4-hydroxy-6,7-dimethoxy-3-oxo-1,3-dihydroisobenzofuran | 182010-21-5

• 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: 4-hydroxy-6,7-dimethoxy-3-oxo-1,3-dihydroisobenzofuran
• 英文别名: 7-hydroxy-4,5-dimethoxy-3H-2-benzofuran-1-one
• CAS: 182010-21-5
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: GVVIJRJAJUNTBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6,7-dimethoxy-3-oxo-1,3-dihydroisobenzofuran 在 吡啶 、 2,6-二甲基吡啶 、 ozone-containing oxygen 、 三甲基锍 、 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 7-(tert-Butyl-dimethyl-silanyloxy)-6-(2-hydroxy-3-methyl-but-3-enyl)-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：

  3,5,6-trimethoxyphthalide 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以61%的产率得到4-hydroxy-6,7-dimethoxy-3-oxo-1,3-dihydroisobenzofuran
  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

文献信息

• SOLVENT CONTAINING 1,2,5-THIADIAZOLE COMPOUND, AND METHOD FOR EXTRACTING AN ORGANIC COMPOUND USING THE SOLVENT
  申请人：Tatsuta Kuniaki

  公开号：US20060287533A1

  公开（公告）日：2006-12-21

  The object of the present invention is to provide a solvent which is free from the risk of destroying the ozone layer surrounding the Earth, hardly toxic, and free from the risk of causing environment pollution problems by polluting underground water or air. The solvent contains at least one chosen from 1,2,5-thiadiazole compounds represented by formula (1) below: (where R 1 and R 2 each represent hydrogen or methyl group).

  本发明的目的是提供一种溶剂，该溶剂不会破坏包围地球的臭氧层，几乎无毒，并且不会通过污染地下水或空气而导致环境污染问题的风险。该溶剂包含至少一种选择自下式所示的1,2,5-噻二唑化合物中的一种：(其中R1和R2分别代表氢或甲基基团)。
• 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.