anthra-9,10-quinone-1-carbonyl chloride | 53453-81-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthra-9,10-quinone-1-carbonyl chloride
• 英文别名: 1-anthraquinonecarbonyl chloride；anthaquinone-2-carbonyl chloride；Anthrachinon-carbonsaeure-(1)-chlorid；Anthrachinon-1-carbonsaeurechlorid；9,10-dioxo-9,10-dihydro-anthracene-1-carbonyl chloride；9.10-Dioxo-9.10-dihydro-anthracen-carbonsaeure-(1)-chlorid；9,10-Dioxo-9,10-dihydro-anthracen-1-carbonylchlorid；9,10-Dioxo-9,10-dihydroanthracene-1-carbonyl chloride；9,10-dioxoanthracene-1-carbonyl chloride
• CAS: 53453-81-9
• 化学式: C₁₅H₇ClO₃
• 分子量: 270.672
• InChiKey: LLSVGXGSYBLMNY-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C
• 沸点：
  463.9±34.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  anthra-9,10-quinone-1-carbonyl chloride 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-aminobutyl)-1-anthraquinonecarboxamide hydrochloride
  参考文献：
  名称：

  Cationic Anthraquinone Derivatives as Catalytic DNA Photonucleases: Mechanisms for DNA Damage and Quinone Recycling

  摘要：

  Ammonium-substituted anthraquinone derivatives have been found to catalyze DNA cleavage upon irradiation with 350 nm light. Picosecond laser spectroscopy demonstrates that the excited quinones react with DNA by two separate oxidative pathways: electron transfer from a nearby base and hydrogen atom abstraction from the deoxyribose component of the nucleic acid backbone. Photo-oxidation of DNA by either pathway yields the one-electron-reduced form of the quinone as a byproduct. Back electron transfer from the reduced quinone to the oxidized base is the predominant decay path for the reduced quinone formed by the electron transfer pathway while that formed by hydrogen atom abstraction is converted back to the ground-state, fully oxidized form by reduction of molecular oxygen. The resulting superoxide anion is detected by its reduction of cytochrome c. Comparison of the spectroscopic data for two quinones with significantly different cleavage efficiencies suggests that DNA cleavage by these quinone reagents results from the hydrogen-abstraction chemistry. The laser experiments further indicate that the quinone completes one cycle of excitation, oxidation of DNA, and reduction of oxygen within 10 mu s, illustrating the potential utility of these agents for double-stranded cleavage of DNA.

  DOI：

  10.1021/ja00101a005
• 作为产物：
  描述：

  蒽 在 氯化亚砜 作用下， 以 二硫化碳 为溶剂， 反应 2.0h， 生成 anthra-9,10-quinone-1-carbonyl chloride
  参考文献：
  名称：

  Bhatt, M. Vivekananda; El Ashry, Shaker H.; Somayaji, Vishwanatha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 6, p. 473 - 486

  摘要：

  DOI：

文献信息

• Photoregulated Transmembrane Charge Separation by Linked Spiropyran−Anthraquinone Molecules
  作者：Linyong Zhu、Rafail F. Khairutdinov、Jonathan L. Cape、James K. Hurst

  DOI：10.1021/ja0545620

  日期：2006.1.1

  formation and decay of two reaction intermediates, identified as 3ZnTPPS4- and a species with the optical properties of a semiquinone radical. Kinetic profiles for Co(bpy)3(3+) reduction under continuous photolysis in the presence and absence of added ionophores indicated that transmembrane redox mediated by SP-AQ was electroneutral, but reaction by the other quinone-containing mediators was electrogenic. The

  酰胺连接螺吡喃-蒽醌 (SP-AQ) 偶联物​​显示出通过外部 EDTA 介导 ZnTPPS(4-)-光敏化的单层磷脂酰胆碱囊泡内封闭 Co(bpy)3(3+) 的跨膜还原。这些反应的总量子产率取决于染料的异构状态；具体而言，闭环螺吡喃 (SP) 部分的 30-35% 光转化为开环部花青 (MC) 形式导致简单共轭体的量子产率降低 6 倍，而含有蒽醌部分上的亲脂性 4-十二烷基苯氧基取代基。瞬态光谱和荧光猝灭测量表明，有两个因素导致了这些光异构化引起的量子产率变化：提高了部花青基团对 1ZnTPPS4- 的荧光猝灭效率，并降低了含有部花青的氧化还原载体的跨膜扩散速率。瞬态分光光度法还揭示了两种反应中间体的连续形成和衰变，鉴定为 3ZnTPPS4- 和一种具有半醌自由基光学特性的物质。在存在和不存在添加的离子载体的情况下，连续光解下 Co(bpy)3(3+) 还原的动力学曲线表明，由 SP-AQ
• Fluorescence as a Means for Kinetic Studies. III. Bimolecular Reaction of Fluorescent Reagent as Quenching Probes
  作者：Hideharu Ushiki、Akio Okamoto、Kazuyuki Horie、Itaru Mita

  DOI：10.1246/bcsj.56.3181

  日期：1983.10

  In order to study the rate of bimolecula reaction between 9-(3-aminopropyl)carbazole and dansyl chloride, the change of fluorescent intensity of dansyl group has been measured. It has been found that the rate of increase in fluorescent intensity of the dansyl group is equal to the rate of decrease in fluorescent intensity of the carbazolyl group during progress of this bimolecular reaction. Another

  为了研究9-(3-氨基丙基)咔唑与丹磺酰氯的双分子反应速率，测定了丹磺酰基团荧光强度的变化。已经发现，在该双分子反应过程中，丹磺酰基荧光强度的增加速率等于咔唑基荧光强度的降低速率。还简要检查了另一种淬灭探针。
• Scholl; Donat, Justus Liebigs Annalen der Chemie, 1934, vol. 512, p. 1,21
  作者：Scholl、Donat

  DOI：——

  日期：——
• Scholl; Dehnert; Wanka, Justus Liebigs Annalen der Chemie, 1932, vol. 493, p. 56,82
  作者：Scholl、Dehnert、Wanka

  DOI：——

  日期：——
• Activation of JNK, p38 and ERK mitogen-activated protein kinases by chromium(VI) is mediated through oxidative stress but does not affect cytotoxicity
  作者：Show-Mei Chuang、Geou-Yarh Liou、Jia-Ling Yang

  DOI：10.1093/carcin/21.5.491

  日期：2000.8.1