4B,12b-epidioxido-dibenzo[a,j]perylene-8,16-dione | 74292-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4B,12b-epidioxido-dibenzo[a,j]perylene-8,16-dione
• 英文别名: 4B,12b-epidioxido-dibenzo[a,j]perylen-8,16-dion；27,28-Dioxaoctacyclo[12.12.2.11,15.12,6.08,13.021,26.014,30.019,29]triaconta-2,4,6(30),8,10,12,15,17,19(29),21,23,25-dodecaene-7,20-dione
• CAS: 74292-77-6
• 化学式: C₂₈H₁₄O₄
• 分子量: 414.417
• InChiKey: YROHSRONVDVSQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4B,12b-epidioxido-dibenzo[a,j]perylene-8,16-dione 生成 dibenzoperylene-8,16-dione
  参考文献：
  名称：

  Mellier, Annales de Chimie (Cachan, France), 1955, vol. <12> 10, p. 666,682

  摘要：

  DOI：
• 作为产物：
  描述：

  dibenzoperylene-8,16-dione 在 二硫化碳 作用下， 生成 4B,12b-epidioxido-dibenzo[a,j]perylene-8,16-dione
  参考文献：
  名称：

  Mellier, Annales de Chimie (Cachan, France), 1955, vol. <12> 10, p. 666,682

  摘要：

  DOI：

文献信息

• Rate parameters for the two-step photofragmentation of aromatic endoperoxides in solution
  作者：K. Jesse、F. J. Comes

  DOI：10.1021/j100156a051

  日期：1991.2

  The formation of dimethylhomoocoerdianthrone (HOCD) following subpicosecond laser photolysis of its endoperoxide (PO) was studied by laser-induced fluorescence (LIF) in the solvents dichloromethane and toluene. The measured rise time of the LIf signal refers to a time constant of tau-2 = 1.7 +/- 0.5 ps at 22-degrees-C. The study of the characteristic rate constant at different temperatures gives an activation energy of E(a) = 5.5 +/-0.5 kcal/mol and a preexponential factor of A = 10(15.7 +/- 0.3) s-1 in toluene. These parameters are consistent with our earlier model for the two-step photofragmentation of aromatic endoperoxides, which assumes a short-lived 1.6-biradical intermediate crossing an activation barrier. The photolysis study of the newly synthesized endoperoxide of anthrabisbenzothiopyran (ABTPO) reveals that photocycloreversion starting from S3(pi-pi*) proceeds with a time constant of tau-2 = 46 +/- 6 ps in dichloromethane (at 22-degrees-C). In this case the activation parameters amount to E(a) = 5.0 +/- 0.6 kcal/mol and A = 10(14.8 +/- 0.3) s-1. The observed activation barrier on the potential energy surface can be a result from resonance effects in the chromophores of the peroxy biradical. The large A factors reflect the importance of internal degrees of freedom in the transition state.
• Photolysis of the endoperoxide of heterocoerdianthrone. A concerted, adiabatic cycloreversion originating from an upper excited singlet state
  作者：R. Schmidt、W. Drews、H. D. Brauer

  DOI：10.1021/ja00528a046

  日期：1980.4