3-(5-Carboxy-3-methyl-pent-2t-enyl)-4-hydroxy-6-hydroxymethyl-2-methoxy-toluol; 6-(6-Hydroxy-4-hydroxymethyl-2-methoxy-3-methyl-phenyl)-4-methyl-hex-4t-ensaeure | 31848-65-4

• 分子结构分类: 有机化合物
• 英文名称: 3-(5-Carboxy-3-methyl-pent-2t-enyl)-4-hydroxy-6-hydroxymethyl-2-methoxy-toluol; 6-(6-Hydroxy-4-hydroxymethyl-2-methoxy-3-methyl-phenyl)-4-methyl-hex-4t-ensaeure
• CAS: 31848-65-4
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: JERAAVMUBLIRBV-ONNFQVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(5-Carboxy-3-methyl-pent-2t-enyl)-4-hydroxy-6-hydroxymethyl-2-methoxy-toluol; 6-(6-Hydroxy-4-hydroxymethyl-2-methoxy-3-methyl-phenyl)-4-methyl-hex-4t-ensaeure 在 水 、 碘 、 镍 、 potassium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 叔丁胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 31.0h， 生成 methyl (E)-6-(2-hydroxy-3-iodo-6-methoxy-4,5-dimethylphenyl)-4-methylhex-4-enoate
  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：

  霉酚酸 在 lithium hydroxide 作用下， 以 水 为溶剂， 反应 96.0h， 以82%的产率得到3-(5-Carboxy-3-methyl-pent-2t-enyl)-4-hydroxy-6-hydroxymethyl-2-methoxy-toluol; 6-(6-Hydroxy-4-hydroxymethyl-2-methoxy-3-methyl-phenyl)-4-methyl-hex-4t-ensaeure
  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