[3,5-Dimethoxy-4-(3-methylbut-2-enyl)phenoxy]-tri(propan-2-yl)silane | 876726-97-5

• 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: [3,5-Dimethoxy-4-(3-methylbut-2-enyl)phenoxy]-tri(propan-2-yl)silane
• 英文别名: [3,5-dimethoxy-4-(3-methylbut-2-enyl)phenoxy]-tri(propan-2-yl)silane
• CAS: 876726-97-5
• 化学式: C₂₂H₃₈O₃Si
• 分子量: 378.627
• InChiKey: AGGATQZBWMNHIM-UHFFFAOYSA-N

物化性质

• 沸点：
  415.1±45.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 potassium osmate(VI) 、 potassium carbonate 、 对甲苯磺酸 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 51.0h， 生成 [3,5-dimethoxy-4-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-triisopropyl-silane
  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-dimethoxyphenoxy)triisopropylsilane 、 1-溴-3-甲基-2-丁烯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.42h， 以98%的产率得到[3,5-Dimethoxy-4-(3-methylbut-2-enyl)phenoxy]-tri(propan-2-yl)silane
  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.