(2S,3S,4R,5R)-tricyclo[4.2.2.22,5]dodeca-7,9,11-triene-3,4-diol | 104286-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R)-tricyclo[4.2.2.22,5]dodeca-7,9,11-triene-3,4-diol
• CAS: 104286-30-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: BPRULWHMTUBJAD-QSTBHEHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-tricyclo[4.2.2.22,5]dodeca-7,9,11-triene-3,4-diol 在 三氟甲磺酸酐 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.12h， 生成 syn-o,o'-dibenzene
  参考文献：
  名称：

  Chemistry of syn-o,o‘-Dibenzene

  摘要：

  Anew and improved synthesis cis, syn-o,o'-dibenzene 1 was developed to obtain 1 in larger amounts with improved purity, syn-Dibenzene 1 undergoes thermolysis to two molecules of benzene at a rate slower than that of the thermodynamically more stable anti-dibenzene 2. Kinetic analysis revealed that the higher thermal stability of 1 is due to the higher heat of activation in thermolysis. Photoelectron spectroscopy of 1 showed that the through-bond interaction between the two cyclohexadiene units in o,o'-dibenzenes is more important than their through-space interaction. A comparative study on the thermolyses of related syn-o,o'arene:benzene dimers suggests that thermolyses of syn-o,o'-arene:benzene dimers proceed via their anti-isomers as an intermediate. syn-Dibenzene 1 also undergoes adiabatic photolysis to one molecule of excited benzene and one molecule of ground-state benzene in goad efficiency. The mechanisms of these reactions an discussed.

  DOI：

  10.1021/ja0023579
• 作为产物：
  描述：

  methyl orthoformate of cis-cyclohexa-3,5-diene-1,2-diol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 生成 (2S,3S,4R,5R)-tricyclo[4.2.2.22,5]dodeca-7,9,11-triene-3,4-diol
  参考文献：
  名称：

  Chemistry of syn-o,o‘-Dibenzene

  摘要：

  Anew and improved synthesis cis, syn-o,o'-dibenzene 1 was developed to obtain 1 in larger amounts with improved purity, syn-Dibenzene 1 undergoes thermolysis to two molecules of benzene at a rate slower than that of the thermodynamically more stable anti-dibenzene 2. Kinetic analysis revealed that the higher thermal stability of 1 is due to the higher heat of activation in thermolysis. Photoelectron spectroscopy of 1 showed that the through-bond interaction between the two cyclohexadiene units in o,o'-dibenzenes is more important than their through-space interaction. A comparative study on the thermolyses of related syn-o,o'arene:benzene dimers suggests that thermolyses of syn-o,o'-arene:benzene dimers proceed via their anti-isomers as an intermediate. syn-Dibenzene 1 also undergoes adiabatic photolysis to one molecule of excited benzene and one molecule of ground-state benzene in goad efficiency. The mechanisms of these reactions an discussed.

  DOI：

  10.1021/ja0023579

文献信息

• YANG, NIEN-CHU, C.;HORNER, M. G., TETRAHEDRON LETT., 1986, 27, N 5, 543-546
  作者：YANG, NIEN-CHU, C.、HORNER, M. G.

  DOI：——

  日期：——