3H-spiro[1-benzofuran-2,1'-cyclopentan]-3'-en-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: 3H-spiro[1-benzofuran-2,1'-cyclopentan]-3'-en-3-one
• 英文别名: Spiro[1-benzofuran-2,4'-cyclopentene]-3-one
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: INCMJRXWRBKARU-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：
  0.25
• 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：

  3H-spiro[1-benzofuran-2,1'-cyclopentan]-3'-en-3-one 在 2,6-二甲基吡啶 、 四氧化锇 、 三氟化硼乙醚 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 二丁醚 、 水 、 丙酮 为溶剂， 反应 4.34h， 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-3-烯基-(2,5-二甲氧基-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 3H-spiro[1-benzofuran-2,1'-cyclopentan]-3'-en-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

• Novel Spiroannulated 3-Benzofuranones. Synthesis and Inhibition of the Human Peptidyl Prolyl cis/trans Isomerase Pin1
  作者：Manfred Braun、Anahita Hessamian-Alinejad、Boris De Lacroix、Birte Alvarez、Gunter Fischer

  DOI：10.3390/molecules13040995

  日期：——

  The novel 3H-spiro[1-benzofuran-2-cyclopentan]-3-one skeleton has been madeaccessible by different routes. One- and two-step protocols lead to tricyclic and tetracyclicbenzofuranones 2 and 3, respectively. A four-step synthesis to spirocompound 4 isdescribed. The novel spirocyclic benzofuranones display modest to no inhibition of thehuman peptidyl prolyl cis/trans isomerase Pin1.

  新颖的3H-spiro[1-benzofuran-2-cyclopentan]-3-one骨架通过不同途径得以合成。一步和两步的合成路线分别得到三环和四环的benzofuranones 2和3。文中描述了一种四步合成螺环化合物4的方法。这些新颖的螺环benzofuranones对人类肽基脯氨酰cis/trans异构酶Pin1的抑制作用表现出适度或几乎没有抑制效果。
• 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.