2-(bromomethyl)-1-methoxy-9,10-anthracenedione | 63965-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(bromomethyl)-1-methoxy-9,10-anthracenedione
• 英文别名: 1-methoxy-2-bromomethyl-9,10-antraquinone；2-bromomethyl-1-methoxyanthraquinone；2-(Bromomethyl)-1-methoxyanthracene-9,10-dione；2-(bromomethyl)-1-methoxyanthracene-9,10-dione
• CAS: 63965-46-8
• 化学式: C₁₆H₁₁BrO₃
• 分子量: 331.166
• InChiKey: QNRDUTDBBOCTQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(bromomethyl)-1-methoxy-9,10-anthracenedione 在 盐酸 、 disodium hydrogenphosphate 、 tetrafluoroboric acid 、 三氯化铝 、 sodium dichromate 、 硼烷四氢呋喃络合物 、 dimsyl sodium 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 58.67h， 生成 1-hydroxy-2-(1'-oxopent-2'-enyl)anthraquinone
  参考文献：
  名称：

  Anthraquinone dye intermediates as precursors of aklavinone-type anthracyclinones

  摘要：

  DOI：

  10.1016/s0040-4020(01)91538-8
• 作为产物：
  描述：

  分散橙11 在 nitrosylsulfuric acid 、 1,3-二溴-5,5-二甲基海因 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 丙酮 、 丁酮 为溶剂， 反应 13.5h， 生成 2-(bromomethyl)-1-methoxy-9,10-anthracenedione
  参考文献：
  名称：

  Anthraquinone dye intermediates as precursors of aklavinone-type anthracyclinones

  摘要：

  DOI：

  10.1016/s0040-4020(01)91538-8

文献信息

• BeCl2 as a new highly selective reagent for dealkylation of aryl-methyl ethers
  作者：Hashem Sharghi、Fatemeh Tamaddon

  DOI：10.1016/0040-4020(96)00815-0

  日期：1996.10

  An efficient and simple method is introduced for the selective removal of methyl group from poly aryl-methyl ethers, in some important derivatives of benzophenones, xanthones, anthraquinones, aryl esters, benzamides and nitroanisoles with BeCl2.

  一个高效，简便的方法被引入用于由聚芳基-甲基醚的选择性除去甲基的，在二苯甲酮，呫吨酮，蒽醌类，芳基酯，苯甲酰胺和nitroanisoles与BECL一些重要的衍生物2。
• Copper Nanoparticles on Charcoal for Multicomponent Catalytic Synthesis of 1,2,3-Triazole Derivatives from Benzyl Halides or Alkyl Halides, Terminal Alkynes and Sodium Azide in Water as a “Green” Solvent
  作者：Hashem Sharghi、Reza Khalifeh、Mohammad Mahdi Doroodmand

  DOI：10.1002/adsc.200800612

  日期：2009.1

  A one-pot procedure for synthesis of 1,2,3-triazole derivatives via the three-component coupling (TCC) reaction between terminal alkynes, benzyl or alkyl halides, and sodium azide in the presences of 1 mol% nanoparticles copper/carbon (Cu/C) catalyst has been developed. The catalyst showed high catalytic activity and 1,4-regioselectivity for the [3+2] Huisgen cycloaddition in water as a “green” solvent

  在1 mol％纳米粒子铜/碳存在下，通过末端炔烃，苄基或烷基卤化物和叠氮化钠之间的三组分偶联（TCC）反应，通过一锅法合成1,2,3-三唑衍生物的步骤已经开发出Cu / C）催化剂。该催化剂在水中作为“绿色”溶剂对[3 + 2] Huisgen环加成反应显示出高催化活性和1,4-区域选择性，在所有情况下均获得了良好或优异的收率。该程序消除了处理有机叠氮化物的需要，并且它们是就地产生的。该反应范围广，对于合成新的三唑氮杂冠醚和蒽醌衍生物特别实用。通过扫描电子显微镜（SEM），原子强迫显微镜（AFM），X射线衍射（XRD），电感耦合等离子体（ICP）分析和FT-IR实验技术对多相催化剂进行了全面表征。催化剂被循环十次而没有明显的活性损失。
• 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.