1,3-二甲氧基-9,10-蒽醌 | 1989-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,3-二甲氧基-9,10-蒽醌
• 英文名称: 1,3-dimethoxy-9,10-anthraquinone
• 英文别名: xanthopurpurin dimethylether；1,3-dimethoxyanthraquinone；1,3-Dimethoxy-anthrachinon；1,3-dimethoxyanthracene-9,10-dione
• CAS: 1989-42-0
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: ILRJFVJXKPFIAB-UHFFFAOYSA-N

物化性质

• 熔点：
  155 °C
• 沸点：
  462.1±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-二甲氧基-9,10-蒽醌 在 sodium hydroxide 、 sodium dithionite 、 氢溴酸 、 溶剂黄146 作用下， 生成 1-羟基-3-甲氧基-2-甲基蒽醌
  参考文献：
  名称：

  Joshi et al., Journal Of Scientific and Industrial Research, 1955, vol. 14 B, p. 87,92

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-dimethoxy-8-nitroanthraquinone 在 硫酸 、 溶剂黄146 、 sodium sulfite 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 5.5h， 生成 1,3-二甲氧基-9,10-蒽醌
  参考文献：
  名称：

  Cameron, Donald W.; Feutrill, Geoffrey I.; Patti, Antonio F., Australian Journal of Chemistry, 1980, vol. 33, # 7, p. 1805 - 1816

  摘要：

  DOI：

文献信息

• Lifetime prediction of laser-precracked fused silica subjected to subsequent cyclic laser pulses
  作者：Faiz Dahmani、Ansgar W. Schmid、John C. Lambropoulos、Stephen J. Burns、Semyon Papernov

  DOI：10.1557/jmr.2000.0167

  日期：2000.5

  Measurements of fatigue failure strength of laser-cracked fused silica in air at room temperature for different numbers of laser shots and laser fluences are presented. The failure-strength variability is found to be due mainly to the spectrum of crack depths. Agreement with theory suggests the incorporation of a residual term into the failure–strength equation. Due to its sign, the residual stress is of mouth-opening displacement nature at the crack. Analysis of the residual stress data shows a linear proportionality with crack depth, whereas the failure–strength is inversely proportional to the square root of the crack depth.

  本文介绍了室温下不同激光发射次数和激光通量下空气中激光裂纹熔融石英的疲劳破坏强度测量结果。结果发现，失效强度的变化主要是由裂纹深度谱造成的。与理论一致的结论表明，应在破坏强度方程中加入残余项。根据其符号，残余应力在裂缝处具有张口位移的性质。对残余应力数据的分析表明，残余应力与裂纹深度成线性比例，而破坏强度与裂纹深度的平方根成反比。
• Utilization of Sulfide, Sulfoxide, and Sulfone Groups as Regiochemical Control Elements in the Diels–Alder Reaction of Naphthoquinones
  作者：Masatomo Iwao、Tsukasa Kuraishi

  DOI：10.1246/bcsj.60.4051

  日期：1987.11

  The Diels–Alder reactions of 2-phenylthio-, 2-phenylsulfinyl-, and 2-phenylsulfonyl-1,4-naphthoquinones, which were unsymmetrically substituted by methoxyl group on the benzenoid ring, with some vinylketene acetals were studied. The regioselectivity of the reactions was cleanly controlled by each of these sulfur substituents. In addition, the reactivity of the naphthoquinones were greatly enhanced

  研究了在苯环上被甲氧基不对称取代的 2-苯硫基-、2-苯亚磺酰基-和 2-苯磺酰基-1,4-萘醌与一些乙烯基烯酮缩醛的 Diels-Alder 反应。这些硫取代基中的每一个都完全控制了反应的区域选择性。此外，通过引入砜或亚砜基团大大提高了萘醌的反应性。作为这项研究的结果，有效地合成了几种蒽醌类化合物，包括天然产物，如 pachybasin 和 phomarin 6-甲基醚，以及 11-脱氧蒽环酮。
• Evaluation of a Series of 9,10-Anthraquinones as Antiplasmodial Agents
  作者：Che Puteh Osman、Nor Hadiani Ismail、Aty Widyawaruyanti、Syahrul Imran、Lidya Tumewu、Chee Yan Choo、Sharinah Ideris

  DOI：10.2174/1570180815666180607085102

  日期：2019.1.15

  The selected compounds were tested for toxicity and probed for their mode of action against β-hematin dimerization through HRP2 and lipid catalyses. The most active compounds were subjected to a docking study using AutoDock 4.2. Results: The active AQs have similar common structural characteristics. However, it is difficult to establish a structure-activity relationship as certain compounds are active

