4-<<(phenoxycarbonyl)oxy>methyl>-2-methoxytetrahydrofuran | 138060-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-<<(phenoxycarbonyl)oxy>methyl>-2-methoxytetrahydrofuran
• 英文别名: (5-methoxyoxolan-3-yl)methyl phenyl carbonate
• CAS: 138060-24-9；138060-25-0；144799-84-8；144799-85-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: FTVXMEWVNVGYSR-UHFFFAOYSA-N

物化性质

• 沸点：
  361.4±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-<<(phenoxycarbonyl)oxy>methyl>-2-methoxytetrahydrofuran 在 Dowex HCR-S-H⁺ 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 49.0h， 生成 2-<methoxy>carbonyl>amino>methyl>pyridine
  参考文献：
  名称：

  4-Substituted 2-alkoxytetrahydrofurans as potent and long-lasting PAF antagonists

  摘要：

  A series of 4-substituted 2-alkoxytetrahydrofuran derivatives featuring an acetal group were prepared and evaluated for PAF antagonist activity in the PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Compound 2-[[N-acetyl-N-[[[2-(octadecyloxy)tetrahydrofuran-4-yl]methoxy]carbonyl]amino]methyl]1-ethylpyridinium chloride (4e, UR-11353) was selected for further development on the basis of its high activity and long-lasting action. The compound maintained a significant activity even 24 h after administration of a single dose of 1 mg/kg iv in the PAF-induced mortality test in mice and 10 h after administration of the same dose in the PAF-induced hypotension test in rats. Comparison with previously reported carba analogues suggests that the presence of the acetal group is the structural characteristic that confers its long-lasting activity.

  DOI：

  10.1021/jm00082a007
• 作为产物：
  描述：

  2-(hydroxymethyl)-4,4-dimethoxybutan-1-ol 在 吡啶 、 pyridin; (+/-)-2-oxo-bornane-10-sulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 4-<<(phenoxycarbonyl)oxy>methyl>-2-methoxytetrahydrofuran
  参考文献：
  名称：

  4-Substituted 2-alkoxytetrahydrofurans as potent and long-lasting PAF antagonists

  摘要：

  A series of 4-substituted 2-alkoxytetrahydrofuran derivatives featuring an acetal group were prepared and evaluated for PAF antagonist activity in the PAF-induced in vitro platelet-aggregation and in vivo hypotension tests. Compound 2-[[N-acetyl-N-[[[2-(octadecyloxy)tetrahydrofuran-4-yl]methoxy]carbonyl]amino]methyl]1-ethylpyridinium chloride (4e, UR-11353) was selected for further development on the basis of its high activity and long-lasting action. The compound maintained a significant activity even 24 h after administration of a single dose of 1 mg/kg iv in the PAF-induced mortality test in mice and 10 h after administration of the same dose in the PAF-induced hypotension test in rats. Comparison with previously reported carba analogues suggests that the presence of the acetal group is the structural characteristic that confers its long-lasting activity.

  DOI：

  10.1021/jm00082a007