(2E,8Z)-13-(4-methoxyphenylmethoxy)-8-methyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]trideca-2,8-dien-10-ol | 1248573-81-0

• 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: (2E,8Z)-13-(4-methoxyphenylmethoxy)-8-methyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]trideca-2,8-dien-10-ol
• 英文别名: (5Z,11E)-13-[tert-butyl(dimethyl)silyl]oxy-1-[(4-methoxyphenyl)methoxy]-6-methyltrideca-5,11-dien-4-ol
• CAS: 1248573-81-0
• 化学式: C₂₈H₄₈O₄Si
• 分子量: 476.772
• InChiKey: KTMQHVKWNLBNDU-HYGMHYJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.44
• 重原子数：
  33
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,8Z)-13-(4-methoxyphenylmethoxy)-8-methyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]trideca-2,8-dien-10-ol 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到(2E,8Z)-13-(4-methoxyphenylmethoxy)-8-methyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-10-[(1,1-dimethylethyl)diphenylsilyloxy]trideca-2,8-diene
  参考文献：
  名称：

  Synthesis of a trans,syn,trans-Dodecahydrophenanthrene via a Bicyclic Transannular Diels−Alder Reaction: Intermediate for the Synthesis of Fusidic Acid

  摘要：

  While thermolysis of the macrobicyclic triene lactone 12 did not produce the expected bicyclic transannular Diels-Alder (BTADA) product 13. heating the corresponding ether 18 to 110 degrees C for 4 h afforded a quantitative yield ol the desired cycloadduct 19. which could be easily reduced to the perhydrophenanthrene. an ABC ring analogue of lusidic acid 1 Theoretical calculations with hybrid density functional theory (B3LYP/6-31G(d)) help rationalize why the lactone does not cyclize whereas the ether does

  DOI：

  10.1021/jo101533h
• 作为产物：
  描述：

  (2Z,8E)-3-methyl-10-[(1,1-dimethylethyl)dimethylsilyloxy]deca-2,8-dienal 、 1-(3-bromopropoxymethyl)-4-methoxy-benzene 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以87%的产率得到(2E,8Z)-13-(4-methoxyphenylmethoxy)-8-methyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]trideca-2,8-dien-10-ol
  参考文献：
  名称：

  Synthesis of a trans,syn,trans-Dodecahydrophenanthrene via a Bicyclic Transannular Diels−Alder Reaction: Intermediate for the Synthesis of Fusidic Acid

  摘要：

  While thermolysis of the macrobicyclic triene lactone 12 did not produce the expected bicyclic transannular Diels-Alder (BTADA) product 13. heating the corresponding ether 18 to 110 degrees C for 4 h afforded a quantitative yield ol the desired cycloadduct 19. which could be easily reduced to the perhydrophenanthrene. an ABC ring analogue of lusidic acid 1 Theoretical calculations with hybrid density functional theory (B3LYP/6-31G(d)) help rationalize why the lactone does not cyclize whereas the ether does

  DOI：

  10.1021/jo101533h

文献信息

• Synthesis of a <i>trans</i>,<i>syn</i>,<i>trans</i>-Dodecahydrophenanthrene via a Bicyclic Transannular Diels−Alder Reaction: Intermediate for the Synthesis of Fusidic Acid
  作者：Michael E. Jung、Ting-Hu Zhang、Rebecca M. Lui、Osvaldo Gutierrez、K. N. Houk

  DOI：10.1021/jo101533h

  日期：2010.10.15

  While thermolysis of the macrobicyclic triene lactone 12 did not produce the expected bicyclic transannular Diels-Alder (BTADA) product 13. heating the corresponding ether 18 to 110 degrees C for 4 h afforded a quantitative yield ol the desired cycloadduct 19. which could be easily reduced to the perhydrophenanthrene. an ABC ring analogue of lusidic acid 1 Theoretical calculations with hybrid density functional theory (B3LYP/6-31G(d)) help rationalize why the lactone does not cyclize whereas the ether does