(E)-7-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]hept-2-ene | 1237766-03-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-7-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]hept-2-ene
• 英文别名: [(E)-7-bromohept-2-enoxy]-tert-butyl-dimethylsilane
• CAS: 1237766-03-8
• 化学式: C₁₃H₂₇BrOSi
• 分子量: 307.346
• InChiKey: ACGDTDHTJNJBBY-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-7-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]hept-2-ene 、 以 二甲基亚砜 为溶剂， 以94%的产率得到(E)-9-[(1,1-dimethylethyl)dimethylsilyloxy]non-7-en-1-yne
  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：

  叔丁基二甲基氯硅烷 、 (E)-7-bromohept-2-en-1-ol 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到(E)-7-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]hept-2-ene
  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