(S)-5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid | 153490-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid
• 英文别名: (3S)-5-acetyloxy-2,2,4,6,7-pentamethyl-3H-1-benzofuran-3-carboxylic acid
• CAS: 153490-89-2
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: SZWLTZXHASLOKP-GFCCVEGCSA-N

物化性质

• 沸点：
  412.3±45.0 °C(predicted)
• 密度：
  1.185±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid 在 dimethyl sulfide borane 、 bromotriphenylphosphonium bromide 、 苯酚 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 85.0h， 生成 (3R)-5-hydroxy-3-<(4-methylpiperazino)-methyl>-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran
  参考文献：
  名称：

  2,3-Dihydro-1-benzofuran-5-ols as Analogs of .alpha.-Tocopherol That Inhibit in Vitro and ex Vivo Lipid Autoxidation and Protect Mice against Central Nervous System Trauma

  摘要：

  A series of a-tocopherol analogues was synthesized with potential therapeutic value for such pathological conditions as stroke and trauma. A set of criteria such as the inhibition of in vitro lipid peroxidation, superoxyl radical scavenging, and brain penetration, as measured by ex vivo inhibition of lipid peroxidation, was applied to select the most effective compound. 2,3-Dihydro-2,2,4,6,7-pentamethyl-3-[(4-methylpiperazino)methyl]-1-benzofuran-5-ol hydrochloride (22) was selected because of its superior antioxidant properties and better brain penetration. This compound also protected mice against the effects of head injury. The criteria thus turned out to be useful for the characterization of a neuroprotective analogue of alpha-tocopherol.

  DOI：

  10.1021/jm00003a008
• 作为产物：
  描述：

  methyl 2,3-dihydro-5-<(4-nitrobenzoyl)oxy>-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylate 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.83h， 生成 (S)-5-acetoxy-2,3-dihydro-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid
  参考文献：
  名称：

  2,3-Dihydro-1-benzofuran-5-ols as Analogs of .alpha.-Tocopherol That Inhibit in Vitro and ex Vivo Lipid Autoxidation and Protect Mice against Central Nervous System Trauma

  摘要：

  A series of a-tocopherol analogues was synthesized with potential therapeutic value for such pathological conditions as stroke and trauma. A set of criteria such as the inhibition of in vitro lipid peroxidation, superoxyl radical scavenging, and brain penetration, as measured by ex vivo inhibition of lipid peroxidation, was applied to select the most effective compound. 2,3-Dihydro-2,2,4,6,7-pentamethyl-3-[(4-methylpiperazino)methyl]-1-benzofuran-5-ol hydrochloride (22) was selected because of its superior antioxidant properties and better brain penetration. This compound also protected mice against the effects of head injury. The criteria thus turned out to be useful for the characterization of a neuroprotective analogue of alpha-tocopherol.

  DOI：

  10.1021/jm00003a008