2,10-Dioxatricyclo[4.4.4.01,6]tetradeca-11,13-diene | 161297-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,10-Dioxatricyclo[4.4.4.01,6]tetradeca-11,13-diene
• CAS: 161297-72-9
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: IKVPWWLINNPPRK-UHFFFAOYSA-N

物化性质

• 沸点：
  306.3±42.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,10-Dioxatricyclo[4.4.4.01,6]tetradeca-11,13-diene 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以53%的产率得到11,12-epoxy-3,4,6,7-tetrahydro-8a,4a-<1>buteno-2H,5H-pyrano<2,3-b>pyran
  参考文献：
  名称：

  Heteroatomic Effects on the Acid-Catalyzed Rearrangements of Dispiro[4.0.4.4]tetradeca-11,13-dienes

  摘要：

  The synthesis of dispiro [4.0.4.4]tetradeca-11,13-dienes containing one or two heteroatoms (O,S) is described. In all cases, a suitably functionalized cyclohexanone served as the precursor. Bromination-dehydrobromination delivered the cyclohexenone, which was subjected to 1,2-reduction and elimination by reaction with 2,4-dinitrobenzenesulfenyl chloride and thermal activation. The pathways by which the 1,3-cyclohexadienes undergo acid-catalyzed isomerization have been identified. The choice between aromatization and conversion to a [4.4.4]propelladiene gives evidence for being dependent on an interplay between steric and electronic factors. The generation of a transient oxonium ion causes both pathways to operate at approximately equivalent levels. When a thermodynamically less favorable thionium ion intermediate is involved, selectivity increases to the point where only aromatization occurs in the presence of p-toluenesulfonic acid. A neighboring sulfhydryl group is shown to be capable of intercepting the spirocyclic carbocationic intermediate. The regiochemistry of the epoxidation of 30 and the stereoselectivity of Diels-Alder cycloaddition of the [4.4.4]propelladienes to N-methyltriazolinedione are also detailed.

  DOI：

  10.1021/ja00096a024
• 作为产物：
  描述：

  (5R*,6S*)-1,7-dioxadispiro<4.0.4.4>tetradeca-11,13-diene 以33%的产率得到
  参考文献：
  名称：

  Branan Bruce M., Paquette Leo A., J. Amer. Chem. Soc, 116 (1994) N 17, S 7568-7667

  摘要：

  DOI：

文献信息

• Paquette, Leo A.; Branan, Bruce M.; Rogers, Robin D., Journal of the American Chemical Society, 1995, vol. 117, # 22, p. 5992 - 5998
  作者：Paquette, Leo A.、Branan, Bruce M.、Rogers, Robin D.、Bond, Andrew H.、Lange, Holger、Gleiter, Rolf

  DOI：——

  日期：——
• Paquette, Leo; Branan, Bruce M., Heterocycles, 1995, vol. 40, # 1, p. 101 - 104
  作者：Paquette, Leo、Branan, Bruce M.

  DOI：——

  日期：——