trans-2,5-cyclohexadiene-1,4-diol | 74894-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2,5-cyclohexadiene-1,4-diol
• CAS: 74894-37-4
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: MMLJDECBZWQXCV-IZLXSQMJSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  271.2±40.0 °C(predicted)
• 密度：
  1.288±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.17
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-2,5-cyclohexadiene-1,4-diol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到(2R,5R)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
  参考文献：
  名称：

  2,3-Dioxabicyclo[2.2.2]oct-7-en-5-one:  Synthesis and Reactions of the Keto Endoperoxide of Phenol

  摘要：

  The photooxygenation of 1,4-cyclohexadiene (3) affords the diastereomeric hydroperoxy endoperoxides exo-4 and endo-4 and the diastereomeric hydroperoxides trans-5 and cis-5 in a ratio of 87: 9:3.5:0.5. Selective reduction of hydroperoxide group in the endoperoxides exo-4 and endo-4 in the presence of titanium tetraisopropoxide-diethyl sulfide gave the corresponding hydroxy endoperoxides exo-7 and endo-7, which on PCC oxidation leads to the phenol-derived keto endoperoxide 2. The triphenylphosphine deoxygenation of the keto endoperoxide 2 produces a 9:1 mixture of 1,2- and 1,4-dihydroxybenzenes 10 and 11, while the CoTPP-catalyzed rearrangement affords the bisepoxide 12, malealdehyde (13), and beta-lactone 14. The mechanisms of these transformations are presented.

  DOI：

  10.1021/jo000120p
• 作为产物：
  描述：

  1,4-环己二烯 在 5,10,15,20-tetrakisphenylporphyrin 、 氧气 、 三苯基膦 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.33h， 生成 trans-2,5-cyclohexadiene-1,4-diol
  参考文献：
  名称：

  2,3-Dioxabicyclo[2.2.2]oct-7-en-5-one:  Synthesis and Reactions of the Keto Endoperoxide of Phenol

  摘要：

  The photooxygenation of 1,4-cyclohexadiene (3) affords the diastereomeric hydroperoxy endoperoxides exo-4 and endo-4 and the diastereomeric hydroperoxides trans-5 and cis-5 in a ratio of 87: 9:3.5:0.5. Selective reduction of hydroperoxide group in the endoperoxides exo-4 and endo-4 in the presence of titanium tetraisopropoxide-diethyl sulfide gave the corresponding hydroxy endoperoxides exo-7 and endo-7, which on PCC oxidation leads to the phenol-derived keto endoperoxide 2. The triphenylphosphine deoxygenation of the keto endoperoxide 2 produces a 9:1 mixture of 1,2- and 1,4-dihydroxybenzenes 10 and 11, while the CoTPP-catalyzed rearrangement affords the bisepoxide 12, malealdehyde (13), and beta-lactone 14. The mechanisms of these transformations are presented.

  DOI：

  10.1021/jo000120p