3,5,6-trimethoxyphthalide | 105518-11-4

• 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: 3,5,6-trimethoxyphthalide
• 英文别名: 4,6,7-trimethoxy-3-oxo-1,3-dihydroisobenzofuran；4,5,7-trimethoxyphthalide；4,5,7-trimethoxy-3H-2-benzofuran-1-one
• CAS: 105518-11-4
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: IPCXXYCURKKDAR-UHFFFAOYSA-N

物化性质

• 沸点：
  436.8±45.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5,6-trimethoxyphthalide 在 三氯化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 7-Allyloxy-4,5-dimethoxy-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid

  摘要：

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.

  DOI：

  10.1021/jm9603633
• 作为产物：
  描述：

  2,4,5-三甲氧基苯甲酸 在 盐酸 、 silver(II) oxide 、 N-溴代丁二酰亚胺(NBS) 、 硝酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.07h， 生成 3,5,6-trimethoxyphthalide
  参考文献：
  名称：

  Evaluation of some preparations of trialkoxyphthalic acid derivatives

  摘要：

  DOI：

  10.1021/jo00378a005

文献信息

• Regiospecific synthesis of 9-ethoxy-4,5,6,8-tetramethoxy-1,3-dihydro-naphtho-(2,3-) furan-1-one: A key synthon of fredericamycin A
  作者：AV Rama Rao、N Sreenivasan、D Reddeppa Reddy、V.H Deshpande

  DOI：10.1016/s0040-4039(00)95755-1

  日期：1987.1

  An efficient and regiospecific synthesis of ABC ring synthon of fredericamycin A has been described.

  已经描述了腓特烈霉素A的ABC环合成子的有效和区域特异性合成。
• Evans, Geoffrey E.; Staunton, James, Journal of the Chemical Society. Perkin transactions I, 1988, p. 755 - 762
  作者：Evans, Geoffrey E.、Staunton, James

  DOI：——

  日期：——
• EVANS, GEOFFREY E.;STAUNTON, JAMES, J. CHEM. SOC. PERKIN TRANS.,(1988) N 4, 755-761
  作者：EVANS, GEOFFREY E.、STAUNTON, JAMES

  DOI：——

  日期：——
• Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid
  作者：Peter H. Nelson、Stephen F. Carr、Bruce H. Devens、Elsie M. Eugui、Fidencio Franco、Carlos Gonzalez、Ronald C. Hawley、David G. Loughhead、David J. Milan、Eva Papp、John W. Patterson、Sussan Rouhafza、Eric B. Sjogren、David B. Smith、Rebecca A. Stephenson、Francisco X. Talamas、Ann-Marie Waltos、Robert J. Weikert、John C. Wu

  DOI：10.1021/jm9603633

  日期：1996.1.1

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.
• Evaluation of some preparations of trialkoxyphthalic acid derivatives
  作者：Kathlyn A. Parker、Denice M. Spero、Kathleen A. Koziski

  DOI：10.1021/jo00378a005

  日期：1987.1