4-Allyl-3,5-dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-cyclohexa-2,5-dienone | 876727-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Allyl-3,5-dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-cyclohexa-2,5-dienone
• 英文别名: 3,5-Dimethoxy-4-prop-2-enyl-4-[(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methyl]cyclohexa-2,5-dien-1-one
• CAS: 876727-00-3
• 化学式: C₁₉H₂₈O₅
• 分子量: 336.428
• InChiKey: XJTJCIJUFBZMRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Allyl-3,5-dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-cyclohexa-2,5-dienone 在 高氯酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以72%的产率得到
  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：

  [3,5-Dimethoxy-4-(3-methylbut-2-enyl)phenoxy]-tri(propan-2-yl)silane 在 三乙烯二胺 、 甲基磺酰胺 titanium(IV) isopropylate 、 palladium diacetate 、 potassium osmate(VI) 、 四丁基氟化铵 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 52.09h， 生成 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

文献信息

• Total Synthesis of Garsubellin A
  作者：Dionicio R. Siegel、Samuel J. Danishefsky

  DOI：10.1021/ja057418n

  日期：2006.2.1

  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.