3,5-Dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-phenol | 876726-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-Dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-phenol
• 英文别名: 3,5-dimethoxy-4-[(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methyl]phenol
• CAS: 876726-99-7
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: ZPNNYNIAJKEPOY-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C(Solv: toluene (108-88-3))
• 沸点：
  404.7±40.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,5-Dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-phenol 、 烯丙基甲基碳酸酯 在 titanium(IV) isopropylate 、 palladium diacetate 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 0.92h， 以62%的产率得到4-Allyl-3,5-dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-cyclohexa-2,5-dienone
  参考文献：
  名称：

  Total Synthesis of Garsubellin A

  摘要：

  A concise approach to the laboratory synthesis of garsubellin A is described. Garsubellin A, an effective inducer of choline acetyltransferase (ChAT), has been shown to have potential as a therapeutic agent for the treatment of Alzheimer's disease. Starting from 3,5-dimethoxyphenol, the synthesis has provided garsubellin A in an 18-step sequence. Notable transformations include dearomative allylation, diastereoselective vinylogous lactonization, iodocarbocyclization, transannular Wurtz, and bridgehead functionalization reactions.

  DOI：

  10.1021/ja057418n
• 作为产物：
  描述：

  1-(2,6-dimethoxy-4-triisopropylsilanyloxy-phenyl)-3-methyl-butane-2,3-diol 在 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.17h， 生成 3,5-Dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-phenol
  参考文献：
  名称：

  Total Synthesis of Garsubellin A

  摘要：

  A concise approach to the laboratory synthesis of garsubellin A is described. Garsubellin A, an effective inducer of choline acetyltransferase (ChAT), has been shown to have potential as a therapeutic agent for the treatment of Alzheimer's disease. Starting from 3,5-dimethoxyphenol, the synthesis has provided garsubellin A in an 18-step sequence. Notable transformations include dearomative allylation, diastereoselective vinylogous lactonization, iodocarbocyclization, transannular Wurtz, and bridgehead functionalization reactions.

  DOI：

  10.1021/ja057418n