methyl 3-methoxy-4-(tosyloxy)benzoate | 773876-08-7

• 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: methyl 3-methoxy-4-(tosyloxy)benzoate
• 英文别名: 3-Methoxy-4-(tosyloxy)benzoic acid methyl ester；methyl 3-methoxy-4-(4-methylphenyl)sulfonyloxybenzoate
• CAS: 773876-08-7
• 化学式: C₁₆H₁₆O₆S
• mdl: MFCD05882612
• 分子量: 336.365
• InChiKey: AXGAYPIRWLFTNE-UHFFFAOYSA-N

物化性质

• 沸点：
  499.2±45.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 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：

  methyl 3-methoxy-4-(tosyloxy)benzoate 、 2,3-dihydro-1H-inden-5-yl trifluoromethanesulfonate 在 氯化镍二甲氧基乙烷 、 4,4-二苯基-2,2-二联吡啶 、 1,4-双(二苯基膦)丁烷 、 lithium bromide 、 palladium dichloride 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以83%的产率得到methyl 4-(2,3-dihydro-1H-inden-5-yl)-3-methoxybenzoate
  参考文献：
  名称：

  磺酸盐与磺酸盐：芳基三氟甲磺酸酯与芳基甲苯磺酸酯的镍和钯多金属交叉电偶联

  摘要：

  虽然苯酚是交叉偶联中常见且方便的芳基来源，通常作为磺酸酯，但两种不同磺酸酯的直接交叉乌尔曼偶联尚不清楚。我们在此报告了针对这一挑战的通用解决方案，该解决方案由 Ni 和 Pd 与 Zn 还原剂和 LiBr 作为添加剂的组合催化。该反应具有广泛的范围，如 33 个实例所示（平均产率 65% ± 11%）。机理研究表明，Pd 强烈偏好三氟甲磺酸芳基酯，Ni 催化剂对甲苯磺酸芳基酯的偏好较小，催化剂之间的芳基转移由 Zn 介导，Pd 通过消耗芳基锌中间体来提高产率。

  DOI：

  10.1021/jacs.0c04670
• 作为产物：
  描述：

  香草酸甲酯 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3-methoxy-4-(tosyloxy)benzoate
  参考文献：
  名称：

  Aminocarbonylation of Aryl Tosylates to Carboxamides

  摘要：

  The palladium - catalyzed aminocarbonylation of aryl tosylates with amines is reported. Suitable conditions were identified by high throughput reaction screening and then further optimized. The substrate scope of the reaction with respect to the aryl tosylate component and the amine component are reported. Competitive aminolysis of the aryl tosylates to afford the amine toluenesulfonamides and the phenol was not observed.

  DOI：

  10.1021/acs.orglett.5b01283

文献信息

• 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.
• Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates
  作者：Kai Kang、Liangbin Huang、Daniel J. Weix

  DOI：10.1021/jacs.0c04670

  日期：2020.6.17

  While phenols are frequent and convenient aryl sources in cross-coupling, typically as sulfonate esters, the direct cross-Ullmann coupling of two different sulfonate esters is unknown. We report here a general solution to this chal-lenge catalyzed by a combination of Ni and Pd with Zn reductant and LiBr as an additive. The reaction has broad scope, as demonstrated in 33 examples (65% ± 11% ave yield)

  虽然苯酚是交叉偶联中常见且方便的芳基来源，通常作为磺酸酯，但两种不同磺酸酯的直接交叉乌尔曼偶联尚不清楚。我们在此报告了针对这一挑战的通用解决方案，该解决方案由 Ni 和 Pd 与 Zn 还原剂和 LiBr 作为添加剂的组合催化。该反应具有广泛的范围，如 33 个实例所示（平均产率 65% ± 11%）。机理研究表明，Pd 强烈偏好三氟甲磺酸芳基酯，Ni 催化剂对甲苯磺酸芳基酯的偏好较小，催化剂之间的芳基转移由 Zn 介导，Pd 通过消耗芳基锌中间体来提高产率。
• Aminocarbonylation of Aryl Tosylates to Carboxamides
  作者：Seungwon Chung、Neal Sach、Chulho Choi、Xiaojing Yang、Susan E. Drozda、Robert A. Singer、Stephen W. Wright

  DOI：10.1021/acs.orglett.5b01283

  日期：2015.6.5

  The palladium - catalyzed aminocarbonylation of aryl tosylates with amines is reported. Suitable conditions were identified by high throughput reaction screening and then further optimized. The substrate scope of the reaction with respect to the aryl tosylate component and the amine component are reported. Competitive aminolysis of the aryl tosylates to afford the amine toluenesulfonamides and the phenol was not observed.