spiro[9H-fluorene-9,2’(5’H)-furan]-5’-one | 114702-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: spiro[9H-fluorene-9,2’(5’H)-furan]-5’-one
• 英文别名: Spiro[fluorene-9,5'-furan]-2'-one
• CAS: 114702-39-5
• 化学式: C₁₆H₁₀O₂
• 分子量: 234.254
• InChiKey: GMZDLGOYQMWCCA-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  471.5±34.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-formyl-9-hydroxyfluorene 在 正丁基锂 、 silver trifluoromethanesulfonate 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 2.83h， 生成 spiro[9H-fluorene-9,2’(5’H)-furan]-5’-one
  参考文献：
  名称：

  Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones

  摘要：

  AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.

  DOI：

  10.1021/ol401824v

文献信息

• ARCADI, A.;BERNOCCHI, E.;BURINI, A.;CACCHI, S.;MARINELLI, F.;PIETRONI, B., TETRAHEDRON, 44,(1988) N 2, 481-490
  作者：ARCADI, A.、BERNOCCHI, E.、BURINI, A.、CACCHI, S.、MARINELLI, F.、PIETRONI, B.

  DOI：——

  日期：——
• Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones
  作者：Masahiro Egi、Yuya Ota、Yuka Nishimura、Kaori Shimizu、Kenji Azechi、Shuji Akai

  DOI：10.1021/ol401824v

  日期：2013.8.16

  AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.