2,2-spiropentanylbenzofuran-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2,2-spiropentanylbenzofuran-3-one
• 英文别名: Spiro[1-benzofuran-2,1'-cyclopentane]-3-one
• 化学式: C₁₂H₁₂O₂
• mdl: MFCD11111662
• 分子量: 188.226
• InChiKey: GWRNCFNBUZVZAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-spiropentanylbenzofuran-3-one 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 6.75h， 生成
  参考文献：
  名称：

  Rapid Assembly of Functionalized Hydrodibenzofurans via Semipinacol Rearrangements

  摘要：

  A distinct strategy via unprecedented semipinacol rearrangements for the synthesis of functionalized hydrodibenzofurans is reported. The versatile reactivity of benzofuran-3-one as a building block enabled the convergent coupling of simple starting materials and, thus, allowed for the facile variation of R group and the construction of hydrodibenzofurans with fused rings.

  DOI：

  10.1021/acs.orglett.5b02202
• 作为产物：
  描述：

  环戊基2-甲氧基苯基甲酮 在 吡啶 、 三氯化硼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 2,2-spiropentanylbenzofuran-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

文献信息

• Rapid Assembly of Functionalized Hydrodibenzofurans via Semipinacol Rearrangements
  作者：Xiaotong Yao、Xiaoni Xie、Chunyu Wang、Liansuo Zu

  DOI：10.1021/acs.orglett.5b02202

  日期：2015.9.4

  A distinct strategy via unprecedented semipinacol rearrangements for the synthesis of functionalized hydrodibenzofurans is reported. The versatile reactivity of benzofuran-3-one as a building block enabled the convergent coupling of simple starting materials and, thus, allowed for the facile variation of R group and the construction of hydrodibenzofurans with fused rings.
• 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.