2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene | 6824-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧戊环
• 英文名称: 2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene
• 英文别名: 2,5-Epidioxy-dihydrofuran；Furanperoxid；2,3,7-Trioxabicyclo[2.2.1]hept-5-ene；2,3,7-trioxabicyclo[2.2.1]hept-5-ene
• CAS: 6824-18-6
• 化学式: C₄H₄O₃
• 分子量: 100.074
• InChiKey: HUNLKXOJSNOFAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene 在 2,3-二巯基丁二酸 作用下， 以 二氯甲烷 为溶剂， 生成 cis-butenedial
  参考文献：
  名称：

  Photooxygenation of furans in the presence of trimethylsilyl cyanide. Oxidative cyanation of furans

  摘要：

  DOI：

  10.1016/s0040-4039(00)84636-5
• 作为产物：
  描述：

  呋喃 在 oxygen 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  将单线态氧添加到共轭二烯中。内过氧化物形成机制

  摘要：

  Etude cinetique des reactors de l'oxygene singulet avec divers furanes substitues-2 et dissubstitues symetriquement-2,5

  DOI：

  10.1021/ja00356a046

文献信息

• Addition of singlet oxygen to conjugated dienes. The mechanism of endoperoxide formation
  作者：Edward L. Clennan、M. E. Mehrsheikh-Mohammadi

  DOI：10.1021/ja00356a046

  日期：1983.9

  Etude cinetique des reactions de l'oxygene singulet avec divers furannes substitues-2 et disubstitues symetriquement-2,5

  Etude cinetique des reactors de l'oxygene singulet avec divers furanes substitues-2 et dissubstitues symetriquement-2,5
• Mechanism of endoperoxide formation. 3. Utilization of the Young and Carlsson kinetic techniques
  作者：Edward L. Clennan、M. E. Mehrsheikh-Mohammadi

  DOI：10.1021/ja00335a040

  日期：1984.11

  Determination des constantes de vitesse d'additions de l'oxygene singulet a trente-neuf furannes et cyclopentadienes

  Determination des constantes de vitesse d'additions de l'oxygene singulet a trente-neuf furannes et cyclopentadienes
• Photooxygenation of furans in the presence of trimethylsilyl cyanide. Oxidative cyanation of furans
  作者：Isao Saito、Yueh-Hsiung Kuo、Teruo Matsuura

  DOI：10.1016/s0040-4039(00)84636-5

  日期：——
• Kinetic Studies of Singlet Oxygen [4 + 2]-Cycloadditions with Cyclic 1,3-Dienes in 28 Solvents
  作者：Jean-Marie Aubry、Bernadette Mandard-Cazin、Michel Rougee、Rene V. Bensasson

  DOI：10.1021/ja00141a006

  日期：1995.9

  The [4 + 2]-cycloaddition of singlet oxygen with 1,4-dimethylnaphthalene (DMN) and derivatives has been studied in 28 solvents by laser flash photolysis and steady state photolysis. The bimolecular rate constants of singlet oxygen quenching by DMN, via a physical process (k(q)) and via a chemical reaction (k(r)), are solvent-dependent and increase by more than 2 orders of magnitude from cyclohexane to formamide. This significant solvent dependence is in contrast with previous investigations conducted in six or seven solvents. It is discussed in terms of the solvatochromic properties of the different solvents. Moreover, for seven water-soluble 1,3-dienes, the overall rate constant k(0) (= k(r) + k(q)) is much higher in water than in methanol. Our results are consistent with a two-stage mechanism implying as a first step an equilibrium producing an exciplex with charge transfer character. A shift toward the formation of this exciplex leading to the cycloaddition product occurs by an increase (i) in the Hildebrand solubility parameter delta(H), (ii) in the dipolarity-polarizability parameter pi* of the solvent, and (iii) in the solvophobicity of the diene.