2-methoxyethoxymethyl (E)-6-[6-methoxy-4-(2-methoxyethoxymethoxy)-7-methyl-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoate | 125198-39-2

• 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: 2-methoxyethoxymethyl (E)-6-[6-methoxy-4-(2-methoxyethoxymethoxy)-7-methyl-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoate
• CAS: 125198-39-2
• 化学式: C₂₅H₃₆O₁₀
• 分子量: 496.555
• InChiKey: VPNYUOVABTVCCO-UBKPWBPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-methoxyethoxymethyl (E)-6-[6-methoxy-4-(2-methoxyethoxymethoxy)-7-methyl-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoate 在 盐酸 、 chromium chloride 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 四丁基溴化铵 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.5h， 生成 (+/-)-methyl 7-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methylhepta-4,5-dienoate
  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：

  2-甲氧基乙氧基甲基氯 、 霉酚酸 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以19%的产率得到2-methoxyethoxymethyl (E)-6-[6-methoxy-4-(2-methoxyethoxymethoxy)-7-methyl-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoate
  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

文献信息

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

  DOI：——

  日期：——