2-acetoxymethyl-[1,4]naphthoquinone | 50371-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetoxymethyl-[1,4]naphthoquinone
• 英文别名: 2-Acetoxymethyl-[1,4]naphthochinon；2-Acetoxymethyl-1,4-naphthoquinone；(1,4-dioxonaphthalen-2-yl)methyl acetate
• CAS: 50371-31-8
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: LVANOIBITFYTLA-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  376.5±42.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetoxymethyl-[1,4]naphthoquinone 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.5h， 生成 2-(hydroxymethyl)-1,4-naphthoquinone N-methylcarbamate
  参考文献：
  名称：

  2-和6-甲基-1,4-萘醌衍生物和潜在的生物还原烷基化剂。

  摘要：

  许多抗肿瘤药同时具有醌核和适当的取代基，这些取代基可使其充当生物还原性烷基化剂。为了开发具有独特性质的此类新化合物，我们合成了一系列2和6-甲基-1,4-萘醌衍生物，并评估了它们对肉瘤180腹水细胞的抗肿瘤活性。这些醌中的几种表现出抗肿瘤活性，从而显着延长了荷瘤小鼠的存活时间。其中活性最高的是2-和6-甲基-1,4-萘醌的甲磺酸酯，甲苯磺酸酯和N-（氯乙基）氨基甲酸酯。

  DOI：

  10.1021/jm00348a023
• 作为产物：
  描述：

  2-甲基萘 在 chromium(VI) oxide 、 氯 、 溶剂黄146 、 三氯化磷 作用下， 生成 2-acetoxymethyl-[1,4]naphthoquinone
  参考文献：
  名称：

  The Synthesis of Some Derivatives of 2-Methyl-1,4-naphthoquinone

  摘要：

  DOI：

  10.1021/ja01218a014

文献信息

• Synthesis of Quinones from Hydroquinone Dimethyl Ethers. Oxidative Demethylation with Cobalt(III) Fluoride
  作者：Ayumi Tomatsu、Syunji Takemura、Kimiko Hashimoto、Masaya Nakata

  DOI：10.1055/s-1999-2875

  日期：1999.9

  The oxidative demethylation of 1,4-dimethoxynaphthalene and 1,4-dimethoxybenzene derivatives with cobalt(III) fluoride proceeded in good to excellent yield to afford the corresponding naphthoquinone and benzoquinone derivatives.

  用三氟化钴对1,4-二甲氧基萘和1,4-二甲氧基苯衍生物进行氧化脱甲基反应，能够获得良好至极佳的产率，从而得到相应的萘醌和苯醌衍生物。
• Cerium catalyzed persulfate oxidation of polycyclic aromatic hydrocarbons to quinones
  作者：Jacek Skar·ewski

  DOI：10.1016/s0040-4020(01)91339-0

  日期：1984.1

  A practical synthesis of polycyclic quinones from the parent hydrocarbons is described. The twophase oxidation of hydrocarbons was accomplished by using ammonium persulfate in the catalytic presence of cerium ammonium sulfate, silver nitrate, and sodium dodecyl sulfate. The reaction conditions and scope have been discussed in detail.

  描述了由母体烃实际合成多环醌的方法。通过在硫酸铈铵，硝酸银和十二烷基硫酸钠的催化存在下使用过硫酸铵完成烃的两相氧化。已经详细讨论了反应条件和范围。
• Development of Novel Quinone Phosphorodiamidate Prodrugs Targeted to DT-Diaphorase
  作者：Carolee Flader、Jiwen Liu、Richard F. Borch

  DOI：10.1021/jm000179o

  日期：2000.8.1

  A series of naphthoquinone and benzimidazolequinone phosphorodiamidates has been synthesized and studied as potential cytotoxic prodrugs activated by DT-diaphorase. Reduction of the quinone moiety in the target compounds was expected to provide a pathway for expulsion of the phosphoramide mustard alkylating agent. All of the compounds synthesized were excellent substrates for purified human DT-diaphorase (k(cat)/K-m = 3 x 10(7) - 3 x 10(8) M-1 s(-1)). The naphthoquinones were toxic to both HT-29 and BE human colon cancer cell lines in a clonogenic assay; however, cytotoxicity did not correlate with DT-diaphorase activity in these cell lines. The benzimidazolequinone analogues were 1-2 orders of magnitude less cytotoxic than the naphthoquinone analogues. Chemical reduction of the naphthoquinone led to rapid expulsion of the phosphorodiamidate anion; in contrast, the benzimidazole reduction product was stable. Michael addition of glutathione and other sulfur nucleophiles provides an alternate mechanism for activation of the naphthoquinone phosphorodiamidates, and this mechanism may contribute to the cytotoxicity of these compounds.
• Potential bioreductive alkylating agents. 4. Inhibition of coenzyme Q enzyme systems by lipoidal benzoquinone and naphthoquinone derivatives
  作者：Ai Jen Lin、Ronald S. Pardini、Brian J. Lillis、Alan C. Sartorelli

  DOI：10.1021/jm00253a002

  日期：1974.7
• Die biologische Aktivität der natürlichen K-Vitamine und einiger verwandter Verbindungen
  作者：H. Dam、J. Glavind、P. Karrer

  DOI：10.1002/hlca.19400230128

  日期：——