(E)-tert-butyldimethyl[1-phenethyl-4-(toluene-4-sulfonyl)but-3-enyloxy]silane | 844475-59-8

• 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: (E)-tert-butyldimethyl[1-phenethyl-4-(toluene-4-sulfonyl)but-3-enyloxy]silane
• 英文别名: tert-butyl-dimethyl-[(E)-6-(4-methylphenyl)sulfonyl-1-phenylhex-5-en-3-yl]oxysilane
• CAS: 844475-59-8
• 化学式: C₂₅H₃₆O₃SSi
• 分子量: 444.711
• InChiKey: ZKCQWZOEHHKDLV-KEBDBYFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyldimethyl[1-phenethyl-4-(toluene-4-sulfonyl)but-3-enyloxy]silane 在 potassium tert-butylate 、 苯基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.75h， 生成 (+/-)-(2S,4S,6S)-4-[2-methyl-1-(toluene-4-sulfonyl)prop-1-enyl]-6-phenethyl-2-phenyl[1,3]dioxane
  参考文献：
  名称：

  Tandem Conjugate Addition−Elimination for the Diastereoselective Synthesis of 4E-Alkenyl syn-1,3-Diols

  摘要：

  We have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syri-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C.

  DOI：

  10.1021/ol701624y
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (E)-1-phenyl-6-tosylhex-5-en-3-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到(E)-tert-butyldimethyl[1-phenethyl-4-(toluene-4-sulfonyl)but-3-enyloxy]silane
  参考文献：
  名称：

  Tandem Conjugate Addition−Elimination for the Diastereoselective Synthesis of 4E-Alkenyl syn-1,3-Diols

  摘要：

  We have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syri-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C.

  DOI：

  10.1021/ol701624y

文献信息

• Tandem Conjugate Addition−Elimination for the Diastereoselective Synthesis of 4<i>E</i>-Alkenyl <i>syn</i>-1,3-Diols
  作者：Delphine Rotulo-Sims、Joëlle Prunet

  DOI：10.1021/ol701624y

  日期：2007.10.1

  We have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syri-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C.