methyl 3-[3-[(4,6-dimethoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)methyl]-2,2-difluoro-1-methylcyclopropyl]propanoate | 125198-37-0

• 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: methyl 3-[3-[(4,6-dimethoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)methyl]-2,2-difluoro-1-methylcyclopropyl]propanoate
• CAS: 125198-37-0
• 化学式: C₂₀H₂₄F₂O₆
• 分子量: 398.404
• InChiKey: PEUDMOYPAZQRNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-[3-[(4,6-dimethoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)methyl]-2,2-difluoro-1-methylcyclopropyl]propanoate 在 lithium hydroxide 、 三氯化硼 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 3-[2,2-Difluoro-3-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-ylmethyl)-1-methyl-cyclopropyl]-propionic acid
  参考文献：
  名称：

  Synthesis and immunosuppressive activity of some side-chain variants of mycophenolic acid

  摘要：

  The syntheses and immunosuppressive bioassays of 12 side-chain variants of mycophenolic acid are described. The compounds were made either from mycophenolic acid itself or from 5-(chloromethyl)-1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisoben zofuran, a versatile intermediate for the synthesis of diverse side-chain variants. Replacement of the methylated E double bond of the natural product with a triple bond, a Z double bond, a saturated bond, or a sulfur atom, with overall chain lengths equal to or greater than that of mycophenolic acid, produced compounds devoid of significant activity. Replacement of the side-chain double bond with difluoro, dibromo, or unsubstituted cyclopropane rings also removed most activity. Replacement of the double bond with an allenic linkage yielded a compound with about one-fifth of the immunosuppressive activity of mycophenolic acid. Some possible causes for the unusual specificity of structure and activity are discussed.

  DOI：

  10.1021/jm00164a057
• 作为产物：
  描述：

  methyl (Z)-6-(4,6-dimethoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate 、 二氟氯乙酸 以89%的产率得到
  参考文献：
  名称：

  NELSON, PETER H.;EUGUI, ELSIE;WANG, CHING C.;ALLISON, ANTHONY C., J. MED. CHEM., 33,(1990) N, C. 833-838

  摘要：

  DOI：