1,3-dihydro-5,7-dimethoxy-6-<(trifluoromethanesulfonyl)oxy>isobenzofuran-1-one | 124200-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1,3-dihydro-5,7-dimethoxy-6-<(trifluoromethanesulfonyl)oxy>isobenzofuran-1-one
• 英文别名: 1H,3H-5,7-dimethoxy-6-((trifluormethyl)sulfonyl)isobenzofuran-1-one；1H,3H-5,7-dimethoxy-6-[(trifluormethyl)sulfonyl]isobenzofuran-1-one；(4,6-dimethoxy-3-oxo-1H-2-benzofuran-5-yl) trifluoromethanesulfonate
• CAS: 124200-75-5
• 化学式: C₁₁H₉F₃O₇S
• 分子量: 342.249
• InChiKey: MQUGYGUHAVUKAC-UHFFFAOYSA-N

物化性质

• 熔点：
  119-121 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  546.9±50.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3-dihydro-5,7-dimethoxy-6-<(trifluoromethanesulfonyl)oxy>isobenzofuran-1-one 在 bis-triphenylphosphine-palladium(II) chloride 甲酸 、 三正丁胺 、 1,3-双(二苯基膦)丙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到5,7-dimethoxyphthalide
  参考文献：
  名称：

  Deoxygenation of highly hindered phenols

  摘要：

  DOI：

  10.1021/jo00290a033
• 作为产物：
  描述：

  3-hydroxy-2,4-dimethoxy-6-(methoxymethyl)benzoic acid 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 1,3-dihydro-5,7-dimethoxy-6-<(trifluoromethanesulfonyl)oxy>isobenzofuran-1-one
  参考文献：
  名称：

  Deoxygenation of highly hindered phenols

  摘要：

  DOI：

  10.1021/jo00290a033

文献信息

• 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.
• SAA, JOSE M.;DOPICO, MERCEDES;MARTORELL, GABRIEL;GARCIA-RASO, ANGEL, J. ORG. CHEM., 55,(1990) N, C. 991-995
  作者：SAA, JOSE M.、DOPICO, MERCEDES、MARTORELL, GABRIEL、GARCIA-RASO, ANGEL

  DOI：——

  日期：——