2-hydroxy-5-methoxy-p-xyloquinone | 25653-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-5-methoxy-p-xyloquinone
• 英文别名: 2-Hydroxy-5-methoxy-3,6-dimethylcyclohexa-2,5-diene-1,4-dione
• CAS: 25653-42-3
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: YYPQLDVIQXWGQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 2-hydroxy-5-methoxy-p-xyloquinone 以 乙醚 为溶剂， 生成 2,5-dimethoxy-3,6-dimethyl-1,4-benzoquinone
  参考文献：
  名称：

  Partial Deacetylation of Asterriquinone Diacetate by Aqueous Sodium Bicarbonate in Pyridine.

  摘要：

  阿斯特里奎酮（ARQ）；2, 5-bis[1-(1, 1-二甲基-2-丙烯基)-1H-吲哚-3-基]-3, 6-二羟基-2, 5-环己二烯-1, 4-二酮和ARQ单乙酸酯是来自干酪芽孢杆菌（Aspergillus terreus）IFO 6123的代谢产物。ARQ二乙酸酯在80°C下用5%水合NaHCO3在吡啶中处理5分钟，转化为ARQ单乙酸酯，产率为93.4%。同样，通过在室温下用5%水合NaHCO3在丙酮中处理，2, 5-二乙氧基-p-木酚醌和2, 5-二乙氧基-p-苯醌分别转化为2-乙氧基-5-羟基-p-木酚醌（产率为85.8%）和2-乙氧基-5-羟基-p-苯醌（产率为66.7%）。

  DOI：

  10.1248/cpb.43.1818
• 作为产物：
  描述：

  3,6-Dimethyl-4,5-dimorpholino-1,2-benzochinon 在 盐酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-hydroxy-5-methoxy-p-xyloquinone
  参考文献：
  名称：

  Synthese und Hydrolyse von 3,6-Dialkyl-4,5-bis[dialkylamino]-1,2-benzochinonen

  摘要：

  DOI：

  10.1055/s-1979-28797

文献信息

• Preparation and Route of Asterriquinone Monoalkyl Ether from Asterriquinone Diacetate by Treatment with a Mixture of Alcohol and Alkali, Followed by Acidification.
  作者：Akira KAJI、Ryo SAITO、Yukako HATA(nee SHINBO)、Noriki KIRIYAMA

  DOI：10.1248/cpb.47.77

  日期：——

  3-Alkoxy-6-hydroxy-p-benzoquinones were prepared by the treatment of 3, 6-diacetoxy-p-benzoquinones with a mixture of alcohol and alkali, followed by acidification. The key intermediate acetoxy-alkoxy-p-benzoquinones were formed by the base-catalyzed addition of an alkoxy anion to the conjugated double bonds in the diacetoxy-p-benzoquinone ring, followed by an acetoxy anion elimination. This method was applied for preparing a novel o-quinone derivative of asterriquinone (ARQ) by the addition of 2-haloethanol and intramolecular O-alkylation.

  3-烷氧基-6-羟基-p-苯醌通过将3,6-二醋氧基-p-苯醌与醇和碱的混合物处理，然后酸化制备而成。关键中间体醋氧基-烷氧基-p-苯醌是通过碱催化将烷氧基阴离子加成到二醋氧基-p-苯醌环中的共轭双键，随后进行醋氧基阴离子消除而形成的。这种方法被应用于制备一种新型的o-醌衍生物阿斯特里奎诺（ARQ），通过添加2-卤代乙醇和分子内O-烷基化实现。
• Partial Deacetylation of Asterriquinone Diacetate by Aqueous Sodium Bicarbonate in Pyridine.
  作者：Akira KAJI、Kengo KIMURA、Tomoki IWATA、Noriki KIRIYAMA

