral envelop, hemagglutinin for the wild type and three kinds of mutants using a model system consisting of a trimeric hemagglutin complex, viral lipid membrane. solvation waters, and ions . A natural product stachyflin, which shows a high level of antiviral activity specific to some subtypes of influenza viruses, was examined on binding to the wild-type hemagglutinin was clarified. Next, 8 compounds were selected from a chemical database by in silico screening, considering the findings from the simulations. Inhibitory activities to suppress the proliferation of influenza virus were measured by cell-based antiviral assays, and chemical scaffolds were found to be potent for an inhibitor. More than 30 derivatives bearing either of these two chemical scaffolds were synthesized, and cell culture assays were carried out of evaluate the compound potency. Several derivatives displayed a high compound potency, and 50% effective concentrations of two synthesized compounds were below 1 mu M

  DOI：

  10.1021/cb200332k

文献信息

• Stereoselective benzylic deprotonation in the enzymatic rearrangement of N-acetyldopamine derived o-quinone to the p-quinone methide
  作者：Martin G. Peter、Axel Merz

  DOI：10.1016/0957-4166(95)00083-2

  日期：1995.4

  (R)-N-acetyl-[β-2H1]-dopamine (R)-1 undergoes an enzyme catalyzed oxidative tautomerization to quinone methide 3 with loss of the benzylic HSi, as proven by isolation of deuteriated rac. N-acetylnoradrenaline (4), while loses the deuterium label. Thus, the o-quinone-p-quinone methide isomerization is a stereoselective enzymatic reaction.

  （R）-N-乙酰基-[ β - 2 H 1 ]-多巴胺（R）-1经过酶催化氧化互变异构化成甲基化醌3，而苄基H Si丢失，这是通过重氢分离rac证明的。N-乙酰基去甲肾上腺素（4）失去了氘标记。因此，邻苯醌-对苯醌甲基化物异构化是立体选择性酶促反应。
• JP5765650
  申请人：——

  公开号：——

  公开（公告）日：——
• Mechanism of Drug Resistance of Hemagglutinin of Influenza Virus and Potent Scaffolds Inhibiting Its Function
  作者：Hiroshi Yanagita、Norio Yamamoto、Hideyoshi Fuji、Xinli Liu、Masakazu Ogata、Mizuho Yokota、Hiroshi Takaku、Hideki Hasegawa、Takato Odagiri、Masato Tashiro、Tyuji Hoshino

  DOI：10.1021/cb200332k

  日期：2012.3.16

  Highly pathogenic influenza viruses have become a global threat to humans. It is important to select an affective therapeutic option suitable for the subtypes in an epidemics or pandemic. To increase the options, the development of novel antiviral agents acting on targets different from those of the currently approved drugs is required. In this study. we performed molecular dynamics simulations on a spike protein on the viral envelop, hemagglutinin for the wild type and three kinds of mutants using a model system consisting of a trimeric hemagglutin complex, viral lipid membrane. solvation waters, and ions . A natural product stachyflin, which shows a high level of antiviral activity specific to some subtypes of influenza viruses, was examined on binding to the wild-type hemagglutinin was clarified. Next, 8 compounds were selected from a chemical database by in silico screening, considering the findings from the simulations. Inhibitory activities to suppress the proliferation of influenza virus were measured by cell-based antiviral assays, and chemical scaffolds were found to be potent for an inhibitor. More than 30 derivatives bearing either of these two chemical scaffolds were synthesized, and cell culture assays were carried out of evaluate the compound potency. Several derivatives displayed a high compound potency, and 50% effective concentrations of two synthesized compounds were below 1 mu M
• [EN] ELECTROCHEMICAL REDUCTIVE COUPLING OF PHENOL DERIVATIVES<br/>[FR] COUPLAGE RÉDUCTEUR ÉLECTROCHIMIQUE DE DÉRIVÉS DE PHÉNOL
  申请人：[en]WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：WO2023278766A1

  公开（公告）日：2023-01-05

  A scalable Ni- or Ni/Pd-catalyzed electrochemical reductive coupling method is disclosed, affording biaryls in good to excellent yield via the electrolysis of lignin-derived aryl sulfonate esters. This method features the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry and the high selectivity for desired biaryls over other side products. The biaryls find applications in building blocks for high-performance polyesters or PVC plasticizers.