2,6-dimethoxy-4-(methoxymethyl)-3-(methylthio)toluene | 128919-99-3

• 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: 2,6-dimethoxy-4-(methoxymethyl)-3-(methylthio)toluene
• 英文别名: 1,3-Dimethoxy-5-(methoxymethyl)-2-methyl-4-methylsulfanylbenzene
• CAS: 128919-99-3
• 化学式: C₁₂H₁₈O₃S
• 分子量: 242.339
• InChiKey: FTSGSFYATVGQNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-dimethoxy-4-(methoxymethyl)-3-(methylthio)phenyl trifluoromethanesulfonate 、 三-N-丁基甲基锡 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦 、 lithium chloride 2,6-二叔丁基-4-甲基苯酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到2,6-dimethoxy-4-(methoxymethyl)-3-(methylthio)toluene
  参考文献：
  名称：

  Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes

  摘要：

  The palladium-catalyzed cross-coupling reaction of highly hindered, electron-rich phenol triflates and organostannanes (Stille reaction) has been studied in a systematic manner. The following are its salient features: (1) electron-rich phenol triflates require triphenylphosphine to undergo palladium-catalyzed cross-couplings; (2) in general, efficient reactions take place only when larger-than-usual amounts (10-15%) of palladium are employed. On the reagent side, alkyl- (methyl only), allyl-, vinyl- and alkinylstannanes undergo efficient cross-couplings with the title substrates. However, some limitations to this novel entry to 2-substituted resorcinols exist in regard to both substrates and reagents. Thus, conformationally rigid (hexasubstituted) aryl triflates behave poorly, demethylation being an important side reaction. Moreover, alkyl groups other than methyl cannot be introduced because beta-elimination occurs more rapidly. The potentially powerful synthesis of hindered biaryls has also been studied briefly. In the present conditions, the reaction appears to be limited by the presence of ortho substituents on the arylstannane moiety.

  DOI：

  10.1021/jo00028a051

文献信息

• Palladium catalyzed cross-coupling of phenol triflates with organostannanes. A versatile approach for the synthesis of substituted resorcinol dimethyl ethers.
  作者：Gabriel Martorell、Angel García-Raso、José M. Saá

  DOI：10.1016/0040-4039(90)80227-d

  日期：——

  -2,6 Dimethoxy-substituted phenol triflates undergo efficient Pd(O) catalyzed cross coupling with organostannanes, thus providing an easy access to substituted resorcinol dimethyl ethers, a common building block of many aromatic polyketides.

  -2,6二甲氧基取代的苯酚三氟甲磺酸酯经过有效的Pd（O）催化与有机锡的交联，从而易于获得取代的间苯二酚二甲醚，这是许多芳香族聚酮化合物的常见组成部分。
• MARTORELLL, GABRIEL;GARCIA-RASO, ANGEL;SAA, JOSE M., TETRAHEDRON LETT., 31,(1990) N6, C. 2357-2360
  作者：MARTORELLL, GABRIEL、GARCIA-RASO, ANGEL、SAA, JOSE M.

  DOI：——

  日期：——
• Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes
  作者：Jose M. Saa、Gabriel Martorell、Angel Garcia-Raso

  DOI：10.1021/jo00028a051

  日期：1992.1

  The palladium-catalyzed cross-coupling reaction of highly hindered, electron-rich phenol triflates and organostannanes (Stille reaction) has been studied in a systematic manner. The following are its salient features: (1) electron-rich phenol triflates require triphenylphosphine to undergo palladium-catalyzed cross-couplings; (2) in general, efficient reactions take place only when larger-than-usual amounts (10-15%) of palladium are employed. On the reagent side, alkyl- (methyl only), allyl-, vinyl- and alkinylstannanes undergo efficient cross-couplings with the title substrates. However, some limitations to this novel entry to 2-substituted resorcinols exist in regard to both substrates and reagents. Thus, conformationally rigid (hexasubstituted) aryl triflates behave poorly, demethylation being an important side reaction. Moreover, alkyl groups other than methyl cannot be introduced because beta-elimination occurs more rapidly. The potentially powerful synthesis of hindered biaryls has also been studied briefly. In the present conditions, the reaction appears to be limited by the presence of ortho substituents on the arylstannane moiety.