1-羟基-3-甲氧基-9,10-蒽醌 | 20733-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-羟基-3-甲氧基-9,10-蒽醌
• 英文名称: 1-hydroxy-3-methoxy-9,10-anthraquinone
• 英文别名: 1-hydroxy-3-methoxyanthraquinone；xanthopurprine 3-methyl ether；xanthopurpurin 3-methyl ether；xanthopurpurin-3-methyl ether；1-hydroxy-3-methoxy-anthraquinone；1-Hydroxy-3-methoxy-anthrachinon；1-Hydroxy-3-methoxyanthracene-9,10-dione
• CAS: 20733-99-7
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: LRCKMFKYRNMGRL-UHFFFAOYSA-N

物化性质

• 熔点：
  193 °C
• 沸点：
  490.3±45.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  1-羟基-3-甲氧基-9,10-蒽醌 在 sodium hydroxide 、 sodium dithionite 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：

  1,3-二溴蒽醌 在 甲醇 、 氢溴酸 、 溶剂黄146 作用下， 生成 1-羟基-3-甲氧基-9,10-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：

文献信息

• Reaction of 2-Acetoxy-3-chloro and 2,3-Diacetoxy Naphthoquinones with 1,3-Dioxy and 1,1,3-Trioxy Butadienes
  作者：Donald W. Cameron、Andrew G. Riches

  DOI：10.1071/ch99179

  日期：——

  Reaction of 2-acetoxy-3-chloro naphthoquinones towards the 1,3-dioxy diene (2) and the 1,1,3-trioxy diene (9) was examined. The competing influence of the acetoxy and chloro substituents was assessed from the regiochemistry of the resulting Diels–Alder chemistry, as was competition between that process and Michael addition/elimination. Reaction of the same dienes towards the less reactive 2,3-diacetoxy naphthoquinone (25) was also investigated.

  研究了 2-乙酰氧基-3-氯萘醌与 1,3-二氧二烯（2）和 1,1,3-三氧二烯（9）的反应。 和 1,1,3-三氧基二烯 (9) 的反应进行了研究。乙酰氧基和氯代 乙酰氧基和氯取代基的竞争影响。 和迈克尔加成/消除之间的竞争。 和迈克尔加成/消除之间的竞争。同样的二烯与反应性较低的 还研究了活性较低的 2,3-二乙酰氧基萘醌 (25) 的反应。 进行了研究。
• 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。
• Reactions of ketene acetals-14 The use of simple mixed vinylketene acetals in the annulation of quinones
  作者：Jacques Savard、Paul Brassard

  DOI：10.1016/s0040-4020(01)91496-6

  日期：1984.1

  α,β- β, γ-unsaturated esters can be converted by strong base and chlorotrimethylsilane to the corresponding mixed vinylketene acetals which are shown to be particularly useful and generally applicable reagents for the regiospecific annulation of halogenoquinones. The reaction proceeds readily with a variety of substrates including benzoquinones.

  α，β-β，γ-不饱和酯可通过强碱和三甲基氯硅烷转化为相应的混合乙烯酮缩醛，这对于卤代醌的区域特异性环合而言是特别有用和普遍适用的试剂。该反应在包括苯醌在内的多种底物下容易进行。
• Regiospecific syntheses of quinones using vinylketene acetals derived from unsaturated esters
  作者：Jacques Savard、Paul Brassard

  DOI：10.1016/s0040-4039(01)86747-2

  日期：——

  A general method of annellating quinones in high yield has been devised using mixed vinylketene acetals obtained directly from the enolate ions of unsaturated esters.

  已经设计了使用直接从不饱和酯的烯醇盐离子获得的混合乙烯基乙烯酮缩醛来高产率环化醌的一般方法。
• 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。