ethyl (E)-10-[(1,1-dimethylethyl)dimethylsilyloxy]dec-8-en-2-ynoate | 1248573-49-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-10-[(1,1-dimethylethyl)dimethylsilyloxy]dec-8-en-2-ynoate
• 英文别名: ethyl (E)-10-[tert-butyl(dimethyl)silyl]oxydec-8-en-2-ynoate
• CAS: 1248573-49-0
• 化学式: C₁₈H₃₂O₃Si
• 分子量: 324.536
• InChiKey: MWJDCRVFYFOUGI-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-10-[(1,1-dimethylethyl)dimethylsilyloxy]dec-8-en-2-ynoate 、 甲基锂 在 copper(l) iodide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 ethyl (2Z,8E)-3-methyl-10-[(1,1-dimethylethyl)dimethylsilyloxy]deca-2,8-dienoate
  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：

  (E)-9-[(1,1-dimethylethyl)dimethylsilyloxy]non-7-en-1-yne 、 氯甲酸乙酯 在 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以74%的产率得到ethyl (E)-10-[(1,1-dimethylethyl)dimethylsilyloxy]dec-8-en-2-ynoate
  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