3-<(ethanoyloxy)methyl>-1,8-dimethoxy-9,10-anthracenedione | 107960-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-<(ethanoyloxy)methyl>-1,8-dimethoxy-9,10-anthracenedione
• 英文别名: (4,5-Dimethoxy-9,10-dioxoanthracen-2-yl)methyl acetate；(4,5-dimethoxy-9,10-dioxoanthracen-2-yl)methyl acetate
• CAS: 107960-78-1
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: WZUZRRAHOMTPJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-<(ethanoyloxy)methyl>-1,8-dimethoxy-9,10-anthracenedione 在 sodium dithionite 作用下， 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Substituent effects upon the peak potentials and reductive cleavage rate constants of hydroxy- and methoxy-substituted 9,10-anthraquinones in 50% aqueous CH3CN: do they correlate?

  摘要：

  A variety of hydroxy- and methoxy-substituted 2-(acetoxymethyl)-9,10-anthraquinones (2a-7a) were reduced electrochemically and with dithionite (S2O-4(2-)) in 50% aqueous CH3CN buffers over a wide pH range. Good to excellent yields of their corresponding reductive cleavage products, the substituted 2-methyl-9,10-anthraquinones 2b-7b, were obtained from most of these anthraquinone acetates, but only at higher pH. Rate constants for the reaction of 2-(acetoxymethyl)-9,10-anthraquinone (1a) with excess dithionite ranged from 1.0 x 10(-4) S-1 at pH values less than 7 to 4.0 x 10(-4) S-1 at a pH of 10, demonstrating that loss of acetate occurs in the rate-determining step and that cleavage occurs slower via the anthrahydroquinone of 1a than the conjugate base of the anthrahydroquinone. Substituent effects upon the reductive cleavage process were determined by measuring rate constants for those acetates that react cleanly with dithionite at pH 8. These effects, which are rationalized on the basis of resonance theory and intramolecular H bonding, correlate fairly well with the peak potentials (E(p)) of the reductive cleavage products of these acetates. Thus, electron-donating substituents on an anthraquinone acetate not only make it more difficult to reduce resulting in a more negative E(p) but also enhance the rate of acetate cleavage in the corresponding anthrahydroquinone.

  DOI：

  10.1021/jo00004a049
• 作为产物：
  描述：

  大黄酚 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氯化碳 、 氯仿 、 丙酮 为溶剂， 反应 19.0h， 生成 3-<(ethanoyloxy)methyl>-1,8-dimethoxy-9,10-anthracenedione
  参考文献：
  名称：

  The influence of ion-pairing on the electroreductive cleavage of substituted 9,10-anthraquinones in DMF solution

  摘要：

  DOI：

  10.1021/jo00386a030

文献信息

• The influence of ion-pairing on the electroreductive cleavage of substituted 9,10-anthraquinones in DMF solution
  作者：Ronald L. Blankespoor、David L. Schutt、Melinda B. Tubergen、Randy L. De Jong

  DOI：10.1021/jo00386a030

  日期：1987.5
• Substituent effects upon the peak potentials and reductive cleavage rate constants of hydroxy- and methoxy-substituted 9,10-anthraquinones in 50% aqueous CH3CN: do they correlate?
  作者：Ronald L. Blankespoor、Elise L. Kosters、Alan J. Post、Derek P. Van Meurs

  DOI：10.1021/jo00004a049

  日期：1991.2

  A variety of hydroxy- and methoxy-substituted 2-(acetoxymethyl)-9,10-anthraquinones (2a-7a) were reduced electrochemically and with dithionite (S2O-4(2-)) in 50% aqueous CH3CN buffers over a wide pH range. Good to excellent yields of their corresponding reductive cleavage products, the substituted 2-methyl-9,10-anthraquinones 2b-7b, were obtained from most of these anthraquinone acetates, but only at higher pH. Rate constants for the reaction of 2-(acetoxymethyl)-9,10-anthraquinone (1a) with excess dithionite ranged from 1.0 x 10(-4) S-1 at pH values less than 7 to 4.0 x 10(-4) S-1 at a pH of 10, demonstrating that loss of acetate occurs in the rate-determining step and that cleavage occurs slower via the anthrahydroquinone of 1a than the conjugate base of the anthrahydroquinone. Substituent effects upon the reductive cleavage process were determined by measuring rate constants for those acetates that react cleanly with dithionite at pH 8. These effects, which are rationalized on the basis of resonance theory and intramolecular H bonding, correlate fairly well with the peak potentials (E(p)) of the reductive cleavage products of these acetates. Thus, electron-donating substituents on an anthraquinone acetate not only make it more difficult to reduce resulting in a more negative E(p) but also enhance the rate of acetate cleavage in the corresponding anthrahydroquinone.