6-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-1-(4-methoxyphenyl)-3,5-dioxohexyl 2-(2-(tertbutyldimethylsilyloxy)-2-(4-(tert-butyldimethylsilyloxy)phenyl)ethyl)-4,6-dimethoxybenzoate | 1449521-93-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-1-(4-methoxyphenyl)-3,5-dioxohexyl 2-(2-(tertbutyldimethylsilyloxy)-2-(4-(tert-butyldimethylsilyloxy)phenyl)ethyl)-4,6-dimethoxybenzoate
• 英文别名: [6-(2,2-Dimethyl-6-oxo-1,3-dioxin-4-yl)-1-(4-methoxyphenyl)-3,5-dioxohexyl] 2-[2-[tert-butyl(dimethyl)silyl]oxy-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]ethyl]-4,6-dimethoxybenzoate；[6-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)-1-(4-methoxyphenyl)-3,5-dioxohexyl] 2-[2-[tert-butyl(dimethyl)silyl]oxy-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]ethyl]-4,6-dimethoxybenzoate
• CAS: 1449521-93-0
• 化学式: C₄₈H₆₆O₁₂Si₂
• 分子量: 891.216
• InChiKey: UWHYKHUASQOBTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  62
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-1-(4-methoxyphenyl)-3,5-dioxohexyl 2-(2-(tertbutyldimethylsilyloxy)-2-(4-(tert-butyldimethylsilyloxy)phenyl)ethyl)-4,6-dimethoxybenzoate 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到3-(4-(tert-butyldimethylsilyloxy)phenyl)-6,8-dimethoxyisochroman-1-one
  参考文献：
  名称：

  Synthetic studies towards tragoponol: preparation of a highly functionalized resorcylate

  摘要：

  Studies on the synthesis of racemic tragoponol are described. The western resorcylate unit of tragoponol was efficiently constructed from appropriate diketo-dioxinone and secondary alcohol intermediates using a ketene generation-trapping and aromatization sequence. Further functionalization provided an advanced diketo-dioxinone intermediate which upon desilylation resulted in the formation of a dihydroisocoumarin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.044
• 作为产物：
  描述：

  [3-[Methoxy(methyl)amino]-1-(4-methoxyphenyl)-3-oxopropyl] 2-[2-[tert-butyl(dimethyl)silyl]oxy-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]ethyl]-4,6-dimethoxybenzoate 、 2,2-dimethyl-6-(2-oxopropyl)-4H-1,3-dioxin-4-one 在 lithium diisopropyl amide 、 diethylzinc 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.33h， 以76%的产率得到6-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-1-(4-methoxyphenyl)-3,5-dioxohexyl 2-(2-(tertbutyldimethylsilyloxy)-2-(4-(tert-butyldimethylsilyloxy)phenyl)ethyl)-4,6-dimethoxybenzoate
  参考文献：
  名称：

  Synthetic studies towards tragoponol: preparation of a highly functionalized resorcylate

  摘要：

  Studies on the synthesis of racemic tragoponol are described. The western resorcylate unit of tragoponol was efficiently constructed from appropriate diketo-dioxinone and secondary alcohol intermediates using a ketene generation-trapping and aromatization sequence. Further functionalization provided an advanced diketo-dioxinone intermediate which upon desilylation resulted in the formation of a dihydroisocoumarin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.044

文献信息

• Synthetic studies towards tragoponol: preparation of a highly functionalized resorcylate
  作者：Hideki Miyatake-Ondozabal、Anthony G.M. Barrett

  DOI：10.1016/j.tetlet.2013.05.044

  日期：2013.9

  Studies on the synthesis of racemic tragoponol are described. The western resorcylate unit of tragoponol was efficiently constructed from appropriate diketo-dioxinone and secondary alcohol intermediates using a ketene generation-trapping and aromatization sequence. Further functionalization provided an advanced diketo-dioxinone intermediate which upon desilylation resulted in the formation of a dihydroisocoumarin. (C) 2013 Elsevier Ltd. All rights reserved.