trifluoromethanesulfonic acid 2-hept-6-enoylphenyl ester | 646522-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trifluoromethanesulfonic acid 2-hept-6-enoylphenyl ester
• 英文别名: Methanesulfonic acid, trifluoro-, 2-(1-oxo-6-heptenyl)phenyl ester；(2-hept-6-enoylphenyl) trifluoromethanesulfonate
• CAS: 646522-80-7
• 化学式: C₁₄H₁₅F₃O₄S
• 分子量: 336.332
• InChiKey: ABHVSVIXQAMFLY-UHFFFAOYSA-N

物化性质

• 沸点：
  404.5±45.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 2-hept-6-enoylphenyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以87%的产率得到2-pent-4-enyl-benzofuran-3-one
  参考文献：
  名称：

  Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions:  Synthetic and Mechanistic Insights

  摘要：

  Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degreesC. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.

  DOI：

  10.1021/jo0352023
• 作为产物：
  描述：

  6-庚烯酸 在 吡啶 、 正丁基锂 、 三氯化硼 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.92h， 生成 trifluoromethanesulfonic acid 2-hept-6-enoylphenyl ester
  参考文献：
  名称：

  Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions:  Synthetic and Mechanistic Insights

  摘要：

  Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degreesC. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.

  DOI：

  10.1021/jo0352023

文献信息

• Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions:  Synthetic and Mechanistic Insights
  作者：Jotham W. Coe、Krista E. Bianco、Brian P. Boscoe、Paige R. Brooks、Eric D. Cox、Michael G. Vetelino

  DOI：10.1021/jo0352023

  日期：2003.12.1

  Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degreesC. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.