Acetic acid 2-methoxy-1,10-dioxo-1,10-dihydro-anthracen-9-yl ester | 84612-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Acetic acid 2-methoxy-1,10-dioxo-1,10-dihydro-anthracen-9-yl ester
• 英文别名: 2-Methoxy-1,10-dioxo-1,10-dihydroanthracen-9-YL acetate；(2-methoxy-1,10-dioxoanthracen-9-yl) acetate
• CAS: 84612-45-3
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: ZTFLNTJFFOSOFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid 2-methoxy-1,10-dioxo-1,10-dihydro-anthracen-9-yl ester 以 苯 为溶剂， 生成 1-acetoxy-2-methoxy-anthraquinone
  参考文献：
  名称：

  Effect of structure of acyl group on photochemical conversions of 1-acyloxy-9,10-anthraquinone derivatives

  摘要：

  Photochemical conversions of O-acyl derivatives of 1-hydroxy-2-methoxy-9,10-anthraquinone have been studied by low temperature and pulsed photolysis. Acyl group structure has a substantial effect on the rate of thermal migration. Replacement of methyl by ethoxy decreases the rate constant by two orders of magnitude; replacement by diethylamino reduces it nearly five orders of magnitude. The log rate constant of the aroyl rearrangement is linearly dependent on the electrophilic constant of the substituents in the phenyl nucleus of the migrant.

  DOI：

  10.1007/bf01184519
• 作为产物：
  描述：

  1-acetoxy-2-methoxy-anthraquinone 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 生成 Acetic acid 2-methoxy-1,10-dioxo-1,10-dihydro-anthracen-9-yl ester
  参考文献：
  名称：

  Effect of structure of acyl group on photochemical conversions of 1-acyloxy-9,10-anthraquinone derivatives

  摘要：

  Photochemical conversions of O-acyl derivatives of 1-hydroxy-2-methoxy-9,10-anthraquinone have been studied by low temperature and pulsed photolysis. Acyl group structure has a substantial effect on the rate of thermal migration. Replacement of methyl by ethoxy decreases the rate constant by two orders of magnitude; replacement by diethylamino reduces it nearly five orders of magnitude. The log rate constant of the aroyl rearrangement is linearly dependent on the electrophilic constant of the substituents in the phenyl nucleus of the migrant.

  DOI：

  10.1007/bf01184519

文献信息

• Laser Flash Photolysis Study of the Primary Processes in the Photochromic Reaction of 1-acyloxy-2-methoxyanthraquinones
  作者：N. P. Gritsan、A. Kellmann、F. Tfibel、L. S. Klimenko

  DOI：10.1080/10587259408037823

  日期：1994.5

  The nanosecond laser flash photolysis (time resolution 3 ns) has been used to study the primary processes in photochromic reaction of three O-acylic derivatives of 1-oxy-2-methoxyanthraquinone with methyl (I), ethoxyl (II) and diethylamino (III) in migrating acyl. The triplet-triplet absorption spectra of the reactive triplet states of quinones II and III were detected. The triplet and ground states absorption spectra of the photoproduct (ana-quinone) were observed; the quantum yields of ana-quinone formation and the rate constants of all elementary steps were measured in toluene at room temperature. It was confirmed in the present work that photochemical migration of acyl groups is an adiabatic process occurring on the triplet potential energy surface.