3,4-Dimethylenefuran | 95406-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3,4-Dimethylenefuran
• 英文别名: 3,4-Dimethylidenefuran-1-ium-5-ide
• CAS: 95406-66-9
• 化学式: C₆H₆O
• 分子量: 94.113
• InChiKey: VFUOKRKJYXGUTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-Dimethylenefuran 在 氧气 作用下， 以80%的产率得到1H,4H-Furo[3,4-d][1,2]dioxin
  参考文献：
  名称：

  3,4-Dimethylenefuran and 3,4-dimethylenethiophene, heterocyclic analogs of the disjoint non-Kekule hydrocarbon tetramethyleneethane

  摘要：

  DOI：

  10.1021/ja00285a035
• 作为产物：
  描述：

  3-Oxabicyclo<3.2.0>hepta-1,4-dien 在 氧气 作用下， 生成 3,4-Dimethylenefuran
  参考文献：
  名称：

  Resonanzenergie von Diradikalen — 1,8-萘醌二甲胺

  摘要：

  Diradicals的共振能量。— 1,8-萘醌二甲烷

  DOI：

  10.1002/jlac.199619961230

文献信息

• Parallel reactivity sequences in cycloadditions of singlet biradicals and Diels-Alder reactions. A common physical basis manifested as entropy control or enthalpy control
  作者：J. C. Scaiano、Veronique Wintgens、Karl Haider、Jerome A. Berson

  DOI：10.1021/ja00205a032

  日期：1989.11

  Reactivite des diradicaux dimethyl-3,4 furanne et dimethyl-3,4 thiophene, generes a partir des diazenes correspondants, vis-a-vis de divers composes vinyliques

  Reactive des diradicaux dimethyl-3,4 furanne et dimethyl-3,4 thiophene，generes a partir des diazenes 通讯员，vis-a-vis de divers composesvinyliques
• Ground-state multiplicities of 3,4-dimethylenefuran and 3,4-dimethylenethiophene. Experimental tests of ab initio and semiempirical theories of heteroatom-bridged disjoint biradicals
  作者：Marc M. Greenberg、Silas C. Blackstock、Keith J. Stone、Jerome A. Berson

  DOI：10.1021/ja00192a026

  日期：1989.5
• Absolute rates of dimerization and cycloaddition of 3,4-dimethylenefuran and 3,4-dimethylenethiophene by nanosecond time-resolved spectroscopy
  作者：J. C. Scaiano、Veronique. Wintgens、Ann. Bedell、Jerome A. Berson

  DOI：10.1021/ja00220a061

  日期：1988.6
• Absolute rates of heterocyclic singlet biradical reactions determined by nanosecond time-resolved absorption spectroscopy. Dimerizations and cycloadditions to alkenes and to dioxygen
  作者：Richard B. Heath、Linda C. Busch、Xu Wu Feng、Jerome A. Berson、J. C. Scaiano、Alain B. Berinstain

  DOI：10.1021/j100152a047

  日期：1993.12

  Singlet biradicals of the 3,4-dimethyleneheterocycle series, where the heterocycle is furan, thiophene, or N-substituted pyrrole, with chromophores in the UV-vis region (560-640 nm), are generated by nanosecond laser flash photolysis of diazene precursors in fluid solution. The rate constants for disappearance of these transients are determined by time-resolved absorption spectroscopy using the long-wavelength band. The rate constants for dimerization are near the encounter-controlled rate. Rates of trapping by alkenes are well described by a frontier orbital model. Oxygen trapping rate constants range between 10(7) and 10(9) M-1 s-1. The ratios of rate constants for trapping of 3,4-dimethylene-N-(p-toluenesulfonyl)pyrrole by pairs of alkenes in preparative competition experiments are in good agreement with those determined by the flash photolytic method. This confirms assignments of the 3,4-dimethyleneheterocycle structure to the chromophore of the biradical transients.
• The first magic angle spinning NMR spectrum of a captive intermediate: direct observation of a singlet ground state biradical, 3,4-dimethylenefuran
  作者：Kurt W. Zilm、Ron A. Merrill、Marc M. Greenberg、Jerome A. Berson

  DOI：10.1021/ja00239a046

  日期：1987.3