  DOI：10.1248/cpb.43.1818

  日期：——

  Asterriquinone (ARQ); 2, 5-bis[1-(1, 1-dimethyl-2-propenyl)-1H-indol-3-yl]-3, 6-dihydroxy-2, 5-cyclohexadiene-1, 4-dione and ARQ monoacetate are metabolites from mycelium of Aspergillus terreus IFO 6123. ARQ diacetate was converted into ARQ monoacetate by treatment with 5% aq. NaHCO3 in pyridine at 80°C for 5 min, and the yield was 93.4%. Similarly, by treatment with 5% aq. NaHCO3 in acetone at room temperature, 2, 5-diacetoxy-p-xyloquinone and 2, 5-diacetoxy-p-benzoquinone were converted into 2-acetoxy-5-hydroxy-p-xyloquinone (yield, 85.8%) and 2-acetoxy-5-hydroxy-p-benzoquinone (yield, 66.7%), respectively.

  阿斯特里奎酮（ARQ）；2, 5-bis[1-(1, 1-二甲基-2-丙烯基)-1H-吲哚-3-基]-3, 6-二羟基-2, 5-环己二烯-1, 4-二酮和ARQ单乙酸酯是来自干酪芽孢杆菌（Aspergillus terreus）IFO 6123的代谢产物。ARQ二乙酸酯在80°C下用5%水合NaHCO3在吡啶中处理5分钟，转化为ARQ单乙酸酯，产率为93.4%。同样，通过在室温下用5%水合NaHCO3在丙酮中处理，2, 5-二乙氧基-p-木酚醌和2, 5-二乙氧基-p-苯醌分别转化为2-乙氧基-5-羟基-p-木酚醌（产率为85.8%）和2-乙氧基-5-羟基-p-苯醌（产率为66.7%）。
• Kaji; Saito; Shinbo, Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 12, p. 2340 - 2341
  作者：Kaji、Saito、Shinbo、Kiriyama

  DOI：——

  日期：——
• SCHILL P.; LOGEMANN E.; DIETRICH B.; LOWER H., SYNTHESIS, 1979, NO 9, 695-697
  作者：SCHILL P.、 LOGEMANN E.、 DIETRICH B.、 LOWER H.

  DOI：——

  日期：——
• Preparation and Structure-Activity Relationships of Novel Asterriquinone Derivatives.
  作者：Akira KAJI、Kengo KIMURA、Masanori TERANISHI、Noriki KIRIYAMA、Masaaki NOMURA、Ken-ichi MIYAMOTO

  DOI：10.1248/cpb.46.1325

  日期：——

  Asterriquinone (ARQ, 1a) is an antitumor metabolite of Aspergillus terreus IFO 6123. To gain insight into the structure-activity relationships of ARQ, a series of chemically modified derivatives (1-6), the ARQ analogues (b-e) and the 2, 5-dihydroxy-p-bezoquinone analogues (f-h), were prepared, and cytotoxic acitivity against mouse leukemia P388 cells investigated. Results indicated that : 1) at least one hydroxy group or acetoxy group in the p-benzoquinone moiety is important to exhibit cytotoxicity; 2) in the p-benzoquinone moiety, a single methoxy group and/or one aceotxy group substitution showed more potent cytotoxicity than when two hydroxy groups are substituted (1); 3) the indole ring is important for the cytotoxicity of ARQ analogues; 4) the 1, 1-dimethly-2-propenyl group in the indole ring is not important for the cytotoxic activity of ARQ.

  Asterriquinone (ARQ, 1a) 是青霉菌 (Aspergillus terreus IFO 6123) 的一种抗肿瘤代谢产物。为了深入了解 ARQ 的结构-活性关系，准备了一系列化学修饰的衍生物 (1-6)，ARQ 同源物 (b-e) 和 2, 5-二羟基-p-苯醌同源物 (f-h)，并研究了其对小鼠白血病 P388 细胞的细胞毒性活性。结果表明：1）在 p-苯醌部分至少需要一个羟基或乙酰氧基才能表现出细胞毒性；2）在 p-苯醌部分，单个甲氧基和/或一个乙酰氧基的取代比两个羟基取代时表现出更强的细胞毒性 (1)；3）吲哚环对 ARQ 同源物的细胞毒性具有重要作用；4）吲哚环中的 1, 1-二甲基-2-丙烯基对 ARQ 的细胞毒性活性并不重要。