tert-Butyl-((E)-1-ethynyl-1-methyl-hex-4-enyloxy)-dimethyl-silane | 131130-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-((E)-1-ethynyl-1-methyl-hex-4-enyloxy)-dimethyl-silane
• 英文别名: tert-butyl-dimethyl-[(E)-3-methyloct-6-en-1-yn-3-yl]oxysilane
• CAS: 131130-48-8
• 化学式: C₁₅H₂₈OSi
• 分子量: 252.472
• InChiKey: HSZGZUBUEOJORX-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  tert-Butyl-((E)-1-ethynyl-1-methyl-hex-4-enyloxy)-dimethyl-silane 生成 tert-Butyl-dimethyl-(1-methyl-2-methylene-3-vinyl-cyclopentyloxy)-silane
  参考文献：
  名称：

  TROST, BARRY M.;LAUTENS, M.;CHAN, C.;JEBARATNAM, D. J.;MUELLER, T., J. AMER. CHEM. SOC., 113,(1991) N, C. 636-644

  摘要：

  DOI：

文献信息

• Trost, Barry M.; Lautens; Chan, Journal of the American Chemical Society, 1991, vol. 113, # 2, p. 636 - 644
  作者：Trost, Barry M.、Lautens、Chan、Jebaratnam、Mueller

  DOI：——

  日期：——
• Pd-Catalyzed Cycloisomerization to 1,2-Dialkylidenecycloalkanes. 2. Alternative Catalyst System
  作者：Barry M. Trost、Donna L. Romero、Frode Rise

  DOI：10.1021/ja00089a016

  日期：1994.5

  The mechanisms by which palladium complexes may catalyze the cycloisomerization of 1,6- and 1,7-enynes to dialkylidenecycloalkanes were probed by exploring a catalyst system different than a ligated palladium acetate which previously has proven to be successful. Although carboxylic acids showed no discernible interaction with palladium(0) complexes, this combination proved to be a powerful catalyst system to effect this cycloisomerization. The fact that the two catalyst systems do not have the same reactivity profile suggests this new catalyst system may operate by a different mechanism. Evidence supporting a pathway invoking formation of a hydridopalladium acetate followed by hydropalladation as initiation is presented. Steric and electronic effects direct the regioselectivity of the termination step to form either 1,3- or 1,4-diene products. The 1,3-diene products participate exceedingly well in Diels-Alder reactions, both inter- and intramolecularly. The presence of an oxygen substituent at the position allylic to the diene served as both a regiochemical control element for the palladium-catalyzed cycloisomerization and a diastereochemical control element for the Diels-Alder reaction. The net result of these two steps, the first of which is a catalyzed isomerization and the second an addition, is a highly efficient approach to complex polycycles in terms of both selectivity and atom economy.