Trifluoro-methanesulfonic acid (1S,4R,5S)-4,8,8-trimethyl-bicyclo[3.2.1]oct-6-en-6-yl ester | 860004-00-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (1S,4R,5S)-4,8,8-trimethyl-bicyclo[3.2.1]oct-6-en-6-yl ester
• CAS: 860004-00-8
• 化学式: C₁₂H₁₇F₃O₃S
• 分子量: 298.326
• InChiKey: QWBGXWQMHBDNFK-KHQFGBGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 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：
  0.83
• 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：

  Trifluoro-methanesulfonic acid (1S,4R,5S)-4,8,8-trimethyl-bicyclo[3.2.1]oct-6-en-6-yl ester 、 一氧化碳 、 三丁基[(1E)-2-(三甲基硅烷基)乙烯基]锡烷 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到(E)-1-((1S,4R,5S)-4,8,8-Trimethyl-bicyclo[3.2.1]oct-6-en-6-yl)-3-trimethylsilanyl-propenone
  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：

  2,8,8-timethylbicyclo[3.2.1]oct-2-en-7-ol 在 palladium on activated charcoal 正丁基锂 、 Celite 、 氢气 、 二异丙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 75.75h， 生成 Trifluoro-methanesulfonic acid (1S,4R,5S)-4,8,8-trimethyl-bicyclo[3.2.1]oct-6-en-6-yl ester
  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