(2E,8Z)-13-(4-methoxyphenylmethoxy)-8-methyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-10-[(1,1-dimethylethyl)diphenylsilyloxy]trideca-2,8-diene | 1248573-52-5

• 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: (2E,8Z)-13-(4-methoxyphenylmethoxy)-8-methyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-10-[(1,1-dimethylethyl)diphenylsilyloxy]trideca-2,8-diene
• 英文别名: tert-butyl-[(5Z,11E)-13-[tert-butyl(dimethyl)silyl]oxy-1-[(4-methoxyphenyl)methoxy]-6-methyltrideca-5,11-dien-4-yl]oxy-diphenylsilane
• CAS: 1248573-52-5
• 化学式: C₄₄H₆₆O₄Si₂
• 分子量: 715.177
• InChiKey: HMEFLAIPDSUHDZ-JUFPIJMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.02
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 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]-10-[(1,1-dimethylethyl)diphenylsilyloxy]trideca-2,8-diene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(5Z,11E)-6-methyl-13-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]trideca-5,11-dien-1-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
• 作为产物：
  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

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