(2,2,4-trimethyl-6-bicyclo[3.2.1]octa-3,6-dienyl) trifluoromethanesulfonate | 654674-00-7

• 英文名称: (2,2,4-trimethyl-6-bicyclo[3.2.1]octa-3,6-dienyl) trifluoromethanesulfonate
• CAS: 654674-00-7
• 化学式: C₁₂H₁₅F₃O₃S
• 分子量: 296.311
• InChiKey: SSOPSXXQGJLSMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2,2,4-trimethyl-6-bicyclo[3.2.1]octa-3,6-dienyl) trifluoromethanesulfonate 在 copper(l) iodide 、 四(三苯基膦)钯 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3aR,4S,8R,8aR)-2,5,5,7-Tetramethyl-4,5,8,8a-tetrahydro-3aH-4,8-methano-azulen-1-one
  参考文献：
  名称：

  Stereoselective Nazarov Cyclizations of Bridged Bicyclic Dienones

  摘要：

  Bridged bicyclic dienones underwent silyl-directed Nazarov cyclization with generally very high diastereoselectivity. In most cases, a strong preference for cyclization to the product with an exo-disposed cyclopentenone was seen. However, the presence of additional unsaturation in the three-carbon bridge of a bicyclo[3.2.1]octadiene system caused complete reversal in selectivity with exclusive formation of the endocyclopentenone. The observed selectivities are believed to result from a combination of steric and electronic effects.

  DOI：

  10.1021/ol051169q
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 2,4,4-trimethylbicyclo[3.2.1]oct-2-en-7-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(2,2,4-trimethyl-6-bicyclo[3.2.1]octa-3,6-dienyl) trifluoromethanesulfonate
  参考文献：
  名称：

  Improved Yields with Added Copper(I) Salts in Carbonylative Stille Couplings of Sterically Hindered Vinylstannanes

  摘要：

  Stille coupling under standard carbonylative conditions proceeds in poor yield when using hindered alkenylstannane and enol triflate partners. The inclusion of 35 mol % CuI or CuBr significantly improves the efficiency of the coupling, providing a variety of complex 1,4-dien-3-ones in good to excellent yield.

  DOI：

  10.1021/jo034788q