  背景：对非洲用于治疗发烧和疟疾的药用植物进行的植物化学研究产生了具有潜在抗疟原虫活性的代谢产物，其中许多是蒽醌（AQ）。AQ具有与萘醌和氧杂蒽类似的亚结构，萘醌和氧杂蒽以前被报道为新型抗血浆药物。 目的：本研究旨在研究具有羟基，甲氧基和甲基取代基的9,10-蒽醌的结构要求，以发挥强大的抗血浆活性，并研究其可能的作用方式。 方法：通过Friedel-Crafts反应合成了31个AQ，并测定了其对恶性疟原虫（3D7）的体外抗疟原虫活性。测试了所选化合物的毒性，并探讨了它们通过HRP2和脂质催化作用对抗β-血红素二聚化的作用方式。使用AutoDock 4.2对最具活性的化合物进行了对接研究。 结果：有源AQ具有相似的共同结构特征。但是，由于某些化合物具有活性，尽管没有其他活性AQ所表现出的结构特征，却很难建立结构-活性关系。它们具有邻位或间位取代基和一个游离羟基和/或羰基。当C-6被甲基取代时，AQ的活性通常增加。1
• Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues
  作者：Muhammad Akhtar、Seema Zareen、Swee Yeap、Wan Ho、Kong Lo、Aurangzeb Hasan、Noorjahan Alitheen

  DOI：10.3390/molecules180810042

  日期：——

  Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC50 = 5.70 ± 0.21 and 8.50 ± 1.18 mg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.

  天然存在的蒽醌类化合物达米卡酸酮（damnacanthal, 1）和北达米卡酸酮（nordamnacanthal, 2）通过改进的反应步骤合成，并分别研究了它们对MCF-7和K-562癌细胞系的细胞毒性。中间类似物2-溴甲基-1,3-二甲氧基蒽醌（5，IC50 = 5.70 ± 0.21和8.50 ± 1.18 mg/mL）、2-羟甲基-1,3-二甲氧基蒽醌（6，IC50 = 12.10 ± 0.14和14.00 ± 2.13）、2-羰基-1,3-二甲氧基蒽醌（7，IC50 = 13.10 ± 1.02和14.80 ± 0.74）、1,3-二甲氧基-2-甲基蒽醌（4，IC50 = 9.40 ± 3.51和28.40 ± 2.33）、1,3-二羟基-2-甲基蒽醌（3，IC50 = 25.60 ± 0.42和28.40 ± 0.79）也在MCF-7和K-562癌细胞系中表现出适度的细胞毒性。其他结构相关的化合物，如1,3-二羟基蒽醌（13a，IC50 = 19.70 ± 0.35和14.50 ± 1.28）、1,3-二甲氧基蒽醌（13b，IC50 = 6.50 ± 0.66和5.90 ± 0.95），也表现出良好的细胞毒性。目标化合物达米卡酸酮（1）在MCF-7和K-562癌细胞系中被发现具有最高的细胞毒性，IC50值分别为3.80 ± 0.57和5.50 ± 1.26。所有化合物的结构通过详细的光谱技术得到了阐明。
• Studies on ketene and its derivatives. CIX. Synthesis of naturally occurring anthracene-9,10-diones.
  作者：NOBUYA KATAGIRI、TETSUZO KATO、JUN NAKANO

  DOI：10.1248/cpb.30.2440

  日期：——

  The synthesis of naturally occurring anthracene-9, 10-diones (12a-c) from ethyl 2-benzyl-4, 6-dihydroxybenzoates (7a-d), prepared by the reaction of diketene with ethyl 4-aryl-3-oxobutanoates (6a-d), is described. Reaction of diketene with 6a-d in the presence of sodium hydride in tetrahydrofuran gave 7a-d. Treatment of 7a-d with methyl iodide in the presence of potassium carbonate, followed by ethanolic sodium hydroxide, gave 2-benzyl-4, 6-dimethoxybenzoic acids (9a-d). Cyclization of 9a-d with trifluoroacetic acid-trifluoroacetic anhydride gave anthrone derivatives (10a-d) which, without purification, were oxidized with chromium trioxide to give the anthracene-9, 10-diones (11a-d). Selective demethylation of 11a-c with boron tribromide gave 12a-c.

  本文介绍了从 2-苄基-4，6-二羟基苯甲酸乙酯（7a-d）合成天然蒽-9，10-二酮（12a-c）的方法，该方法由二酮烯与 4-芳基-3-氧代丁酸乙酯（6a-d）反应制备。在氢化钠存在下，二酮烯与 6a-d 在四氢呋喃中反应，得到 7a-d。在碳酸钾存在下用碘甲烷处理 7a-d，然后用乙醇氢氧化钠处理，得到 2-苄基-4，6-二甲氧基苯甲酸（9a-d）。9a-d 与三氟乙酸-三氟乙酸酐环化后得到蒽酮衍生物 (10a-d)，无需纯化，用三氧化铬氧化后得到蒽-9，10-二酮 (11a-d)。用三溴化硼对 11a-c 进行选择性去甲基化，得到 12a-c。